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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…
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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,…
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For my last coaching session, I brought a list of questions about our team setup. One product manager wants to move to our managed service, so who takes over the areas that become free? My coach listened and then said that all of it was tactics and that the business strategy behind it was missing:…
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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…
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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…
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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…
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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…
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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.
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Around the third report a team lead’s job changes. We treated it as a coaching problem, not a ceiling, and our player-coaches learned to run teams of four or five.
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An enterprise customer we had built toward for months backed out, late and without warning. The gut punch lasted twenty minutes. What mattered was the next few hours: what we told a team of forty, and in what order. Here is the playbook, and where we went off script.