Why smart leaders can get stuck (and what to do about it)

Have you ever had the feeling of working away at a problem that you just can’t seem to solve?

You've analysed it. You've discussed it. You’ve set it aside and come back to it in the hope that you’ll have some fresh insights. But nothing works.

In fact, the more you think about it, the harder it is to even articulate exactly what the problem is.

If that sounds familiar, this might help.

I want to offer you a distinction that can change how you approach the most stubborn challenges.

In everyday language, complicated and complex mean roughly the same thing. But in leadership, the difference matters enormously.

Complicated problems are problems that are difficult, but solvable.

There are one or more solutions that can be worked out in advance if you apply the right knowledge, analysis, or expertise. Think of restructuring a process, drafting a legal document, or building a financial model. These might be hard, but they are do-able when you bring rigour and skill to the tasks.

As an individual (pre-leadership), these would have been the problems you were paid to solve. You were good at them. They gave you confidence.

Complex problems are different in kind, not just degree.

In a complex situation, cause and effect are impossible to predict in advance. Patterns only become visible in hindsight. No amount of analysis will give you a definitive answer, because the answer doesn't yet exist.

This understanding of complexity comes from complexity theory, which is concerned with uncertainty and non-linearity in systems.

Although we don’t usually think of it this way, we all function within various complex systems, made up of people, processes, relationships, interactions, and norms. Examples include our families, workplaces, and industries. With so many variables, dependencies and interacting elements, these systems become so intricate that predicting outcomes, such as “what would happen if…” is impossible. Complex problems reside within these systems.

Here's a simple way to see the difference between a problem that is complicated and one that is complex:

 And graphically:

This matters because you can’t solve complex problems in the way that you would if they were complicated. Therefore, when you recognise which type of problem you're dealing with, everything changes.

This is a critical distinction for leaders to grasp because, as leader, you are inevitably operating within complex systems. Much of what you are dealing with is therefore unpredictable. Problems are often complex. Change doesn't happen in a straight line.

This is why many new leaders feel like they've lost their footing. You are often appointed as a leader because you are excellent at solving complicated problems. Now you're expected to lead through complex ones, and by you're applying the same toolkit.

The disorientation you may feel isn't a sign that you're not cut out for leadership. It's a sign that you're encountering genuine complexity and that you need a different approach.

The first step is to simply ask: is this a complicated problem or a complex one?

Look out for the signs that you're dealing with complexity: the problem keeps shifting; previous solutions haven't stuck; multiple people have tried to fix it with different methods; tensions and relationships are part of the issue.

If that's what you're looking at, stop trying to resolve it through analysis alone. You definitely won't find the answer by thinking harder.

In complex situations, solutions can’t simply be imposed; they emerge. Your job is to create the conditions for that emergence to happen.

The most practical way to do this is through small, contained ‘safe to fail’ experiments. Try something. Observe what happens. Adjust. Try again.

For example, if you're struggling with low engagement in your team, you don't need a comprehensive engagement strategy before you act. Try one or two small things (a different format for your weekly meeting, a brief individual check-in with each person, greater transparency on decisions you'd normally just announce). See what changes. Build on what works.

This can feel uncomfortable when you're used to having the right answer, because you probably want a fix that can give you give you immediate solution you crave. But in complexity, experimentation is the method to adopt.

The discomfort you feel is natural. Complex environments are inherently uncertain. They generate anxiety. That's almost unavoidable and, if you are anything like me, accounts for the low-level sense of apprehension, you often feel in your working day.

But you need to be able to manage the anxiety that complexity creates because otherwise it will push you towards a behaviour that tends to make things worse: excessive control.

If you feel the urge to micromanage, over-communicate, or take back delegated tasks, that's usually anxiety rather than judgement. As I've written before, that kind of reactive control tends to undermine the very outcomes you're trying to protect.

Your job in complex situations, therefore, is to maintain enough composure (in yourself and in your team) to keep thinking clearly and acting thoughtfully. That means acknowledging uncertainty openly. It means saying "I don't know yet, but here's what we're going to try." It means staying curious.

Complex problems are rarely solved by the most senior person in the room. They tend to resolve through diverse thinking, increased interaction, different perspectives and better conversations.

The person closest to the issue often has the most insight. The team member who approaches it from an unusual angle might see something you've missed entirely.

So, rather than driving towards a predetermined solution, open things up. Ask better questions. Create the conditions for your team to think together. This is real leadership; in a sophisticated form.

The shift from complicated to complexity thinking is one of the most important cognitive transitions in leadership. It doesn't come naturally, particularly for people who've built their confidence on having the right answers.

But once you make it, you can stop waiting for certainty and move towards solutions carefully, experimentally, and with considerably more confidence than before.

All of my posts on complexity are here. Posts for new leaders are here.

Are you stuck in complexity right now?

If so, I can help. Book a one-off Clarity Coaching Session now. Click the link to see exactly how I can help you get unstuck.

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