CEO-CTO Therapy Part 4: What Are You Even Doing?

A major point of contention that often arises in relationships between tech executives and their CEOs is that the latter does not understand what the former are actually doing and where their time is going. They wonder whether things are doing fine and whether they ought to be doing better.

They hear you describing a team that’s always working hard and busy, yet by their judgement output is thin. Add to that the daily increase of questions to the tune of “why aren’t you all already doing 10x better with AI?” (Or, which I’ve also heard, “why aren’t you getting rid of anyone who isn’t 10x better so we move faster?”).

If you’re wondering why they’re thinking like that, you should also consider whether you’ve made it easier to for them to see things differently. It’s not like this can be solved magically, but understanding the common causes for this can help. Let’s go over that.

Note: the previous parts of the series are available here: I | II | III.

The Reason Behind This Gap

I’m sure your team’s not just sitting there twiddling their thumbs. However, it’s often that their work isn’t visible or understood. For example, you might be investing a lot of effort into tackling bugs that come up regularly. That quality debt definitely needs handling, but your CEO likely doesn’t let those “count” as “output” (and, let’s be honest, pretty rightfully so).

Then there are the projects that you’ve accepted as too big and never broke them down effectively. Multi-month efforts that create radio silence without showing progress. Silence creates tension.

And as you’re working on these things, priorities change and drift. By the time you’re done with something, the CEO has already moved on and forgotten about those tasks, shifting focus to something else.

There’s also the invisible work, like learning new things, experimenting, investing in scaling improvements, and more. These efforts often go unnoticed, and you don’t “get credit” for them, even when they were direly needed.

What To DO About It

First, if a good chunk of your time goes into quality issues, you have to fix them. There’s no putting a positive spin on it. Quality issues actually aren’t a communication problem like others discussed here, but rather just a… quality problem. Sack it up and make things better.

Chunk things into the smallest genuinely shippable pieces. This might mean cutting the scope down, but it could also just be about reshaping the order of the work. Doing so immediately improves visibility and means things are less likely to go “stale.” It also makes it easier to react to changing priorities faster without losing work already done. And while this was common advice for a couple of decades (though not really adhered to by many), this is one of those things that AI really makes easier to achieve.

Aim for cascading releases. Stagger teams and work so something is always going out. No more six-week silences. With continuous deployment and some pacing teams differently, you get the benefit of demonstrating more progress without really any disadvantages. I’d even say it might make things easier on leadership, because it means you don’t have to squeeze all planning work across the organization into the same week. While you’re at it, make sure that these releases are well communicated outside the organization.

Lastly, when it comes to handling non-feature work, you have to manage it correctly, in a way that involves Product and your stakeholders. That’s covered in depth in this three-part series.

Closing Thoughts

Of course, I’m not pretending any of the steps in the previous section are easy to perform. They’re often the focus of my work with clients, but we’ve repeatedly shown that dramatic progress can be made within a couple of months in most cases.

To do that, you need to stop making excuses, realize that the CEO asking what you’re doing isn’t always bad faith, and accept that making the work legible is actually part of the job.