The sitcom-worthy moment: CEO barges into the room with three new “must-haves” for the current version. The CTO, with ruffled hair and bags under the eyes, pleads for a breather. “Oh, you’re always complaining,” the CEO mutters on the way out. Roll credits. You’ve lived this scene. Probably more than once this quarter.
Note: You can find the previous two parts here: Communication and Measuring Engineering.
Inherent Friction
The tension is here to stay. The fact that it exists isn’t a dysfunction. Actually, its absence usually is. The CEO’s job is to chase opportunity. The CTO’s job is to protect the system that delivers on it. The mistake is treating the tension as a problem to eliminate rather than a dynamic to manage well.
While it often gets too extreme and is one of the main causes for problematic relationships between CEOs and CTOs, it can also be a useful tool. In fact, it can become the basis for healthy prioritization, but it requires stopping the failure modes.
The Two Failure Modes
Two lazy CTO responses make this tension worse.
The Wall: “We can’t, the version is locked.” Process as a shield. You might feel like you’re doing the principled thing, but it usually reads as obstruction. A CTO who’s always seen as opposed to what the business wants to do.
The Doormat: “Sure, we’ll figure it out.” Buys peace today, burns trust (and the team) tomorrow. It’s not effective, and doesn’t utilize your leadership abilities. And, often, it just leads the team to utter failure.
Both approaches are often people’s default stances; they follow them almost without thinking—even when they might be telling themselves otherwise. And when that’s the case, when your reactions are so obvious ahead of time that people know they don’t even have to ask you, what are you there for? It doesn’t matter whether you always say “yes” or “no”; if you always say the same thing, you’re redundant. Both are abdications. You can do better.
Understand Their POV
As annoying or stressful as it might be, your CEO isn’t asking for more things just for the heck of it. I’ve yet to come across a founder who was thinking, “let’s see how much work we can stack on their backs before they finally snap.”
They’re doing what they think is the right thing. They want to get more work done because they see the business need, or have their own stressful issues to handle. They often also don’t have enough understanding, and many think that applying more pressure from their end is needed to ensure that the team doesn’t slack off (even without attributing any malice to the team). You’re all in the same boat.
Conversation Tactics
Speak in tradeoffs, not verdicts. Replace yes/no with “if we do X, then Y slips / Z gets cut / quality on W drops.” Make the cost visible instead of making yourself the villain.
Speak in spectrums. Almost nothing is binary. The answer to a request doesn’t have to be a simple yes or no. Can a stripped-down version ship now, and the full thing land next sprint? CEOs often want the signal of progress more than the full feature.
Don’t buffer. Padding estimates “just in case” insults the CEO’s intelligence and erodes your credibility when they find out (they always find out). Give honest numbers and honest ranges. That’s not to say that you cannot gain some wiggle room. But that needs to be done in the open, and not hidden behind estimates. Aim to not allocate 100% of the team’s capacity, knowing full well that something will crop up.
Ask to break work into small chunks. The smaller your units of work, the cheaper it is to change direction. Long monolithic efforts are what make every reprioritization feel like a catastrophe. Agility is a function of batch size. Yes, ideally, you wouldn’t have to change plans in the middle of a two-week sprint. But if you had to, wouldn’t it be better to at least be able to do it without losing what you were already working on?
Go Upstream
Conversation tactics only get you so far. Find where decisions actually get made. If the CEO is committing things to clients in sales calls without you, no amount of clever framing in the meeting room will save you. The fight you’re having is downstream of a process you haven’t fixed.
Make commitment-making a shared act. You don’t want to be the veto, but it would be nice to be present. You want to be in the room when promises are formed, not when they’re delivered to you as fact. That will help you understand where it’s coming from, what exactly is needed by the client, and come up with the best approach to tackle it. It also helps ensure you won’t be surprised by things that were decided but only communicated to your team too late.
Get an Outside Read
The uncomfortable possibility: you might both be wrong, in opposite directions. Sometimes the CEO’s expectations are genuinely unreal. Maybe it’s anchored on competitor PR, outdated past experiences, or pure wishful thinking.
Sometimes the CTO has slowly acclimated to a sluggish rhythm and doesn’t even notice anymore. You’re breathing your own exhaust on velocity.
An outside perspective (a peer CTO, a coach, a board member who’s seen other engineering orgs) is often the best way to realize whether there’s a bias one way or the other.
The Work
In closing, the friction isn’t a sign that something is wrong. If you feel that it’s a fight, then that’s a problem and means the relationship might be breaking.
Bring it back to the therapy frame from the series.
You should be disagreeing, or pushing back, thoughtfully: with shared language, shared visibility, and the humility to check whether your own calibration has drifted.