People sometimes ask me why, after running companies for most of my career, I've chosen to spend this chapter of my life working on the CEO role itself. Why not retire to the board circuit, write the occasional check, and offer advice when asked?

It's a good question, and it comes down to two primary reasons.

Frustration

The first is simple frustration. Over four decades in business, I have seen, more times than I care to count, companies with everything going for them fail because of poor leadership from the CEO seat. These businesses had a real market, a product customers wanted, talented people who showed up ready to do great work—i.e., everything you need for a home run. But then the ball gets chopped into the infield for a single. Or worse, the company strikes out entirely. Everyone involved is left scratching their head: How did we mess up such a sure thing?

With all the other pieces there, the answer is usually: the CEO. What makes it frustrating to watch is that the CEOs who preside over these misses are usually extremely smart and accomplished. They have a track record of achievement. They excelled at everything they did before becoming CEO.

But there was a problem. The CEO job is different from “everything they did before.” Nobody trained them for this role. They came to work on Day 1 not realizing they didn’t know the rules of the game they would be asked to win. They didn’t know how the pieces moved. They had not built the skills.

So they improvise. And the CEO job—a tightrope walk, as I describe it—does not reward improvisation. The cost of failed improvisation isn't borne by the CEO alone. Employees’ careers are affected when the company stalls out or goes under. Customers don’t get what they wanted. Investors and shareholders who backed the vision are left holding the bag. Thus, when a CEO fails, the failure cascades through hundreds or thousands of lives. Not to mention, such losses are huge sources of squandered value in the economy.

So one reason I am driven to help CEOs understand the job and do it well is that it’s really hard to watch preventable mistakes. And they are preventable. Every good sales executive, HR leader, CFO, etc. has a clear system and tools for delivering results. Such a system and tools are available to the CEO too. The problem is one of information sharing and good training. That is the gap I aim to fill when I write books on the role, teach classes on it, and develop tools for CEOs.

With a real operating system, the opposite of the needless strikeout can happen, too. I have also seen companies that should have been modest successes turn it into something remarkable. I’m highly motivated by my desire to see more of that kind of winning rather than strikeouts that should have been home runs.

What I Hope to Leave Behind

The second reason I spend my time working with CEOs is more personal. It took me longer to figure out how to articulate.

At a certain point in life you start thinking about what you'll leave behind. Will your professional legacy be a monument to the past? A company you grew decades ago? Your name on a building? I decided I don’t primarily want to be remembered for that kind of thing. I’d much prefer to be remembered for something I offered that’s helping people now.

That is a demanding standard, because it means the work can’t be frozen at a certain point in time. It has to stay alive. I find myself asking what I can do now to help others in their own future. If I can guide a first-time CEO through her first board meeting this quarter, or help a stagnated CEO see his blind spot that has cost him two great executives this year, that is success to me. By that definition, legacy is about whether you are still useful right now, to people navigating the highest-pressure job in business today.

This is why I keep writing, keep teaching, and keep building tools for the role. Not because the world needs another retrospective from a former CEO, but because there are 200,000 sitting CEOs who got handed the most consequential job in their company with no manual and no support system. Every one of them is one bad quarter away from becoming another cautionary tale about wasted potential. I want to be their first call when they have an issue.

If I can help a CEO run their company a little better because of something we worked on together, that's the only kind of legacy I'm interested in anymore.

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America has had transcontinental rail service since 1869, but no single company has ever owned track from one coast to the other. Freight crossing the country still gets handed off from a western railroad to an eastern one somewhere around the Mississippi, which adds days. Union Pacific’s roughly $85 billion bid for Norfolk Southern would end that handoff and put one owner’s track from Los Angeles to the Atlantic. The Surface Transportation Board accepted the merger application in May and is still reviewing it, and a decision isn’t expected until 2027.

Three of the big US railroads reported last week, and the merger features in each call. We have Union Pacific (the buyer), Norfolk Southern (the target), and CSX (the one large railroad …

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Quote of the week

The US trucking industry is short roughly 82,000 drivers this year, its first shortage in four years, according to the American Trucking Associations. The average driver is now around 57 years old, and retirements are outpacing new entrants. Spot rates for hauling freight have climbed to two-year highs, and a federal roadside inspection blitz in May pulled enough trucks off the road to tighten the market further. Analysts are clear that the squeeze is coming from a shrinking supply of trucks and drivers, not a surge in shipping demand.

Much of J.B. Hunt’s earnings call this week was about how the company, one of the country’s largest truc…

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The social contract we all sign includes a prominent clause regarding agreeableness. We are rewarded socially for saying nice things. Someone looks tired? Tell them they look great anyway. Their pitch was mediocre? Say it was really good. We regard these as the most benign of white lies, the lubricants that keep daily life easy.

Is there a deeper harm in the small compliments you don’t really mean? That is ultimately a question for the ethicist or philosopher. But I can tell you what these false compliments do from a leadership perspective.

When Tim’s peer says “Great work!” after Tim phoned in his presentation, Tim takes the moment of satisfaction and moves on. Relatively harmless. But when Tim’s CEO says “Great work!” after the same phoned-in presentation, Tim’s whole perspective gets skewed. Tim takes it as a signal that he should repeat this behavior. He feels he has the CEO’s seal of approval. Maybe he now thinks he can judge by proxy the work of others. With a simple, tossed off c…

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Quote of the week

RIP Spirit Airlines. The ultra-low-cost carrier filed for bankruptcy and shut down in May, a casualty of the jet fuel spike that followed the war in the Middle East. But Spirit is far from the only airline affected. The International Air Transport Association (IATA) now expects industry profits to be cut roughly in half this year, with jet fuel averaging about 70% more than in 2025.

On Friday, Delta CEO Ed Bastian led an earnings call in which he got into how all this has affected his company. He explained how the world has changed for carriers, especially those on the lower end—fuel hedges are largely a thing of the past, and other costs (labor, airports, etc.) are growing too. Hence Delta’s commitment to “stay in its lane” in terms of strategy rather than making any moves to fill the gap left by Spirit. He also seemed upbeat around the idea that higher ticket prices would stick even after fuel costs fall.

Along with Delta’s call, we’ll also look at Levi Strauss, which raised guidance while sitting on a tariff refund it refuses to count, and Kura Sushi, the conveyor belt sushi chain whose competitors raised prices five times faster than it did.

Here’s what the CEOs had to say.

Delta Air Lines (DAL)

Q2 2026 Earnings Call

Results: strong, with record revenue up 14%, EPS of $1.56 beating estimates, and full-year guidance affirmed despite a multibillion-dollar fuel headwind.

Delta is the most profitable US airline, and 61% of its revenue now comes from sources other than main cabin tickets: premium seats, its American Express partnership, cargo, and maintenance work for other carriers.

Delta raised fares to cover record fuel costs and expects them to stick

Fuel expense hit $4.4 billion in the quarter, up nearly $2 billion year over year and the highest in Delta’s history. The industry passed the cost through in fares faster than in any previous fuel cycle.

“High fuel prices have proven to be the most powerful catalyst for change in our industry.”
—Ed Bastian

Bastian argued the new prices will hold even if fuel keeps falling: airfares have risen 10 to 15 points less than overall inflation since COVID, and by Delta’s estimate, the low end of the market still needs another 5% in fare increases just to break even at current fuel prices.

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I have been doing this CEO gig for a long time. And for as long as I can remember, CEOs have been looking for what I call the “God system.” This system would gather all the data about everything happening in the company, then present it in a way that lets the CEO make informed, near-perfect decisions.

First, it was ERP systems. They seemed like the God system for CEOs back in the 1990s. The next couple of decades saw the rise of the dashboard. The new God system was a single view of all company analytics—revenue, pipeline, margin, hiring, churn, engagement. The ultimate dashboard would give the CEO something close to omniscience. Those promises never panned out. Today, AI has put us on a new quest for El Dorado. What if a model could understand all the data inside my company, then help me crunch it, analyze it, make decisions based on it? Maybe it could even make the decisions for me!

I understand the pull. I really do. After enough years in the CEO chair, the sheer volume of things you…

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In this edition

Quotes of the week

The defining fact of the current era of business leadership is that we’re all having to learn to work with a strange new colleague: AI. It’s a lot like trying to get value out of a genius-level person who happened to be raised on Mars. It can do so much… and yet it still requires so much from its human handlers.

This week’s earning calls (from FactSet, FranklinCovey, and Concentrix) sketch in a bit more detail on how B2B companies are using AI, how it is affecting their workforce, and how it’s impacting their ability to sell to customers. We see one company this week citing internal AI use as a driving force for a 10% reduction of the technology team. But we also see evidence that this kind of move is more a reshuffling than a slashing, not equating to large reductions in total headcount. Moreover, growing AI use among customers doesn’t seem to be reducing their need for these companies’ products. The correlation in fact seems to be reversed.

Ongoing disruption is a certainty, but it still feels like we’re learning what form it will take from week to week.

FactSet (FDS)

Q3 FY2026 Earnings Call

Results: Strong. Adjusted EPS of $4.53 beat by $0.08, revenue rose 6.4% to $622.9 million, organic ASV growth accelerated to 7.1%, and the stock climbed about 6% on the day.

FactSet’s workstation puts financial data, analytics, and portfolio tools in front of about 250,000 users at banks, asset managers, and wealth firms, mostly under subscription. Its headline metric is ASV, or annual subscription value: the forward revenue from everything clients currently pay for.

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I’ve been telling people to think of AI as a brilliant new college graduate. It has a degree in everything—at least everything a university knows how to teach. Ask Claude or ChatGPT or Gemini about finance, and it answers like a finance major. Ask it about marketing, and it answers like a marketing major. Ask it about operations, law, medicine, coding and it knows the answer. It walked out of “graduation” with more knowledge than any human could absorb in a lifetime.

But here’s the problem CEOs encounter with AI: There’s no degree for being a chief executive.

Not even in business schools. In these schools, you find specialization in functional areas. You can take classes in finance, marketing, operations, and organizational behavior. These produce graduates who are genuinely good at their chosen function.

What you will not find in business schools is a department that teaches the job of integrating all of this knowledge into a practical theory of the organization. This is the essence of …

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Quote of the week

White-collar hiring has been shrinking for years. Professional and business services payrolls have contracted YoY for 31 straight months, a streak that former Glassdoor chief economist Aaron Terrazas says has no precedent outside a recession.

The most cited reason for job cuts is—you guessed it—AI. That has been true for three months running, according to the outplacement firm Challenger, Gray & Christmas. A recent example: ServiceNow’s messy AI-related headcount reduction, months after the CEO pledged to hold headcount steady.

Three companies that reported last week sell labor-heavy services into that market, and each is building AI into its own work while drawing a line ar…

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In today’s article, I’m going to encourage you to consider the gap between (a) what you think your team knows and (b) what they actually know. It’s probably wider than you realize.

Part of my work is helping CEOs turn the strategy in their heads into shared knowledge employees understand and act on. One of the ways we do that is ChatCEO, our new AI platform built for the CEO. We are happy to show you how the product can quickly make your communication job as CEO notably easier.

Get started with ChatCEO here.

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Quote of the week

In 2026, every company has an AI narrative. Right now a lot of them are broadcasting positive stories of AI adoption while nervously eyeing the new tech. Is it friend or foe? A bit of both? Can the business AI eats up be compensated for by new AI-driven services?

Our three companies this week are pretty different from each other (a legacy publisher, a consulting titan, and a business analytics platform) but all are grappling with that question. Here’s what the CEOs had to say.

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Some CEOs put in great performances at the all-hands.

They talk about people being the company’s most important asset. They eloquently speak about respect, growth, treating employees well. You feel like you’re at a motivational TED talk!

But then that same CEO can walk back to their office, reschedule their 1:1s for the third week in a row, fire off a terse message to the CMO, and shrug when they find out the engineering team has lost another employee.

No matter how invigorating the speech at the all-hands, employees will base their actions on what they see from the CEO. That’s especially true for managers. If they see the CEO slacking off on basic management duties, why should they put in the effort?

When you attain the level of CEO, you might assume you get to do just the exciting stuff. You make the big calls, raise capital, craft strategy, work with the board. It’s heady stuff.

But the truth is, you’re still a manager, and you’re the most influential one in your company. You can’t give…

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Quote of the week

Over the past year, the frontier AI labs have moved strongly into education. OpenAI built a tutor mode for ChatGPT, made a free version for teachers through 2027, and released a tool to measure whether student AI use improves or erodes how people actually learn. Google and Anthropic are pushing into the same space.

For the companies that already sell software to schools and employers, that raises a question: Is a chatbot a threat to these businesses or a tailwind? Three of them reported in the past week, and all th…

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Below are the short remarks I gave at the ceremony last month.

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If you could use help setting up AI that works this way rather than tossing away tokens and hoping for the best, we built ChatCEO for you. CEOs who lead a company of 50+ employees are eligible to become founding users and get one year of ChatCEO free.

Apply for ChatCEO Access

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Quote of the week

One hundred years ago, the 1920s were roaring despite the fact that the beer, wine, and spirits industry was technically illegal. The speakeasies were packed and bootleggers were making a pretty penny.

Flash-forward to today, and we have an inside-out version of that situation. Alcohol is legal, abundantly advertised, but Americans are less interested in the stuff than ever. A Gallup poll released last August found that only 54% of Americans say they drink, a record low in Gallup’s data going back to 1939. Young adults, once the heaviest drinkers, now report drinking at rates below middle-aged and older Americans. The spirits category p…

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Most leadership development focuses on the “how” question. And for good reason: for most leaders, including executives, the “what” of the job is relatively clear. A sales VP knows the objective is to close more deals. A CFO knows the goal is to strengthen the balance sheet. A head of product knows she needs to ship features customers will pay for.

The hard part of these jobs is figuring out how to get there. How do we improve our close rate? How do we reduce our cash burn? How do we prioritize the roadmap?

The CEO Job Is Figuring Out What to Do

But the CEO role is fundamentally different, and most people don’t realize it until they’re sitting in the chair. When you become a CEO, the “how” problems are still there, but you’ve got a bigger fish to fry first: “what” to do in the first place.

This might seem like an absurd thing to say, since CEOs have infinite things to…

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Quote of the week

Phil has a point. It’s nice to be selling a relatively mandatory good, like car parts and maintenance, in a tough economy. Things like car parts and maintenance are inelastic, or at least only elastic to the point that something snaps. You either fix your car now… or deal with a bigger repair bill later.

In addition to hearing more from AutoZone’s CEO, we’ll also check in this week with a couple of other CEOs whose product is decidedly elastic, namely clothes and electronics. We’ll see that despite that, the US consumer is still showing up in those stores, for now.

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I talk to a lot of CEOs. Ask a hundred CEOs what got them to the top, and you will hear a hundred different stories.

But one trait does show up again and again: an unshakeable belief in their own judgment.

Call it confidence, ego, self-reliance, or even vision, but it’s the single most common characteristic in people who reach the CEO seat. Every time I teach a CEO Masterclass, I chuckle when we place them on the DISC Wheel, because they’re all clustered in the D quadrant. That’s D for Dominance, and despite the fact that D-type people make up only around 9% of the population, they make up somewhere north of 70% of CEOs in my experience. That relates closely to the classic self-assurance of the CEO.

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