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How to Hit the Ground Running as CTO/VPE

When starting a new role as a tech executive, it is common to feel slightly disoriented at first. That’s because, in most startups, you’re not going through a ready-made orientation process. More often than not, you have to carve your own path forward without a lot of guidance.

Having aided many CTOs and VPs of Engineering during their onboarding, I have thoughts about this. Your personal onboarding can feel overwhelming, especially when you are taking over an organization that is already up and running. However, once you acknowledge that you are supposed to take charge and organize this for yourself, you should already be better off. Remember, you have agency here. 

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Intention, Inertia, and Introspection

The best tech leaders I’ve seen and who remain remarkable over the years are those who are never "done." They evolve, learn, experiment, and change their minds routinely. The constant need to undergo personal growth is both the most fascinating thing about leadership and a source of anxiety and fatigue. It can feel like a never-ending struggle where you can’t stop. Issues and problems keep piling on your plate, and what used to work for you last year no longer seems to be cutting it. 

I’ve seen this struggle repeatedly when working with my clients. In coaching them, I’ve learned that naming some of the everyday occurrences of this growth effort and their relationships can help reduce stress and make priorities more straightforward. My recently published book, The Tech Executive Operating System, covers many aspects of managing your focus and energy. In this article, I want to focus on a part that can be utilized by itself without needing to go through the entire book. That is understanding the mechanism of balancing Intention and Inertia with Introspection.

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The Fallacy of Meeting Expectations

Coding is magic. Leading an engineering organization is like being in charge of a cadre of brilliant wizards. At least, it should be.

The experienced and calloused tech executive has learned—often the hard way—that things are not as easy as they seem. As the team grows, complexity prospers. This intrinsic perfectionism engenders a vicious, negative feedback loop forming an organization on an incessant drive to… meet expectations.