Category: Field Note
-
My co-founder and I have been building our company together for several years. Not long ago, I learned that one of our investors had started to worry about our co-founder relationship. The reason was a group chat in which the two of us had gone quiet. The worry was understandable, but it was wrong. We…
-
On the last Monday of September, I saw the same build vs buy decision from both sides of the table, a few hours apart. In the morning, one of our customers called to say they would end a service we run for them. From January, a team elsewhere in their group would have spare capacity,…
-
One of our first enterprise deals fell through after months of work. The customer believed in the product and trusted us to deliver. In the analysis afterwards, and through conversations with a coach, it became clear that a significant part of the problem was how we had negotiated. That led me to start reading Negotiation…
-
Once a quarter, we sat down and rated team members on two dimensions: work performance and social behaviour. Each received a score from 1 to 10. The assessment was relatively informal, with room for individual judgement. We used these ratings mainly to follow development over time. Looking across several quarters helped us notice who worked…
-
As implementation gets faster and cheaper, the bottleneck in product development can shift toward product management and design. Engineers can turn an idea into working software while the team is still figuring out which problem matters, how people will use the solution, and whether anyone will pay for it. Product and Design Are Getting Faster…
-
For the past two years, the loudest debates inside our company have used the same vocabulary: scale, productivity, AI. Every quarter delivered a fresh version of the same conversation. How do we scale sales? How do we make customer success more productive? Which AI tool takes which workload off whose desk? The vocabulary came from…
-
A generalist we hired early ended up doing several jobs under one title, and the debate about it went in circles. Writing the job description again, years after hiring, turned a stuck title discussion into a package both sides could negotiate.
-
AI agents are great at gathering context for 1:1s and coaching prep. But the judgment stays human. Here is the line between errand and judgment.
-
Turning how your best people work into an AI Skill sounds like a documentation job. It isn’t. The hard part is judgment, and the moment you try to write it down you hit a forty-year-old problem that AI has quietly moved rather than solved: the work is no longer getting the knowledge out, it is…
-
We’re a small company selling into a narrow, heavily regulated market. There are maybe a few dozen buyers that really matter, and most of them are cautious about anything new. For a long time I treated getting our first real customers as a search problem. Looking at where those customers actually came from, I realized…