A Lighthearted Field Guide to Fundraising Disasters

Tom Iselin
16 minutes ago
4 min read

A Lighthearted Field Guide to

Fundraising Disasters!

Here’s a crash course in what “not” to do when fundraising, what donors secretly loathe, and a short list of how to ask for money without breaking into hives.

Yes, you'll chuckle because if you've raised money, you've experienced many of these things. So enjoy this lighthearted field guide to fundraising disasters . . .

13 Ways to Ensure Fundraising Failure

Force someone who fears fundraising to fundraise. It’s like making a cat take a bubble bath—messy, loud, and no one’s happy at the end.
Hire a CEO who breaks out in hives at the words fundraising, you, and donor when mentioned in the same sentence—and then act shocked when revenue drops. Same for some board members.
Let the intern design your major donor strategy. What could go wrong? (Everything.)
Treat your fundraisers like background extras in a movie they’re supposed to star in. Don’t thank them, buy them coffee, and be sure to have them work late and on the weekends—ok, holidays too.
Spend 30 hours writing a $1,500 grant while ignoring the potential donors who want to hand you BIG checks over lunch meetings.
Obsess over finding new donors while forgetting the ones already on your Christmas card list.
Pop the question before the first date. If you ask too soon, expect awkward donor silence.
Wing it! Planning is for those who enjoy success and lower blood pressure.
Let board members ghost fundraising responsibilities like it’s a bad Tinder date.
Set fundraising goals based on unicorn math and wishful thinking.
Task your fundraiser with designing the gala and fixing the office printer and the spotty Wi-Fi, and running to the store to buy Fritos for the kids’ lunch program.
Make your newsletter look like a 1997 PowerPoint and call it “marketing.”
Treat fundraising expenses like a splurge, not an investment. Penny wise, donor foolish.

16 Things That Annoy Donors

Treating donors like ATM machines with email addresses.
Making them navigate your organization like it’s a DMV.
Acting like you’re selling used cars, not saving puppies.
Treating the thank-you process like an Amazon delivery notification – “Your generosity has shipped” and nothing else.
Ignoring their interests, passions, or their obsession with pickleball.
Sending the tax receipt like it’s a breakup text—short, cold, and no explanation.
Mistaking “cultivation” for “confession hour” about your own greatness.
Showing zero proof their gift helped anything besides your office coffee budget.
Daily emails, weekly voicemails, monthly carrier pigeons... it’s too much.
Fake enthusiasm. Overdoing the pep like a cheerleader who missed the actual game.
Forgetting what your nonprofit does, which is only slightly worse than forgetting your own name.
Acting like non-cash gifts don’t count. Spoiler: they do.
Not saying thank you. Not saying thank you. Not saying thank you.
Dropping balls, missing deadlines, and sending “Dear [Insert Name]” emails.
Reading straight from the script like it’s a high school play.
Giving no say in how or when they hear from you . . . like an uninvited telemarketer.

10 Key Pieces of Data to Collect from Donors

Donor information is gold. Don’t trust your brain to remember it—your brain still forgets where your keys are.

1. The basics. Address, mobile, birthday, favorite social network to ignore you on.

2. Fun stuff. Their hobbies, music tastes, and guilty-pleasure TV shows. (“The Bachelor”)

3. Their motivation and why. (Hint: it’s rarely because your annual report was riveting.)

4. Appeal strategy. How do they like to be asked? For Boomers, it’s probably not via TikTok.

5. Giving history. Amounts, frequency, and whether you’ve sent them a thank-you in the last decade.

6. Event attendance. What they’ve come to, what they liked, and if they danced at the gala.

7. Affiliations. Clubs, boards, organizations—and if they once chaired something fancy.

8. Achievements. Medals, books, honors, patents. Basically, their donor resume.

9. Internal connections. Who do they know on your team? Leverage those relationships, don’t leave them collecting dust like the office treadmill.

10. Correspondence history. How they like to communicate and how often. (Nobody asked for 8 emails in 3 days.)

5-Step Fundraisers Training Regimen

Want to fundraise like a pro? Lace up your learning shoes and turn on your favorite Jane Fonda video. Here’s your workout plan:

1. Learn your nonprofit facts. If you don’t know what you do, why should anyone give?

2. Practice storytelling. Ditch the stats—bring the heart. Stories beat spreadsheets.

3. Role-play. It’s cheesy. It’s awkward. It works. Get over it and practice.

4. Learn about your donors. Stop short of stalking, but do some in-depth research.

5. Go live. Start small, ask safe, and work your way up to the big leagues. That’s when you can swing for the fences.

About the Author

Tom Iselin has built nine sector-leading nonprofits (yes, he sleeps… occasionally). He’s written six books, sits on several boards, and is considered one of the nation’s top experts on building high-performance nonprofits. Oh, and he’s been rated one of America’s 10 best retreat facilitators—though his mom insists he’s #1. Tom is the president of First Things First, a business specializing in board retreats, strategic planning, fundraising, and executive coaching.

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