Get in touch

What Happens When You Take a Group of Leaders Into a Prison?

A guest perspective from Karen, who leads a service-based business and joined The Alliance for a very different kind of leadership experience at Thorn Cross Prison in September 2026.

There aren’t many leadership organisations that invite you to spend the day inside a prison, so when The Alliance gave me the opportunity to experience something very different, I jumped at it.

The Alliance brought a group of leaders together at Thorn Cross, a Category D men’s prison in Cheshire, to step into a world most of us knew very little about. Around 90% of the leaders in the room had never been inside a prison before. I was one of them.

There’s something bigger behind experiences like this too. The Alliance talks about creating a movement of leaders who want to be a force for good, people who are willing to look beyond their own organisations, learn from each other and use their influence to make a difference.

Sitting in that room at Thorn Cross, that vision felt very real. These were leaders who cared about the businesses they lead and the people and communities around them. It was heartening to see that movement already happening around me, in the conversations, the connections being made and the leaders already thinking about what they could take back into their own worlds.

It was an opportunity to listen to people with lived experience, employers already creating opportunities for prison leavers, and organisations working between prisons and businesses to make those opportunities possible.

It was also an invitation for us all to be curious. To step outside our usual circles, hear different perspectives and perhaps challenge some of our own.

The experience had been billed as one of those that might change the way you think.

And it did!

Seeing things differently

As the conversations unfolded at Thorn Cross, I could feel perspectives shifting too.

We listened to people talk openly about their experiences of prison, the work they had done on themselves and what it meant when somebody was prepared to see beyond their past and give them an opportunity.

And around me, I could hear leaders being inspired and beginning to think differently too.

One described the experience as a real eye-opener and talked about wanting to go back into their own organisation and do things differently. Another was already thinking about conversations they wanted to have with their team.

What stayed with me was how open those leaders were to having their thinking challenged and how quickly that turned into conversations about what they could do differently.

Stepping into somebody else’s world

I always think there’s something powerful about deliberately stepping outside the world you know. And something brave about being vulnerable enough to admit that you don’t have all the answers.

People wanted to understand, asking thoughtful questions about what worked, what support was needed and what they might do differently themselves.

For me, this was purposeful leadership in action; listening, questioning our own assumptions and being open to what we might learn from each other.

I hadn’t anticipated the depth of self-reflection I would hear from people talking about their experience of prison: rebuilding their lives, educating themselves, developing skills and doing some incredibly difficult work on who they were and who they wanted to become.

It made me think about the things we ask of ourselves as leaders.

Know yourself. Understand your impact. Take responsibility. Be prepared to learn. And a big one for me is to have the courage to examine the things that are uncomfortable.

I think we learn when we’re prepared to look beyond the obvious places.

A leadership community making a difference

One leader shared they were “popping with ideas”. Another wanted to take the conversation back to their team. Someone else was already thinking about what they could put in place with their Board.

And there were employers already doing it.

Hearing from organisations creating opportunities for prison leavers brought it to life. This was social value you could see and feel, meaningful opportunities creating real change in people’s lives.

I came away with huge admiration for the work Laing O’Rourke is doing. What inspired me was the action. They were making things happen, learning as they went and openly sharing that learning so others could follow.

Alongside them were organisations creating the bridge between employers and people leaving prison. What stayed with me was the passion of the people doing this work. You could feel that this was about more than their role, they genuinely believed in the difference they could make.

And it’s this willingness, I think, that helps shape a movement: people who believe in the change they want to see and using whatever influence they have to help make it happen.

What happens after we leave the room?

Not surprisingly the conversations didn’t stop at the prison gates.

I went home and talked about the experience with my family. Then I talked about it with my team.

One leader shared “I’ll encourage my clients to consider offering opportunities to people they may previously have dismissed. There is so much talent in prison – talent we can make use of in the outside world.”

Another said “This was an extremely eye opening experience for me, one that will stick with me because I want to be one of those people that can help make a difference and provide opportunities that are different to the normal conventional way.”

It was so good to see people thinking differently, behaviours beginning to change and, importantly, action already starting. And all from one experience. It was one event but there are so many ripples from it. I love that!

Thank you to Karen for sharing her perspective, and for capturing some of the conversations, connections and moments that stayed with her after her visit to HMP Thorn Cross with other leaders.

Want to be part of a leadership community making a difference?

If you’re looking for a leadership community that will introduce you to different perspectives, challenge your thinking and connect you with other leaders who want to make a difference, you’ll find it at The Alliance.

Come and experience it for yourself at one of our taster events.

Or, if you’d like to stay connected, subscribe below for more thinking from The Alliance on leadership, people and purpose.