I recently facilitated a session with a small group of people who had deep experience in their sector and strong views about what needed to change. The conversation sat within some genuine constraints, particularly around funding. There were difficult choices ahead, and any realistic way forward would involve trade-offs.

Conversations like this can make organisations understandably cautious about how much context to share. Explaining the constraints too early may narrow people’s thinking or cause the discussion to gather around one solution before the issue has been properly explored. Yet once people have been invited to contribute, holding too much of the difficult context back can limit how useful that contribution is.

What stayed with me from this workshop was how comfortably the participants handled the complexity. They understood that there was no magical pot of money waiting to be discovered and did not need the difficult parts softened for them. As more of the complexity surfaced through the conversation, they were able to think more deeply about what might actually be possible.

Getting to the hard mahi

I had deliberately allowed time at the beginning for people to understand why they were there and get a sense of one another before we got into the harder questions.

That can feel slightly indulgent when there is a full agenda and somebody is waiting for tangible outputs. People have given up their time, the clock is moving and we haven’t filled a single sheet of butcher’s paper yet.

However, people are already working things out during that early part of the session. They are listening for which perspectives seem to carry weight and noticing what happens when someone disagrees. They are also forming a view about me and whether I am interested in what they have to say.

I find that if I rush this part it affects the rest of the facilitation, and I'm pushing harder for thoughts and opinions. When I give participations the time they need in this "settling" phase, they have had time to understand who else is there and what sits behind their views, the conversation starts to shift. Someone makes a connection they had not seen before, while another person questions an assumption they came in with. The group becomes more willing to explore what is difficult because disagreement no longer feels quite so risky.

In this facilitation the participants, after a good period of "settling" spoke plainly about what they believed needed to change and listened carefully when others saw it differently. They were able to name problems without allowing those problems to swallow the possibility of something better.

The insights became richer as the conversation deepened, and the participants were willing to stay with the tension for a little longer, even though nobody could offer them a solution.

What are we worried will happen?

I keep coming back to our nervousness about difficult context, and the innate caution organisations have that skirts around difficult conversations. Hard conversations can equal big emotions - something I wrote about on LinkedIn last week. But big emotions are something we should allow, rather than shut the door on before they can surface. 

People may react strongly because the issue affects something they care deeply about. They may also carry frustration from earlier decisions or previous attempts at engagement. Bringing more context into the conversation can expose tensions the project team would prefer to manage carefully.

Timing plays an integral role in helping people make sense of information and reducing overwhelm caused by too much information. People need enough information to understand what they are being asked to consider, without having to wade through everything the organisation knows. That's the tricky part, right? We need to apply our judgement in figuring out what enough looks like.

I ask myself (this works most of the time):

• What does someone need to understand to contribute to this particular question?
• Which constraints genuinely shape what is possible?
• Is there anything that would materially change their advice if they knew it?

Those questions are a useful starting point to create the conditions for a calmer conversation, but calm is not always the same thing as useful.

Finding the question underneath the brief

By the time I arrive with my Sharpies and Post-it notes, a significant part of the facilitation work has already happened. The preparation involves understanding why the organisation wants to bring people together now, what it is genuinely trying to work through and how the insight will be used afterwards.

The first version of a brief may describe a broad conversation about the future. As we work through it together, a more immediate decision often comes into view, along with the constraints around what can realistically change. That deeper understanding influences the questions I prepare and the context participants will need if their contribution is going to be useful.

If the purpose remains too broad, participants and the organisation can leave the same session with quite different ideas about what took place. Participants may believe they were being invited to imagine the future freely, while the organisation was listening for insight that could inform a particular decision. Both may have approached the conversation in good faith, but they were working towards different destinations.

The discussion may still generate thoughtful ideas, although connecting them to the decision becomes much harder. Later, when participants see the outcome, they may struggle to recognise where their contribution went. This kind of frustration can begin well before the session, while the purpose is still being worked out and before anyone has considered what participants need to understand about the decision ahead.

Taking a leap of faith with complexity

What struck me about these participants was their ability to care deeply about the future of their sector while also recognising the limits of what could be funded. They challenged parts of the current approach and listened when somebody else’s experience complicated their own view. Nobody needed to abandon what mattered to them for the group to think seriously about what might work.

These participants had spent much of their working lives dealing with complexity, so their ability to work constructively with it should not have surprised me. Even with an experienced group, though, there is a leap of faith involved in putting the full weight of a difficult issue in front of people when you cannot be sure how they will respond or where the conversation will go.

Providing the information in plain English gives people a better chance of working with it. They need enough context to understand why the constraints matter and how those constraints shape the choices ahead, while still having space to respond emotionally. I’m comfortable when that happens because emotion often shows us where the consequences are felt, or reveals the earlier experiences that have made part of the issue feel particularly raw.

The facilitator then needs to hold that response without allowing it to close down everybody else’s ability to keep thinking together. My preparation begins with working out what people need to know about the issue and how much time they may need to make sense of one another. The history surrounding a group will affect that, as will what people believe is at stake for them, so experience and judgement matter far more than a standard workshop formula.

This session reminded me to have more confidence in the process. When we translate the complexity without stripping it away, people may be far more capable of working constructively with the hard parts than we expect.

Before your next workshop or stakeholder session, what complex information could help people contribute more usefully if it were explained in a way they could work with?