Working with tech executives, one thing becomes obvious very quickly: the CEO relationship is the most important one you have, second only to Product. And yet, it’s often fragile, strained, or quietly dysfunctional. Even among co‑founders. It doesn’t have to be that way.

This is a problem I’ve dealt with repeatedly in client work. Not in theory. In strategy sessions, one‑on‑ones, and uncomfortable conversations that people avoid for years. The good news is that in most cases, the relationship can be materially improved with deliberate effort.

We’ll start with communication, because it’s the part leaders most confidently believe they’re doing well, and most consistently get wrong.

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Making Space

You probably speak with the CEO often. But how often do you actually talk?

Not status updates. Not Slack pings. Not a drive‑by comment at the end of a meeting. Real conversations. The kind that builds context, trust, and mutual understanding over time. Without that space, depth never develops. Without depth, the relationship stays transactional.

Many executives hesitate to ask for dedicated time with the CEO. They don’t want to be perceived as “another thing on their plate.” Two things about that. First, good CEOs aren’t quite that brittle. Second, and more importantly, you have to actively work against becoming exactly that.

If your meetings are just a string of complaints, escalations, or problems, they will be experienced as a burden. If, instead, they are a place where you:

• offer insight, not just issues
• surface patterns the CEO can’t see
• propose options and trade‑offs
• help remove bottlenecks beyond your org
  

… then those meetings start taking weight off the CEO’s shoulders rather than adding to it.

Yes, ask for feedback. Talk about your own goals and development. Some CEOs will engage deeply, others won’t. But naming it explicitly often creates the possibility for it to happen later. It also makes clear that you take your role and personal growth seriously.

More often than not, your conversations should create value for the CEO, not consume it.

Speaking Value

Effective communication with the CEO isn’t about vocabulary sophistication. It’s about mutual understanding. When I assess communication as one of the core leadership traits with clients, I’m very blunt: it doesn’t matter how technically correct you are if the other person didn’t understand you or you didn’t understand them. That requires deliberate translation to match the discussion with how your interlocutors think.

In an ideal world, a CEO never hears words like refactoring or tech debt. These are implementation details. Your interface with the executive team—your API, if you’ll allow the metaphor—should be value‑oriented.

With all due respect, a large portion of executive teams would happily replace an engineering org with “a few LLMs” if they thought it would achieve the same outcomes. Your ability to frame work in business terms is one of the main things still justifying the role. That’s an exaggeration, but not by much.

So don’t assume that invoking “tech debt” grants you a free pass.

For many executive teams, it simply doesn’t land. And in organizations where it does work, it often works the way a mechanic telling you your “thingie‑ma‑bob” is broken works: you nod, you pay, and you quietly wonder whether you’re being taken for a ride.

Suspicion is a terrible foundation for partnership. Instead, explain benefits, trade‑offs, and consequences in terms the business understands. Yes, that takes more effort. Yes, it increases accountability, because now you’re stating outcomes you can be held to. That’s not a downside. If you’re uncomfortable standing behind the value of a commitment, it’s worth asking whether it truly deserves priority in the first place.

If you have questions or reflections about the CEO–CTO relationship, reach out. My email is easy to find. And if you want the next parts in this series, sign up for the newsletter below.