Close Enough to Influence, Independent Enough to Be Honest
Recently, four people I mentor brought me different versions of the same problem in the span of a few days. One CTO was dealing with a founder-developer who still had strong opinions about how software should be built. Another had an operator CEO who was hands-off on technology until something broke, at which point they overreacted. A third had just discovered that their CEO was making decisions affecting their team without consulting them. And a fourth was trying to figure out how to respond to a CEO who had vibe-coded a prototype and couldn’t understand why the engineering team needed more than a few days to build the production version.
Stepping back, there are some familiar patterns here: each scenario involved a disconnect between the CTO and CEO on expectations, communication, and decision-making. Whether the CEO was too hands-on, too removed, or making unilateral decisions, the shared challenge was finding the right balance of influence, alignment, and honest partnership. These patterns are common for technology leaders, and recognizing them early helps you map your own challenges and approach.
Four people. Four different situations. All with the same core question: how do you build an effective relationship with your CEO?
This led me to reflect on my own experiences. I’ve reported to about half a dozen CEOs across companies of different sizes and stages. Every one of those relationships was different in ways that mattered. Not just because of personality, but because of what the CEO cared about, what they expected from me, and how much room there was for honest disagreement. The lesson that keeps coming back is that this relationship is something you have to build deliberately. It doesn’t just happen because you’re both competent.
Why this relationship is different
To understand why these relationships are challenging, consider how the CTO-to-CEO relationship is asymmetric, setting it apart from other working relationships. The CEO hired you (or chose not to let you go when they joined). They can fire you. They set your compensation. They determine how much room you have to operate. That part isn’t different from any boss-employee dynamic. But they also depend on your judgment in domains they often can’t evaluate themselves. They need to hear things honestly from you. And they have very narrow windows into your part of the organization: a weekly one-on-one, a staff meeting, maybe a few ad hoc conversations. That’s it. What they understand about your world comes almost entirely through what you choose to surface.
You need to be close enough to influence, independent enough to be honest, and aligned enough to execute even when you disagree. If you’re too close, you become a yes-person and stop adding value. If you’re too independent, you look like you’re running your own company inside the company. If you suppress every disagreement in the name of alignment, you let the company make avoidable mistakes.
When this relationship breaks, it rarely stays contained. The exec team senses it. The board senses it. Your directs sense it, and they start hedging. If the CRO sees you disagree with the CEO and still get respected, they’ll feel safer doing the same. If they see you get shut down, they learn to keep quiet. The CTO-CEO dynamic models what honesty and partnership look like for the entire leadership team.
Different CEOs, different problems
Each CEO has distinct attitudes and preferences, which present unique challenges. However, CEOs can be grouped by shared traits, which create distinct dynamics.
The founder-developer CEO still has strong opinions about how things should be built. When your CEO built version one, they have opinions wired differently than those of a CEO who came up through sales or marketing. Some of those opinions are gold. Some of them are artifacts of how they used to build things. Your job is to figure out which is which without being dismissive. I’ve worked for a founder who was a brilliant product mind and an exceptionally fast developer, but whose approach to building code worked well for a solo builder and wasn’t something you’d want to build an engineering organization around. Navigating that meant figuring out which areas they cared deeply about and which areas they’d acknowledge they didn’t know well. You push forward where you have room and tread carefully where you don’t.
I also worked for a founder-developer CEO who was very narrowly technical rather than broadly so. Deeply knowledgeable in specific areas, but without a full picture of the platform. That created a different challenge: they felt qualified to weigh in on technical decisions, and in their areas of depth, they often knew more than I did. In those areas, I deferred completely. In the areas where they didn’t claim expertise, I had more room to work.
The operator CEO, as is most common in my experience, is hands-off when it comes to technology. That seems freeing, but it isn’t. These CEOs lack context to judge severity, timing, or reasons for failures, and swing from ignoring problems to overreacting. A surprised CEO makes poor decisions. With this type, proactively build context: provide regular, concise updates, link technical health to business outcomes, and alert them before problems escalate.
Visionary CEOs, usually founders, bring constant new ideas and a strong drive for innovation. Their entrepreneurial mindset fuels company growth, but following every idea can drain focus from the core business. If you always say yes, you’ll be overwhelmed; saying no all the time may sideline you. Find areas to invest in, leveraging credibility so you can advise the CEO when an idea isn’t feasible right now.
The challenge isn’t finding the ‘best’ CEO type. The real test is recognizing who you’re working with and intentionally adapting your approach to make the relationship work.
The four foundations of CEO trust
Every successful CEO relationship I’ve seen shares four key foundations: competence, candor, commitment, and context. These consistently determine whether the partnership is strong or fragile.
Competence seems obvious, and technical leaders often assume it. But to a CEO, it’s not just technical depth. It’s your ability to translate technical details into business reality, deliver results, and spot problems early. CEOs judge competence by outcomes, not by engineers’ standards.
Candor is the hardest foundation to build and the easiest to lose. CEOs are surrounded by people who have incentives to shade the truth. If you become one of those people, you lose the thing that makes you most valuable. But candor without judgment is just complaining. Candor means: here’s the real situation, here’s what I think we should do, and here’s what I need from you. It also means telling the CEO when they’re wrong in your domain, and doing it in a way they can hear. Privately. With data. With a proposed alternative. Not in front of the board. Not in a group setting.
Commitment is what separates senior leaders from everyone else. Disagree and commit is easy to say and genuinely hard to do. It means your team never hears you undermine the decision. It means you run at it with full effort, not with one foot out the door waiting to say, “I told you so.” If your team can tell you disagree with the decision you’re executing, you’ve already failed the commitment test. Your behavior teaches the organization whether decisions are real or negotiable.
Context is the one most people miss. Competence, candor, and commitment can all be undermined if you and the CEO are operating from different mental models of how the business works. Building context means constantly translating between the engineering and business worlds. “We need to replatform” means nothing to most CEOs. “Our current architecture limits how fast we can ship features customers are asking for, and that’s contributing to churn” means everything. Building context goes both ways, though. You need to understand what the CEO is dealing with that you don’t see: board pressure, investor expectations, competitive moves, and how the rest of the exec team is pulling on them. When the CEO makes a decision that seems wrong to you, the first question to ask is: What context do they have that I don’t?
Making the relationship work day to day
Weekly one-on-ones with the CEO are non-negotiable. Protect them. If the CEO cancels frequently, that’s a signal you need to address directly. Use that time to pre-wire. Nothing that comes up in a staff or board meeting should be the first time the CEO hears it from you. Lead with conclusions, not context. Tell them what you think, then offer the supporting detail if they want to dig in.
Handle disagreements deliberately. Raise concerns before decisions are made. Bring data, not just opinions. Frame feedback as “here’s what I see and what I’d advise” instead of “I disagree.” If overruled, commit fully. Execute as if it were your idea. If it fails, you’ll have standing to revisit, having genuinely tried.
I learned about handling disagreement the hard way. At one company, I saw us heading in a direction I disagreed with. I raised my concerns. They were heard. We kept moving in that direction. I continued advocating until another member of the exec team pulled me aside and said, “This one’s over. This is the way we’re going now.” I hadn’t read the room. The decision had been made, and I was still arguing. I had to shift fully into execution mode, and I should have gotten there sooner.
Watch for the strategic vacuum. If you’re the only person on the exec team thinking past the current quarter, writing strategy documents, doing competitive analysis, pushing the team to plan for what’s coming, that’s both valuable and dangerous. Valuable because somebody has to do it. Dangerous because if the CEO isn’t co-owning that work, it can create resentment on both sides. If you’ve come from companies with more structure and you’re now at a place that doesn’t operate that way, the instinct to fill that gap is strong. But your current company exists because whatever they’ve been doing has worked for them so far. If you feel yourself becoming the lone operator, surface it directly: “I notice I’m driving a lot of the longer-term strategic thinking. I’m happy to do it, but I want to make sure we’re aligned on that being part of my role.”
When trust is eroding
By the time most leaders recognize that trust has eroded, it’s often too late. Here are the signals.
Signs the CEO is losing confidence in you: they start asking your directs for information instead of you (and not in the healthy way where you’ve pre-wired those relationships). They bring in outside advisors or consultants for things that should be your responsibility. Your one-on-one gets shorter, less frequent, or more transactional. You find out about decisions affecting your team after they’ve been made.
Signs you are losing trust in the CEO: you start building a case file of bad decisions, collecting evidence for an argument you haven’t made yet. You explain the CEO’s decisions to your team in ways that distance you from them (“the CEO wants us to” instead of “we need to”). You spend more energy managing around the CEO than working with them. You stop bringing up problems because you don’t think they’ll be heard.
If you catch yourself translating the CEO’s decisions into something your team can stomach, the relationship needs attention. You’re not a translator. You’re supposed to be a partner.
Understanding the human side
Most CEOs at growth-stage companies are under a lot of pressure from the board and investors that the rest of the exec team doesn’t fully see. They’re being evaluated quarterly. When a CEO takes a struggling function under themselves or suddenly elevates the priority of something that seemed peripheral, it’s often because that issue has reached the board level or they are concerned it will if it isn’t handled.
Understanding that pressure doesn’t mean excusing bad behavior. But it does mean adjusting your approach. A CEO isn’t going to blame the board, just like you aren’t going to blame the CEO to your team. If you sometimes see unusual behavior or weird pressure, there may be something going on that you don’t have visibility into. The best CEO relationships I’ve had are those in which the CEO trusted me enough to say, “The board is aware of this, and they’ve raised the priority.” Even when they can’t share that, recognizing the possibility changes how you respond.
When it’s time to go
Sometimes the relationship can’t be fixed. If the CEO consistently overrides you in your domain without engaging your reasoning. If your values don’t align with how to treat people or make decisions. If you’ve surfaced the issues directly multiple times, and nothing changes. If you’re staying because of inertia or compensation rather than belief in the direction. Those are signs of a role fit problem, not a relationship problem.
If you’re not that far gone, repair requires both sides. Be direct: “I think our working relationship isn’t where it needs to be, and I’d like to talk about what we can do about it.” That is a very hard sentence to say, but it is the only honest one. Propose specific changes. “I’d like us to use our one-on-one to pre-wire any staffing or budget decisions before they go to the broader team.” That’s actionable. “We should communicate more” is not. If you agree on specific changes, give it 90 days of real effort before deciding whether it’s working.
If you’ve done the work and the trust still isn’t there, leaving is a reasonable decision. It’s not failure. It’s recognizing a fit problem. The worst outcome is staying in a broken CEO relationship and letting it erode your judgment, energy, and your team’s trust. And if you’re feeling that the trust has broken down, they’re feeling it too. Every CEO I’ve worked with, when that alignment is gone, they’re already thinking about who comes next. By the time you’ve decided it’s not repairable, they’ve probably already made that decision and may already be interviewing.
What I got wrong early on
Earlier in my career, I thought the CEO relationship was mostly about competence. Deliver results, and the relationship takes care of itself. That turned out to be incomplete. Competence is table stakes. The relationship lives or dies on candor, commitment, and shared context.
I also used to think that disagreeing with the CEO was inherently risky, something to be done sparingly and carefully. Over time, I learned that the opposite is true. A CEO who doesn’t hear honest pushback from their CTO is flying blind. The risk isn’t pushing back. It’s not pushing back. You just have to do it the right way.
Working with founder-developer CEOs taught me something specific. Their technical opinions aren’t obstacles to manage. They’re signals about what the CEO values. Learning to distinguish between “I built this, and I’m attached to it” and “I’ve been watching customers, and I see something you don’t” made me a much better partner to founder-CEOs.
The CEO relationship is the highest-leverage relationship in your career as a technology leader. It determines your scope, your influence, your ability to protect your team, and whether you can do the job you were hired to do. If you want a starting point, ask yourself four questions before your next one-on-one: Does the CEO hear the truth from me? When we disagree, do we have a reliable process for working through it? Do I understand what they’re dealing with that I can’t see? And does my team see a partnership when they look at us, or a hierarchy?
If the answer to any of those is uncomfortable, you have work to do. And that work starts with you.
To hear an extended discussion of this topic, please listen to my recent podcast episode: Working with the CEO: Close Enough to Influence, Independent Enough to Be Honest.
Originally published in my newsletter at: https://kevingoldsmith.substack.com/p/working-with-the-ceo