In rowing, the coxswain watches everything. How hard you pull on every stroke. Whether you’re in time with the rest of the boat. How your form breaks down when you’re tired. They’re among the most valuable people in a rowing team.
At work, I don’t have a coxswain. So I built a robotic one.
Every night it reviews my meetings & coaches me on how to improve, whether they’re one-on-ones, pitch meetings, or other calls.1
At work, success is subjective. So I built a rubric spanning five dimensions, each scored 0 to 10 : active listening, empathy, questioning effectiveness, communication clarity, & technical depth.
It looked reasonable on paper. Then the real work began. Here’s what the AI told me after reviewing a week of meetings :
Pitch Meeting Analysis (Jan 22) : “Interrupted founder 6 times in first 10 minutes, primarily when explaining technical architecture. Pattern : you ask clarifying questions before they finish establishing context. Recommendation : wait 15 seconds after they pause before responding. Founders need space to demonstrate depth.”
One-on-One Analysis (Jan 24) : “Asked 12 questions in 30-minute check-in, but only 2 were follow-ups to previous answers. Pattern : moving to next topic before exploring depth. This can signal you’re checking boxes rather than genuinely curious. Try : 3 questions deep before moving on.”
Investor Update Call (Jan 26) : “You delivered the portfolio news update in 4 minutes with zero pauses. Empathy score : 2/10. The founder just shared they’re struggling with retention. Your response was immediate pivot to metrics. Recommendation : acknowledge the emotional weight before problem-solving.”
My wife would say I don’t need a machine to tell me I lack empathy. She’s been saying it for years. But the AI is harder to argue with.