In this episode, Sherry Bevan talks with Stephen Gilpin of Wolverhampton Wanderers Football Club about his thoughtful and refreshing approach to leadership that goes far beyond the world of sport.
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Episode 15: Adaptive Leadership
In conversation with Stephen Gilpin, Wolverhampton Wanderers
Sherry Bevan: Today, my guest is Stephen Gilpin. Stephen is the Assistant Director of Performance at Wolverhampton Wanderers Football Club and co-founder of the charity Prostate United. Stephen, a very warm welcome.
Stephen Gilpin: Thank you, Sherry. Good morning, and thanks for having me on.
It would be great to start by hearing a little about your career and how you came to be in your current role.
Stephen: It all goes back to university. In 2009 I went to Sheffield Hallam to study physiotherapy, and during my third year I completed an internship at Sheffield Wednesday Football Club. Looking back, that internship was probably the reason I got my foot in the door of professional sport so early in my career.
After graduating I spent a short time working in private practice, but during my internship I’d volunteered virtually all my free time – weekends, evenings, anything I could give. I’d almost created a role before there was actually a vacancy.
When I qualified and moved into private practice, that left a gap. The Head of Medical at the time, Paul Smith, gave me a call and offered me a role as First Team Physiotherapist. I was very junior and inexperienced, but it was an incredible opportunity to begin my career in elite Championship football.
I spent four years at Sheffield Wednesday during a period of major change. The club came under new ownership, significant investment came in, and overnight the environment was transformed. We were able to develop a much more progressive medical and performance department, and many of the players joining the club had experienced world-class environments elsewhere, so expectations were high.
As one of the junior members of staff, I was exposed to everything. I travelled to specialist appointments in the UK and abroad and had the opportunity to learn from some of the best rehabilitation experts in Europe. Those four years became my deep dive into learning – making mistakes in a supportive environment, developing quickly, and preparing myself for the next stage of my career.
On the pitch we had some incredible experiences too. We reached a play-off final, then a play-off semi-final, although unfortunately we fell short both times. It was a brilliant period for developing both professionally and personally, surrounded by fantastic colleagues.
In 2017 I moved to Rotherham United as Head of Medical. It was my first real leadership role, moving from leading myself to leading other people. It was also a smaller organisation with fewer resources, which meant culture became incredibly important.
I was brought in by Ross Burbeary, who later became a great friend and my co-founder at Prostate United. Working under Paul Warne, I learned the value of creating an environment where everyone moves together with a shared purpose. We had around 20 players and a dozen staff, but there was a real sense of collective commitment.
We consistently punched above our weight. We won promotion to the Championship in my first season, and although we bounced between the Championship and League One over the following years, we were competing against clubs with budgets four, five or even seven times larger than ours. What kept us competitive wasn’t resources – it was the culture we’d built.
That period was also my first real experience of leading people. Like most new leaders, I made plenty of mistakes. I probably thought there was a “right” way to lead, when actually leadership is far more nuanced than that. Fortunately, I was in another supportive environment where mistakes were seen as part of learning rather than something to be punished.
From there I was headhunted by Nottingham Forest to lead their rehabilitation programme, working under Martin O’Neill and Roy Keane. For a variety of reasons, including management changes and uncertainty around the club, it didn’t work out as planned, and I moved to Hull City.
At Hull I returned to a more technical role as Senior Physiotherapist. The club had just been relegated from the Premier League, so it was another opportunity to help stabilise an organisation going through significant change. I really enjoyed my year there.
Then Paul Warne called again and invited me back to Rotherham, this time to oversee all performance services. That was my first experience of leading people outside my own technical expertise – sports scientists, athletic development coaches, nutritionists and psychologists.
That was a huge learning experience because I wasn’t the subject matter expert in every area anymore. My role became enabling others to be the experts while bringing everyone together around a common philosophy and way of working.
That eventually led me to Wolverhampton Wanderers. Initially, I joined to help create greater alignment between the academy and the first team, bringing together medical and performance services across the club.
Very quickly that role evolved into my current position as Assistant Director of Performance. I now work across the Boys’ Academy, Women’s First Team and Men’s First Team, supporting Phil Hayward, our Director of Performance, on people and strategy, while also leading significant parts of our academy and women’s programmes.
It’s a hugely varied strategic leadership role. Rather than delivering everything myself, my role is to work through other leaders. I have heads of department who each lead their own teams, and together we’re focused on creating a high-performance environment where people can do their best work.
Looking back, it’s been an incredible leadership journey. I’ve invested heavily in my own development through Premier League programmes, further study and vocational learning.
What’s given me a really broad perspective is experiencing both ends of the spectrum. I’ve worked in clubs with very limited resources, where culture means everything, and now I work in an organisation with significant resources, large teams and complex systems. The challenge today is how you create that same strong culture in a much bigger, noisier and more complex environment.
That’s the journey that’s brought me to where I am today.
From physiotherapist to performance leader
It sounds as though that internship at Sheffield Wednesday was one of those real sliding-door moments. If you hadn’t secured that opportunity – and then committed all those hours volunteering – your career could have looked very different.
I think a lot of people have those sliding-door moments. When I talk to colleagues, there’s often one opportunity they said yes to that changed everything.
My philosophy has always been simple: say yes first and figure it out afterwards.
With that internship, while friends were enjoying holidays or travelling, I committed all of my free time to what I knew was my long-term goal – getting into elite sport. I didn’t necessarily mind whether that was football or another sport, but football became the platform that allowed me to build my career.
Getting the internship wasn’t a given. I applied, went through a recruitment process and earned the opportunity. Once I was there, I knew I had to make the most of it. I said yes to everything, became someone people could rely on, and looked for every opportunity to learn.
At that stage in my life I didn’t have the responsibilities of a family, so I could afford to prioritise experience over salary. I could have earned more working in the NHS or staying in private practice, but I knew what my long-term goal looked like. The environment, the role and the learning opportunities were far more valuable than the extra money.
Leading across teams with very different seasons
You’re now at Wolves, and anyone who follows football will know it’s been a difficult season for the men’s team, while the women’s team has enjoyed a fantastic year. How do you balance leading across teams experiencing such different levels of success?
It’s been fascinating because my three major areas of responsibility – the Boys’ Academy, the Women’s First Team and the Men’s First Team – have all had completely different seasons.
The men’s programme has faced significant challenges. The academy has had a hugely positive year, with some exciting young players progressing into the first team, which is ultimately what the academy exists to do. And the women’s programme has achieved promotion, moving from a hybrid part-time set-up into the Women’s Championship for the first time.
Each programme has been on its own journey.
We’re incredibly proud of what’s happening with the women’s team. It’s a progressive group of players and staff, led by a head coach who’s created enormous momentum. The club has invested significant time and resources into building an environment that allows that programme to keep growing.
The men’s season, on the other hand, has provided a different kind of opportunity.
By Christmas, when we were sitting on just two points, there was a very real possibility of relegation. As difficult as that was, it forced us to stop, reflect and ask some challenging questions.
For probably the first time in a long time, the club was prepared to be genuinely vulnerable. We held up the mirror and asked ourselves what wasn’t working, what we wanted to keep, and what kind of football club we wanted to become.
Alongside changes in senior leadership and the arrival of Rob Edwards, we’ve created much greater collaboration across the organisation. We’ve involved people throughout the club in some deep and honest conversations about our purpose, our values and the direction we want to take.
Knowing there was a realistic possibility of relegation actually gave us several months to prepare – not just operationally, but culturally.
We asked ourselves:
- What do we stand for?
- Who are we here to serve?
- How do we reconnect with supporters?
- How do we create the energy we’ll need for what’s ahead?
Those conversations have been incredibly valuable.
When people ask what the atmosphere is like around the men’s team, they’re often surprised by my answer. If you walked into the training ground today, you probably wouldn’t guess we were bottom of the league.
That’s because the leadership team has worked hard to create an environment built on honesty, accountability and optimism. We’ve acknowledged where we’ve fallen short, but we’ve also created a shared belief about where we’re going next.
We’ve also sought ideas from outside football. We’ve worked with some fascinating people, including Steve Hewitt, the former CEO of Gymshark, who has helped us rethink our business model, purpose and identity.
Ironically, if we’d survived by a single point, some of those difficult conversations might never have happened. Sometimes failure creates the opportunity for the most meaningful change.
At the same time, we have an academy that’s thriving and a women’s programme that’s full of energy. The challenge is making sure one programme doesn’t define the mood of the whole organisation.
We’re fortunate to have strong leaders within each area who act as cultural architects. Dan McNamara, our Women’s Head Coach, is a great example. He’s created tremendous belief and energy within that programme, and that’s something worth celebrating.
My role is to move across all three environments while remaining consistent in how I lead. On a Monday morning, the men’s team may have lost 3-0 while the women’s team has won 7-0. Those conversations require different approaches, but the leadership principles stay the same.
That’s a challenge – but it’s one I genuinely enjoy.
Purpose, trust and adaptive leadership
I think the work you’re doing around purpose, values, collaboration and connection is going to benefit the whole club. Those values run across every part of the organisation, and I imagine they’ll make a huge difference as you rebuild and move forward.
Absolutely. If you’d stopped people around the club five months ago and asked, “What’s the purpose of this organisation?”, I think a lot of people would have struggled to answer.
What we’ve tried to create is clarity. We want everyone to understand why they come to work, what their role is, and how that contributes to the wider organisational objectives.
It doesn’t matter where you sit within the club – we’re all working towards the same goal. But first we had to define that goal. We had to be really clear about where we’re heading and then help everyone understand how their role contributes to the bigger picture. That creates ownership.
Alongside that, we’ve spent a lot of time focusing on trust.
How do you build trust when people are naturally anxious about relegation, the financial implications, and the uncertainty that follows? How do you keep people motivated, engaged and believing in what Wolves is trying to achieve?
That’s been a huge focus over the past few months.
For me, it’s all about clarity, trust, purpose, understanding our audience and strengthening the connection between the club and the people we serve.
That’s something I see in every organisation I work with. Having a clear purpose is important, but making sure everyone understands that purpose is fundamental. If people aren’t all pulling in the same direction, it’s very difficult to achieve anything meaningful.
I’m also really interested in your own leadership journey. You’ve gone from being a technical expert to leading people across multiple specialist disciplines. What have you learned about your own leadership style?
It’s definitely been a journey – and one that’s still evolving. I’ve made plenty of mistakes along the way.
One of the biggest lessons was realising that before I could lead other people effectively, I had to learn how to lead myself.
I started asking myself questions like:
- How do I become a high-performing individual?
- How do I show up consistently?
- What am I like on a good day? On a bad day?
- What are my values?
- How do I respond to feedback?
Over the last ten years I’ve invested a lot in understanding myself through 360-degree feedback, psychometric profiling, Insights Discovery and, more recently, Hogan Assessments.
That process has helped me understand both my strengths and my blind spots, and it’s given me a much clearer development plan.
The word I keep coming back to is consistency.
Earlier in my leadership career, I probably wasn’t as consistent as I wanted to be.
People often talk about authenticity, and I’ve been on quite a journey with that idea. Where I’ve landed is that I don’t aspire to be an authentic leader as much as I aspire to be an adaptive leader.
The Hogan work really helped me think about this differently. I almost picture it like a DJ mixing desk. Depending on the situation, the person or the context, I can turn different aspects of my personality up or down.
If I approached every conversation in exactly the same way simply because I was being “authentic”, I don’t think I’d always get the best outcome.
Earlier in my career I probably tried to lead in one particular style. I might have focused on being more data-driven, more direct or more objective, but I realised that approach didn’t connect with everyone.
Now I think much more about the situation I’m walking into.
Sometimes I need to be the quietest person in the room and allow someone else to lead. If I speak too early, I might unintentionally shut down creativity.
Other times I need to bring more energy, more presence or more strategic thinking.
Sometimes I need to stay at a helicopter level, looking three years ahead. Other times I need to get into the detail and understand exactly what’s happening on the ground.
For me, that’s adaptive leadership.
My values stay constant, but how I express them changes depending on what the situation needs.
People sometimes think authenticity means being exactly the same in every circumstance. I don’t see it that way. I think you can remain true to your values while still flexing your leadership style.
That’s been one of the biggest lessons in my leadership journey.
Leading people is difficult, but it’s also a real superpower.
I’ve been fortunate to work with some outstanding leaders and mentors, and seeing them up close has shown me the impact great leadership can have. Often it isn’t about systems or technology – it’s about presence, consistency and the way people make others feel.
When I think back to Paul Warne at Rotherham, we didn’t have outstanding facilities or huge budgets. The pitches weren’t always great, the resources were limited, but people bought into something much bigger than that.
That’s people leadership.
It can be every bit as powerful as investing in expensive technology or new systems. Those things absolutely matter, but without the people element, they rarely deliver their full potential.
So I’m still learning.
I hope that journey never stops because leadership is something that’s always evolving.
Leadership is a journey
It’s interesting because quite a few of the leaders I’ve spoken to for the Team Talk podcast have said something similar. I recently interviewed John Dutton, who has more than 30 years’ leadership experience, and he’s still learning, still adapting and still looking to improve.
That willingness to keep learning seems to be one of the defining characteristics of great leaders.
I completely agree, because the context is always changing.
The environment changes. The people change. The challenges evolve. The performance landscape we’ll be working in by 2050 will look completely different to today.
As leaders, we’ll be navigating AI, new technologies and innovations that we can’t fully predict yet. So the question becomes: how do we continue learning from great people and keep evolving ourselves?
When I compare the leader I was in 2017 with the leader I am today, it’s night and day. I know I need to keep that momentum going because I’m passionate about leadership and the impact it has – not just on performance and results, but on people.
Ultimately, I want to help people in my teams grow into leaders themselves. If someone I’ve worked with goes on to have a successful leadership career, that’s success for me.
That’s what gives me purpose.
Every environment I step into is another opportunity to learn.
Most of my learning has come through failure. Looking back, I can see that the biggest lessons didn’t happen immediately. They unfolded over time.
Even now, I can reflect on situations from two years ago and only just realise how I could have approached them differently. Sometimes the learning comes long after the event.
People often say, “Fail fast, learn fast.” There’s certainly value in immediate feedback, but I think real learning is much slower than that. It’s thoughtful, deliberate and reflective.
That’s something I’ve come to appreciate through further study and research, and it’s really influenced how I develop as a leader.
I completely relate to that.
Even now I find myself reflecting on situations from 20 or 30 years ago and thinking, “If I knew then what I know now, I would have handled that differently.”
Sometimes you don’t even realise you’ve made a mistake until years later, when you’ve gained more experience and perspective.
Absolutely.
Building Prostate United
I’d love to talk about the work you’re doing at Wolves all day, but I also want to shine a light on Prostate United. Tell me how it started and how you became a co-founder.
This is my passion project.
It’s something that gives me enormous energy, both personally and professionally.
My grandad died from prostate cancer in 2010. He was a hugely inspirational figure in my life and I always knew I wanted to do something in his memory. At first, I imagined that might simply be a fundraising challenge or a physical event.
Then, in 2018, while I was at Rotherham, I spoke to my colleague Ross Burberry.
I said, “What if we ran 10 kilometres every day throughout November? I’ll also run the London Marathon afterwards. Let’s use our football fixtures to raise awareness and see if we can raise some money.”
Ross thought about it for about 30 seconds and simply said, “I’m in.”
That’s how it all began.
At that stage it wasn’t even called Prostate United. It was simply a fundraising challenge for Prostate Cancer UK.
In that first year we raised around £7,500, and I was absolutely delighted.
But something interesting happened.
As we travelled around the country, people at other clubs kept saying, “I’ll join you next year.”
Ross and I looked at each other and laughed because there wasn’t supposed to be a next year.
But after hearing that over and over again, we realised perhaps there should be.
So in 2019, instead of two of us taking part, there were ten people from clubs across the country.
The fundraising doubled.
Then it kept growing.
People started saying, “I can’t run, but I can cycle.”
Great.
Others said, “I can walk.”
Fantastic.
The challenge evolved into something that anyone could take part in.
The fundraising grew from £7,500 to £15,000, then £50,000, £125,000, £250,000, £350,000, eventually reaching almost £500,000 in a single campaign.
Today, after eight campaigns, we’ve raised more than £1.5 million.
It’s been an incredible journey.
Prostate Cancer UK has become a fantastic partner, working closely with Ross and me to help grow the campaign. We now have branding, merchandise, marketing campaigns and agency support. Together we’re building something much bigger than we ever imagined.
Football gives us an amazing platform.
We all know about events like Soccer Aid, but beneath that there wasn’t really a national football movement bringing supporters together around prostate cancer awareness.
Sadly, prostate cancer affects one in eight men, and one in four Black men.
Football reaches exactly those communities.
The idea is simple. Support your football club while taking on a challenge that means something personally – whether that’s for your dad, your grandad, your brother, your uncle or a friend.
That’s the magic of it. It’s not my challenge anymore. It’s everyone’s challenge.
People tell me, “You’ve given me a way to honour someone I loved.”
That’s incredibly powerful.
The more people who get involved, the more awareness we create, the more money goes into research and the closer we get to changing those devastating statistics.
That’s what keeps us going. Every year we set ourselves bigger goals. This year we’re aiming to raise £750,000.
By our tenth campaign in 2027, we want to raise £1 million in a single year.
When I think back to two friends running around Rotherham in 2018 hoping to raise £7,500, it’s amazing to see how far it’s come.
And I genuinely believe it’s only just getting started.
It sounds incredible, and your passion really comes through. I’m curious – are there things you’ve learned through Prostate United that you’ve brought back into your work at Wolves?
Absolutely.
One of the biggest things has been understanding how different organisations operate. Working in the charity sector has given me a completely different perspective on stakeholders, governance, ownership and decision-making, and that’s been invaluable in my role within professional football.
I’ve also learned a huge amount about scaling projects.
How do you grow an idea? How do you become a better project leader? How do you create clear accountability, involve the right people, consult effectively and keep everyone informed? Those lessons transfer directly into the workplace.
Another area is communication.
I’ve really come to appreciate the power of storytelling – how sharing your own story can inspire other people to become part of something bigger.
If storytelling can create a movement around Prostate United, then why can’t it create momentum behind a workplace project or organisational change?
The other lesson is the power of collective effort.
One thing we often say at Prostate United is that we’re standing on the shoulders of giants. None of this has happened because of one or two people. It’s happened because thousands of people have chosen to get behind the cause.
Great things are rarely achieved alone.
If I’m trying to achieve something on my own, I’ll only ever get so far. If I can bring ten people with me, we’ll achieve far more together.
I’ve taken so much learning from building Prostate United over the last decade, and it’s undoubtedly made me a better leader in the professional environment as well.
That really comes across.
The thread running through everything you’ve talked about today – whether it’s Wolves or Prostate United – is purpose. You have such a clear sense of what you’re trying to achieve, and that enables everyone around you to work towards the same goal.
I honestly feel like I could spend all day talking to you because you’ve shared so many fascinating insights about leadership and team performance.
Favourite sporting moment
Before we finish, I always ask my guests the same question.
What’s your favourite sporting moment? It doesn’t have to be football – it could be anything – but what’s the one moment that stands out for you?
For me, a great sporting moment is one where you can remember exactly where you were, who you were with and how you felt.
A few immediately come to mind.
David Beckham’s free kick against Greece. I know exactly where I was standing when that went in.
Johnny Wilkinson’s drop goal to win the Rugby World Cup in 2003.
Tiger Woods winning The Masters while playing through injury.
And Sergio Agüero’s last-minute goal against QPR to win the Premier League for Manchester City.
Those moments stay with you because they create memories.
You can ask almost anyone, “Where were you when Beckham scored against Greece?” and they’ll immediately have a story.
That’s what makes sport so special. It brings people together through moments that become part of our shared history. The excitement, the emotion, the sense of belonging – those are the things that make sport so powerful.
I completely agree.
Johnny Wilkinson has actually come up before with another guest, and I think that’s exactly what sport does. It creates those shared moments that bring people together and build a real sense of community and connection.
It’s one of the reasons I love working in this world.
Stephen, thank you so much for joining me today.
I’ve really enjoyed hearing about your leadership journey, your commitment to continuous learning, and your perspective on adaptive leadership – staying true to your values while adapting your approach to the individual, the situation and the challenge.
It’s been a fascinating conversation.
Thanks, Sherry. I’ve really enjoyed it. Thanks for having me.
Important links
About Stephen Gilpin
Stephen is Assistant Director of Performance at Wolverhampton Wanderers Football Club and co-founder of Prostate United.
About the Host
Sherry Bevan believes that high-performing teams start with confident leadership.
Before becoming a Leadership Consultant, she spent more than 25 years working alongside technology teams, including in organisations such as McDermott Will & Emery, Credit Suisse and Arthur Andersen. That experience gives her a deep understanding of the challenges facing today’s IT leaders, particularly within law firms.
Through her consultancy, coaching and leadership development programmes, Sherry combines commercial understanding with honest conversations, skilled facilitation and practical leadership support to help leaders build confident, high-performing teams.
A former racing cyclist and lifelong sports enthusiast, Sherry is fascinated by what enables teams to perform under pressure. That’s why Team Talk goes behind the headlines to speak with the coaches, performance directors, and leaders who create the environments where success becomes possible.
Because whether it’s a law firm, an IT department or an elite sporting environment, great results rarely happen by accident. They happen when leaders create the conditions for people to perform at their best.
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