When it's time

When an impulse hits you that it’s time to move on, what do you do? Your next impulse might be to suppress and put off the feeling. If you’re naturally given to fighting and “making it work”, the thought of leaving may be so unpleasant and unwanted that it’s all around just easier to kick it away for another day. Yet delaying the right decision has its costs. I probably don’t need to tell you that staying in a bad situation will often negatively affect one’s creativity, growth, and even mental health....

July 8, 2022

Do the low-tech thing first

When building at a startup, sometimes you envision an ideal solution first, making it hard to see anything else. “Do the low-tech thing first” is the rebuttal to this. It’s a simple team value that challenges the sneaky and wasteful instinct to over-engineer, over-analyze, over-anything-but-ship. Primarily, the expression means: give yourself permission to be simple and unsophisticated, when doing so works, and when the fancier option isn’t obviously justified right now....

May 25, 2022

Failing slowly

Plenty of tech companies tout a cultural value of “fail fast”: Accept that you will make mistakes; make those mistakes as promptly as you can; and learn from them so that you don’t make them again. It’s a liberating concept and great value. But to truly succeed at a “fail fast” culture, it’s not sufficient to simply sit back and appreciate this value. You must also identify, and then root out, the causes of slow failure....

May 9, 2022

Better living through visibility

As a people manager or team lead, you are juggling multiple responsibilities. Two responsibilities that probably come with the territory, week in and week out, are: Prioritizing your time well. Creating visibility for your boss, peers, and team. Of managers I’ve mentored and supervised, most had an innate understanding that they must prioritize their time. But very few arrived with a system for creating visibility1, or even thought about that as a necessary function....

April 4, 2022

The CTO and VP of Engineering fork

During the growth of a tech startup, the founding technical leader will likely make an important change to their organization: They will hire or promote someone to be the VP of Engineering, and redefine their own role and duties as CTO in the process. When I went through this process, although I sought and received plenty of advice, I didn’t find a perfect playbook for this change. This post is no exception, but collects and summarizes some of the key aspects of the change that helped me....

October 15, 2021 · 14 min