Leadership Lessons

I recently stepped down as VP of Engineering at Chef. This was a new experience for me as I’d never been responsible for the entirety of product engineering before. I’m immensely grateful for the experience and humbled by the confidence placed on my abilities by the engineers and company leadership. I feel I did a good job but, as with any human endeavor, there’s always room for improvement.

Over the years I’ve gotten in the habit of summarizing lessons learned whenever I change jobs. I thought it’d be helpful to share the lessons I learned leading Chef’s engineering teams since there aren’t many resources available for technical leaders. Becoming a good technical leader is a unique challenge quite different from the hands-on “doing” expected of developers, sysadmins, etc. This is doubly true at the higher leadership levels. You can read books like Rand’s Managing Humans and Lister & DeMarco’s Peopleware (I highly recommend both) but there’s no substitute for the lessons taught by real-life experience.

Here are mine.

  • Be genuine. You are not your title.
  • Invest in the growth of those you lead. Never forget your success is measured by the successes of the team(s) you lead.
  • Be honest. Hiding or ignoring a problem is never the right solution.
  • Understand and internalize the parable about teaching a person to fish. Aspire to be the teacher not the doer.
  • Try to make timely decisions based on the facts at hand.
  • Strike a balance between flexibility and certainty. Change your mind and/or direction when the facts change.
  • Always bias for action over inaction.
  • As much as possible, grow leaders from within. Delegate important work to your strongest team members. Avoid becoming a bottleneck for either information or decisions.
  • Hire smart generalists with solid communication skills. The “rockstar” attitude is toxic and destroys teams. 10x productivity is useless without a team.
  • Hire carefully. Fire quickly.
  • Foster an open and honest environment which encourages respectful dissent. Deter poisonous debate techniques like ad hominem attacks.