What specific collaboration challenges do philanthropists face?

It is rarely easy to launch complex collaborations from the ground floor, to build and sustain them over time, or even to make a compelling case for collaborative approaches in the first place.

Especially given that the needs, interests, and capacities of partners tend to shift over time, collaboration requires an ongoing commitment to sharing time, trust, turf, and treasure.

I recently conducted informal listening sessions with 30+ philanthropists and leaders of networked organizations to learn how they think about complex, multi stakeholder initiatives.

Here are 10 questions interviewees asked that point to the specific challenges of collaborations in philanthropy and among networked organizations:

1. How do we shift funder and grantee mindsets from "go it alone" to "we’re better together"?

   
   

2. How do we convince decision makers that a change in the status quo siloed approach is needed even though the wheels haven't (yet) fallen off the wagon and, in many cases, independent operators are getting good-enough results?

   
   

3. How do we encourage our teams and grantees to look beyond their silos for opportunities to build and leverage partnerships?
   

4. How can we support efforts to bubble up potential mutual-leverage opportunities among potential partners without exerting undue influence by virtue of being a donor?

   
   

5. How can we, as donors, effectively convene and support groups of organizations wishing to develop and execute complex projects given their limited capacity, need for autonomy, real or perceived competition for resources and media hits, pressure to demonstrate unique efficacy in the space, and sometimes wildly different resource environments?

   
   

6. What’s the best way to steward complex, multi-stakeholder initiatives given they necessarily  belong to everyone, yet ultimately benefit from being somebody’s responsibility?

   
   

7. How can we lubricate the work of the full ecosystem so that our philanthropic investments can make a more certain and swift impact?

   
   

8. How do we move beyond loose coordination or cooperation into deep collaboration?

   
   

9. How can we identify could-be collaborators in an ever-changing field of actors seeking to make change across an ever-expanding range of needs?

   
   

10. How can we best support organizations as they navigate challenging inflection points including sunsetting collaborative initiatives, getting derailed collaborations back on track, and merging organizations?

These questions suggest a real curiosity and interest across the board about how best to motivate, structure, and deepen collaboration with both internal and external stakeholders.