I recently encountered a word we don’t hear often in nonprofit work: counterfactual.
The timing was interesting because I had been doing something similar in conversation—taking statements that “didn’t make sense” and flipping them to see what assumptions were underneath.
In research, counterfactual thinking asks what would have happened if things had turned out differently. Evaluators use it to test cause and effect. You don’t hear the term much in nonprofit work because most organizations are focused on delivering programs, not studying populations that didn’t receive them.
But the underlying exercise—imagining the opposite explanation—is a powerful thinking tool for revealing assumptions. In decision science, it’s called inversion: turning a problem upside down to examine the assumptions behind it. Investor and thinker Charlie Munger popularized the idea, borrowing from the mathematician Carl Gustav Jacobi, who advised (as translated):
Invert, always invert.
Jacobi’s advice turns out to be surprisingly useful in everyday conversations.
Statement:
“X doesn’t make sense.”
Inversion:
“X does make sense. Here’s why.”
The point isn’t to prove the opposite is true.
The point is to surface the assumptions hidden inside the original statement.
Why this matters
When we say something doesn’t make sense, we’re usually revealing a belief about how the world should work. That belief is a mental model.
Psychologists call one part of this tendency confirmation bias—our habit of favoring explanations that reinforce what we already believe. In Thinking, Fast and Slow, Daniel Kahneman describes a related dynamic: once we construct a story from the information we have, our minds treat it as complete. He calls this “what you see is all there is.”
Inversion interrupts that reflex.
Flipping the statement forces us to ask: What assumptions made the original statement feel obvious?
Once those assumptions are visible, new explanations—and better questions—appear. Inversion helps us change the frame long enough to see the system more clearly.
Here are a few from my last two weeks.
Example 1: Compliance training
Statement
People are too busy for compliance training. It takes time away from their work.
Inversion
Compliance training saves time, money, and risk. It is part of their work.
What assumptions make the original statement feel obvious?
- Training is separate from real work
- The biggest cost is the hour spent in training
- Compliance content has little operational value
- Compliance training is inevitably poorly designed
Once those assumptions surface, the inversion begins to make sense.
Well-designed compliance learning strengthens worker-related practices and helps keep people safe. When people understand the rules, they avoid mistakes. When they avoid mistakes, organizations avoid injuries, investigations, penalties, and corrective action plans.
The issue isn’t compliance training itself. The issue is how it’s designed.
Poor training wastes time. Well-designed training prevents problems.
It doesn’t make sense that donors aren’t focused on outcomes.
Donor behavior makes perfect sense.
What assumptions are hiding inside the original statement?
- Donors are rational.
- Donors give primarily to maximize impact.
- Outcomes are visible and easy to understand.
In reality, many donors give for other reasons: a friend asked, the organization reflects their values, tax avoidance, or long-standing traditions that shape how people think about charity or virtue.
Seen this way, donor behavior reflects the information and motivations available to them.
The question shifts from “Why don’t donors care about outcomes?” to “What system is shaping donor attention away from outcomes?”.
As long as we stay in the space of something “not making sense,” we limit our ability to identify solutions.
The mental models behind inversion
Inversion doesn’t stand alone. It sits within a cluster of mental models that help us challenge assumptions and see systems more clearly. Together they form a small toolkit for questioning our understanding of things.
| Mental model | Why it matters | How inversion helps |
|---|---|---|
| Inversion Learn more |
Turning a problem upside down reveals assumptions we couldn’t see before. | Flip the statement: “X doesn’t make sense” → “X actually makes perfect sense.” |
| Confirmation bias Learn more |
We tend to favor explanations that reinforce what we already believe. | The original statement feels obvious because it fits our existing story. |
| Map vs. territory Learn more |
Our explanations are simplified models of reality, not reality itself. | “This doesn’t make sense” often reflects the limits of our mental model. |
| First principle thinking Learn more |
Strip away inherited assumptions and rebuild from fundamentals. | Ask: what must be true for the inversion to work? |
| Double-loop learning Learn more |
Real learning happens when we question the beliefs behind our actions. | Inversion challenges the governing belief behind the problem. |
As systems thinker Donella Meadows argued in Thinking in Systems, one of the most powerful leverage points in any system lies in the paradigm behind it.
Change the assumption, and the system begins to look different.
Inversion is a simple way to expose those assumptions.
A thinking habit
The next time you hear yourself say: “That doesn’t make sense.” Try this:
Statement
It doesn’t make sense that ______.
Inversion
______ actually makes perfect sense.
Then ask: What assumptions made the original statement feel obvious?
You don’t have to believe the opposite explanation.
The moment you question your assumptions, you begin to see the system more clearly. Once you can see the system, you can start to change it.