“You can’t wing it or outsource it, even at the CEO level. You need to work at it daily — so AI learns you and you learn AI.” —Jim VandeHei, CEO, Axios

At this point I have driven nearly 100,000 miles using Tesla’s Full Self-Driving, and I have become so used to it that flying somewhere presents a problem. I like having my own car at my destination rather than relying on Uber, but if I rent anything other than a Tesla, I barely trust myself to drive it anymore. I have gotten that accustomed to the car that drives itself.

I know some people (though fewer by the day) who insist they would never trust self-driving technology. Usually, they change their mind after one ride. “I could never” suddenly becomes “I need this.”

In a world being remade by AI, more CEOs are starting to have similar experiences. AI has already transformed the work of programmers, technical writers, designers, and other specialists. But its applications to the core responsibilities of the CEO are less obvious. What does it actually mean to use AI to become a better chief executive?

As I wrote last week, AI and the CEO job share an unusual characteristic: both are so broad in scope that figuring out what to do in the first place is a significant challenge. Give a CEO a powerful general-purpose AI tool, and there are a thousand ways to put it to work. Many of those applications have little to do with the CEO’s own responsibilities.

This has created an interesting divide among early adopters. I know CEOs who have become extraordinarily proficient with AI, using it daily to perform complex technical work. But I’m increasingly convinced that some of these enthusiastic adopters are overlooking the applications that could make the greatest difference in their performance as CEOs. Meanwhile, another group is beginning to develop an entirely different way of running their companies with AI assistance. I believe the gap between these groups is going to become much more consequential over the next few years.

The 3 types of CEOs

When a new technology comes along, some people jump in early, tolerate its imperfections, and invest time learning how to use it. Others wait for the technology to mature, avoiding the inconvenience and expense of being an early adopter.

The determining factor, for me, is conviction. If I have doubts about whether a technology will become important, I’m comfortable letting others experiment with it. But when I believe something is going to fundamentally change the way business is conducted, I want to get good at it as soon as possible.

I think it’s clear to all of us that AI is in the former category. While most CEOs I know share that conviction, I increasingly notice three distinct approaches to personal adoption:

I personally know several CEOs in that second category, who have gone deep into AI. Some are building whole apps or full websites, developing sophisticated tools, and doing other technical work that would have required a specialist just a few years ago. This is genuinely cool stuff.

But is this adding to the CEO’s effectiveness as CEO, or is it giving them the illusion of productivity without helping them lead the organization? Much of the typical CEO’s AI activity — from basic tasks like summarizing meetings to grand experiments in building — has little to do with the actual responsibilities of the CEO.

In a company of any significant size, the chief executive should have people responsible for building software, analyzing functional data, and producing marketing materials. The CEO is responsible for setting the company’s direction, allocating resources, building an effective executive team, and making sure the organization delivers on its commitments. I wonder how many of these AI enthusiasts have devoted comparable attention to using the technology to improve their performance in those areas.

There’s evidence that business leaders are still concentrating their personal AI use on relatively routine activities. A 2026 survey by General Assembly and EZRA found that among more than 500 business leaders, 69% used AI to search for information, 68% to summarize documents, and 58% to draft emails. Just 27% used it for scenario planning, and the same percentage for organizational design. Meanwhile, BCG reports that only 15% of CEOs are generating meaningful value from AI.

There’s no question in my mind that it is the third group of early adopters, those applying AI to the fundamentals of the CEO job, who will see the greatest return. We’re beginning to see AI systems capable of providing robust CEO-specific support, drawing on detailed knowledge of the company and its management processes plus frameworks for how CEOs create value.

Five CEOs who are applying AI to the CEO job

We are beginning to see fascinating examples of chief executives putting AI to work on their own responsibilities. Here are some of my favorites:

1. Robin Vince, BNY

Seeing the whole business and deciding where to focus

Robin Vince runs BNY, America’s oldest bank, with approximately 46,000 employees. In an August interview with Axios, he described a use of AI that gets at one of the CEO’s most fundamental responsibilities: understanding the business as a whole.

The CEO occupies a unique position in the organization. Every functional executive is responsible for a particular area of the business, but the CEO alone is responsible for the enterprise in its entirety. The CEO must understand how the functions interact, balance their competing priorities, and make decisions that optimize the performance of the whole company. That requires maintaining a perspective that no individual functional leader can provide.

Vince sees an extraordinary opportunity for AI here. As he observes: “There’s no person who can see the picture as completely.” By drawing on information from across the organization, AI can help the CEO understand the relationships, tensions, and tradeoffs among its functions, including connections that might otherwise go unnoticed.

Vince is also using that broader understanding to decide how to spend his own time. His AI “coaches me at the beginning of the day, with how I should approach my day proactively.” This is enormously valuable, and something I’m working with CEOs on as well. A CEO has tremendous freedom to choose how to spend the day, which is one reason so many fall into a pattern of constant firefighting. An AI that understands both the CEO’s responsibilities and the company’s current circumstances can help identify where the CEO’s personal attention will make the greatest difference.

These two capabilities reinforce each other. The more complete the AI’s understanding of the business, the better it can help the CEO decide where to focus.

2. Carla Vernón, The Honest Company

Keeping the board relationship strong

Carla Vernón became CEO of The Honest Company in 2023 and led a difficult turnaround involving shrinking margins, limited cash, and pressure to demonstrate profitability. She has also become an enthusiastic AI user.

In an interview with Harvard Business Review, she described spending her spring break exploring tools and developing AI agents for her own use. One of those agents helps prepare her for biweekly meetings with her board chair:

One of the things that I do now is for my meetings with my board chair, which are every other week, I have AI prepare a summary of our recent performance results, the outlook as we’re looking ahead, and some key themes that my board chair and I want to pick up every time we talk. Now I don’t have to write that report. AI gives me the first draft.

This is an example of taking what we all recognize as a core AI capability (summarizing notes and data) and applying it where it matters most to the CEO, in this case her relationship with the board chair. That distillation of companywide results into key themes relevant to the board is a great example of a CEO who understands the AI advantage.

3. Jim VandeHei, Axios

An operating system for the CEO

Axios CEO Jim VandeHei has spent the past year making himself an AI test subject. In his “Confessions of an AI Lab Rat,” he says:

On a personal level, I use ChatGPT or Claude for one to two hours daily, usually in the early mornings, and control an AI personal operating system via my phone. That’s connected to an always-on computer that runs several agents, including one that scans daily for CEO-related data and trends.

A personal operating system for the CEO — music to my ears! VandeHei’s experimentation gives him firsthand knowledge of what the technology can accomplish and where it still struggles. That knowledge is extremely valuable for someone responsible for directing an organization’s AI strategy. He also explicitly points to the problem of shallow AI usage by many CEOs:

You need to go beyond chat. The life-changing work happens in projects or with agents. You need to feed in files of information and direct it with specific skills on how you want it to write, think, fact-check and cite actionable research and intel. This is where your company is headed. Only by doing it yourself will you discover new ways to apply it internally. And you can't delegate this. Your team copies what you do, not what you mandate. Adoption rises and falls based on whether the CEO is hands-on, especially at smaller orgs.

Amen.

4. Matt Blumberg, Markup AI

A virtual board of directors

Matt Blumberg has taken another approach that I find particularly interesting. The CEO of Markup AI constructed what he calls a “fantasy board of directors,” populated by AI versions of 15 prominent thinkers and business leaders, including Warren Buffett, Steve Jobs, and Oprah Winfrey.

As Fortune reported, Blumberg and his executive team created approximately 5,000-word profiles for the individual personas using publicly available material. They then combined those perspectives with information about their company.

Blumberg uses this virtual board to examine strategic proposals, prepare for presentations, and anticipate questions from his actual directors. He even asked it to give him a 2025 performance review, which he found surprisingly insightful. The entire system reportedly took just an hour or two to create.

5. Dara Khosrowshahi, Uber

Rehearsing for the CEO

A story from Uber CEO Dara Khosrowshahi illustrates another fascinating application: using AI to simulate conversations with senior executives.

In an interview, Khosrowshahi revealed that some of Uber’s engineering teams have built a “Dara AI.” Before presenting a proposal to the real CEO, employees can rehearse their presentation with an AI version of him.

Think about the potential of that practice. Employees preparing major proposals can pressure-test their arguments, anticipate objections, and refine their presentations before consuming executive time. The same principle works for the CEO preparing to speak with an investor, negotiate with an important customer, deliver difficult feedback to an executive, or present an unpopular decision to the board.

I am a big believer in rehearsing important conversations. AI makes it possible to do this repeatedly, with different personalities, objections, and scenarios, whenever the CEO has a few minutes available. It is one of the simplest ways I know to make a consequential conversation more productive.

The window is still open

Every CEO I talk to uses AI. But smart applications like the above — and many others — are still something of a rarity. More common is AI used as a better search engine, a quick summarizer, a drafter of low-stakes emails. All good stuff. But even a CEO who becomes exceptionally proficient with AI for peripheral activities can still be late to adopting its most consequential applications to their specific role.

Every CEO should be asking how AI can strengthen the five fundamental responsibilities of the job: owning the vision, providing resources, building the culture, building a decision-making organization, and delivering performance. Those activities determine the success of the enterprise. Improvements in the CEO’s ability to perform them can create extraordinary value.

I want to help more CEOs have the experience I’ve had with Tesla: the moment when an unfamiliar technology becomes something you use so naturally, and find so valuable, that you can scarcely imagine going back. That is an advantage worth pursuing today. Because within a few years, running a company without a powerful AI operating system will seem essentially unthinkable.

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Your airport lounge options are about to expand thanks to a player many didn’t expect: Southwest Airlines.

Since CEO Bob Jordan took the reins (I had the privilege of interviewing him on his first day), much has changed. Open seating and free checked bags are things of the past. The addition of Southwest’s first “Icon Lounges” in 2027 will be a further shift in amenities, and identity.

The first four Southwest lounges will pop up at hubs central to the airline’s strategy:

• Austin-Bergstrom International Airport (AUS)

• Baltimore/Washington International Thurgood Marshall Airport (BWI)

• Nashville International Airport (BNA)

• Daniel K. Inouye International Airport (HNL) in Honolulu

The airline also announced plans for a premium credit card and more generous loyalty benefits.

The announcements came as Southwest reported record third-quarter revenue and strong returns from the aforementioned overhaul of seating, fares, and fees. We will look at those developments below, along with Bloom Energy’s remarkable growth and some significant decisions at American Express.

Southwest Airlines (NYSE: LUV)

Q3 FY2026 Earnings Call

Higher fares and fewer perks are not weakening demand

Southwest’s decision to abandon several longstanding practices, including free checked bags and open seating, has produced a remarkable improvement in revenue.

Average fares rose approximately 27% year over year, yet passenger volumes remained strong. Revenue per available seat mile increased 21.6%. Business travel was particularly encouraging, with passenger counts up roughly 9% and revenue up 29% on essentially flat capacity.

Bob Jordan, Southwest’s president and CEO, said:

So while fares have accelerated certainly a lot here in 2026, and you’ve got to remember that while they’re up, they remain below 2019 in real terms. Our customers are continuing to respond, and we’re seeing -- Justin said this, we’re seeing that both in higher passenger volumes and in yield. So it’s not -- those higher fares are not causing an erosion of volumes.

The changes are also having a substantial impact on profitability. Southwest expects assigned seating and extra-legroom products to contribute approximately $1.5 billion in incremental operating earnings in 2027, up from $1 billion in 2026.

Southwest is building a premium loyalty business

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Your board should be rooting for you. If you win, they win.

But most CEOs say it doesn’t feel that way. Amid the strife of the job, it is easy to slip into negative thoughts. “My board doesn’t understand.” “They have no faith in me.” “They’re gonna fire me!” According to Spencer Stuart, only 37% of CEOs said their board had their back. (Meanwhile, 47% of directors believed their boards had the CEO’s back — a telling misalignment.)

Boards are hardly blameless here. Some are dysfunctional and meddle incessantly. But in the majority of cases I have seen, there is a lot of unnecessary worry in the CEO’s head, sometimes to the point that it becomes a self-fulfilling prophecy. The CEO can sink so far into concerns about what the board is thinking that they don’t take a breath and do the #1 thing that would help them in the next board meeting: proper preparation.

Blindsided by the board

I visited recently with a CEO who was thoroughly demoralized by his board’s reaction to a plan he presented. He had walked into the meeting feeling optimistic about what he wanted to accomplish, but then the directors responded with a level of skepticism he hadn’t anticipated. He felt shot down.

As he told me what happened, I found myself thinking that I could have predicted much of the reaction. Not because I’m some sort of board whisperer, but because I have spent enough time on both sides of the table to recognize the kinds of objections that naturally arise. Plenty of experienced directors and CEOs would have seen them coming.

I suspect that if this CEO and I had talked before the meeting, we could have worked through those objections and refined his approach. He might have come away from the meeting energized by a productive discussion instead of questioning whether his board had any faith in him.

The lesson is that CEOs shouldn’t be discovering how the board will react to a key message as they are presenting it. A bit of anticipation, preparation, and scenario modeling goes a long, long way.

What comedians know about preparation

Comedians have a tough gig: they walk onto a stage night after night and must induce an involuntary response from a roomful of people. You can explain why a joke ought to be funny, but the audience laughs or it doesn’t. Period.

It looks spontaneous, although it’s anything but. Even pros at the level of Chris Rock and Jerry Seinfeld go through a rigorous trial period with new material, testing and tweaking and often bombing in smaller clubs. By the time it’s on the HBO special or your YouTube algorithm, it’s been finely tuned for the best impact.

Comedian Yannis Pappas had a bit about his girlfriend telling him she needed space, which he translated for the audience as “I need you to help me break up with you.” It didn’t get laughs. The breakup was still raw, and the crowd felt sorry for him. So he changed one word. “Girlfriend” became “girlfriends,” and suddenly the joke was about everyone who has ever been dumped. It started landing, and the bit went on to anchor his first Comedy Central special.

In my view, CEOs are wise to bring that preparatory discipline to their board meetings.

Every director arrives at your conference table with a different set of experiences, priorities, and mental models. One may have lived through a disastrous acquisition and consequently view your growth plan through a skeptical lens. Another might be concerned about the balance sheet, while a third is primarily interested in the strength of your executive team. They aren’t immersed in your business every day, and they don’t necessarily see the logic that seems self-evident to you.

That’s why I strongly encourage CEOs to practice important board discussions with someone capable of playing devil’s advocate. More on that momentarily.

Improv in the boardroom

Once you’ve anticipated how your message is likely to land, you can also prepare for what comes next: the questions, objections, and unexpected turns in the conversation.

To return for a moment to the world of comedy, consider the rising popularity of crowd work. Some of today’s most popular comics have built enormous followings through clips of these impromptu interactions. The exchanges look entirely off the cuff, and sometimes they are. But experienced comics also know the kinds of responses they’re likely to get and have developed ways of steering the conversation depending on what comes back.

There’s a reason improvisational comedy has become a discipline of its own. Its best-known principle, “yes, and,” encourages performers to accept what another person introduces and build on it rather than shutting it down. In fact, a 2020 study found that just 20 minutes of improv exercises could make people more comfortable with uncertainty, an effect that wasn’t observed in a comparison group doing scripted exercises.

CEOs can benefit from a similar mentality when dealing with their boards. Many a CEO has walked confidently into a board meeting only to break out in a sweat at the first pointed question. Suddenly they are arguing over a director’s premise, correcting a perceived misunderstanding, or hurrying to the next slide. A perfectly reasonable challenge becomes an uncomfortable confrontation.

The better approach is to remain genuinely open to what the director is saying. You might acknowledge the concern, explain how you’ve thought about it, or explore what circumstances would cause you to change course.

Board members are looking for evidence of sound judgment. A CEO who can discuss the risks candidly, entertain alternative scenarios, and still articulate a clear recommendation does far more to build confidence than one who delivers a polished sales pitch and becomes defensive when questioned.

A little bit of practice goes a long way

Before your next board meeting — especially if you will be presenting something new or uncomfortable — find a trusted adviser, an experienced board member, or another CEO who can examine your presentation without sharing all your assumptions. (Heck, I’m happy to work on it with you.) Have them challenge the weakest parts of your plan, question your evidence, and raise the objections you least want to hear.

A trusted chief of staff can play the role of a skeptical director. So can a mentor, an experienced CEO, or anyone who has spent a lot of time in boardrooms. The trick is finding someone willing to be candid with you, not just tell you that your presentation looks great.

Ask for the support you need

There is one more thing worth remembering if you don’t feel that your board has your back. You can actually tell your directors what kind of support you need from them.

I recommend establishing a Board-CEO Operating Agreement that clarifies which decisions belong to the CEO, which require board involvement, and how the two sides will communicate. It’s a way of getting expectations out in the open rather than leaving each side to guess what the other wants.

The Spencer Stuart research I mentioned earlier found that 68% of CEOs who had explicitly discussed with their boards the support and input they should expect felt effectively supported. Among those who hadn’t had those conversations, the figure was just 50%.

That’s a pretty good argument for having the conversation rather than sitting around worrying about what your directors think.

P.S. If you’d like to see how ChatCEO can help you rehearse for your own board, I’m happy to show you what we’re doing. You can get started here or reach out to me directly.

PowerPoint makes presentations. Nobody has to explain that. You click around, you try a few things, and you figure out how to build a better deck. The purpose is built-in. We even call the software’s output the same thing as the application: PowerPoint.

Nearly every tool a company buys has a similarly well-defined purpose. A CRM tracks customers. Accounting software keeps the books. A spreadsheet does math. You never have to wonder what to do with the tool.

AI is different. Very different.

AI Was Not Designed for One Purpose

AI is not designed for one particular job. It is general-purpose intelligence. It can write, analyze, plan, summarize, argue, and advise on almost anything you put in front of it. It is like a person with a degree in everything.

That sounds like a gift, and it is. But it is also a problem. Once you open an AI tool, you usually get a blank box staring back at you. Many AI providers try to help by putting suggested prompts and workflows in front of you — but the fact remains that those suggestions represent a tiny sliver of its capability, chosen by someone who isn’t you.

With AI, the ultimate generalist, it’s hard to know where to start. It can do anything, but what should it do for you?

It’s the Same Problem the CEO Has

I have written before that the CEO job is unique because nobody tells you what to do. Every other executive runs one function, using a scoreboard and a clear set of responsibilities. But the CEO runs the whole company with no instructions. Figuring out WHAT to do in the first place is usually the hardest part of the job.

If your executives’ jobs are like those specialized apps (PowerPoint, Salesforce, QuickBooks), yours is like the “everything” app: AI.

Now let’s put the two together: AI is a general tool with no assigned purpose. The CEO is a general role with no assigned function. Hand one to the other and you get the same question twice: What should I do?

A CEO who is unclear about how to spend their own time will be unclear about how to use AI. They will aim it at the small-scale tasks everyone else is using it for: drafting emails, summarizing documents, replacing Google. Useful, sure. But it’s not giving you an edge as CEO.

One Answer to Both Problems

If AI and the CEO role share the same inherent problem, they also share a solution: having a system for the CEO role.

A systematic approach to being CEO answers the “What should I do?” question with specificity. It tells you what the job is and how it differs from other executive roles. It points your attention where it needs to be and suggests what to do next. It shows you the shape of the job and the basic constituencies it serves.

When you have a mental model for those things, the AI question gets much smaller. “How can I use this broad, universal tool?” becomes “How can AI make me more effective in my CEO activities?”

The idea behind the Chief Executive Operating System — the framework I developed over my career — is to give CEOs that clarity. Once you have it, you have simultaneously given yourself a map for how to use AI effectively.

It’s a big topic, but no CEO has to tackle it alone.

My team and I are developing ways to help CEOs apply AI to the things that matter most: setting direction, building the right team, making decisions, and keeping the company on track.

If you are a CEO who feels you are only scratching the surface of what AI could do for you, reach out. I would be glad to talk through your situation and share some approaches I have seen work for other chief executives.

Further reading

The pizza chain is getting more orders, including from lower-income customers, but people are buying fewer items each time. The company lowered its growth expectations, and its shares fell about 3% in early trading after the announcement.

More on how Domino’s is responding below, along with some encouraging hiring trends reported by ManpowerGroup and a telling development in the warehouse industry.

Read more

Learn About ChatCEO

The AC in my Tesla went out a few weeks ago.

This is my fifth Tesla and the first time I’ve had to take one to the dealer for a repair, so I wasn’t too upset. Then I found out the first appointment I could get was four weeks away. In Texas, four weeks with an AC that only works when it feels like it isn’t a fun prospect.

When the day finally came, I dropped the car off and picked it up that evening. They had worked on the AC, but it still quit working on the way home. Aaargh. Now I was frustrated, disappointed, and looking at another four-week wait.

It’s not like I needed my Tesla to fly. I just needed cool air.

I completed the customer survey form they emailed me, but I didn’t think it would matter.

I was wrong. Today, I got an unsolicited call from a rep who scheduled a new service visit in just a few days. Now I’m impressed. Instead of being frustrated and disappointed, I’m certain my next car will be a Tesla.

To get this outcome, I never called anyone or escalated anything. I filled out a survey I assumed nobody read. Somebody did read it, and that somebody had the authority to act.

It seems simple, but at a lot of companies, the authority to act just isn’t there. And it’s often a downstream effect of a misalignment at the top of the company.

The question to ask

Most CEOs think they know how their customers feel. That is usually a comforting belief that isn’t quite true. Unless there is well-tended machinery to get customer feedback to them, they are likely living in a bubble.

Once a quarter, ask your leadership team this:

How many times did we hear about disappointing a customer?

A big number is uncomfortable, but it tells you the news is getting through and you can do something about it. A zero should really worry you. If you have hundreds or thousands of customers, you didn’t get through the quarter without letting some of them down. You just didn’t hear about it.

Most of the time, customers won’t tell you when you disappoint them. They just move on and engage less. They stop returning calls and start perusing alternatives. Then at renewal time, they tell you it’s a budget issue. By the time it reaches the CEO, it’s a churn number, and it’s too late to fix anything.

There’s a simple structural fix that is the first step to solving this: The Customer Success department reports directly to the CEO.

Why not put Customer Success under sales?

Plenty of companies put Customer Success under the Sales department. I understand why. Sales sold to the customer initially. Sales knows them, and it looks more efficient on the org chart.

But look at what the sales leader is paid for: bookings, pipeline, momentum, etc. A struggling customer threatens all three, because that customer was supposed to be a reference, an expansion, or the proof point for the next deal. So when Customer Success reports to that leader, bad news has to pass through someone with every reason to wait a quarter and try to fix it quietly, under the radar.

It’s not that the sales leader is hiding customer dissatisfaction on purpose. But when your boss’s bonus depends on the story being good, the story gets softer. The edges get sanded off.

The other thing that happens when Customer Success reports to sales is that the department’s function turns into account management. The job becomes protecting renewals and finding upsells. Those things matter, but they are measured in revenue, not in whether the customer got what they paid for. A customer can renew for two years out of inertia and be unhappy the whole time. A good Customer Success function reads between those lines.

Customer Success is the one function that sees the gap between what was sold and what was delivered. That gap is where a lot of disappointment starts. Whoever sees it must be able to act on it and tell someone upstream, and it can’t be someone who reports to the sales leader.

Sales and Customer Success shouldn’t be rivals, but there is a natural tension between them. They need a clean handoff and respect for each other’s work. And in a young company, the CEO usually is Customer Success. Once you’re a mid-market company with real revenue and customers you can’t afford to lose, that stops working.

Where the CEO comes in

The CEO job exists because there must be someone who manages the business across all functions. Customer Success must report to the CEO because customer problems often span different functions. It’s usually not something wrong in Customer Success itself.

The customer’s dissatisfaction may come from one of the other core areas of the business: issues with the product (like faulty ACs), promises made during the sales process that weren’t fulfilled, pricing that feels out of step with the value derived, and so on. No single function is equipped on its own to diagnose the issue and decide on the proper resolution. It requires the CEO’s 10,000-foot view. The solution will involve balancing across those departments—sales, marketing, product, etc.

This is why you need Customer Success reporting directly to the CEO. It’s not a subsidiary of another function; it is its own core function, serving one of the business’s core constituencies (customers, employees, shareholders). Customer Success needs a proverbial seat at the table precisely so the constituency of customers has a voice to the CEO.

When the head of Customer Success reports to the CEO, three things happen.

1. Bad news reaches you without passing through someone who has a stake in how it sounds.

2. Product, sales, and marketing all hear the customer’s side from someone who isn’t defending their own numbers.

3. And somebody owns customer outcomes, which is a different job from just keeping customers from leaving.

What it looks like

The reporting line is the starting point. Here’s how to make it work in practice:

• Customer Success reports to the CEO and sits on the leadership team.

• The leader is measured on retention and customer outcomes, not bookings.

• Keep a running count of every time a customer was let down and review it monthly. If it’s suspiciously empty, be suspicious.

• Anyone in Customer Success can take a serious problem to the CEO without asking permission first.

• You get on the phone with customers yourself, a few calls a month, and compare what you hear with what you’re being told.

I encourage CEOs to ask these two questions.

1. How many times did we hear about disappointing a customer?

2. And would we even hear it when we did?

I filled out a survey I figured nobody read, and somebody did. Would that happen at your company?

Before we get to today’s article, a bit of positivity:

CEOs showed more appetite to invest and hire in Q3 2026.

In the Business Roundtable’s latest CEO Economic Outlook survey, the index ticked in the right direction:

52% of CEOs expected to increase capital spending over the next six months, up from 50% last quarter.

CEOs’ hiring intentions strengthened more sharply: 36% planned to add employees, up from 30%.

The combination suggests that confidence is broadening. It may not be a hiring boom, but executives see reason to expand both capacity and headcount, an encouraging signal for economic growth. And for the economy, it means a firmer foundation—should those plans become action.

AI’s Real Value Is Upstream

Every CEO I talk to has an AI initiative underway.

But once you probe into what has actually changed, the answers get thin. Where has AI improved the bottom line? Where has it created significant value for customers or employees?

The usual explanations for disappointing AI returns focus on the technology: wrong tools, inadequate training, immature capabilities. But I think many CEOs are looking for the payoff in the wrong place.

Most companies are applying AI downstream, helping employees perform individual tasks more efficiently. There is certainly value in drafting emails faster, summarizing meetings, and automating routine work. But the much bigger opportunity is upstream, in the CEO’s strategic work: setting direction, allocating resources, making decisions, and keeping the organization focused on its goals.

It’s the difference between doing more stuff, and doing more of the right stuff.

This is where I believe AI has the potential to create enormous leverage. Properly deployed, it can dramatically extend the CEO’s reach and influence throughout the organization. It can sharpen the CEO’s decision making, improve resource allocation, and build strategic alignment, up, down and across the organization. It can also give the CEO greater visibility into how the company is performing and where intervention is needed.

But to do that upstream stuff well, AI needs a clear understanding of how the company operates. And in many companies, those things aren't nearly as clear or well documented as they should be.

If you point AI at a company with a clear strategy, defined roles, measurable goals, and disciplined management rhythms, it can make that company faster and sharper.

But if you point it at a company where priorities live in the CEO’s head, accountability is fuzzy, and decisions get remade every week, it will produce more disorder at greater speed and with more confidence.

That is why I believe one of the most important things a CEO can do to prepare for AI is something I have been advocating for decades: make the implicit explicit.

Writing the Unwritten

One of the central ideas I’ve taught CEOs for years is the importance of making the implicit explicit.

A surprising amount of what determines how a company operates is never formally articulated. The CEO may have a clear idea of where the company is headed, how it will win against competitors, and which priorities take precedence over others. But how much of that understanding has actually been put into words, much less written down?

Often, the people who have worked closely with the CEO for years have learned these things through experience. They know what the CEO means, even when the CEO has not been particularly clear. Everyone else has to figure it out.

I call this leadership by ESP. The CEO communicates something broad, people try to infer the intended meaning, and the organization moves forward based on a collection of educated guesses.

This has never been a good way to manage people. And now there is another reason to fix it.

AI can absorb vast amounts of information, reason through problems, and increasingly figure out how to accomplish complex tasks without detailed instructions. But it needs to understand the company it is working for.

Interestingly, as AI becomes more capable, we need to spend less time telling it how to accomplish things. Ethan Mollick makes this point in a recent article about the “Bitter Lesson”: increasingly, AI can figure out how to organize and execute work on its own.

That should sound familiar to anyone who has managed talented executives. The better your people are, the less you need to dictate their methods. But you still need to give them clear objectives, appropriate authority, and enough context to make good decisions.

The same management discipline that allows people to work effectively with greater autonomy is now essential to getting the most out of AI.

Five Things Your AI Needs to Know About Your Company

An effective AI system for CEOs needs a sound, differentiated framework for the CEO role (the reason we built ChatCEO around the Chief Executive Operating System), but it also needs an understanding of the company itself. Here are five things I would want any such system to know.1

1. Where you are going

Every company should have a clear, concise strategic plan that articulates its mission, vision, differentiating values, and long-term objectives.

I’ve always advocated getting this onto one page. The discipline of doing so forces the CEO to make choices and gives everyone in the organization a common understanding of where the company is headed.

It also provides essential context for AI.

Suppose you ask AI to evaluate a new market opportunity. Without knowing your strategy, it can assess the market, analyze competitors, and recommend ways to enter. But it has no basis for judging whether that opportunity is right for your company.

With a clear strategic plan, AI can evaluate opportunities against the direction you have established, identify potential conflicts with existing priorities, and help you make decisions that reinforce your competitive position.

2. Who is responsible for what

In my CEO methodology, I describe the structure of a mature company through what I call the Two Triangles.

The first consists of the three core business functions: product, marketing, and sales. The second represents the three constituencies a company must create value for: employees, customers, and shareholders.

Together, these six areas define the essential work of the business. Each needs a clear executive owner, with the CEO occupying the shareholder seat and managing the balance of resources and value creation across all six.

This structure is important context for AI because it establishes who is responsible for which outcomes and how the pieces fit together.

Think of AI as adding new intelligence and capacity to each executive’s area. An AI working with your head of product needs to understand the product strategy and current development priorities. One working with your head of sales needs to understand your sales objectives and how the company competes for customers.

And AI supporting the CEO needs to understand the entire picture, including how decisions in one area affect the others.

Without that understanding, AI may be very effective at optimizing individual activities while doing little to improve the performance of the company as a whole.

3. Who can decide what

Clear ownership is a starting point. The next question is what authority each executive actually has.

I recommend that every executive have an Executive Performance Profile that defines their responsibilities, their authority, and the metrics by which their performance will be judged.

Consider a decision about changing prices. AI can analyze customer data, competitive positioning, and the financial implications of a proposed change. But who has the authority to make that decision? Under what circumstances should the issue be escalated to the CEO? What other parts of the business need to be involved?

These are questions that a well-organized company should already have answered.

Making those answers available to AI allows it to operate within the company’s established management structure, direct recommendations to the appropriate people, and recognize when a decision requires additional input or approval.

4. What matters right now

Your strategic plan establishes where you’re going. Your quarterly goals establish what you’re trying to accomplish next.

Every executive should have a small number of measurable goals, typically three to five, that reflect their contribution to the company’s larger objectives.

These goals give AI something concrete to work toward.

For example, suppose the head of customer success has a quarterly goal to reduce onboarding time while maintaining customer satisfaction. AI can help analyze the existing process, identify opportunities for improvement, and evaluate the results of changes.

Compare that with simply asking the department to find ways to use AI. You will probably get plenty of ideas and experiments, but it will be difficult to know whether any of them are making a meaningful difference.

When AI understands the goals that matter to the business, you can put its capabilities to work directly against those goals.

5. How you keep the company on track

Finally, AI needs to understand how the company manages its ongoing work.

A well-run company has established rhythms for executive meetings, one-on-ones, quarterly planning, performance reviews, and the other recurring activities that keep the organization aligned and accountable.

These routines generate valuable information about the state of the business: current priorities, progress against goals, unresolved problems, decisions made, and commitments that need follow-up.

Imagine an AI system preparing for your weekly executive meeting. With access to the right information, it can identify which goals are at risk, which decisions need attention, and which commitments from previous meetings remain outstanding.

It can also help executives prepare for their one-on-ones, track important decisions, and surface issues before they become serious problems.

The underlying information needs to be captured and kept current. But once it is, AI can become a valuable participant in the ongoing process of keeping the company on track.

Management Discipline for the AI Era

None of these five things should be new to an experienced CEO. They are fundamental elements of running a good company, and I’ve spent much of my career helping CEOs put them in place.

For years, I’ve argued that CEOs need to get this information out of their heads, put it on paper, and communicate it throughout the organization. When people understand the company’s direction, their responsibilities, and the expectations placed on them, they can work more independently and make better decisions.

AI makes that same discipline even more valuable. The information that helps your executives run their departments effectively can now serve as the foundation for an entirely new source of intelligence and productive capacity.

So before investing in another AI initiative, consider a simple question: If a capable new executive joined your company tomorrow, could you hand them a set of documents that clearly explained your strategy, organizational responsibilities, decision rights, current goals, and operating rhythms?

If those documents do not exist, creating them may be the most valuable thing you can do to prepare your company for AI.

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Should Ed Bastian, Delta Air Lines’ CEO since 2016, be worried about his job?

Elon Musk seems to think so. After Delta chose Amazon’s Leo satellite internet service over SpaceX’s Starlink, Musk predicted that Bastian “will lose his job.” The remark followed unverified reports that Bastian had criticized Musk in conversations with Delta employees. United and American Airlines even joined the fun, trying to lure away Delta customers.

But Bastian says there’s no feud. He brushed off Musk’s remarks during a CNBC appearance Friday. “I drive a Tesla,” he said. He later explained that Delta and Starlink had disagreed about business terms, including access to the customer relationship.

That relationship was also on Bastian’s mind during Delta’s earnings call Friday, when he discussed the threat from AI shopping agents (are they the new Priceline or Expedia?) and why he is reluctant to sell a stake in the airline’s enormously valuable loyalty business.

More on that below, along with PepsiCo’s efforts to revive its North American business and Applied Digital’s plans to build billions of dollars in AI infrastructure.

One thing to notice in these calls is how differently two major American consumer brands are responding to an economy that is strong on paper but that feels tough to many. Delta is seeing high demand from affluent travelers, who have shown little resistance to airfares rising roughly 20% this year. But PepsiCo is working with a different consumer profile, one whose financial pressures have prompted the company to cut snack prices and reconsider its product mix.

The contrast offers a glimpse into how differently American households are experiencing the same economy.

Delta Air Lines (NYSE: DAL)

Q3 FY2026 Earnings Call

Delta expects higher airfares to stick

When we last covered Delta’s earnings in July, CEO Ed Bastian was arguing that airlines would be able to retain their fare increases even after fuel prices declined. Three months later, he is more confident in that prediction.

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For CEOs, the next couple of months have a way of evaporating.

Now is an ideal moment to tame the chaos, get a real operating system in place, and make sure you enter the holidays with a plan for 2027 instead of coming back in January to figure one out.

That’s what we built ChatCEO to help with: giving the CEO a system, along with an AI that understands the company well enough to make that system useful. Today’s article gets into why those two things matter.

I encourage you to sign up for your own ChatCEO here and we will get you all set up!

The Internet changed how leaders get advice. Previously a cottage industry, business guidance grew into an industrial complex.

Founders became thought leaders. Companies became case studies. Academics became gurus. CEOs, previously starved for help, had blog posts, podcasts, Amazon bestsellers, and LinkedIn manifestos galore.

But all that content was a mess, and much of it contradicted itself.

Take a simple question every CEO runs into quick: How much should you listen to your customers?

The Internet has a clear answer. Listen to your customers. It is close to gospel. Put yourself in the customer’s shoes, build what they ask for, let their feedback drive the roadmap. “Customer obsession” is Amazon’s first Leadership Principle, and (the implication is) it should probably be yours too. You will find this advice everywhere, repeated with total confidence, usually attributed to someone successful.

The Internet also has a different clear answer. Customers don’t know what they want until you show them. This one comes with its own patron saints, legends like Henry Ford and his apocryphal “faster horse” quote, or Steve Jobs, who famously refused to run focus groups.

So what is the right answer? Both arguments have produced successful companies. But both cannot be true at the same time. And yet both are endlessly cited.

Synthesis is now cheap

For years, the CEO’s problem was sorting through all of this contradictory advice. Not anymore. Today, AI has given us the next evolution: effortless synthesis.

I just now asked ChatGPT how the CEO of a midsize company should think about customers. Here is a condensed version of what it told me:

Good job, ChatGPT. That is a good answer. It is well-balanced and difficult to object to.

And that is the problem.

The Internet gave us a thousand contradictory answers. AI can now read all thousand, reconcile the contradictions, sand off the sharp edges, and hand us a polished synthesis. It is masterful at caveats. Give it two opposing views and it can find the respectable middle between them almost instantly.

• Listen to customers, but do not listen too much.

• Trust your vision, but remain open to evidence.

• Move fast, but be thoughtful.

• Empower your people, but maintain accountability.

Eventually, much of the existing business advice converges on the same conclusion:

It depends.

Of course it depends! The whole reason the CEO exists is because they look at “It depends” and say “We’re doing this, and here’s why.” It is a painful responsibility, but good CEOs do it every day. If that’s the job, a bot giving you hyper-nuanced both-sides maxims is not too helpful.

Taking the average of opposing advice does not produce a good decision. In fact, taking averages is a pretty reliable way to keep a company average.

Tell me what I want to hear

There is another problem with generic AI advice: It mirrors the person asking.

Based on how you position your query, it may lean toward one side of its synthesis. If I’m anxious about customer churn and turn to my LLM for help, it is likely to extrapolate from my wording that I need to listen more closely to customers. But if I come to it with my conviction that the company has discovered a new category, it will dutifully explain why visionary companies cannot let customers design the future for them.

It can make either case persuasively because both cases are well represented in the material on which it learned. However, what is it really doing here? It’s telling me what it thinks I want to hear.

If AI is simply reflecting your framing back at you, more fluently and with better bullet points, you have confirmation bias on steroids.

How to make your AI CEO-grade

That is not a reason for CEOs to avoid AI. Quite the opposite. The most capable CEOs I know are finding ways to make AI part of how they think.

But they are giving it two things generic AI does not have.

The first requirement is a system for the CEO job.

A customer decision is never only a customer decision. The CEO operates at the intersection of three constituencies: customers, employees, and shareholders. Pushing hard toward one corner of that triangle means the force moves through the other two.

Suppose customers are demanding extensive customization. Looking only at the customer, saying yes may seem obvious. But that decision may increase product complexity, require additional people, reduce margins, slow the roadmap, or make the company less attractive to the broader market.

Those consequences must inform the CEO’s decision. A functional executive can reasonably advocate for one corner of the problem. Sales wants the deal. Product wants architectural coherence. Customer Success wants retention. Finance wants margin.

But the CEO has to see the whole triangle move.

That is why a system matters. It gives the AI—and the CEO—a framework for asking what a decision does to the entire business rather than generating a sophisticated answer to whichever part of the problem happened to appear in the prompt.

The second requirement is operating context.

CEOs should not casually pour proprietary company information into public AI models. But when AI can securely understand the company’s strategy, market, goals, economics, organization, and current situation, something important changes.

Now it can move beyond “it depends.”

It can begin asking: What does it depend on?

Let’s return to the customer question.

An established company improving a mature product in a known market may need to listen extremely closely to customers. Those customers understand the shortcomings of the product because they live with them every day. Their behavior may expose where the company is losing relevance or where a competitor is beginning to win.

A company creating a genuinely new product faces a different problem. Customers can usually describe their frustrations better than they can imagine a product category that does not yet exist. Following their requested solutions too literally may pull the company back toward the familiar thing it is trying to replace.

The nature of the product matters. The maturity of the market matters. The company’s financial position matters. Its strategy matters. Its competitive position matters.

These are the inputs required to make the decision. That is the opportunity AI creates for the CEO. Once it understands your operating context, it can take meta-rules from its system and show you how they apply.

The bottom line

The Internet gave executives more advice than they could ever read.

Generic AI can summarize all of it.

The real prize is an AI that knows enough about the CEO’s job and the company in front of it to know which advice matters now.

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Micron had a good week. The chipmaker reported revenue of $54.2 billion, more than four times what it did a year ago, and told investors it still cannot see when supply will catch up with demand. More than 75% of its 2027 output is already committed. The AI memory boom is still booming.

This week we look a little closer at Micron’s situation, along with manufacturer Jabil, which is also feeling the boom’s reverberations, and CarMax, which is embracing an upside amid increased pricing regulation from the FTC.

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Welcome back to Managing the Future.

If you’re new, welcome. On this Substack I look at topics of interest to CEOs and boards, which increasingly intersects with AI.

To any currently serving CEOs:

Please reach out if you’re experiencing any of the common struggles of the job. Pressure. Isolation. Feeling like you’re turning the ship’s wheel… but the ship just isn’t turning. I would love to hear what is on your mind and see how I can help.

For most of human history, we have treated mathematical ability as one of the clearest signals of intelligence.

Picture a brilliant person at work. What do you see? Probably a chalkboard filled with arcane, scribbled math equations. Something like in A Beautiful Mind or Good Will Hunting.

These people who can manipulate complex equations, construct proofs, recognize abstract patterns, and reason logically through difficult problems are obviously doing something most people could not do. The great mathematicians were therefore regarded as some of the smartest people in society.

Today, that image may be due for an update. Math is still hard, but now everyone has access to tools that can do astoundingly complex mathematics work for us.

In 2025, a version of Google’s Gemini solved five of six problems at the International Mathematical Olympiad, earning a gold-medal-level score. While that achievement doesn’t make mathematicians obsolete, it does make me wonder whether the ability to reason through difficult abstractions will remain our most persuasive proxy for intelligence.

Jensen Huang recently made waves with comments along these lines on The Ezra Klein Show.

“Basic math is being forgotten. Does it matter?”

When the question was put back to him by Klein, he said:

“Yeah. I don’t think it does.”

The Economics of Intelligence

Lots of people disagreed with Huang, but he raises a pertinent question about what happens when abilities we once considered rare become abundant.

Technology has done this before. Calculators reduced the value of doing long calculations by hand. Spreadsheets reduced the value of constructing financial models manually. Search engines reduced the value of simply remembering large amounts of information.

AI is now moving higher up the intellectual stack. It is making sophisticated analysis cheaper and more widely available.

What we regard as intelligence is partly a function of scarcity. Mathematical ability has historically carried such prestige because it is difficult and relatively rare among humans. If machines can perform more of that work better than we can, the skill may become less useful as a proxy for who is smartest.

Try ChatCEO, the first AI built for the chief executive officer.

What CEOs Already Know

The business world offers a useful preview of what that shift might look like.

A good CEO is not supposed to be the best analyst, salesperson, marketer, engineer, or accountant in the company. In fact, one of the CEO’s most important skills is recognizing people who know more than he does and putting their expertise to use.

Nor should the CEO personally analyze every piece of data coming out of the business. That is the job of the executives responsible for those areas. The CEO has a different job: to synthesize information across functions, balance competing interests, see the whole system, set direction, and make decisions.

In other words, the CEO’s intelligence has always depended less on personally producing every answer than on knowing what to do with the answers other people produce. AI pushes more of us in that direction.

The hardest questions a CEO faces are rarely mathematical:

• Should we enter this market?

• Should we fire an executive who has been with us for ten years?

• Should we abandon a product in which we have invested millions of dollars?

• How do we persuade the organization to follow a new strategy?

• How do we get six capable executives with different interests and personalities to agree on a course of action?

AI can already help enormously with the analytical side of these questions. It can examine the market, model scenarios, identify risks, challenge assumptions, and propose alternatives.

But none of those activities settles the question. Someone still has to decide which considerations matter most, reconcile conflicting information, understand the people involved, and act under uncertainty.

That should also change how leaders think about talent. If analytical horsepower becomes abundant, the scarce forms of intelligence inside an organization may increasingly be the ability to frame the right problem, exercise judgment, connect ideas across domains, recognize good work, understand people, and turn knowledge into action.

Those are the capabilities CEOs should be looking for and developing.

What the Question Is Now

The same logic may eventually affect how we think about education and even national competitiveness. We still need people who understand mathematics. But the strategic advantage may shift as extraordinary mathematical capability becomes available almost everywhere.

The question has traditionally been:

Who can do the math?

Increasingly, it may become:

Who can use the machines that do the math to accomplish something important?

That is a much bigger change than simply giving people a better calculator.

The scarce capability will increasingly be not producing the technically correct answer, but applying judgment to it: What question should we be asking? Which answers matter? How does this fit with what we know from other domains? What tradeoffs are we willing to make? How will human beings respond?

The people who can do that kind of work well may be the savants of the coming era.

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When I first became a CEO, there was almost nowhere to go to learn the job. This was before the internet put everything one search away, and back when the business section of a bookstore was the best resource most of us had for learning leadership.

What you found on those bookshelves fell into two categories. The first was the celebrity CEO memoir, the Lee Iacocca genre, in which a famous executive recounted his career with the benefit of hindsight and a ghostwriter. These books were entertaining, and occasionally wise, but they were stories about one person in one company at one moment. They told you what someone did, not how the job works. The second category was the promotional book: a consultant or academic with one idea about strategy, quality, or culture, stretched to three hundred pages and often sold as a singular solution to a problem in business. Some of those ideas were good. None of them gave a view of the whole CEO job.

What was missing was a holistic account of the chief executive role itself. What does a CEO do that no one else in the company can do? How should the job be structured week to week and quarter to quarter? How do you balance the competing demands of customers, employees, and shareholders when they pull in different directions, as they always eventually do? Nobody had written that down, so every new CEO had to reconstruct it from scratch, usually by making expensive mistakes.

Today, the problem has flipped. Anyone with a LinkedIn account can post a thread about what great leaders do, and generative AI means anyone can produce a polished article, a course, or even an entire book on the subject in an afternoon. A leader looking for help in 2026 no longer looks at slim pickings on a Barnes & Noble shelf; they now face an ocean of advice and a much larger cast of people claiming expertise. And while truly CEO-specific advice is still relatively uncommon relative to leadership content, there are now far more people now who claim to help the CEO: coaches, consultants, and self-described thought leaders of every kind.

I want to make a claim that may sound immodest, so let me make it plainly and then try to earn it. I believe I am the best resource available to a working CEO who wants to understand how to do this job at scale. That is not because I think I am smarter than everyone else writing or teaching on the subject. It is because I have had an unusual combination of experiences: doing the job repeatedly with success, teaching it to other CEOs for over a decade, developing a complete system for it, and having that thinking tested in public over time.

Here is the test I would apply to anyone offering CEOs advice, and I invite you to apply it to me.

• First, has the person done the job, more than once, in companies large enough that the CEO cannot personally touch everything? Running a company of fifteen people and running one of five hundred are different jobs. Much of what the founder of a small company learns is exactly what must be unlearned at scale. I have been a CEO more than a half dozen times, in companies of varying sizes and circumstances, and the lesson that repetition teaches is that the job has a structure that holds across companies, even when the specifics change.

• Second, has the person taught the job to others and watched what happened? Doing something well and knowing why it works are not the same thing. For more than fifteen years I have taught a class for sitting CEOs. This teaching forces a discipline that practice alone does not. You must explain your reasoning to skeptical, experienced people who will go back to their companies and try it. The ideas that don’t survive that process get discarded. The ones that do get sharpened.

• Third, can the person describe the whole job, not just a piece of it? This is where most CEO advice fails. It is the same failure I saw on the bookstore shelf decades ago. A framework for hiring, a theory of culture, a tactic for board meetings: each may be useful, but a CEO does not experience the job in pieces. Every decision touches the others. Over the years I developed what I call the Chief Executive Operating System, a systematic way of approaching the role as a whole: what the CEO owns, how the job is organized in time, and how the competing interests inside and outside the company are held in balance. You may disagree with parts of it. But it is a complete system, and a complete system can be examined, argued with, and improved in a way a collection of tips cannot.

• Fourth, has the person’s thinking been exposed to criticism over time? Anyone can be correct in a single post. I have written two books on the role and hundreds of articles in this newsletter over many years. That body of work is public. It has a paper trail. If my thinking were inconsistent or wrong, the evidence would be there for anyone who wanted to look.

These are the questions I would ask if I were a new CEO trying to decide whose advice to trust. In an age when “expertise” can be generated on demand, the most reliable signals are the hard-to-fake ones: years of doing CEO work with a track record of success, years of teaching the CEO job, and a coherent account of the whole role.

That is why I have spent the last several years putting that system into a form CEOs can use every day rather than only in a classroom. But the more important point is not about me. It is that CEOs should hold every source of advice to a real standard, because the cost of following confident but incoherent guidance falls entirely on them and their companies.

I leave you with this question: When you last took advice on how to do your job as CEO, did you know whether the person giving it had ever done it, and could they have explained how that advice fit into the job as a whole?

As I often say, the more my inbox is brimming with requests for support from CEOs, the happier I am. Be in touch if you are interested in maximizing your chance at success as a chief executive.

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Cracker Barrel’s new CEO had been on the job for only six weeks when he held his first earnings call on Wednesday. David Deno (former COO of Yum! Brands and president of Quiznos) arrived after a rough stretch for the 57-year-old restaurant chain, including a rebranding controversy that helped precipitate the departure of his predecessor.

His first move was not to announce another reinvention. Deno told investors that Cracker Barrel was largely working on the right things already; his job was to sharpen the focus. “A big part of my management philosophy is doing fewer things better,” he said.

More on that earnings call below, along with TD SYNNEX’s view from inside the AI infrastructure buildout and Stitch Fix’s effort to keep its turnaround moving through a tougher consumer environment.

TD SYNNEX (SNX)

Q3 FY2026 Earnings Call

AI growth is soaking up cash at TD SYNNEX

The AI infrastructure boom is producing tremendous growth for TD SYNNEX, but it is also requiring the company to put a lot of money to work before it gets paid.

Read more

Most CEOs I work with do not buy diesel.

They run software companies, professional services firms, specialty manufacturers, healthcare practices. When they see headlines about refining margins, they file it under “energy sector problem” and move on. This week, I think that is a mistake.

Torsten Slok, chief economist at Apollo Global Management, published a short note on Wednesday that highlights one remarkable number. In August, the spread between the price of diesel and the crude oil it is refined from, what traders call the crack spread, went above $100 a barrel on the U.S. Gulf Coast for the first time on record. The normal range is $15 to $30. S&P Global reported this week that the spread remains near record levels.

Slok’s concern is what happens after diesel gets expensive. Diesel underlies freight, rail, agriculture, construction and much of the physical economy, so higher diesel costs work their way through supply chains and eventually into the prices of goods and services. In other words, the inflation does not necessarily remain neatly contained in the energy category. “Diesel margins are now setting the long end of the curve,” says Slok, because the market sees them as a signal of future core inflation.

All CEOs should pay attention to that.

The P&L impact arrives late

A diesel shock does not appear in your P&L all at once. Some suppliers will absorb higher freight costs for a while. Others have fuel surcharges that reset periodically. Still others will wait until a contract renewal or annual price increase and try to recover the accumulated cost then.

That delay can make the problem easy to miss. The economics underneath your vendors can be changing for months before anything obvious changes in your own numbers. By the time the increase reaches you, the budget may already be set and commitments to the board already made.

So I would use the lag. Ask your operating and finance teams to trace the exposure one level deeper than they normally would:

Where does diesel enter our cost structure?

Freight is the obvious place, but it can also sit inside the cost of raw materials, packaging, facilities maintenance, waste removal, field service, construction and any vendor whose people or products spend a lot of time on the road.

The point is to know where the pressure will surface before a supplier tells you.

Your customers are doing the same math

Then turn the analysis around and look at your customers. Many of them are dealing with the same problem, and some may have much more direct exposure than you do.

This is the kind of external shock that puts the CEO’s three constituencies, customers, employees and shareholders, into tension at the same time. If your own costs rise, protecting shareholder returns pushes you toward higher prices. Your customers, meanwhile, may be facing their own cost increases and looking for places to cut. Employees will have their own response if those higher costs begin showing up in everyday living expenses.

Start with the customer. Raise prices too quickly or too broadly and you may give a competitor an opening. Wait too long and you can give away margin that will be difficult to recover later.

There is no formula for that judgment. I would decide your pricing posture before the first big increase lands rather than improvising in response to it. Which costs will you absorb? Which will you pass through? Which customers are especially price-sensitive? Where would you rather trade some margin for share?

And if an increase looks likely, talk with your largest customers early. A price change discussed as part of a business conversation is very different from one discovered on an invoice.

Employees may feel it next

If Slok is right about higher diesel costs feeding into core inflation, the pressure eventually reaches employees as well. They experience inflation through groceries, services and household expenses long before anybody on your executive team is discussing the latest CPI release.

That matters when you build next year’s compensation plan. A budget based on the wage pressure you have experienced recently may prove too neat if inflation remains elevated. I would at least model the higher-compensation case now and understand what it would do to margins and hiring plans.

You do not need to change the budget today. You should know what you would change if the assumptions behind it do.

Higher rates change the capital math

Slok’s chart points to another consequence that can reach your company much faster. The bond market is already repricing inflation risk. The 10-year Treasury moved above 5 percent this week, reaching 5.18 percent on September 24.

That changes the arithmetic on capital decisions. The acquisition you were considering, the facility expansion, the debt you planned to refinance next year: all were evaluated against some assumption about the cost of money.

For private-equity-backed companies, higher long-term rates can matter twice, through financing costs today and through the exit math your sponsor is using for tomorrow.

I would go back to any major capital commitment approved under materially lower rate assumptions and run the numbers again. Some projects will still clear the bar. Others may look different now, and I would rather discover that in a planning meeting than explain it later in a board meeting.

Put some ranges around the risk

I do not know where the diesel crack spread will be six months from now. It could remain elevated. Additional supply, weaker demand or some easing of the disruptions in global fuel markets could also bring it down sharply. Crack spreads are volatile by nature.

For a CEO, the useful exercise is not to try and guess exactly what the numbers will be. Instead, it’s to put ranges around the exposure now.

• What happens to our margins if transportation and supplier costs rise another 10 or 20 percent?

• How much can we recover through pricing?

• Which customers are most exposed themselves?

• What would a higher compensation budget do to the plan? Which capital projects become less attractive if long rates stay above 5 percent?

None of those questions requires you to know where diesel will trade next March. They require you to know which decisions inside your company become different if it stays expensive.

That is the value of catching a signal like this early. If diesel prices settle back down, you have spent some time understanding an exposure in your business that you probably should have understood anyway. If they remain high, you have already had the pricing, customer, compensation and capital conversations before they become urgent.

Part of the CEO’s job is maintaining enough distance from today’s operating problems to notice the forces that may alter the next quarter or the next year. Most of those signals will not arrive with a memo addressed to the CEO. Sometimes they show up as a strange number in a market you have never paid attention to before.

So here is the question I would leave you with:

If freight and supplier costs rose meaningfully next quarter, would your leadership team already know what to do, or would you be starting the conversation then?

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We would love to have you join us at Texas CEO Ranch, near Bastrop. You will enter the holiday season with the peace of mind that you have a clear, tested plan for 2027.

Shoot me an email at joel@xpertloop.ai to reserve your spot. Registration includes private lodging and all meals.

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An executive recruiter once said to me, “CEOs are often the first people who call you back.”

I think that’s true. It captures something important about the people who make it to the CEO chair. They move quickly. Whatever the issue is, they are on it. They have a bias for action.

This responsiveness is a fantastic trait for most professionals, all the way up to executive roles. It’s part of the reason people move up the proverbial ladder.

But once you take on a CEO role, responsiveness and fast reactions can become a trap. In fact, they can easily degrade into the greatest affliction of CEOs: chronic firefighting.

A Harvard study of 27 CEOs found that 36% of their working time was reactive. Even their time alone was usually broken into short stretches. It is remarkably easy to spend the entire day being useful while repeatedly postponing the work that only the CEO can do.

I think about this every time we put together a CEO Masterclass. One of the most common reasons CEOs hesitate to attend is simple: three days is a long time to be away from the business.

I understand. I really do. But sometimes taking the time away from the business is exactly the point.

In almost every case, the business won’t go down in flames if you step aside for three days. To the contrary, the very practice of taking time for intentional strategy work and development of your CEO skills will pay huge dividends.

That’s why Bill Gates had his famous “Think Weeks.” Sometimes you have to get far enough away from the business to think seriously about the business.

This is the dynamic we create in the Masterclass. It isn’t remedial. The CEOs who get the most from it are often already very good at the job and want to become more deliberate about how they do it. They understand the value of a system, especially at the top of the organization. And almost invariably they find that a good system helps them be more intentional and less reactive to every seeming emergency that crosses their desk.

What happens in the CEO Masterclass?

Over three days, we work through specific tools for the CEO role, mental models that apply uniquely to the person accountable for the whole company, and practical ways to improve decisions, resource allocation, strategy and execution.

We also spend time on how CEOs can apply AI intelligently to the strategic core of the business, rather than treating it as another productivity app.

Our last Masterclass of the year is November 11–13 outside Austin. The timing means you can step out of the day-to-day for three days, pressure-test how you’re approaching the role, and go into the holidays with a clear, tested plan for 2027.

The business will survive a few days without you. (But yes, we also have fast Wi-Fi at the ranch, thanks to a new fiber install. We won’t stop you from checking in, I promise.)

Email me at joel@xpertloop.ai to reserve your spot.

Download CEO Masterclass Brochure

Every week, roughly a Dallas Cowboys stadium’s worth of Americans turn 65.

Chase Idleman is quick to reassure those of us nearing that milestone that 65 is “the new 35.” But he also thinks we’re nowhere near ready for the caregiving demands that are coming.

Idleman is founder and CEO of Arlow, a company that combines AI-powered tools with human advisors to help older adults and their families manage the day-to-day realities of aging. It’s part of the emerging category known as AgeTech—one Idleman sees as a greenfield.

His route to founder and CEO wasn’t exactly direct. He grew up expecting to take over his parents’ air ambulance business, spent two decades in medtech instead, then had what he cheerfully calls a “midlife crisis” and finally started a company of his own.

Chase and I talked about why startup life turned out to be 10 times harder than he expected, the founder’s 3 a.m. anxiety, how his years in the corporate world prepared him for entrepreneurship, and how Arlow is trying to help families navigate aging before a crisis hits.

Our conversation has been lightly edited for clarity.

When you went to Baylor for undergrad, the internet bubble was peaking. Did you want to get into that tech world?

Not exactly. I actually planned to get into the family business. I was born and raised in Fort Worth, Texas, and my parents were entrepreneurs—they ran a fixed-wing air ambulance company. They had a whole fleet of airplanes they used to fly patients long distances. From a young age, I always thought I was going to take that business over. At four years old, I was sweeping the hangars at Meacham Field.

So I went on and got my EMT certification, started working in the back as a second medic, and got my commercial pilot’s license. Going to Baylor, I still had that path in mind. My entrepreneurship major was with an emphasis in family business. The double major in marketing was basically because my parents weren’t strong in that area. They were great operators but always had a need for marketing and sales experience.

But funny enough, once I was in school, my parents said, “You know, second generations always screw up the business.” They really encouraged me to leave the family nest. So I went to North Texas for grad school.

By the time you graduated, the job market was a little different than when you went in. What was your first job?

When I finished grad school circa 2006, everyone was either going into oil and gas or this new tech sector. I had a friend who worked for J&J, and she’s the one who introduced me to medtech, medical devices, all that.

Here in Fort Worth, there’s a very prominent company called Alcon, the world’s largest ophthalmology-based company. Alcon said, “Hey, we’ll give you a job, but you got to move to Atlanta.” And I was like, “Please don’t make me.” [laughs] But ultimately, I said yes, moved to Atlanta, and then as quickly as possible jumped back to Texas and moved to Austin shortly thereafter.

You spent many years after that in medtech, kind of in the same realm as your parents, actually. Now you’ve founded your own company, Arlow. I assume you always had this idea in your head that you wanted to do something entrepreneurial. Is that right?

So the short story: I stayed in medtech, went into the operating room with a company called Intuitive Surgical, and had a hand in a startup that created a robot called ROSA for neurosurgery. We got bought by Zimmer Biomet, and I moved into leadership at ZB.

I’m 44 years of age, and about a year and a half ago I had a midlife crisis. My parents sold their business after 41 years, so there was nothing to go back to. And I was like, “Man, I never got to live the dream I had as a five-year-old boy of taking over the family business.” I’d always wanted to do that.

I met an individual about a year and a half ago whose parents were in the crisis mode of aging. He was looking at the tools and solutions that could help support him, his siblings, and his aging loved ones. He was like, “They all suck. They’re not good. We can do better.” So we went out, high-fived, and started Arlow on March 26 of last year and got running.

You had seen your parents’ business, so you knew something about running a business. But what surprised you most about moving from the corporate world to a startup environment?

I think people sometimes paint the corporate world in a really negative light compared to owning your own business. But the corporate world teaches you a lot of good things. It teaches you discipline. It teaches you the fundamentals of business. You get to see how things work at scale.

Moving over to the startup side of things is hard. I told a friend this the other day: If you think you know it’s going to be hard, expect it to be 10 times harder than that.

But I rely on my corporate background and the diversity and development I got there every single day. I don’t think I would be as successful as I am now if it weren’t for the blueprints and ingredients that 20 years of experience provided me before this opportunity.

Was there any experience you wish you’d had in the corporate world that would have helped?

Well, there’s part of me that is like, “Why didn’t I do this when I was 27?” I think about that all the time because time is my worst enemy right now. But again, I wouldn’t have the network and skill set at that age.

One of the biggest realizations for me comes from being on the other side of the table now, especially when it comes to mergers and acquisitions, business development, and so on. In that world, you’re sitting on one side of the table. Then you start a company and you’re raising capital, and suddenly you’re on the other side.

Now you’ve got to learn how to build a pitch deck. You’ve got to learn how to communicate with institutional venture capital and family offices. That’s been a big education.

There’s also a whole different language in the startup world. I didn’t know a TAM from a SAM. I remember meeting with our board of directors, and they asked me, “Tell me what you know about QSBS and 83(b) elections and 409A valuations.” And I’m thinking, I have no idea what you’re talking about.

It’s a whole different world. You have to surround yourself with people who will help you, or you’ll be flying blind on some of this stuff.

People in the corporate world often talk about feeling fenced in. They want to run and knock down all these fences blocking them in. But when they come work at a startup, there is no fence. You have to figure out which way to run in the first place.

Exactly. One of my closest friends, who is still a VP at my last job, asked me, “What is the one skill set that you absolutely need for this new role?” I said, “Initiative.” That’s something I feel like I have always had.

You have to wake up and figure out which direction to go. You not only have to have the initiative to get out of bed, but you have to know which way to run. When you have a million different directions you could go, that’s the challenge. You can do anything you want.

Do you notice a different feeling being responsible for investors’ money in a way you weren’t before?

I absolutely feel that fiscal responsibility to the investors, and I’m beyond grateful for them. But I also feel that responsibility for the team. They have all taken a chance by leaving their previous jobs and joining what we are building at Arlow. They have made a big sacrifice to be here on this ship with us. So there is a different level of anxiety you have to navigate day to day.

That’s often the biggest difference CEOs talk about: the anxiety.

I don’t say this the way some people talk about not sleeping as a badge of honor. But I get up at 3:00 a.m. almost every day. I am thinking about how we accomplish our mission around the clock.

The other factor people talk about is a certain loneliness because there are not a lot of people you can talk to about stuff.

I have a co-founder and she’s phenomenal, and I have a great team. I also have a circle of friends that I commiserate with, but it’s a very close circle. It’s not a lot of people. And the reality is they can’t always understand what I’m going through. Unless you’ve lived it or been there, it’s hard to relate sometimes.

Let’s talk a little bit about Arlow, because I think it’s addressing something almost everybody has some experience with. How are you addressing aging and eldercare?

Let me start with some data that helps frame this up. Every day in the U.S., about 11,000 people turn 65. That’s roughly a Dallas Cowboys stadium full of people every week. Senior housing is already tight. Assisted-living communities in major U.S. markets are nearly 88% occupied, and very little new supply is being built. And three out of four adults 50 and older say they want to remain in their current homes as they age.

We as a society are not ready for that reality.

And the problems are complex because aging doesn’t create just one problem. An older adult may be concerned about loneliness. A caregiver may be thinking, I want to make sure Mom has groceries in the cupboard. Or, My mom has dementia. Where do I need to take her? What does reimbursement look like? How do I ensure the house is safe for her? Arlow is designed to help people navigate those different needs as they arise, rather than having to figure each one out on their own.

The other important point is that turning 65 doesn’t suddenly mean you need care. If you look at the five stages of aging, someone turning 65 just means they’re 65. It doesn’t mean they’re getting old. It’s the new 35. The needs develop over time, and our goal is to start helping people and their caregivers well before they reach a crisis.

Thank you. I’m getting too close to 65, so I was getting concerned.

[Laughs.] It’s the new 35.

The first stage where people begin to need help is what we call slightly interdependent. That’s when hearing may start to go, mobility may start to go, and you need a little more assistance. Then you move into full dependency, where you may need around-the-clock help. After that comes crisis mode and end of life.

Eighty-nine percent of aging happens in the independence, slightly interdependent, and full dependency stages. So our objective is: How can we help people who are getting older, and their caregivers, when the aging process first starts?

We offer a human element through multidisciplinary teams, but our anchor point is our CSAs, or certified senior advisors. They’re generalists across the entire spectrum of aging. If you call and say, “Hey, my mom has dementia. What does reimbursement look like?” they can help you navigate the situation and get an answer.

But our bread and butter is our tech stack. We’ve created a conversational AI that allows for self-management. So instead of having to call someone, you can ask the AI a question and it gives you what we call golden responses, which are trained responses.

Within the app, we also have things like a smart locker, where you can put a will, an advance care directive, an insurance card, and it automatically organizes everything. We have a medication management tool where you can take a picture of a supplement, an over-the-counter medication, or a prescription, and it looks at drug interactions. We have an integration with Cost Plus Drugs, Mark Cuban’s company, so you can see low-cost pricing.

It’s really a suite of offerings designed to provide support and guidance based on whatever situation that caregiver is facing.

The last piece is who we sell to. We sell predominantly to employers whose workforces include people in the sandwich generation. You’ve got someone who’s 45, they’re caring for their kids at home, and at the same time their parents are aging and need help.

So our fight is against absenteeism, decreased presenteeism, and the impact of taking FMLA leave as a result of caring for older adults. And right now this is insanely novel. Only 7% of employers offer any form of assistance for employees helping older adults at home.

We’ve been talking about the aging boomer generation forever, but I haven’t seen a lot of other efforts in this space. Is it kind of greenfield at this point?

There are a handful of companies. But by 2030, one in five Americans is projected to be 65 or older. That’s an enormous population, and yet there’s still very little penetration in this category. So it is a massive greenfield opportunity.

We sell into the enterprise space through employers, but we’re also bullish about a consumer model, and right now our consumer offering is no cost. It’s free. We’re trying to get the word out: Go download it and get experience with it.

We are evolving and scaling fast. Ultimately, the community is going to help inform our roadmap, but we have a really exciting next six to 12 months of things we’re building. I also think there needs to be much more attention on this category. We call it AgeTech, and it’s an emerging field. I come from medtech. Medtech has 6,500 different companies in the U.S. There are probably fewer than 300 in the AgeTech space.

Obviously, you’re creating a product that involves AI. How does AI affect your day-to-day work as a CEO and how your team operates?

I think about AI in three parts: from a team perspective, from a tech stack perspective, and in terms of what it can do for our end users.

From a team perspective, we have to understand people’s different backgrounds and how they’re using AI day to day in their roles. From a tech stack perspective, it’s hard to keep up with, quite frankly. Are we using the right tools at the right time? Are we paying the right amount? Are these tools allowing us to go faster without getting bogged down?

And then the question I ask our team every single day is: If we’re using AI in our product, are we doing it just because we can, or are we using it to actually make someone’s life easier—to help them be more efficient, more organized, and get more accurate information?

That’s the real question: How do we make AI not just a feature, but a benefit in what we build?

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The Fed raised interest rates this week for the first time in three years. The next morning, Lennar—one of the country’s largest homebuilders—described a housing market already struggling with high borrowing costs: mortgage rates near 7%, many prospective buyers unable to qualify, and growing competition from existing homes.

More on how Lennar is responding below, along with Forgent Power Solutions’ rapid expansion to serve data centers and the early results of Vera Bradley’s effort to revive its brand.

Lennar Corporation (LEN)

Q3 FY2026 Earnings Call

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All CEOs encounter a basic problem as the company scales: they can’t be in every room.

When a company is small, the CEO can make or directly shape most of the important calls: which customers to pursue, which features to build, which people to hire, where to spend, what to prioritize. At 500 people, those decisions are being made all day, every day, throughout the organization, often by people several layers removed from the CEO.

Leaders have always had to solve some version of this problem, whether they were running GE or commanding a Prussian army.

In the nineteenth century, Helmuth von Moltke helped institutionalize the Prussian concept that became known as Auftragstaktik. A commander made the objective and his intent clear, then relied on subordinates to use their judgment as conditions changed. The Prussian army spent a lot of time building that mechanism with doctrine and training designed to help officers understand the larger purpose and act without waiting for instructions.

A good CEO needs the same capability. So they can, in effect, be in every room.

Early last year, before I was thinking as deeply as I am now about AI and the CEO, I wrote about the idea of “multiplying yourself” as chief executive. My point was that a good management system turns managers into extensions of CEO intent. Which is still true.

What’s different now? Today, AI can supercharge the CEO’s influence inside the organization.

A Better Enterprise Use for AI

Many CEOs still use AI as a fancy search engine. My mission today is helping them find the highest-leverage uses (see: ChatCEO). One of those uses is extending intent throughout the organization.

Imagine giving every employee access to an AI that understands how the CEO wants the company to operate. It knows the long-term mission and vision. It knows the values that differentiate the organization and how those values guide tradeoffs. It knows the measurable strategic objectives. It understands how the CEO thinks about creating value for customers, employees and shareholders, including how to balance those interests when they come into tension.

All of that can live in an LLM that employees consult when they face a decision.

It’s a 24/7 version of commander’s intent, available across the company. It can work in endless ways, but here are a couple of examples:

• Picture a salesperson several time zones from headquarters negotiating with an important prospect. The prospect asks for a discount. The company’s AI knows that protecting margin is a current strategic priority, that the company competes on service rather than price, and that the CEO and sales leader have established a specific discount range that salespeople can approve themselves. The rep can use that context as a sanity check, then decide how to handle the customer.

• Or consider a software team several layers below the executive team deciding whether to interrupt its roadmap to fix a quality issue affecting a subset of customers. The AI can surface that reducing enterprise churn is a strategic objective and that reliability is one of the company’s differentiating values. The team still brings the facts the AI cannot see: the severity of the bug, the technical risk and what customers are telling them.

Thinking Partner vs. Oracle

The AI should be a thinking partner, not an oracle. Employees closest to a situation will usually have information that the CEO and the AI do not. Their judgment about the customer, people, technical constraints and immediate circumstances remains essential.

The AI contributes organizational context. Does this choice advance a strategic objective? Is it consistent with our values? Does it help one stakeholder at an unacceptable cost to another?

Also, to be clear, the CEO must still communicate abundantly and constantly.

Commander’s intent only works when the intent is clear, and the same is true here. The CEO has to keep explaining the mission, priorities, objectives and tradeoffs. AI can reinforce that communication, distribute it farther and make it available at the moment an employee needs it.

This complements the management system rather than replacing it. Managers still translate strategy, coach employees and exercise judgment. Employees still respond to the facts in front of them. AI gives both groups a better way to stay grounded in the principles and priorities of the organization when the CEO cannot be in the room.

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We built ChatCEO around a simple idea: the CEO job deserves its own AI.

Generic AI can answer almost any question. But it doesn’t inherently understand the CEO role—how strategy, people, resources, execution, stakeholders, and performance fit together in a proven framework.

ChatCEO is different because it does understand exactly those things, being based on 30+ years of my real experiences as chief executive. It pulls together the two pieces you need to get useful support: a framework for the CEO job, plus the context of your company: your strategy, goals, executive team, board, operating cadence, personality, and more. All of that is private and secure.

The result takes you far beyond chatting with generic ChatGPT or Claude. Here are five conversations worth having with ChatCEO.

1. Decision testing

CEOs make decisions where the second- and third-order effects matter.

Give ChatCEO a decision you’re considering and ask it to stress-test it. Who benefits? Who might resist? What assumptions are you making? How could customers, employees, shareholders, or your leadership team react? What possible effects or fallout am I not thinking about?

The goal isn’t to have AI make the decision. It’s to make sure you have thought through it comprehensively and had your blind spots pointed out.

2. Goal drafting

Q4 is almost here (yikes), so it’s a good time to make sure your goals actually connect to the strategy.

ChatCEO can help map quarterly goals across the functional areas of the business, recommend goals you may be missing, and pin down the best ways to measure success.

Once you decide on your goals, it can also help you record them in ChatCEO, communicate them to the team, and keep them front and center over the quarter.

3. Meeting brief

Before an important external meeting, ChatCEO can research the people and organizations involved and combine that research with what it already knows about you and your company.

You will go into the meeting knowing recent developments, commonalities, likely priorities, useful questions to ask, and the outcome you should try to drive toward.

Think of it as the briefing a great chief of staff would put on your desk.

4. Board meeting prep

Board meetings often hinge on one or two difficult issues. If there’s a thorny topic coming up, ChatCEO can role-play the conversation with you, challenge your argument, and help hone the way you present it.

And once ChatCEO knows who your board members are, it can help you think through how individual directors may react based on their backgrounds, priorities, and personalities—and tailor your message accordingly.

5. Team alignment

Misalignment is often hard to see until it becomes a problem.

The more you use ChatCEO as a hub for your strategy and goals, the more context it has to surface disconnects: competing priorities, unclear ownership, goals that don’t support the strategy, or blockers between functional leaders.

Instead of waiting for execution to break down, you can ask where the cracks are forming now.

The most interesting use of AI for a CEO isn’t asking questions you could Google.

It’s giving AI enough understanding of (1) the CEO job and (2) your specific company that it can help you think through decisions, strategy, people, communication, and execution.

That’s what we built ChatCEO to do.

Bonus: 10 More Things to Ask ChatCEO

• “If we had to cut spending by 10%, where would you start—and what would you protect?”

• “What assumptions does our strategy depend on?”

• “What would have to be true for this strategy to work?”

• “What traits should I look for in our ideal CMO?”

• “What questions should I ask CMO candidates in the interview?”

• “What am I not paying enough attention to right now?”

• “Which of our goals look most at risk?”

• “Where are responsibilities unclear on my executive team?”

• “What questions should I be asking my board?”

• “If one of our competitors made an aggressive move tomorrow, where would we be most vulnerable?”

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EOS (the Entrepreneurial Operating System) is a fantastic playbook. In an ecosystem glutted with advice for business owners, EOS gives founders a structured way to gain traction. Instead of running the company out of their head, they get a cadence and tools that turn vision into execution. This kind of framework is an appreciating asset in the world of LLMs:

The Marketplace by Quy Ma

Frameworks Are the Next Gold Rush

TL;DR…

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7 months ago · 211 likes · 60 comments · Quy Ma

But as a framework, EOS also has its limits.

It begins to creak as the company scales past 50 or so employees. But it really starts to break down when the leader is no longer the owner of the business. The fundamental issue is this: EOS is designed for owner-operators, not for CEOs with a board and shareholders. These two jobs share a superficial resemblance, but in reality? It’s apples and oranges.

You can see the distinction most clearly in private equity. Say a PE firm buys a founder-led company. The founder is at the same desk, but the job is now a very different one. There are now outside shareholders and a board with real authority. This transition is such a struggle that 65% of PE firms reported CEO turnover during the holding period, with a good chunk of those being unplanned.

Two different jobs

The gulf between owner-operator and board-accountable CEO is wide enough that a good framework needs to account for it.

For one, EOS assumes a single decision maker at the top (usually the “Integrator,” in EOS terms), while the board-accountable CEO faces a more complex reality. In addition to accountability to the board, they also must build out an executive team and delegate authority and decisions down to them properly.

Here is how I would sketch out the biggest differences between the EOS-style owner-operator and the CEO of a company of 50+ employees:

EOS Worldwide itself notes that EOS “was not created for companies with investors and boards of directors.” It says the system can work in that environment, but requires customization. As great as EOS is, I think its strengths lie in helping owner-operators run an entrepreneurial company, while board-accountable CEOs need a system of their own.

An operating system for the chief executive

The Chief Executive Operating System is my take on that system. It is designed from the ground up to put a structure around the CEO who must run a company that has shareholders and a board. It is built for those particular challenges that characterize the CEO job once the company is past 50–100 employees. Those challenges are remarkably persistent all the way up to thousands of employees.

Bottom line:

EOS is an operating system for the owner-operator.

The Chief Executive Operating System is built for the CEO with a board, shareholders, and full executive team.

If you are a CEO with a board, a board member, or a PE firm responsible for portfolio-company leadership, the practical question is: Does the CEO have an operating system built for their real job?

If not, there are a few places to start.

1. Grab a copy of my book The Chief Executive Operating System for a full presentation of the framework.

2. Come to my CEO Masterclass this November.

3. Sign up for ChatCEO to see how we are putting the system into practice with AI.

4. Email me at joel@xpertloop.ai if you’d like to talk about training or implementation. I would genuinely love to have my inbox flooded with CEOs looking for help.

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