Stardate S03E25

Mood: 🤒. Managed to be everywhere I needed to be, but it took its toll.

Outdoor chess and checkers at Parc des Bastions

🌹 What am I grateful for this week?

To round off our bench project, I took the opportunity to host a retrospective similar to one I ran in April with a different group of product strategists. I miss getting in the weeds with the teams, and it was certainly fun to get a firsthand account of what’s been working well and needs tweaking in the work we do.

Time pressure and documentation gaps are ongoing challenges, but some new areas like structuring hypotheses and creating compelling landing pages were really helpful to bring to light. It’s a clear set of focus areas where we can make the next run of the process even smoother.

🌵 What do I wish could have gone differently?

One challenge I had in April was with the follow-up — it was similarly difficult to dole out action items at the end of our retro, with most of the team moving on to new work. How we fund this work internally is a different matter, but investing time to improve documentation is always a double-edged sword.

Why is that? Well, a desire for documentation burns strongest when you lack the knowledge. Once you have it, documentation feels more like a nice to have. A bit like planting a tree under whose shade you may never sit.

For the documentation that we do have in place, there’s a different smell test it needs to pass — is it faster to ask someone to help you solve their problem vs. wade through the docs? If so, then what you’ve written (or are describing in your writing) is probably too complicated. But finding the friction in documentation is tricky when it’s something you’ve produced, and already believe is fit for purpose. Fresh eyes are key to see it for what it is.

All this is to say, I think we need to get smarter about how we maintain and improve documentation on an ongoing basis. Having it as an afterthought isn’t going to cut it in the long run.

💡 What do I need to remember?

To look for and name undeniable shifts. Not starting with the problem, or the solution, or the vision, but framing any high-impact conversation with a particular worldview. If this much isn’t in alignment between parties, none of your other conclusions will follow.

It’s a lesson that extends well beyond pitching and sales environments, and feels relevant any time you’re looking to influence others. And it goes hand in hand with advice about picking an edge, to make sure that you don’t live in the inoffensive, uninspired, unremarkable middle. Naming a big change is already a step towards picking an edge, because you’re raising the stakes against the status quo, and by proxy, conventional wisdom.*

Someone might take offense — that’s okay! Big changes are anything but average (and average ideas aren’t memorable).

Want to combat indifference and average thinking? Start by naming an undeniable shift.

📚 What did I discover?

Visionary underdogs who tell their own story, obsess about their customer experience and ship gems early and often. Sounds like a winning recipe for product leadership!

I’m digging Martin’s framing of business design as a distinct skillset from product management — so often it gets glossed over in that classic product Venn diagram of tech, design and business.

We don’t need to fear the end of a cycle; it’s all been done before. So goes the reasoning in this Cliff Notes version of Ray Dalio’s latest book.


You know how they say the iron triangle of time, scope and cost/resource hides a fourth variable of quality? I think I ran afoul of that trap in a personal sense, jet setting between cities and spending just 48 hours in London on my last stay, with the hidden fourth variable being my health. Thankfully it’s just a head cold, but getting sick is really annoying and I know I’m not in my twenties anymore. I need to let time or scope flex (or else delegate to increase resource!) so I don’t end up flexing my health in the balance.

*There was a Seeking Wisdom podcast with an important corollary around groupthink. The goal for inclusive leadership should be to seek feedback, not consensus, to answer questions like “why now?” Because consensus is a reflection of average thinking, and the middle is where ideas go to die. It’s a bold frame, one not everyone might agree with — that’s precisely what makes it interesting.



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Sean K. Gabriel

Aloha (🤙。◕‿‿◕。)🤙 big on building teams & lean products. Author @ Thinking aloud with #weeknotes. Works best when caffeinated ☕️