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.
Want your own ChatCEO?
Shoot me an email at joel@xpertloop.ai and we will get you started.
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?”