Think about the biggest challenge you are wrestling with right now: Is it a problem (solvable) or a dilemma (unsolvable)?
Most leaders miss this critical distinction—at their peril.
“The space between judging too soon (the classic mistake of problem solvers) and deciding too late (the classic mistake of academics) is a space that leaders of the future need to love—without staying there too long.”
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You don’t have to go far to find an abundance of dilemmas — whether it’s in the news right now or in your personal experience. Here’s a classic one:
- How do we cut costs, navigate a rapidly changing political and economic landscape, and innovate our way out?
What Makes Something a Problem
- Can be solved definitively
- Temporary – once fixed, it’s gone Has clear right/wrong answers
- Examples: Website crash, budget shortfall, scheduling conflict
What Makes Something a Dilemma
- Cannot be solved – only managed and leveraged
- Recurrent – keeps showing up in new forms
- Interconnected with other complex issues
- Threatening and confusing – but also potentially positive
The Leader’s Decision Rule
“If you are not sure if you are dealing with a problem or a dilemma, it is better to assume it is a dilemma. If it turns out to be a problem you can solve, you will get extra credit.”
The path out requires a repivot mindset through dilemma-flipping. Instead of asking “How do we solve this?” ask “How can we turn this into an advantage?”
A “flip” turns a dilemma around. You move from hand wringing to analyzing potential opportunities.
Dilemmas require seeing multiple perspectives simultaneously – like the famous duck-rabbit optical illusion. The image is neither a duck nor a rabbit, and it is both a duck and a rabbit, depending on how you look at it.
Why This Matters Now
The days when leaders solved only problems are gone. In our BANI world (Brittle, Anxious, Nonlinear, Incomprehensible), most challenges are dilemmas disguised as problems.
Leaders who master dilemma-flipping create competitive advantages from ongoing tensions.
What You Can Do Today
- Audit your current “problems” – which ones keep recurring?
- Ask: “What am I trying to solve that should actually be flipped?”
- Remember: Most leadership challenges are dilemmas disguised as problems
In a world where AI can solve problems faster than ever, your competitive edge isn’t in the solving—it’s in recognizing what shouldn’t be solved at all.
Image credit
Donaldson, J. (July 2016), “The Duck-Rabbit Ambiguous Figure” in F. Macpherson (ed.), The Illusions Index. Retrieved from https://www.illusionsindex.org/i/duck-rabbit.