Wool&Prince Founder Finds Value in Applied Improv

Mac Bishop, founder of the Portland-based apparel company Wool&Prince, wasn’t looking for traditional team building when he reached out to us. His team was already close-knit and highly functional. What he wanted was something that would push them out of their comfort zone together — an experience that would strengthen the communication patterns they’d built while revealing new ones they hadn’t considered. What he found through applied improv was more than he’d expected.

The session focused on the fundamentals of collaborative communication: active listening, building on each other’s ideas, and staying present in conversation rather than planning ahead. For a small, fast-moving company where decisions happen quickly and everyone wears multiple hats, these skills turned out to be surprisingly relevant. The exercises surfaced subtle dynamics that the team hadn’t noticed — moments where certain voices dominated, where good ideas got lost in the speed of conversation, where assumptions went unchecked because everyone was moving too fast to question them.

What resonated most with Mac and his team was the directness of the feedback loop. In an improv exercise, you know immediately whether you’re truly listening or just waiting to talk. You can feel the difference between building on someone’s idea and subtly redirecting to your own. There’s no hiding behind email tone or meeting formality. The exercises strip away the usual workplace buffers and reveal how people actually communicate — and that honesty, delivered in a supportive and playful environment, turned out to be exactly what the team needed.

The impact showed up in tangible ways after the session. Team meetings became more inclusive, with quieter members contributing more frequently. Brainstorming sessions produced more diverse ideas because people practiced the discipline of building before evaluating. And the shared experience created a common language — phrases like “yes, and” became shorthand for a communication approach that the whole team understood and valued.

Stories like Wool&Prince’s are why we love this work. Not because the outcomes are dramatic — though sometimes they are — but because they’re real. A team that communicates a little better, listens a little more carefully, and trusts each other a little more deeply. Those incremental improvements compound over time into something that fundamentally changes how an organization operates. And it starts with a willingness to try something different.