Five Problems Teams Get Stuck On (and five ways to address them)

Hadassah Damien
3 min readSep 23, 2019
When you’re stuck-stuck, then what? (public domain image)

I’m becoming fascinated by “stuckness”.

I used to think that “stuck” was only for solopreneurs or underfunded arts orgs (like the ones I was part of); I thought it was a symptom.

Fast forward years through projects, launched products and orgs I’ve run to today, as I coach teams to focus on human needs and individuals to experiment with economic solutions. Now, it’s with both relief and fascination that I realize stuckness is endemic: how is it that smart people and well-equipped teams get stuck?

What’s in the way — and what works to unstick people?

I did a snapshot of work requests my team — a cadre of design thinking facilitators at a VC — received over the last year. I was curious about the patterns we encounter and work on with the startups, enterprise sales teams, and internal departments we support.

I identified five key places that teams seem to get stuck (eg that they’re asking us for help with*):



Hadassah Damien

design strategist & facilitator // economics researcher @rffearlessmoney // progressive technologist // performer