The Hired TechExec Pitfall

This one is for those founders who don’t have a technical founder that wants to lead R&D/Engineering and also for the hired VPEs/CTOs who want to understand their bosses better. Running a startup, especially in the first 3-4 years, without a technical cofounder is a bit like deciding not to castle in chess. It’s possible, and sometimes it’s the right move, but one has to do it fully aware of the consequences and weaknesses it might create in your organization. Let’s set you up for success.

Woe is me, for I am a sole founder

Don’t get me wrong; being an employee-VPE is not bad. Some of the best executives I worked with, even at early-stage startups, weren’t founders. Nevertheless, a significant portion of the problems founders face boils down to the performance and fit of their hired executives. While this is true for most senior leadership roles, in a tech startup, the role of leading product engineering is vital.

So, let me say right off the bat that if you’re reading this while spinning up a new venture, reconsider your decision not to have a technical partner. Without a doubt, cofounders tend to stick around much longer than most for-hire executives, which can save a lot of precious time during your startup’s formative years.

Hiring the Right Leader

Now, assuming that ship has sailed for you (or you’re considering taking on such a position yourself), how do you track down a terrific leader and help them maximize their potential?

First, one of the main issues I hear from founders is that their tech executives “operate as an employee.” Guess what? They are one! This sort of attitude is often the case when the leader is a first-timer that was previously just a team lead or even a senior engineer. I’m not saying hiring someone new is necessarily a mistake—definitely not. I am saying that, especially in those cases, assessing the “executive mindset” of those hires is essential as part of the interviewing process.

The executive mindset is a concept that I covered in The Tech Executive Operating System, which talks about one’s ability to view things with agency and take the initiative. It is about being optimistic and providing an “anything is possible” attitude as opposed to the embittered, cynical senior engineer archetype. Your leaders should themselves be quasi-entrepreneurs. These people have the drive and instinct to be proactive and suggest things, not the type waiting to be told what to do. As I have seen many times in my work, first-timers often have this ability but need active coaching to make this shift quickly.

Further, as I point out in chapter 2 of Capitalizing Your Technology, your tech executives should be treated as fully-fledged executives. That means they join board meetings, help shape the strategy, etc. For that, two things have to be in place. The founders themselves have to treat these leaders appropriately. They should not be expected to be simple executors, for example. Second, look for people with a leadership cachet in your interviewing process. Are they assertive? Do they have enough charisma to lead a conversation?

Whereas most good leadership work is not powerful and should be focused on helping your people shine, when push comes to shove, you’re going to want to have these charismatic types on your side. Whether hiring someone who’s “done it before” or a potential-based star, look for these traits ahead of time and align your partners on the fundamental role of “geeks in the boardroom” to assure maximal success.