What’s Your Problem?
Author: Thomas Wedell-Wedellsborg
A systematic framework for reframing problems before solving them. Wedellsborg argues that in a surprisingly large number of cases, solutions depend not on technological but on mental breakthroughs.
Why This Book Matters to Me
As a PM and startup operator, I’ve learned that the most expensive mistake isn’t building the wrong solution—it’s solving the wrong problem. Key questions I keep returning to:
- Frame Before Solve: How do you resist the urge to jump to solutions?
- Self-Imposed Limitations: What constraints are you assuming that aren’t real?
- Look in the Mirror: What’s your role in creating the problem you’re trying to solve?
The reminder that “assumptions that other people are stupid, selfish, lazy, or uncaring always deserve a second, deeper look” is humbling and practical.
The Problem-Solving Cycle
Tackling problems involves three activities you cycle through repeatedly:
- Framing: Determining what to focus on
- Analyzing: Studying the chosen framing in depth
- Solving: The actual steps to fix it
There are two ways to find new angles:
- Exploring the frame: Delving deeper into the details of the first framing
- Breaking the frame: Stepping away entirely, putting a different spin on it
“You have to zoom out before you dive in: don’t tinker with the specifics before you are fairly confident that you are looking at the right problem.”
The Five Reframing Strategies
- Look outside the frame: What are we missing?
- Rethink the goal: Is there a better objective to pursue?
- Examine bright spots: Where is the problem not?
- Look in the mirror: What is my/our role in creating this problem?
- Take their perspective: What is their problem?
Diagnostic Questions
When examining your problem statement, ask:
- Is the statement true?
- Are there simple self-imposed limitations?
- Is a solution “baked into” the problem framing?
- Is the problem clear?
- With whom is the problem located?
- Are there strong emotions?
- Are there false trade-offs?
“To find self-imposed limitations, simply ask: How are we framing this? Is it too narrow? Are we putting constraints that aren’t necessarily real?”
On Goals Behind Goals
“What is your goal? Why is that goal important to you? Once you reach it, what will it help you achieve?”
Surface higher-level goals by asking: Why do we want to achieve this goal? What is the benefit? What is the goal behind the goal?
Surface subgoals by asking: What is stopping us from reaching this goal?
Look for other goals by asking: What else is important?
On Perspective Taking
Three crucial steps to getting perspective taking right:
- Make sure it happens
- Escape your own emotions
- Look for reasonable explanations
Effective perspective taking has two parts: anchoring (switching on your other-people simulator) and adjustment (adjusting away from your own preferences, experiences, and emotions).
“Don’t stop at the first right answer.”
On Finding Bright Spots
- Have you already solved the problem at least once?
- Are there positive outliers in our group?
- Who else deals with this type of problem?
- Can we broadcast the problem widely?
The Bottom Line
Where other people do a cost-benefit analysis and pick the least painful option, expert problem solvers try to explore the issue in more depth and generate a new, superior option. As Rita Mae Brown put it: “Insanity is doing the same thing over and over again, but expecting different results.” The first step to breaking that cycle is asking whether you’re solving the right problem in the first place.