Your Board Isn’t Working: Why a Board Retreat Might Be the Best Investment Your Nonprofit Makes This Year
Release Date: 06/05/2026
Your Board Isn’t Working: Why a Board Retreat Might Be the Best Investment Your Nonprofit Makes This Year
The Nonprofit Mentor -- Tips, Tools & Tactics from the Trenches for Nonprofit Leaders -- by Tom Iselin
Your Board Isn’t Working: Why a Board Retreat Might Be the Best Investment Your Nonprofit Makes This Year Most nonprofit leaders know the scene. You’re sitting in a board meeting watching the same three people carry the conversation while two members scroll their phones, one asks a question already answered in the pre-read materials, and another slips out early because “something came up.” The meeting ends politely. No one throws a chair. But nothing really moves forward. This is how board dysfunction often shows up—not through dramatic conflict, but through something quieter...
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Building a Donor Pipeline BEFORE You need It!
The Nonprofit Mentor -- Tips, Tools & Tactics from the Trenches for Nonprofit Leaders -- by Tom Iselin
Building a Donor Pipeline BEFORE You need It! Here’s a truth most development directors don’t want to admit out loud: Your donor base is quietly shrinking. Not because you’re doing bad work. Not because your mission isn’t compelling. Not because your fundraising team isn’t trying. But because donors are human. They retire. They relocate. They redirect their giving. They get distracted by grandkids. They fall in love with a new cause. And sometimes, without warning, they just have a change of heart before writing that six-figure check you were sure was coming. If you are not...
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Board Retreat Blunders and Mistakes that Sabotage Retreats
The Nonprofit Mentor -- Tips, Tools & Tactics from the Trenches for Nonprofit Leaders -- by Tom Iselin
Board Retreat Blunders and Mistakes that Sabotage Retreats Board retreats are supposed to be powerful. They’re supposed to create clarity, alignment, momentum, unity, and ownership. They’re meant to be the moment when a board steps out of the day-to-day grind and finally gets honest about where the board is—and where it’s going. Instead? Too many retreats feel like a long, expensive meeting with better snacks. People show up with good intentions. They sit through presentations. They nod politely. They eat. They participate just enough to feel engaged. And then they leave. And...
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Part 3 of 3: Ask Better, Raise More Money -- Fundraising Ask Tactics and Strategies
The Nonprofit Mentor -- Tips, Tools & Tactics from the Trenches for Nonprofit Leaders -- by Tom Iselin
Part 3 of 3: Ask Better, Raise More Money -- Fundraising Ask Tactics and Strategies Most fundraisers spend far too much time worrying about the “perfect ask,” as if somewhere out there is one magical sentence that makes every donor instantly reach for a checkbook. There isn’t. Fundraising is not a Jedi mind trick, and donors are not slot machines you jiggle until money falls out. The truth is much more practical: different donors respond to different types of asks, and the best fundraisers know how to choose the right one for the right person at the right moment. ...
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Part 2 of 3: Ask Better, Raise More Money -- Fundraising Ask Tactics and Strategies
The Nonprofit Mentor -- Tips, Tools & Tactics from the Trenches for Nonprofit Leaders -- by Tom Iselin
Part 2 of 3: Ask Better, Raise More Money -- Fundraising Ask Tactics and Strategies Most fundraisers spend far too much time worrying about the “perfect ask,” as if somewhere out there is one magical sentence that makes every donor instantly reach for a checkbook. There isn’t. Fundraising is not a Jedi mind trick, and donors are not slot machines you jiggle until money falls out. The truth is much more practical: different donors respond to different types of asks, and the best fundraisers know how to choose the right one for the right person at the right moment. That’s why...
info_outline
Part 1 of 3: Ask Better, Raise More Money -- Fundraising Ask Tactics and Strategies
The Nonprofit Mentor -- Tips, Tools & Tactics from the Trenches for Nonprofit Leaders -- by Tom Iselin
Part 1 of 3: Ask Better, Raise More Money -- Fundraising Ask Tactics and Strategies Most fundraisers spend far too much time worrying about the “perfect ask,” as if somewhere out there is one magical sentence that makes every donor instantly reach for a checkbook. There isn’t. Fundraising is not a Jedi mind trick, and donors are not slot machines you jiggle until money falls out. The truth is much more practical: different donors respond to different types of asks, and the best fundraisers know how to choose the right one for the right person at the right moment. That’s why...
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Unresponsive Donors: A Smarter Way to Respond
The Nonprofit Mentor -- Tips, Tools & Tactics from the Trenches for Nonprofit Leaders -- by Tom Iselin
If you’ve spent any time in fundraising, you know this moment well. You send the email, make the call and follow up—politely, professionally, thoughtfully. And then… nothing. No reply. No acknowledgment. No signal of interest or disinterest. Just silence. For many fundraisers, donor silence feels personal. It triggers doubt. Did I say the wrong thing? Did I wait too long? Did they lose confidence in us? Should I push harder—or back off completely? Here’s the truth most fundraisers need to hear—and hear often: Donor silence usually has very...
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The Year-End (Holiday) Fundraising Secrets Nobody Uses
The Nonprofit Mentor -- Tips, Tools & Tactics from the Trenches for Nonprofit Leaders -- by Tom Iselin
The “Notify First” Trick There’s one move that can turn your ho-hum year-end appeal into a home run: notify first! Before you send a single email or stuff a single envelope, reach out to donors—by phone or email—and announce your campaign is coming. This one act can boost your response rate up to five times higher. If you actually reach a donor and they feel connected to your cause, half of them will give. Do it well, and that number can soar 70%. Incredible. But skip the notification and rely only on a generic appeal letter or email? Expect a limp response rate of...
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Specialty Events: How To Turn Small Gatherings into Big Gifts
The Nonprofit Mentor -- Tips, Tools & Tactics from the Trenches for Nonprofit Leaders -- by Tom Iselin
Let’s be honest: most nonprofits don’t need another event. They need better ones. The kind that doesn’t drain staff, exhaust volunteers, or leave donors wondering why they just spent two hours listening to speeches when they could have been home in slippers. That’s where specialty events come in. Savvy fundraisers love specialty events—typically gatherings of 10 to 75 people—because they create something you simply can’t replicate at a big gala. Donors see friends they respect, meet peers they admire, and experience your mission together. There’s energy in the...
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How to Fund Your Next Board Retreat or Strategic Planning Session
The Nonprofit Mentor -- Tips, Tools & Tactics from the Trenches for Nonprofit Leaders -- by Tom Iselin
Every nonprofit eventually hits a moment of polite stagnation. Board meetings are full, calendars are packed, and everyone is working hard—but progress feels heavier than it should. Conversations repeat themselves. Decisions take longer. Direction becomes unclear. Passion wilts. The organization isn’t broken, but it isn’t quite clicking either. That’s usually when someone finally says what everyone else is thinking: “We should probably do a board retreat.” Or, “Maybe it’s time for a planning session.” The idea hangs in the air for a moment, feels responsible and hopeful,...
info_outlineMost nonprofit leaders know the scene. You’re sitting in a board meeting watching the same three people carry the conversation while two members scroll their phones, one asks a question already answered in the pre-read materials, and another slips out early because “something came up.”
The meeting ends politely. No one throws a chair. But nothing really moves forward. This is how board dysfunction often shows up—not through dramatic conflict, but through something quieter and more damaging: under-engagement. Board members attend meetings but contribute little. They skim materials, avoid difficult conversations, they fail to respond to staff emails, and they remain observers rather than active leaders.
At first glance it seems harmless. Meetings are calm. Disagreements are rare. But the cost is real. A few members end up carrying the entire board. Strategic discussions become shallow. Staff grow frustrated presenting ideas that receive little response. And gradually, expectations decline. Leadership turns into attendance.
At that point the board meeting starts to resemble a pleasant dinner party—friendly conversation, plenty of nodding, and very few decisions. And when that happens, the organization begins to drift.
When this type of drift happens, one of the smartest investments a nonprofit can make is a well-designed board retreat—an opportunity to step back, address culture, under-engagement, and reset expectations before the board stops leading and starts simply showing up. Listen in!