Why The CTO Sucks

I know the title might be a bit provocative, but life’s too short to always sugarcoat harsh feedback. This article is a collection of real things I regularly hear from CEOs, other executives, and employees. Too often, people don’t feel comfortable saying these things to your face, so you can be wasting precious months and years without tackling issues. Perhaps something on this list is what you need to be aware of to set yourself on the right path for 2024.

Edit: Part 2 is available here.

Ivory Tower

Often coming from your employees, this is a general complaint about you no longer being involved in how things are done. Perhaps they’ll describe you as being disengaged or too high-level. Common examples of issues that arise from this problem are disagreement about how long something should take or about not being approachable by your people so you don’t hear what’s actually taking place.

As with any complaint, there are two possibilities here. Either you are too disengaged, or you aren’t (I know, groundbreaking stuff). If it’s the former, then you definitely should think about ways to become more involved with the team. I’m not saying you have to be coding, but there’s benefit in popping into some of the meetings, having regular skip-level one-on-ones, etc., so that you are a present leader and not someone who never gets to understand how things actually are.

However, I’ve seen cases where teams complain about this even when the tech executives aren’t disconnected from what’s happening—they’re just focusing on other things or demanding more of the team. That might happen when you’re thinking about an upcoming change that you’re aware of but that they aren’t, for example. Or because you understand why they think “X Project” will take five weeks, but you disagree that should be the case. When that happens, communicate what’s going on and bring them into the fold.

Poor Role Models

This is a tougher one to manage. You might have directors or other senior people on the team who are thinking about their future and careers and don’t view you as the leader who’ll get them there. Coaching should always be a central part of your day-to-day, yet many executives stop doing it with time or were never good at it.

Considering your star people, how many of them do you think really look up to you and are regularly growing thanks to your mentoring and coaching? Wouldn’t having your best director leave because she feels stuck in place be a shame? I’ve worked with a VP who just seems to insist on dropping this ball, closing his eyes, and hoping things will work out eventually. That’s not leadership.

Being Lost

An issue cofounders and CEOs bring up is when tech executives are unsure of their position in the company and, therefore, stop being “there.” I’ve talked about this recently on a podcast episode about the difference between wandering and being lost. Perhaps you’re thinking of the meaning of your role after a couple of years and having a solid team under you. Or maybe the team has changed so much that you no longer feel like you fit in.

Either way, your partners, your team, and you deserve better. It’s okay to wander as long as you realize it and do it purposefully, giving yourself permission to research and find your new purpose in the company. But a leader that’s neither here nor there, stuck in some sort of limbo, is problematic for the entire company.

Jargon Speak

Good executive teams are… teams. That means that you should be able to collaborate with your peers. Such collaboration often requires your efforts to convince them a certain initiative makes sense. There are two ways to do it. The first, which many geeks-turned-leaders like, is overwhelming the other side with jargon. Sometimes, we don’t even do it consciously, but we claim something is required or the right thing to do because of $techstuff and, for all intents and purposes, are twisting people’s arms to do what we want.

Admittedly, getting your way like that might be easy, but it’s not how partnerships are established. You need to learn to discuss things in ways that convey the value of the work, the business risks and possible gains, etc. Without that, don’t be surprised when people eventually automatically glaze over whenever you speak.

Requires Manual Operation

I’ve yet to meet the CEO, who wanted executives to overwhelm them with even more issues. Unsurprisingly, people who are already quite busy don’t feel the need to hear about more problems, even if those are important ones. Moreover, they rarely have the attention and time to invest in tailoring specific instructions for each of their executives.

Often, when CEOs feel like they have to “operate” their tech executives, they eventually grow tired of it. You can turn things around. Don’t wait to be told what to do. Don’t assume you can’t act before being given direct orders. Come up to the CEO with ideas about tackling issues and taking the responsibility to execute them. Do things without asking for explicit permission ahead of time, especially when we’re not talking about critical matters. Frequently, it’s better to ask for forgiveness later than for permission in advance.

Seeing this is already quite long, and I’m only halfway through my list of issues, I’ll stop here. If you’d like to see part 2, subscribe to my newsletter below and let me know!

Edit: Part 2 is available here.