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*):

As, essentially, a team innovation coach, my role is to provide methods and support by which the intelligent and driven people I work with can gain insight, clarity, and discover both their next steps and the why’s driving them.

From the five common types of problems we get asked to work on, I identified a few methods I and my team commonly use to address these requests and get folks moving forward:

For the projects I work on, this looks like creating design-thinking sessions that are:

  • customized engagements to focus teams on high-value business and product problems,
  • delivered via one-off in-person retreats, remote workshop sprints, and/or coaching.

*Obviously, there are issues that facilitators DON’T get asked to support on: funding and hiring come to mind.

However, understanding the business case (identifying user need or product market fit elements or meaningful metrics for funders) and creating more functional teams to hire into (by clarifying roles and decision-making processes) do come across the docket often.

As I analyze this work, a key question I have is: Are these types of problems ones you face on your team — or are there other things you’re getting stuck on or seeing others stuck on? Is this insight true for you? What’s sticky for you?



Hadassah Damien

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