Jason and Eiso continue their deep dive on different engineering leadership roles, sharing their thoughts on CTOs, VPs, and Managers, how to hire for these roles, and adopting organizational structures that promote transparency and trust in the decision-making processes that shape your business.


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Get the full transcript here

Listen to part one of this three-episode series here

Here are a few of our favorite moments from the conversation

I think that everyone is looking for a unicorn at the CTO role, and that unicorn is someone who can think about product, tech, think about the organization, and think about execution. And, truthfully, there are so few people like that in the industry that what you actually will end up doing is augmenting that CTO's strengths with somebody else in the VP of Engineering role's strengths. Usually, if the CTO is hyper-technical or product-oriented, you're going to add a VP of Engineering who is execution-oriented, career ladder-oriented, and organizationally oriented.

I don't believe that hiring a nontechnical VP of Engineering is a good match because I don't think that they have the right mindset to go in. This is a trend that we saw briefly. I don't think it ever fully took, but there was a time in Silicon Valley where they said, "you just need people skills to be a VP of Engineering or an Engineering Leader." And that does not work. It would help if you had some domain expertise to be able to do that. But I don't think that you need to over orient to that as well.

I have a couple of principles I live by. One is, I want less communication overhead, so fewer times that one team has talked to another team to get something done. I like more autonomy for teams, so they have wider areas of control to control more of the product surface area or their own destiny and ability to get things done. And I want to optimize for execution speed, velocity, and learning

One of the more frustrating things I see in the industry is that people who have been in a role for three, four, five, six months think they are ready for the next position. And one of the more interesting things is managers saying, "Hey, I've been a manager for six months or a year. I'm ready for director." or "I've been director for six months or a year. I'm ready for VP." The problem is you don't know if the decisions you're making at the VP level are good or bad, sometimes for years.

You've heard me say this before on this podcast, but I'll reiterate it, there are basically four different kinds of things that are just in limited supply in general in the world: money, time, ideas, and people. But in reality, in our industry, money is all over the place. It's super prevalent. There are enough ideas inside your own company, and you're saying "no" more than you're saying "yes," so there's plenty of ideas. Time is constant. So really, the entire game at this point is people. And its people who use the money efficiently to implement the ideas in a timely manner.