One of the recurring patterns I see in my work with CTOs and VPEs is the creeping tension between them and their CEOs. It’s natural: CEOs are wired to be antsy about performance, and in tech organizations that tension often centers around the performance of the tech leadership team.
When there’s no technical co-founder around to serve as a trusted advisor, this unease gets amplified. Suddenly, every missed update or delayed deliverable becomes a question mark. CEOs start to micromanage, trust erodes, and your freedom to operate shrinks.
Often, the way this tension shows up is in that loaded phrase: “I don’t feel a sense of urgency.” That’s rarely what they actually mean. What they’re really saying is: “I don’t know if things are moving as they should, and I don’t know if I can trust you to make it happen.” And if you let that perception fester, it doesn’t end well.
Here are a few ways to counteract it.
Speak their language, not yours
You hate it when the car mechanic explains your problem with auto shop mumbo-jumbo that makes you feel clueless, right? Don’t do the same to your CEO.
Translate your updates into business terms. Not throughput, story points, or microservice migration stages. Instead, focus on customer impact, time-to-value, cost tradeoffs, and risk management. The less they have to “decode” your updates, the more competent you’ll come across.
Double-click on their stress
When your CEO asks a clarifying question or seems hung up on a detail, don’t just answer and move on. Pause. Ask yourself: What’s really behind this question?
Often it’s not about the task itself but about an underlying fear: missed deadlines, ballooning scope, or lack of visibility. Every time they feel the need to double-check you is a learning moment. Adjust your communication so next time, they don’t need to ask. Otherwise, those small disconnects snowball into mistrust.
Don’t ignore the anecdote trap
CEOs have to keep tabs on a million different areas, most of which they’re not experts in. So they often latch onto anecdotes. One story from an engineer, one customer complaint, one late delivery, and suddenly it’s “this always happens.”
You can’t change their wiring, but you can counterbalance it. Share positive datapoints proactively. Highlight small wins, steady progress, and moments of excellence. If the only things they ever hear about your org are when there’s a fire, you’re letting anecdotes shape the narrative against you.
Kill the radio silence
Silence breeds suspicion. Break your work into visible, bite-sized milestones and communicate them as they happen. Provide timely updates even if they’re short. The goal isn’t to flood your CEO’s inbox but to ensure they never have to wonder, “What’s engineering even doing right now?”
This is just one example of being proactive that will really help turn things around in your relationship with the CEO and your peers. Just think about the difference you feel between someone coming and letting you know what’s been going on, as opposed to being left to wonder till you eventually ask and receive a brisk “all good!”
The bigger picture
“Sense of urgency” is usually a proxy. What your CEO really wants to feel is confidence that progress is happening and that they can trust you to lead without hand-holding.
Conveying competency isn’t about working faster. It’s about making progress visible, translating it into terms that resonate, and showing them you’ve got the wheel firmly in your hands. That’s how you shift the relationship from tension and micromanagement to trust and empowerment.