A CTOs Life: Damned if You Do, Damned if You Don’t
Why Being a CTO is One of the Most Difficult Executive-Level Roles
The Executive Brief
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 a CTO. Shouldering blame is part of the job.
I wish this article gave you the secret to avoiding those no-win situations.
(It doesn’t)
What it does instead to share with you my strategy for dealing with it. Hope it helps.
A CTOs Life: Damned if You Do, Damned if You Don’t
A CTO friend of mine 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 scrum teams.
She couldn’t believe the CEO was upset with her. “I worked so hard to make the team fungible and hot-swappable across the platform and instead its interpreted as me creating a giant team. Obviously I would never do that!”
I can’t tell you the number of times CTO colleagues have complained about things like this. They go off and do something good for the business. It’s completely misinterpreted by the business stakeholders. And they get knocked for it.
Even when there isn’t a misinterpretation CTOs can get knocked for doing the right thing.
Although it’s pretty strange it does seem to be a part of a CTOs life to get in trouble for doing good things. In fact, most of the time a CTO is living in a world of “damned if you do, damned if you don’t.”
Let me give you examples that I’ve seen in the past. I’m sure many of these will resonate with your own experience.
The CTO solves a critical bug that’s been plaguing the software for years. The response from the business? “Why was this there in the first place?” The fact that the CTO wasn’t around when the bug was created is irrelevant to them.
The CTO stops a bunch of security breaches from happening. The response from the business? “That took way too long!” Never mind that the CTO probably just saved the company from being headline news!
The CTO builds and launches a complex product in half-the-time the business expects. The response from the business? “Well, we knew you were good. So, can you do that 5 more times for us?!” Uhm, yeah…
The CTO dramatically improves uptime for a highly scaled product with 10s of millions of users. The response from the business? “I mean that’s your job anyway, so…” Just, wow.
The CTO does an incredible job building the Engineering/Product Team, filling it with A players. The response from the business? “Yeah, these folks are good but what have they accomplished?” The fact that the team just joined is irrelevant to them.
The CTO gets rid of a 3rd party people provider that was essentially minting money of the company and hires one that is cheaper and does a better job. The response from the business? “What? There was a 3rd party involved? Oh, OK.” Yeesh!
The CTO manages to exit a toxic staff member with lots of tribal knowledge without causing any disruption to the team. The response from the business? “Why did you let this person on your team anyway?” Never mind that the CTO didn’t hire them!
The CTO realized the product was heading nowhere because of its current design and suggests and alternative that creates a revenue uptick. The response from the business? “The head of product really is inspirational.” 🤷
The CTO realizes that there’s tons of fat in the budget and painstakingly trims it down by 30%. Huge win, right? But the response from the business? “Great, we’ll take those savings. Plus you’re a fiduciary so no big deal.” Greeaaaaat.
The CTO remediates years of technical debt with some clever technological breakthroughs that made the team 10% faster. Th response from the business? “What is technical debt anyway and why are you focused on that?” Good, God the sheer stupidity.
I guarantee that if you’ve ever lead technology for a company larger than a startup that you’ve encountered at least one of those scenarios in your career.
So, now, here’s the secret to dealing with all of this:
Smile, educate your stakeholders and move on to the next thing, because this is the life of a CTO. Very few other executive roles are as hard for stakeholders on the business side to comprehend.
The answer is to keep doing the right things for the business, one after another. If you get knocked for it defend to a degree but educate others more. Then do the next thing and the next thing.
Over time as you aggregate the wins the business usually can’t ignore your accomplishments.
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Great post on capturing the unique challenges and paradoxes that CTOs face in their roles, and highlighting the often thankless task of navigating through no-win situations. As a technology leader, I agree with your observation that Chief Technology Officers (CTOs) often don't receive sufficient recognition for their multifaceted responsibilities. However, I believe this extends to other C-Suite roles as well. Consider the Chief Product Officer (CPO), who manages the intricate interplay of user requirements, market dynamics, and technical viability. if the predictions don't go as expected and the outcomes falls short, they will be questioned on why they didn't follow alternate paths. Similarly, Chief Customer Officers primarily shoulder the responsibility of retention, but it's important to acknowledge that they aren't solely responsible for the company's current situation.