Questions CEOs ask

Because being CEO is a high-stakes job with little built-in support, and we believe that AI can meaningfully improve a chief executive’s odds of success.

Every other executive has a function, a scoreboard and someone who defines what success looks like. The CEO has none of that. You're accountable for everything and could, in theory, work on anything. Yet no one tells you what to do next. The pressure doesn't let up, and the fear of getting a big call wrong rarely goes away. The people around you, including your team, your board and even your family, can't fully see what the role asks of you.

Joel Trammell has done this job four times and has spent years teaching it to hundreds of CEOs. He built ChatCEO so no CEO has to figure it out alone. It gives you a partner that understands the role, knows your company, and helps you see what matters most right now.

Joel Trammell, a four-time CEO who has spent his career defining what the CEO job actually is.

Joel led companies to multiple nine-figure exits, including NetQoS (acquired by CA Technologies) and CacheIQ (acquired by NetApp), and served as CEO of NASDAQ-listed Black Box Corporation. He wrote The CEO Tightrope and The Chief Executive Operating System, is a member of the Austin Tech Hall of Fame, and publishes the Substack Managing the Future. ChatCEO is built on the Chief Executive Operating System, the methodology he developed over his career. It's made by his company, XpertLoop.

Meet Joel →

It's your CEO coach and your chief of staff in one place.

As a coach, it helps you think through hard decisions, difficult conversations and leadership problems, using a proven method for the CEO role. As a chief of staff, it handles the recurring work that keeps a company aligned. It prepares you for meetings, drafts board-ready materials and communications in your voice, helps you set quarterly goals, and flags competitor moves. Because it learns your strategy, your team and your goals, you don't have to re-explain your company every time.

For the same reason the CEO job is hard: nobody tells you what to use it for.

Most software has one obvious purpose. AI can do almost anything, so you open it and face a blank box. The CEO role works the same way, because it comes with no instructions. Put the two together and you get the same question twice: what should I do? Without a clear model of the job, most CEOs aim AI at small tasks like emails and summaries. ChatCEO starts from a system for the CEO role, so the AI is pointed at what matters most: setting direction, building the team, making decisions and keeping the company on track.

Read Joel's essay: "AI Has the Same Problem as the CEO Job" →

ChatCEO runs on those same leading models, but it adds expertise in the CEO role and knowledge of your company.

A general AI assistant can help you draft quarterly goals. ChatCEO can draft them from your documented two-to-three-year objectives, last quarter's results and your goal structure, then help you track progress after they're set. It also brings a CEO-specific methodology, a management rhythm that runs every week, scheduled briefings, and a human team that helps you put it all in place.

A dedicated XpertLoop Operator sets everything up with you over 90 days, and you never start from a blank page.

During the ChatCEO Quick Start, your Operator sets up your private ChatCEO, loads it with your company's context, and produces ten deliverables for your approval. These include your 1-Page Strategic Plan, org chart, executive performance profiles, board map, company and cascaded quarterly goals, and a 12-month operating calendar. ChatCEO drafts, your Operator edits, and you decide.

Your time commitment is one 60-minute intake interview and a 30-minute working session each week. At day 90, you can run the system yourself or keep working with your Operator.

No.

Building your 1-Page Strategic Plan is part of onboarding. It's drafted from whatever strategy material you already have and refined with your feedback. You supply the judgment; ChatCEO and your Operator do the drafting.

It comes to you, so you don't have to remember to open it.

Every weekday morning, your Daily Brief highlights your most important opportunity or meeting, shows your calendar, and can produce a full brief for any meeting on request. Every Saturday, an intelligence brief covers news and competitor activity in your market and what it means for your business. ChatCEO also supports your management rhythm: the weekly leadership meeting, 1:1s with direct reports, protected strategic thinking time, board meetings and quarterly offsites.

Yes, if you use its Goals module.

Each Friday, goal owners rate how likely their goal is to be achieved and the quality of the work so far. Those updates roll up to company goals, so you can see which priorities are at risk, drill into the goals underneath, and ask ChatCEO questions such as "Who hasn't updated their goals in two weeks?" or "Where are at-risk goals concentrated?"

Yes, and they're often where CEOs need help most.

ChatCEO can help you plan a difficult conversation, explore different approaches, and rehearse your wording. If you've loaded personality assessments such as DISC or CliftonStrengths for you and your team, it uses them to suggest how a message is likely to land with a particular person. The final call is always yours.

Yes. We never share your content with AI companies or use it to train models.

CEO conversations often contain sensitive information, and ChatCEO is built on that assumption from the ground up. We use industry-leading encryption and privacy measures to keep your content and interactions safe, confidential and fully under your control. General AI tools carry real discovery risk: CEO conversations run through unprotected platforms have appeared in legal proceedings. That doesn't happen here.

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