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Why so Many Board Retreats Fall Flat–and What to Try Instead
A senior leader from a large nonprofit reached out about designing a retreat for one of their key departments. Here’s what struck me: The retreat was just two weeks away. A handful of team members had already been tasked with designing the day. Each person had ownership over one chunk of the agenda—and they hadn’t been in touch with each other about plans or possibilities. And, there was a palpable sense of uncertainty about what the retreat was actually supposed to accomplis

Deb Mashek
Aug 27, 20252 min read


When Collaboration Feels Like a $300 Salad Hat
A few summers ago, I was sitting in a creaky lawn chair on the patio of a run-down lakefront shack I’d rented for the season—scrolling through Facebook, as one does when avoiding real life. That’s when the ad found me. An end-of-season clearance sale: a patio set with a loveseat, a captain’s chair, and a table—all for $300. What a deal! I looked up from my screen and instantly imagined it: this tired patio transformed into an Instagram-worthy oasis. I could already see myself

Deb Mashek
Aug 13, 20252 min read


When Giving Feels Hard, Turn to Collaboration
Even the most committed donors sometimes hesitate to give boldly—overwhelmed by decisions, uncertain about the landscape, afraid of scrutiny, pressed for time. The barriers are real. A recent report from the National Center for Family Philanthropy (check out the full report here ) outlines ten of the most common psychological barriers to giving. Among them: Fear of scrutiny Feeling unqualified to act Discomfort with risk Not enough time What struck me most? Collaboration can

Deb Mashek
Jul 23, 20251 min read


The Best Collaborative Programs Start with Conversations, Not Solutions
Collaboration starts long before launch. If you're at a foundation that's getting ready to design a program for others—say, a shared service hub or a capacity-building initiative—pause and consider this: Are you collaborating with the people you hope to serve? Too often, well-intentioned efforts fall into the “build it and they will come” trap. A new offering is designed, resourced, and launched—only to be met with low engagement, confusion, or unintended consequences. Not be

Deb Mashek
Jul 9, 20251 min read

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