Fundraising Table Talk
I start arguments with my kids at the dinner table so you don't have to fight with your donors
Last week when the four of us sat down to an inexpertly (but lovingly) carved turkey dinner, we each came prepared to actively contribute to vibrant dinnertime conversation.
By and large, dinnertime conversation around here can be tough. Old standbys like “What did you do at school today?” and “How was work?” never really take flight. But after many, many false starts, we’ve worked through how to talk to each other. And our family’s approach to dinnertime conversation works as much in my fundraising as as it does with my wife and kids. Spoiler alert: it starts with acknowledging what we think we want to talk about vs. what we actually want to talk about.
In a moment of truly visionary family leadership, I assigned each of the four of us a night to be in charge of generating (and sustaining!) dinnertime conversation. Below are 100% accurate sketches of my family’s sundry conversation styles and topics:
Monday: Child #1
Conversation style: 1990s Jerry Seinfeld impersonating a TV reporter
Child #1 kickstarted the first night by sounding weirdly like Jerry Seinfeld rattling off headlines he very clearly just Googled: “So what’s the deal with this war in Ukraine, huh? Anybody?” and “So, bees are coming back? Have you heard about this in the news? The bees?” Good effort, bud, but none of the topics caught fire.
Tuesday: Child #2
Conversation style: Ice-T from Law & Order SVU if on duty during the Spanish Inquisition
Child #2 asked a few opening questions and then interrogated us all like we were a bunch of degenerate mall shoplifters. She really turned the heat up on Child #1 (who confessed to crimes both real and imagined). Child #2 keeps these conversational streets safe, but her cross-examination is harrowing.

Wednesday: Wife
Conversation style: US General George S. Patton reincarnated as a Mead Trapper Keeper (but prettier, kinder, lovelier, nicer, and funnier)
Wife whipped the troops into fighting shape by having us each report our weekend plans, what homework is due (and when), and what upcoming things we collectively need to schedule ourselves around. Plans were articulated, coordinated, filed away, and organized. Conversation then proceeded to strategy for storming Omaha Beach on our next family vacation.

Thursday: Yours Truly
Conversation style: Socrates meets butt-hole Uncle Frank from Home Alone
I like to voice strong opinions about things I know nothing about. And then pose questions that provoke my teenagers into an argument:
“I’m pretty sure I could drive our car onto the flatbed of a moving semi. I could probably also deliver a baby in the back of a NYC taxicab if I had to.”
“David Bowie was totally miscast in Labyrinth. Am I right, Child #2?”
“I don’t care for Gen Z’s taste in music. It’s…sub-musical. I can’t be convinced otherwise!”

Four valiant attempts at dinnertime conversation. Zero progress. We each wanted something different: current events, plans for the week, or to start a fight.
We didn’t meet for dinner on Friday night.
We couldn’t face each other.
Kidding.
Once we began being attentive to what we really wanted to talk about (and I stopped baiting my kids), dinnertime conversation took off!
Child #1 was downright eloquent about two kids in his class—both named Liam. He and his classmates nicknamed one “Good Liam” and the other “Bad Liam.” (Bad Liam sounds like a total nightmare, but so much fun.)
Child #2 reported finding one of her former teachers on Instagram who left teaching and started a yoga studio. Apparently, she’s thriving.
Spouse and Yours Truly talked about some new babies of people we work with, the funny things people do/say at work, and the celebrities Grandma Kitty thinks I should ask money from.
Conversation at my dinner table is best when it resembles light workplace gossip. We try to turn “What did you do today?” into “Who did you talk to today?”
It’s not hard to swing this approach back to our fundraising and how we talk with our donors (and each other)—with curiosity and genuine interest. Am I interested in why donors give and where they direct their gifts? Of course I am. But that’s just the start of the discussion.
If they play pickleball, I want to hear about their third shot drop.
I want to know what they’re reading. And if I should be reading it, too.
Do they have a dog? Do they want to meet mine?
What do they like to talk about at dinnertime?
Do they think I could drive my car onto the back of a semi if (a) conditions were totally clear, (b) I was on a straightaway on the Pennsylvania turnpike between the Bedford and Midway exits, and (c) I had US General George S. Patton riding shotgun while I attempted it?
I want to know what they like about their job (and if they have any good workplace dirt I can share with my family at dinner tonight)
Relationships are the bread and butter of fundraising, and they start with conversations you actually want to have so you can learn something that lives beyond the moment. Does this lead to better relationships with my donors? I hope so.
But in the moment, there’s nothing wrong with wanting a little gossip, learning something we didn’t know about each other before, and creating the kind of conversations we both want to keep having together.
My dear waffle eaters: I regret to inform you that every word in this post is true.
I wasn't sure where you were going at first - tied together so well - loved it. Yes! I want to know about the donors - what are their interests, do they intersect with mine, can I learn something new. Connected to this I tell my colleagues use your vacation time, go out and be in the world, we need to have interests, hobbies, experiences, trips, etc. to connect with those 100+ people in our portfolios. Nobody wants to talk with boring people. We have to be interesting people and be people that are interested in other. Great post as usual Dan, and thank you for the Home Alone reference. It was needed! One of the best holiday movies!