Managing up is the skill most CTOs and CPOs never got taught. Your good at building teams, shipping product, and navigating technical complexity. The relationship with your CEO is a different kind of problem, and quietly, it’s where some of the most capable technical leaders I coach and advise come unstuck.
For CTOs and CPOs, managing up to the CEO is often the leadership skill they were least prepared for. The problem rarely looks like a problem at first. You’re delivering. Your team is shipping. The CEO seems satisfied. And then, often suddenly, something shifts. You find yourself out of sync. Decisions begin to happen without your input, with your CEO working around or beneath your role to move things forward. Your strategic proposals don’t land the way you expected. The CEO seems to be operating from assumptions about your team that aren’t accurate, and you’re not sure how that happened.
What I’ve observed, across a lot of these relationships, is that the breakdown rarely starts with a single incident. It accumulates through a pattern of missed expectations, ones the CTO or CPO didn’t even know existed.
Why Managing Up to the CEO Is Hard for CTOs and CPOs
The CTO and CPO roles sit in a uniquely difficult position when it comes to managing up. Unlike a CFO or CMO, whose domains are reasonably legible to most CEOs, your world, whether that’s engineering architecture, technical debt, or product strategy, is opaque in ways that matter. The CEO can’t easily assess whether your team is performing well, whether the risks you’re describing are serious, or whether the timeline you’ve committed to is realistic.
That opacity creates a relationship that depends almost entirely on trust. And trust, in this context, relies on a very specific kind of communication: the ability to translate what’s happening in your world into language that connects to what the CEO cares about most.
Most CTOs and CPOs are never taught how to do that translation well. So they default to what they know: status updates, technical briefings, roadmap reviews. These feel thorough, but they often miss the point entirely.
Five Patterns That Erode the Relationship
These are the patterns I see most consistently when CTOs and CPOs struggle with managing up to their CEO:
The Common Thread
None of these patterns stem from incompetence or bad intent. They develop because most CTOs and CPOs are never given a map for managing up. The encouraging thing is that all five are addressable, not through dramatic behaviour change, but through more deliberate communication habits applied consistently.
What Strong Managing Up Looks Like for CTOs and CPOs
The CTOs and CPOs who excel at managing up to their CEO aren’t necessarily the ones doing the best technical work. They’re the ones who’ve developed a specific set of communication habits that make their work legible, their risks visible, and their judgment trustworthy.
The Underlying Principle
Across all five habits, there’s a consistent thread. The CTO or CPO who manages up well isn’t trying to impress their CEO. They’re trying to make the CEO’s job easier. That shift in intent changes almost everything about how you communicate upward.
Your CEO will never fully understand your world. But you can fully understand theirs. That asymmetry, when you lean into it, is where the strongest CTO/CPO-CEO relationships take root.
A Note on Timelines and Commitments
The timeline question deserves its own attention because it’s where managing up most often breaks down for CTOs and CPOs. “When will it be done?” is one of the most loaded questions a CEO can ask, and almost nobody answers it well.
The wrong answer is false precision: a specific date given under pressure that becomes an anchor in the CEO’s mind, surfaces in board conversations, and lingers long after you’ve forgotten you ever said it. Evasion is no better: “it depends,” “we’re still scoping it,” or an answer so hedged it communicates nothing.
The right answer is confident uncertainty. Something like: “Based on what we know today, we’re targeting the end of Q2. The biggest risk to that is X, and here’s how we’re managing it. I’ll give you an updated view in three weeks when we know more.” This gives the CEO what they actually need: a planning horizon, the key risk, and a date when they’ll have better information. It also models the kind of thinking that builds credibility over time.
The same principle applies to scope. When a CEO asks “can we add this feature?” the answer almost always involves a trade-off. The CTO or CPO who says “yes, and here’s what moves” is far more useful than the one who says “it’s complicated” or, worse, says yes and quietly absorbs the cost into the team.
Questions to Sit With
If you’re a CTO or CPO thinking honestly about managing up to your CEO, these are worth working through:
- If your CEO had to describe to the board what your team accomplished last quarter, what would they say? Is that what you would say? If there’s a gap, that’s a communication gap, not a performance gap.
- When did you last raise a meaningful risk to your CEO before you had a plan to address it? If you struggle to find an example, consider what that pattern is costing you in terms of trust.
- Do you have a consistent, self-initiated cadence for the CEO relationship, or does most of your upward communication happen reactively, when something is needed or something has gone wrong?
- Does your CEO understand the key constraints your team is operating under, such as the architectural decisions, the accumulated technical debt, and the hiring gaps, or would those feel like surprises if they came up in a board conversation?
- What does your CEO actually care most about right now? Not what they say in 1:1s, but the things driving their decisions. How explicitly does your work connect to those things in the way you communicate it?
A Final Thought
Managing up well doesn’t mean being political. It doesn’t mean softening hard truths or packaging bad news attractively. It means developing the discipline to communicate your world in terms that are useful to the person you’re communicating with. And it takes real courage to do it consistently: to raise the uncomfortable thing early, to push back on the unrealistic expectation, to say “I don’t know yet” to someone you want to inspire confidence in. If that’s a dimension you want to explore further, our Courage to Lead series goes deep on exactly that.
Your CEO is making decisions about the whole business, often with incomplete information and real time pressure. The more you can make your piece of the business legible to them, the better those decisions get. That’s good for them, good for your team, and ultimately good for you.
The CTOs and CPOs who build strong upward relationships aren’t the ones who have the smoothest delivery or the most polished presentations. They’re the ones who understand that their job doesn’t stop at the boundary of their own organization, and who invest in the relationship with the same seriousness they bring to everything else.
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