Why The CTO Sucks: Part 2

Seeing that the first part got some people thinking and that I managed to share some non-trivial examples of problems, here are some instances of issues you might be having and not aware of.

A bit of follow-up on comments: Yes, probably the most common argument I hear is that the tech leadership is plainly inadequate. For example, not delivering. However, the tech executives are rarely unaware of this, so I thought it would be less interesting to discuss. Let me know if you’d be interested in reading about handling that as well!

Zero-Sum Game Thinking

More often than not, this manifests in tech leadership’s relationship with product leadership. It’s when the whole mode of collaboration with other functions in the company seems to be argumentative and stems from an overly protective mindset. That is, any change or agreement comes at the cost of their own people and resources.

I completely understand the need to keep things real and say when something is just plainly not feasible. However, I also have seen how some executives, with time, grow to believe this is their role: to be the one that says no. However, that couldn’t be farther from the truth. An effective executive is often the one that comes up with inventive ways to accomplish things. Saying no is easy; finding the right path is where the secret sauce is. Also, you shouldn’t view your peers as enemies.

Warm and Fuzzy

I sometimes hear CEOs bemoaning that their VP Engineering is acting as a “union leader.” When they say that, they mean that the focus seems to be on keeping the team happy, even when that happiness harms the company’s long-term goals. You shouldn’t be looking to your team for love and acceptance. That’s not the right way of doing things.

Instead, work on yourself to realize that providing harsh feedback, setting higher expectations, letting go of people, and all those things that rarely feel “nice” make teams grow the most. You’re not Barney the dinosaur. And I genuinely believe that when we’re coddling people for too long, we’re actually doing them a huge disservice. That’s because they’re slowly becoming used to a certain level of performance that will not cut it in their next roles.

Delegation Oblivion

The contrast extreme of the micro-management described in part 1. Sometimes, there are executives who provide their teams with too much freedom. Yes, there is such a thing. First, this is a frequent complaint by other executives who feel like their peer is “out of the picture” and has no idea what’s happening in their organization. Second, it’s also something that many senior ICs notice when they’re looking for some leadership that’s just absent.

And in my coaching, I see this is actually something people get to solely due to good intentions. They’re so afraid of appearing to be micromanaging their teams or not trusting enough. They’ve heard too many times that Steve Jobs quote about bringing brilliant people and getting out of their way. The critical thing to remember is that Steve Jobs never “disappeared” but was actually there and provided people with lots of feedback. Perhaps even too much.

You definitely don’t need to aim to know which tasks each of your ICs are currently assigned. Nevertheless, you should be involved enough to know what’s going on and be able to spot issues. Two things I recommend clients do are management-by-walking-around and regular skip-level one-on-ones. While you shouldn’t be required for day-to-day operations, you shouldn’t aim to get to the point where no one would notice it if you were gone.

Perfectionism / Dogmatism

We all reach a point where we have to grow up. Yeah, I used to demand everyone TDD every single line of code or that no changes will ever be made mid-sprint, etc. I still believe these are good things and should be the default. However, we cannot turn these things into religious wars.

Striking the right balance between idealism and pragmatic solutions is a requirement. Yes, it means you’re going to have some tech debt or do things that aren’t optimal. Results are what we’re after; improvements and honing can come next.

Floating Leadership

Lastly, there’s the issue of not knowing where you’re headed or being unable to convey your vision to your team effectively. Leadership is about taking the lead. You cannot lead from behind. You should be taking the initiative and acting as a propellant.

However, this is not something I often hear described by others, at least not directly. They will mention some symptoms of this. Because it’s such a profound issue in leadership, I’ve dedicated a whole article about self-diagnosis and treatment here.