Seasonal Reset

Feb 27
3 min read

Updated: 7 days ago

Unlocking the Answers:

Over the past few days, I shared three reflections, not as riddles to solve, but as clues pointing to patterns that show up again and again in leadership and fundraising.

Here’s what those clues were quietly pointing toward, and why they matter.

Clue# 1:

What do fundraisers assume they have, but few actually do?

This clue was about shared clarity.

As Duke Haddad writes, nonprofits must show donors, and all stakeholders, that their gifts are investments yielding tangible community impact. That requires clear alignment between mission, strategy, and programs, along with consistent ways of naming and measuring what success actually looks like.

In many organizations, clarity is assumed rather than shared. Leaders may know what matters, but that understanding isn’t always held in the same way across staff, boards, or donors.

A simple test: if people across the organization describe priorities differently, clarity isn’t missing, it isn’t shared.

When clarity lives only with a few people, belief stays fragile. People may care deeply about the mission, but struggle to articulate why it matters right now, which makes it harder to act, advocate, or confidently invite others in.

Clarity isn’t a document.

It's a shared understanding.

Clue# 2:

Why do boards hesitate, even when they care deeply?

This clue pointed to belief alignment, not motivation.

BoardSource’s Leading with Intent research shows that fundraising consistently ranks among the areas where boards perform weakest, and that many boards don’t fully prioritize clarity around mission, role, or community context, which often shows up as hesitation or uneven engagement.

In other words, people pull back when they don’t feel confident explaining the “why,” not when they don’t believe in the work.

That hesitation is information, not resistance.

Clue# 3:

Most donors won’t call you up and say something has changed. They will just silently change direction.

This clue was about timing, trust, and belief.

As Cherian Koshy has noted, trust isn’t a vague feeling, it’s a biological state. Drawing on neuroscientist Paul Zak’s research on oxytocin, he shows that trust measurably increases empathy and prosocial behavior. When trust is high, people are more likely to give, and to keep giving.

But that state is fragile.

Donor behavior consistently shows that pauses are rarely about dissatisfaction. More often, they signal a moment where connection wasn’t reinforced, a delayed thank-you, stewardship outreach that didn’t quite land, or messaging that felt muddy or unclear.

Pauses don’t mean belief is gone.

They mean it hasn’t had a chance to settle.

And belief that hasn’t settled doesn’t disappear, it waits.

What these clues point to:

Taken together, these patterns point to what I call the Squish Factor, the human space between intention and action, where belief is still forming, confidence is uneven, and trust takes shape.

Most fundraising strategies are built for action: campaigns, timelines, asks.

Very few are designed to care for belief before the ask.

But belief doesn’t harden on demand.

It starts squishy.

And when it’s cared for, it becomes sticky.

If this way of seeing resonates, you’re welcome to continue in whatever way feels right:

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