Case study: creative-thinking workshop for 14 founders at Toronto Tech Week
A room of technical founders, each stuck on a hard problem in a familiar way. The workshop was about changing the angle, not handing out answers.
- Format
- In-person workshop. 14 attendees. Toronto Tech Week 2026, Toronto, Canada.
- Problem
- Founders were looping on hard problems, pattern-matching to past challenges instead of seeing the current one clearly. The thinking was strong. The framing was borrowed.
- What I did
- Delivered creative-thinking strategies for mindset reframing, then ran team exercises on sample challenges so attendees practised the moves in the room rather than filing them away as theory.
- Outcome
- Attendees left with new perspectives, a small toolkit for troubleshooting their own challenges, and a clearer read on the experiential biases shaping their decisions.
Working on sample challenges instead of live company problems is deliberate. It lowers the stakes enough that people will try the uncomfortable version of a move, which is the only version that teaches anything.
Mixing teams matters too. A founder explaining a problem to someone outside their domain has to drop the shorthand, and the shorthand is usually where the unexamined assumption is hiding.
Most of the useful moments were not the exercises themselves. They were the pauses afterward, when someone noticed they had approached a brand new problem exactly the way they approached their last one.
The takeaway toolkit was intentionally short. Founders do not need another framework library. They need two or three moves they will actually reach for on a bad Tuesday.