11 Things a CTO Should Never Say to a CEO

Andrew Weaver
May 29, 2023

The CEO:CTO relationship is often pivotal to an organisation but is not without its challenges and that’s often down to the very different personalities who can typically fill each role.

So we had some fun this week when asking our community of global tech leaders for suggestions about what you should avoid saying to the CEO unless you have your tongue firmly in your cheek …

From the many contributions that landed with us at CTO Academy, we selected the following “11 things a CTO should never say to a CEO”:

1. “Have you tried turning it off and then on again?”

It’s always the obvious method to start with, then we’ll dive a little deeper …

2. “Is there any chance we can take a more scattergun approach?”

Spray and play is important in early-stage start-ups but there comes a point when you have to settle down a little …

3. “IMO, empathy is overrated.”

This might be more a reflection on you but if you’re tasked with building a high-performance team; then it’s maybe not the thing to say to the CEO

4. “What do you do?”

I once knocked on the door of a former CEO and asked him this very question after he’d pushed a difficult conversation with one of my team. It didn’t go down well and I’ll be honest, made things a lot worse so this is a personal recommendation to avoid …

5. “Have you seen this great CEO role that’s become available?”

Nudge, nudge, wink, wink …

6. “I’ll take over this investor presentation.”

They might respond with … “but this is what I do” … in sarcastic reference to point No.4 above, which of course you’d never say after reading this article.

7. “KPIs? Remind me again…”

KPIs, OKRs, SLOs … what will it be next week?

8. “Let me write it down for you.”

Sometimes there is no other way forward …

9. “Sure we can ship by tomorrow.”


10. “Do you think you will still want this next week?”

I refer the jury back to No.2 mentioned earlier and how do we put it, this relates to the ever-changing strategy of some CEOs we’ve known …

11. “Why?”

OK, I get it … I’m looking for a new role from Monday.

But … if you can avoid saying some/all of these things; i.e., what your brain might be thinking, then your relationship with the CEO will be a bed of roses, maybe something like this:

Things a CTO should never say to a CEO to maintain a good relationship.
Yeah, we’ve been playing with generative AI also…can you blame us?
List of 11 things a CTO should never say to a CEO
(click to download)

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