Five Things I Would Have Done Differently

I don’t have many regrets in my professional career. In fact, I have none. Regretting is useless and a waste of time.

Yet…

As I’m currently on a bit of a sabbatical, I can’t help reflecting. If I could go back in time and give myself some advice before taking my last VP Engineering role, this would be some of it:

About 80% of issues at work stem from lack of explicit expectations. At first, I didn’t do a great job of getting and setting clear expectations with the CEO, resulting in some unnecessary dissonance. Later on, I took an interim VP Product role, and managed to do a better job in defining expectations, leading to a much smoother collaboration. The lesson is if you can’t get a clear answer, try harder. Extract it, force it out, do whatever it takes. If all else fails, create your own and validate them.

The takeaway: Have early conversations with those you work closely with, seeking to understand what is important to them and what their mental models are. Give them yours in return. And ask yourself, "what needs to be discussed now in order to avoid bad surprises later?"

For a long time, I was so heads-down building the Engineering team that I forgot to look around me. By learning how others view the world, and educating them on how Engineering works, you build healthy connective tissue and trust. Otherwise, silos quickly emerge as everyone just focuses on their own thing. But everything needs to work in tandem for the company to succeed.

The takeaway: Leverage cross-functional rituals, such as 1:1s and inter-departmental meetings, to foster your understanding of others' priorities and help them understand the respective Engineering trade-offs.

How do we run Marketing? What is hitting Customer Support and is that trickling down to Product? How’s the company budget allocated? What’s our burn? How do we know we’re moving in the right direction as a company? What is the engine of our business? Do we have a flywheel? I learned the hard way that when you’re part of a Leadership Team, being at least literate in all these (and more) is non-negotiable. In fact, let me rephrase that: you’re borderline useless otherwise.

The takeaway: Stay curious. Use self-awareness to gauge which adjacent topics you need to improve on, identify the people and other resources that can help fill in those gaps, and make a conscious decision to spend time around them.

While I was aware that every team inevitably goes through different stages of development, it took me too long to realize the importance of monitoring high-level team metrics for speed and quality of delivery. With them, you can be proactive in addressing issues and consistently communicate progress both to the team and upstairs. Without them, you’re flying blind, relying solely on observation and gut feelings – yours' and others' – that don’t scale.

The takeaway: Can you objectively show someone outside of tech how well your team is doing and trending over time? Can you objectively assess the impact of a change in process or personnel? If not, figure out what metrics would be need to be able to do so and start tracking them.

Although I communicated often to my teams through “top of mind” emails and All Hands Meetings, their schedule was erratic and topics were all over the place. Sure, there’s a lot going on in startups and getting your shit together is an ongoing struggle. But past a dozen people, communication won't sort itself out anymore. Your messaging needs to be consistent, clearly highlight what’s most important, and arrive at a predictable cadence. Otherwise, shared context decreases, everyone perceives things a little bit differently or, worse, simply makes up their own facts to fill in the gaps you left.

The takeaway: Plan your communication, communicate your plan, and stick to it. Follow up "low-bandwidth" events (such as all-hands) with "high-bandwidth" 1:1s to ensure the message landed.

I don’t beat myself up. I got as much imposter syndrome as the next guy or gal, but I remind myself that growth mindset is a thing: “I wasn’t able to do X… yet.” Now that I know, I can give it another, better shot next time.