Mike Cannon-Brookes, co-founder and co-CEO of Atlassian, has said publicly that most days he doesn't know what he's doing. That he's felt like a fraud for fifteen years. That he's petrified, at any moment, someone is going to call him on it. He said this as a billionaire running a company worth tens of billions of dollars.

I'm not a billionaire. Neither are you, probably. But if you're a CTO and you recognise that feeling — the quiet dread that someone will figure out you got lucky, that you've been smiling at the right moments, that you don't actually know enough — then you're in good company. Neil Gaiman wrote that maybe there aren't any grown-ups. Just people who work hard, go slightly out of their depth, and do the best job they can. He said Neil Armstrong felt like an imposter too.

I've felt this way for most of my career. The feeling doesn't disappear when you get the title. For most people, it gets louder. What changes — what has to change — is your relationship to it.

The knowledge surface is impossible Infrastructure, security, architecture, AI, hiring, board communication, product strategy, data — the CTO is expected to hold a view on all of it. No human being is an expert in all of it. The feeling that you don't know enough isn't weakness; it's an accurate reading of the situation. The question is what "good enough" looks like at your level of the organisation.
The role has no output metric Engineers ship code. You can look at a commit and know it works or it doesn't. CTOs make decisions. Decisions have long feedback loops, many variables, and outcomes that depend on factors outside your control. When there's no direct signal that you're doing your job well, doubt fills the vacuum.
You're comparing your insides to everyone else's outsides The other CTOs you see at conferences, on LinkedIn, in investor meetings — they look certain. They have frameworks and opinions and they deliver them without visible hesitation. You're hearing their public performance and comparing it to your private experience. It's not a fair comparison. I know this because I've had the private conversations.
You got here because you were exceptional at something specific And now the role rewards entirely different skills. You were promoted for your technical depth. You're now evaluated on your judgment, your communication, your ability to build a team that doesn't need you. That recalibration — from expert to multiplier — takes time, and in the gap it feels like you're failing.
You have to perform certainty you don't feel Board meetings, all-hands, investor calls, difficult conversations with the CEO. The role asks you to project confidence precisely when you're most uncertain. Most people handle this by faking it. There's a better way — but it requires being clear about what you actually know versus what you're navigating.
The isolation makes it worse You can't show doubt to your team — it undermines their confidence. You can't show it to the board. Your peer group from before you got the title has a different relationship with you now. When there's nobody to think out loud with, the imposter feeling compounds in private. This is the part of the problem most people don't name.

I've felt like a fraud since high school. That feeling that at some point someone would find out — that I got the job because I smiled at the interview, that I passed because the question was easy, that the delivery happened because of lucky circumstances. I still feel it. What changed is that I stopped trying to make it go away, and started understanding what it was telling me. That's the work.

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You feel like a fraud. So does the co-founder of Atlassian.

Why imposter syndrome hits hardest at the CTO level.