Are You a CT-NO?

Photo by Morgan Bryan on Unsplash

A CEO once told me it felt like the CTO misheard and thought his title was CT- N O. “Can we do that? No. Is that feasible? No.” After wiping myself from having spilled my coffee laughing, I realized that’s such a common stance tech executives take that I’m surprised I hadn’t heard the term earlier. Let’s discuss why so many people have this issue and how you can become a force-multiplying CTO instead of a backlog gatekeeper.

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Fear and Authority

You’re not alone if you recognize a bit of yourself in that CEO’s complaint. The fact is that many tech leaders, consciously or not, address most incoming requests and ideas as interruptions and issues. Why is that?

Leaders I’ve worked with were often burned in the past by tech leaders who-in their view-didn’t say ‘no’ often enough. Occasionally, it’s their past as ICs or team leads under tech executives who allowed changes to occur without seemingly any thought. Some have even done the same themselves and now have ‘repented,’ choosing the austere position of the senior techie: Everything is expensive, will take four times longer than you expect, will be a nightmare to maintain, and won’t be useful anyway.

This is natural overcompensation for having suffered in the past, but that’s not all of it. Some executives I’ve coached had an issue of wanting to feel like they have a say. That’s another very natural part of being in a role with a lot of responsibility: we expect it to come with more authority. The issue is when we start wielding that authority for the sake of doing so. If you want to become a leading tech executive, you’re going to have to drop that mindset and learn how to say ‘yes’ correctly. Of course, fixing this default negative stance does not mean we aim to have all tech executives turn into order-takers.

End of Binary Thinking

As part of helping executives fulfill their potential, one of the most effective tools I’ve seen is helping leaders break the habit of supplying knee-jerk reactions. It doesn’t matter if your default is yes or no. We strive to see anything as the complex wave function that it is. Rarely is anything in our world as simple as a binary decision. That’s overly simplistic and means that we’re often missing opportunities or trying to take on too many things simultaneously.

Decide to view requests and suggestions as a peer. You’re not “protecting your team.” You’re trying to achieve the best ROI for the company. When your peers ask a simple yes/no question, imagine that you’re expanding it into the continuum of possibilities for achieving it.

Let’s consider a common example. The CEO asks whether it would be possible to integrate some new capability announced by a vendor. The CT-NO would take a second to consider it, realize it would derail the current projects, and reject it. However, imagine the whole spectrum of ways of doing it.

• You can have an entire team drop what it’s doing to address it immediately, at the cost of delaying other commitments.
• If you decide to implement a basic POC, it would only take half a day. Do we need an operational product or something to show prospects?
• A wizard-of-Oz solution that works for 50% of the use cases and puts the rest of the strain on customer success/operations initially, until automated, is possible. Will that answer business needs?
• You can implement a solution that would work for 80% of use cases in a few days. Would that be a good compromise for this quarter?
• You could hire a few freelancers to work on it alongside the team.
• You could get world-class experts in this technology and pay their boutique a high price but have this done within a few days.

And those are just some generic options that are almost always applicable, without getting into the actual details. In any real-world scenario, you could get into your SLAs, operational costs, deadlines, long-term maintenance, specific edge cases, and more that you could tweak to reach a solution that works. Should any question you get in the hall between meetings warrant such a deep deconstruction? Probably not. But by defaulting to viewing things like this instead of viewing things in black-and-white or yes-or-no, you will stand out as a tech executive.

© Aviv Ben-Yosef 2024 — Originally published on the best newsletter for tech executives