Three Questions That Can Save Thanksgiving (and Your Foundation’s Strategy)
Unconventional Facilitation - Part 1
Ever left a strategy meeting thinking, Well… that went sideways? You’re not alone. In multi-generational philanthropy, feelings run deep—especially when values collide. Younger generations want to change the world; older generations want to preserve hard-earned wisdom. Somewhere between “save the planet” and “respect the legacy,” dinner gets awkward.
Enter Dialectical Behavior Therapy (DBT)—a psychology tool that sounds clinical but is secretly brilliant for family facilitation. I use DBT’s three magic questions to help families separate emotion from evidence and keep conversations moving:
Is it valid?
Does it fit the facts?
Is it effective?
Let’s unpack these.
Is it valid?
Here’s the sometimes mind-bending truth: ANY emotion ANYONE is feeling at ANY time is valid. Emotions are not right or wrong. They simply are. And they are caused. Whatever is coming up in your retreat or strategy session came from somewhere. And it is that person’s authentic experience. One of the worst things a facilitator can do with strong emotions is try to reason out of them. Emotions aren’t rational, and the first thing to do when navigating them is: validate, validate, validate. A simple recognition and naming of the feeling is often all it takes; “I’m sensing some withdrawal here – can you tell me what’s feeling unsafe?” (Note: whatever you do don’t mistake “I’m sorry you feel that way” for validation)
Does it fit the facts?
Emotions are real—but not always accurate. Once we validate the feeling itself, we check the facts. What evidence supports the reaction? What contradicts it? Often, assumptions crumble under inspection. That sigh across the table wasn’t judgment—it was fatigue. The lack of eye contact wasn’t avoidance—it was someone scanning notes. This step builds empathy and accountability. Everyone gets to test their interpretation. Fact-checking feelings is powerful—it helps separate stories from reality.
Is it effective?
Here’s the clincher. Even if the story is true… does the reaction help? Anger might be justified. But if it pushes others away, it’s not effective. DBT helps families ask: Does this behavior get us closer to our shared goal? If the goal is unity, generosity, and impact—maybe we need a different approach.
Notes of Caution
I don’t announce, “We’re doing therapy now.” Instead, I weave these questions into conversation:
“What tells you that’s true?”
“Is there another interpretation?”
“What outcome are we hoping for here?”
Over time, families start using the framework themselves. The room softens. Curiosity replaces defensiveness. You can feel trust rebuilding.
Whatever you do, don’t weaponize DBT. (“Dad, does your anger fit the facts?” is not a winning move.) This is a gentle inquiry, not a courtroom cross-examination.
Why It Works
DBT keeps families anchored in reality and purpose—especially when emotions swirl. It moves the group from reactive to reflective and transforms conflict into collaboration.
So next time the conversation heats up, try this examination. Three questions. One calmer family. A better path forward.