What I’ve Learned as a Coach

My very cold sailing team at the Downeast Regatta in Maine

For the last few months, I’ve combined a couple of my passions. I’m coaching a high school sailing team and the engineering team of a recently funded startup. I would love to say it was planned, but in both cases someone I know well asked if I could step in and help. I’m no coach Taylor from Friday Night Lights, but the experience has been gratifying and a great interlude in my career. What have I learned?

  1. Being a coach is fun: Helping smart and committed folks improve is satisfying on many levels. Despite the differences in age and experience, coaching high school kids and adults is remarkably similar. The hardest thing is the few folks who don’t want to be there. Mom made me, or I hate this place, but I need the paycheck are tough things to hear, but so far those instances have been few and worked themselves out pretty quickly.
  2. You aren’t the player: I’ve gotten into coaching because I’ve been there and done that on a number of occasions. Although tempting, I can’t just take over. My tenure is limited and I need to leave the the players in a better place than I started. Most often that means asking a lot of questions and making sure they are reflecting on ways to improve their performance.
  3. Meet them where they are: When I started coaching the sailing team I was eager to tell them everything I knew — after all I’ve been sailing for longer than they’ve been alive. My great lectures led to them going out and losing their first 6 races. A lot of my “genius” wasn’t sinking in. Instead I need to meet them where they are. Basic rules of thumb like “cross when you can” and “down in the puffs” along with a solid dose of encouragement went a lot farther. After my retooling, they went out and won the next 5 races. Maybe those coaches who have a few keywords on the wall “Commitment, Excellence…” are onto something. The engineering team was struggling getting to a solid agile process. Over 50% of all tasks were being delivered late or being added after a sprint started. Rather than focusing on everything that could be improved, we started with just getting to a point where we could predictably plan and execute a sprint. We’ll get to the more advanced topics, but big improvements come from getting the basics right.
  4. Listen a Lot: Prior to my arrival, the engineering team had gone through a lot of changes that left more than a few people bruised and sensitive. A not-unusual story of a smart VP of Engineering flaming out and losing the trust of those around him had led to a team in disarray. A lot of the coach job is talking with folks about their aspirations and what they can do to improve today. Just being listened to goes a long ways. In the office, I’ve planted myself at a desk in the middle of the team so I can hear the on-going conversations. Similarly with the sailing team, I try to carve out time with each person to talk about what they want to work on.
  5. Get in the boat: Sometimes the best way to teach something is to get in the boat. Feeling a roll tack and experiencing the footwork is a lot more impactful than listening to a lecture. Being a part of grooming and planning meetings makes it easier to find areas of improvement. Important things like how hard it is for remote employees to join in — or that no one was capturing notes — are easy fixes if you are watching.
  6. Do the important, but not urgent, tasks: For the engineering team, there are a bunch of important activities that were simply not being done as the team put out fires and delivers on their commitments. Important, but not urgent tasks like setting individual goals and building an automated dashboard for metrics has helped the team do a better job on their core tasks of delivering amazing results. My goal now is to hand this over to the internal team to keep going.
  7. It takes time: Built in habits and ways of working are not changed overnight. We all backslide under pressure. I thought my team had nailed starts, but they got to the big regatta in Maine and seemed to have forgotten everything they had learned.
  8. Keep Learning Yourself: One of the joys of life is learning new things. Whether it is learning how to apply the concepts of Lean Startups and Smart Canvas or the latest team racing techniques, there is always more to learn. Some of which will inform my coaching going forward.

Bottom Line: Both teams are doing well. We have the state championships coming up — and although not favored to win we should be near the top. The engineering team is doing better. Sprints are more predictable, and the rest of the company is gaining confidence in them. Even after my coaching job ends, I’ll move seamlessly into the cheerleader role. (Did I mention I look great in Spandex?)