In a previous article, I looked at the three features of wicked problems. One of these features, knowledge uncertainty, is when we don’t know everything we need to know in order to solve the problem effectively. This vacuum in understanding provides a conundrum for leaders. How to lead when you don’t know the answers; how to mitigate risks when you can’t see them; and how to maintain authority when you can’t dictate what’s to be done?

Typically, when leaders find themselves having to make decisions with incomplete information, the first port of call is to get more of it. And the go-to place to seek this information is through the analytic method: get the data. This sounds perfectly logical, but ‘getting the data’ is problematic with wicked and complex problems because our usual data-collection approaches are not designed for wicked problems. In this article I’ll explain why and what to do instead.

Our usual way of gaining knowledge

Organisations are managed by specification, inspection, measurement and targets. Whether we’re trained as engineers, marketeers or accountants, we’re taught the analytic method – to collect and analyse data – as the key tool in our decision-making. This analytic method involves breaking the problem down into its most simple unit of analysis so that you can collect data that is easy to work with. Think call-centre response times; EBITDA; or customer numbers.

In most cases, this is appropriate and it works well. These ‘most cases’ have one thing in common: the thing we’re measuring is deterministic – that is, it doesn’t act back on us when we act on it. Kicking a football is deterministic. You kick the ball, the ball moves based on the force you’ve placed on it, and it goes in the direction determined by the kick (although that may be quite different from your intention!). A cat, in contrast, is not deterministic. If you kick a cat, it will respond, but how it responds will be totally unpredictable, and the next time you kick it, it will respond differently again – this time perhaps anticipating your action.

Wicked problems are more like cats than footballs. Even collecting data about a wicked problem can change it. Imagine for example that you are trying to build a bypass and you ask local residents their views on two options. The very action of seeking the data stirs up the energies of those residents and the problem begins to morph before your eyes.

That’s if you can even gain access to the data! Collecting and having access to data is not politically neutral, and stakeholder groups may be highly reluctant to engage with any and all attempts to understand them if they suspect that data will be used to ‘manage’ them. Gaining valid and reliable data in these situations can be extremely challenging.

And then there’s the issue of defining what data you’re looking for. In order to collect data, you have to have made a decision about what aspects of the problem to foreground and what to ignore. But wicked problems are in part wicked because they are defined differently by different stakeholder groups. Seeking views from your own perspective may miss the core of the issue as it appears to others – so your data may be useless in capturing the essence of the problem.

What should we do then, when confronted with uncertainty in wicked problems? We need a shift from analytical thinking – that is, the science of dealing with independent sets of variables – to systems thinking: a leadership practice that works with the interdependence of variables and the full complexity of the problem at hand.

Leadership as convening

Given that a wicked problem is interconnected and ‘owned’ by many different groups, it stands to reason that no one group can solve it independently of other groups. Accepting this as a leader, our focus shifts from collecting data towards convening the problem owners in dialogue where the ‘people with the problem’ become the ‘people with the solution’. Convening, in effect, becomes our leadership task.

Convening aims to work with groups who have a shared ownership of a wicked problem, and help them to move forward by clarifying their shared intent.  This can be a major breakthrough as groups come to realise that, at some level, their members share goals, when before they assumed otherwise.

In these situations, the work of the leader is as much about presence as it is about action. That is, bringing disparate groups together in a safe space so that a generative process can occur where commonality is created and greater knowledge can be found. This is still data gathering – but of a very different type than we’re used to in organisations. It’s not just the contrast between quantitative and qualitative ways of knowing. It involves a leader having a very different relationship with the data that is emerging.

To do this, a leader must abandon their preferred outcome – no matter how convinced of it they may be – in order to enable the group themselves to find the answers that suit them. This is deeply challenging because it goes against everything we have been taught about effective leadership. According to the conventional wisdom, leaders have a compelling vision (in practice, this often means they think they have the right answer) and they pursue this vision with vigour until it’s been executed. By contrast, when leading as convening, leaders must decide what’s more important: being right or getting it right.

The views, opinions and perspectives of different stakeholder groups will be full of subjective realities and deeply held emotions. Acknowledging this means that leaders must be able to contain the groups’ anxiety as they move through the process. Creating a safe ‘container’ for complex problem-solving to take place means leaders have to abandon other leadership stereotypes: always have the answer and avoid showing weakness. When the stakes are high, the group will look for strength in the leader, but not in the way we might expect. Groups wishing to carry out problem-solving want a leader who can stay with them through the difficult emotions without bolting straight to a simple answer. Strength, in these situations, is in notknowing and in being okay with not knowing.


It is much easier to be the kind of leader who, when confronted with a problem, moves into action. And it feels better in such situations to feel like we are getting things done. As leaders confronted with wicked problems, we’re invited to exercise a different type of leadership and adopt different information-gathering practices. It is painstaking work, but it’s the only kind that works with wicked problems.

In my next article I’ll explore further how to reconcile differing values amongst stakeholder groups when working with a wicked problem.

By Jacqueline Conway…

Dr Jacqueline Conway works with CEOs and executive teams as they fully step into their collective enterprise-wide leadership, helping them transform their impact and effectiveness.

Jacqueline is Waldencroft’s Managing Director. Based in Edinburgh, she works globally with organisations facing disruption in the new world of work.