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.

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.

Leigh Newsome

Partner, Hoola Hoop · CTO & CPO Coach

Leigh Newsome is a Partner at Hoola Hoop and a CTO & CPO coach with 25 years of experience scaling product and engineering teams. He has worked with a wide range of startups and global enterprises, including Avid, Digidesign, WPP, and Kantar/Millward Brown, and successfully led TargetSpot (backed by Union Square Ventures, Bain Capital Ventures, and CBS) through its acquisition to Radionomy Group (Vivendi). When he’s not coaching CTOs, you’ll find him teaching digital audio to graduate students at NYU, building audio and signal processing applications, or flying fixed-wing aircraft, but never all three at once.

That’s exactly why I do what I do. And it’s what CTO coaching is for.

What is CTO Coaching?

CTO coaching is a structured working relationship between a technology executive and an experienced coach, designed to help the CTO grow as a leader, make better decisions, and perform more effectively in their role.

It’s very different from consulting. A consultant gives you answers. As a CTO coach, I help you to develop the skills, self-awareness, and judgment to find better answers yourself.

My approach is grounded in 25 years of hands-on experience as a technology and product executive — having served in CTO, CPTO, and CEO roles across a range of growth-stage companies. What I value most about the team I work with at Hoola Hoop is that every partner and coach brings that same perspective. We’re all former operators who have navigated exactly the challenges our clients face. Not theorists. Practitioners. The guidance is concrete because the experience is real.

Who Needs CTO Coaching?

In my experience, CTO coaching is highly valuable at multiple career stages, but it tends to be incredibly impactful in a few specific situations.

Areas CTO Coaching Addresses

Effective CTO coaching covers both the technical leadership dimension and the human side of the role. In my work with technology leaders, these are some areas that come up consistently:

What Makes A Good CTO Coach?

Not all coaches are created equal. Here’s what I’d tell any leader looking for a CTO coach:

• Real operating experience in technology leadership First and most importantly, look for a coach with real operating experience in technology leadership. A coach who has never scaled an engineering team, managed technical debt under growth pressure, or navigated a difficult CTO-CEO dynamic will struggle to give you relevant, credible guidance. I’ve spent decades doing exactly that, and it’s the foundation of every coaching relationship I have.
• Someone who asks great questions, not just dispenses advice Second, look for someone who asks good questions rather than just dispensing advice. The best coaching unlocks your own thinking. A coach who just tells you what to do creates dependency, you want someone who builds your capacity to think through hard problems independently.
• Honest and willing to challenge you Third, look for a CTO coach who will be honest with you and challenge you. As a CTO, you often don’t get candid feedback from your teams or peers. A good CTO coach will tell you what you need to hear, not just what you want to hear.

What to Expect from CTO Coaching

My coaching engagements typically involve regular one-on-one sessions usually weekly or bi-weekly, focused on whatever is most pressing for you at that moment and on the goals we have set together. Sessions are confidential, which creates the space for the kind of honest conversation that’s hard to have with a direct report, peer, or investor.

I often start with an interview-based 360 review speaking directly with your peers, direct reports, and CEO. This helps get an honest, multi-perspective picture of where you are excelling and where the real development opportunities lie. Then we define 3 to 5 goals to work on. This gives our CTO coaching sessions a grounded starting point rather than relying solely on self-assessment.

From there, coaching sessions evolve to address real-time issues as they arise such as team performance challenges, a board presentation, technology decisions, a team restructure, or a conflict with the CPO or CEO. I also facilitate CTO leadership roundtables, bringing together technology leaders from across our client base and portfolio to share experiences, challenge each other’s thinking, and learn from peers who are navigating similar inflection points. Many CTOs find these peer sessions as valuable as the one-on-one coaching itself.

Leigh Newsome

Partner, Hoola Hoop · CTO Coach

Leigh Newsome is a Partner at Hoola Hoop and a CTO coach with 25 years of experience scaling product and engineering teams. He has worked with a wide range of startups and global enterprises, including Avid, Digidesign, WPP, and Kantar/Millward Brown, and successfully led TargetSpot through its acquisition to Radionomy Group (Vivendi). When he’s not coaching CTOs, you’ll find him teaching digital audio to graduate students at NYU, building audio and signal processing applications, or flying fixed-wing aircraft — but never all three at once.