The Questions That Turn Messy Problems into Clear Ones
The art of not wrestling in the mud
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“Never wrestle with a pig. You both get dirty, and the pig likes it.”
There are moments in leadership when you feel like you’re pushing through mud. You’ve had the meetings, redrafted the plans, sent the follow-up emails… and yet nothing changes. The harder you push, the murkier things become. It’s easy to start believing that the problem lies with them — whether that’s the resistant colleague, the slow department or an impossible client (you know who you’re thinking about!).
Performance psychologists Pete Lindsay and Mark Bawden have a term for this: pig wrestling. Their book of the same name opens with the line above, then builds an entire philosophy around it. The problem, they argue, isn’t the pig: it’s that we keep stepping into the pen. We engage with messy problems in messy ways, full of assumption and ego.
Their insight is deceptively simple: most problems stay stuck because we’re solving the wrong version of them. An important skill you can develop is to clean the problem first: to strip it back until you can see what’s actually happening.
And the most effective cleaning tools are questions and reframing techniques: things that calm emotion and invite new movement.
Here are three approaches to transform any muddy situation into one you can actually work with.
The Question That Stops the Struggle
“What am I really wrestling with?”
When a problem refuses to budge, our instinct is to push harder. We gather data, escalate and tighten control in line with the methods we’ve learned in school or through practice. But this sort of pressure only amplifies confusion. Every extra email and meeting becomes another layer of mud.
At that point, curiosity is not a luxury, it’s the only way out! Asking “What am I really wrestling with?” interrupts the pattern. It forces a moment of self-awareness before reaction.
This question invites you to separate fact from interpretation. Facts are what anyone could observe. Interpretations are the meanings you’ve attached to those facts. A missed deadline is a fact; “they don’t respect me” is an interpretation. The more we fuse the two, the dirtier the problem becomes.
In Pig Wrestling, the authors describe how people load problems with invisible baggage: memories of previous failures, unspoken rivalries, stories about motive and character. Once that baggage is attached, the problem feels enormous. But when you strip it away, what’s left is almost always something smaller and behavioural: things like an unclear handover or an overloaded schedule.
Here, curiosity acts as a solvent. Instead of “Why won’t they collaborate?”, you might ask, “What specifically breaks down when we try?” or “Where exactly does the delay begin?” The moment you ask those questions, you shift from frustration to observation.
So our first strategy is about precision. Leaders don’t have to be as calm as a monk (though that doesn’t hurt!), they just have to see clearly enough to act effectively. And clarity begins the moment you stop wrestling.
From Certainty to Open Enquiry
When problems feel vague or conversations stall, it pushes you to ask sharper questions and pay closer attention. Used strategically, curiosity turns uncertainty into clarity by revealing what’s really happening beneath the surface. With that understanding, you can make better decisions and identify logical next steps even in complex situations or environments.
The Question That Brings Clarity
“When does this not happen?”
Once you’ve named the real problem, the next step is to look for exceptions: these are the overlooked moments when the issue disappears or doesn’t occur. It’s an unusual form of curiosity because it asks you to find evidence of success within failure.
In practice, it sounds like:
When does this tension ease up?
When do these two teams actually work well together?
What’s different about those situations?
This is the question that transforms blame into insight. Most of us default to asking why: “Why do they resist change?” or “Why does communication break down?” But “why” questions tend to invite justification and speculation. They lead us deeper into theory and away from evidence. By contrast, “When does this not happen?” anchors you in observation. It assumes the system already contains the seeds of a solution.
In Pig Wrestling, this idea is symbolised by the “gold nuggets” buried in the mud, the rare moments of alignment that prove the problem isn’t absolute. When you identify those, you can study the conditions that allow them. Maybe collaboration improves when meetings are informal, or when a certain person facilitates or when decisions are made earlier in the week.
Psychologists call this positive deviance: it’s about looking for the outliers who succeed under the same constraints as everyone else. Leaders who ask these questions are able to both see problems and map contexts. They realise that what looked like a personality clash might actually be a scheduling issue or a missing feedback loop.
As W. Edwards Deming said, “Every system is perfectly designed to get the result that it does.” So the trick is to look for the moments when the design accidentally produces something better and then make those moments the norm.
When curiosity turns to pattern-spotting, problems shrink. They lose their moral weight and become design puzzles instead.
The Question That Opens Possibility
“What would I like to see instead?”
Once the problem is clean and contextual, it’s time to move forward. But even here, leaders fall into another trap: trying to fix rather than design. Fixing assumes control, whereas designing assumes learning.
The question “What would I like to see instead?” shifts you from analysing the past to shaping the future. It’s borrowed from solution-focused therapy, where clients are asked to imagine that overnight, a miracle occurred and the problem vanished: “What would be the first sign that things were better?”
It’s a deceptively powerful exercise. You can’t answer it with abstractions. For example, answering “Better collaboration” doesn’t work: that’s a slogan, not a vision. To describe the future, you have to picture it: who’s talking to whom, what decisions happen earlier, what the atmosphere in the room feels like.
That image then reveals the first small, concrete steps toward it. Maybe what’s missing isn’t commitment but shared context; not motivation but clarity. You can test that hypothesis with incrementally, for example with one change of format or one shared document.
The miracle question also clarifies what matters most. In any complex issue, there’s usually a handful of essential conditions and a long tail of preferences. Once you distinguish between them, the design space opens up.
Leaders often equate authority with having answers. But the reality is that questions design reality. Every question presupposes a frame: what counts as relevant, what success means, where agency sits. When you choose your questions deliberately, you also choose your frame; and, by extension, the kind of organisation you create.
The Leader Who Doesn’t Step in the Pen
The pig, of course, is always waiting. But maturity in leadership is about recognising the moment when the fight itself has become the problem.
Curiosity offers a clean route:
What am I really wrestling with? cuts through story and emotion to reveal structure.
When does this not happen? replaces blame with observation and evidence.
What would I love to see instead? turns insight into design.
These questions don’t (and can’t!) guarantee comfort alone. But they do guarantee an opportunity to make concrete progress: they restore movement where frustration once reigned.
The best leaders clarify conversations and highlight better frames. They know that asking the right question at the right time is the discipline that keeps them out of the pen.
In the end, curiosity doesn’t solve the mess. It simply points to the part that can be cleaned, and that’s always where change begins.
I’m Andrea, a management consultant with over a decade of experience across industry and academia. I work with commercial, non-profit, academic and government organisations worldwide, helping them capture meaningful insights through mixed methods research.
I write about practical frameworks to help you discover what others miss. My main goal is to translate complex concepts into techniques that readers can use immediately.
I came for the opening quote. I stayed for the incredibly pragmatic and actionable advice that I immediately applied at work today with great results. Your brain is wondrous, Andrea! Thank you. 🙏🏾
So very very true. Instead of adding to the chain of cc's and emails, get to the real issue. Try a conversation, go see someone face to face if you can. It's much harder to ignore someone who's facing you!