Tech Exec—Cofounders Fit

We all know that whenever someone interviews for a role, they should also do their due diligence and interview the company. Having seen many times when a tech executive joined a company as a CTO or VPE only to realize later they do not work well with the founders, I decided to lay out a recommended agenda for your next interview. If you’re already in your role, I believe these aspects can also help you realign yourself for success or gain clarity about where you should be heading.

(If you’re a founder hiring a tech executive, I will cover this subject from your perspective in my work-in-progress book. Subscribe below to get updates.)

Leadership Style

There are many different sorts of leaders, and some of those do not fit other certain company cultures. Discussing your leadership style is a way of assuring the culture fit right off the bat. For this, I think it is essential to go over different parts of how you view your day-to-day work and the company’s trajectory. For example, let us consider some elements of your leadership style.

Hands-on intensity: Especially relevant for smaller companies, though I’ve seen this come up at organizations with dozens of engineers as well. How hands-on you will be is something that sometimes might be completely up to you, meaning that if you’d like to do it and you find the time, no one will tell you not to and vice versa. However, some founders expect their tech executives to be completely up to date regarding every bit and tactical decision. That might be great for you, but it could also be entirely in contrast with how you would like to spend your days.

Growth: Similarly, there are different schools of thought when it comes to company size and headcount. If you’ve been following my writing online, you know that I prefer tight-knit teams as opposed to mindlessly reaching for the hyper-growth lever, but to each their own. Ensure that it aligns with the company’s strategy, whichever you prefer or believe in. I have seen many VPs that were expecting to lead a rocket ship, hiring dozens of people rapidly. For them, the interesting part is managing managers of managers, not the small startup level. However, a year later, they would realize it would not happen and be completely discouraged.

Culture and values: There are many different aspects that comprise a company’s culture, and some might be especially critical for you. Consider work-life balance. I have seen companies where the founders expect people to burn the midnight oil regularly, completely against their tech executive’s preference. And I’ve seen the opposite, where the executive wanted to go into blitz mode for a bit and was told that is not something that company does. Will they treat R&D as first-class citizens in the company or as code monkeys? Is this a company with many perks or one morally opposed to them? You will have to sell these values and culture to many new hires, so make sure you can live with them.

Metrics for Success

Another very critical aspect to consider is how your bosses will determine whether you are doing your job well or not. Somewhat surprisingly, this is often not discussed before both parties decide to work together. If you do not know what would be a success, how can you ensure that you aim there? Further, you will not be able to say whether that metric for success is one you agree with.

Some leaders care deeply about the personal growth of their people and investing in coaching. Others might focus more on technological advancements, while other tech executives would only look at team velocity. For me, a team not innovating regularly cannot be considered genuinely successful (more in this free sample chapter here).

Level of Freedom

Some say that they care the most about the autonomy they will be given in their roles. This has many different manifestations, and you might care differently about each, but you should nevertheless take the time to discuss them. The level of freedom you receive often boils down to whether the founders are looking for an executive or merely an executor.

For example, will you be given control of your budget, or will you have to approve every single hire or decision to expense a SaaS tool or offsite? Can you decide who and where to hire? For example, I’ve seen tech executives that desperately needed to create another level of management but were not allowed to do so by the CEO for some reason. Other times, they wanted to hire people remotely or use an agency for a certain project and were not given the freedom to do what they judged was best. Of course, there are also the stories of VPEs that had to live with hires they didn’t want and who objectively were a bad fit for the role because they were shoved down their throats by the founders.

Assess how open the founders are to give you the room you need to perform your role optimally. If you are a first-timer and one is experienced in the area, perhaps less leeway makes sense as you will be coached and grow. However, this should not be left unaddressed before taking on the job.

Be an executive, not an executor.