The CTO Life: Damned if You Do, Damned if You Don’t

We Deep-Dive into the Catch-22 of the CTO Role

Welcome Leaders!

There are a lot of metaphors that describe no-win situations, but “damned if you do, damned if you don’t” is especially true for the CTO role.

Shouldering the blame and being criticized is part of the job. (I’m sure a lot of you have experienced what I’m talking about.)

In today’s article we’ll cover why this phenomenon exists and what executives should do about it.

Cheers,

Bobby

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Have you ever accomplished something you thought was really valuable only to later be criticized for it?

Well, join the club!

This is a pretty typical part of a CTOs life 😛

CTOs lead organizations that do the kind of technical work that is often misunderstood by other executives and stakeholders.

So, an accomplishment in the mind of a CTO or their team may not be an obvious accomplishment in the mind of other stakeholders.

Here’s an example:

A CTO friend once complained to me that her boss (the CEO) had gotten upset with her because she had created “one giant team” instead of several smaller engineering teams.

She couldn’t believe the CEO was upset with her 😢

“I worked so hard and it took so long to design the engineering team to be flexible across our ecosystem of projects and instead (the Boss) thinks I was silly to create ‘one giant team.’ Obviously I would never do that! He’s misunderstanding the situation.”

I felt bad for her but I know how often big accomplishments by CTOs can be completely misunderstood by others. In fact, I can’t tell you the number of times CTO colleagues have complained to me about this kind of thing.

The frequent scenario is: CTOs / Engineering will get something big accomplished for the business such as saving a lot of money 💰 or solving a long-standing product issue, and instead of a pat on the back they will get criticized for it or at least not properly acknowledged.

Let me give you several more common examples I’ve seen in the past.