When a lot of people see or hear the word "strategy," they might picture something big: enterprise boardrooms thick with tension, slide decks bristling with SWOTs, or those ambitious five-year roadmaps, you know them, the ones that quietly gather dust after year two (or sooner!). At times strategy feels corporate, institutional, enterprise-y and removed from the messy reality of everyday problems.
For a while I’ve felt that strategy is for everyone: a creative pursuit, about bold choices and imagining a different future, so much so I even created a whole workshop and template on the topic.
But more than that it's about deciding where to focus your energy, what to let go of without guilt, and how to create momentum when everything feels a bit stuck. Whether you're running a large company or—as in this case—breathing life back into an AI community meetup.
AI for Deep Learning in Enterprise (AIDLE) was a community that had been going for quite a few years, with thousands of people signed up on Meetup, but despite some high points in 2023 a trend was beginning to emerge: the numbers turning up in person were dwindling and by early 2025 were hovering at around 15-20 people from an occasional high water mark of 70-80.
In truth some things were easy to identify than others as the symptoms were very visible. The brand felt a bit like a leftover from a very academic conference; volunteers were getting harder to come by and speakers were becoming thinner on the ground; the community itself had just gone quiet and the buzzing energy had taken a significant dip.
This ‘energy crisis’ is something I’d seen before. Not just with meetups, but with products, teams, even entire companies. All the right pieces in place, but something fundamental was missing. The machinery was running, lots of tactical stuff but no clear direction and momentum. So the first task was clear: to really understand what was going on and ‘diagnose the drift’.
Steve Pearlman of the Critical Thinking Institute points out that our brains are wired to scan for signals of threat and reward before deciding how to act.
In many ways, that’s the foundational first step in strategy: what’s going on here, and what does it mean for us?
When Hugh first asked me to help with his Meetup community, the easy move would have been to jump straight into promotion ideas or growth tactics. But the more useful move was to slow down and ask critical questions: Why are people turning up? Why aren’t more staying? What’s working and what isn’t?
That act of pausing to observe and challenge assumptions gave us clarity on the real issues and from there, the strategy almost emerged naturally. Critical thinking might sound abstract, but in practice it’s what stops you from playing the wrong game.
"Before we fix anything," I said, "let's figure out what we're actually trying to fix."
The questions weren't particularly complex: