You started your career at Dunfermline Athletic and later returned to East End Park as an established player. What was it like coming through the system at the club and then working under Jimmy Calderwood?
“I loved my time as a young player at Dunfermline. I was fortunate to be part of a Scottish BP Youth Cup-winning squad, but I knew I wouldn’t be kept on at that time. There were players ahead of me, and sometimes that’s the hardest thing for young players to accept.
“I went back to play junior football in Scotland and loved it—my confidence grew again, and I was able to rebuild my playing career, which took me around the world before returning to East End Park almost ten years later.
“The period working under the late Jimmy Calderwood and Jimmy Nicholl was amazing. It was four years of continued improvement, culminating in a Scottish Cup final and a return to European football.”
You spent a significant part of your career at Sheffield Wednesday. What were your most memorable moments there?
“Without a doubt, the greatest game of my playing career was captaining Sheffield Wednesday to victory in the 2004-05 League One play-off final.
“The club had been on a downward spiral for quite a few years, so to be part of its rebirth—and to do it with the armband on—was incredible.
“I ended up spending over 16 years at the club as a player and coach. It’s an amazing club with an amazing fanbase.”
You also played abroad during your career in Hong Kong and Greece. What was that experience like, both on and off the pitch?
“I loved life abroad. I really embraced the people and cultures of the countries I lived in.
“If I had any advice for a player moving overseas, it would be to try to learn the language and integrate into the local scene.
“Travel is the best education you can get, and some of the life and football experiences I had will stay with me forever.”
You coached at Sheffield Wednesday alongside managers like Carlos Carvalhal and Steve Bruce, and you also took charge of the club on a caretaker basis several times. What were those experiences like?
“Working and learning from experienced coaches was invaluable for my own coaching journey. Observing how they communicated with players and staff was fascinating, as was seeing the variety of playing philosophies they implemented.
“Because of those experiences, when I had the opportunity to lead the club on three different occasions, I felt comfortable and was able to handle the ups and downs that come with first-team management.
“I think my overall record was pretty decent, especially considering that 99% of the time an interim coach takes over, it’s when a team is struggling.”
You were known for your leadership on the pitch. How did you develop those qualities, and was it always a given that you would move into coaching and management?
“I always wanted to go into coaching, but it was never a certainty. I didn’t break into full-time football until I was a bit older, so I really appreciated the opportunity I was given. That journey made me value my career more, and it became a cornerstone of how I led.
“I gave respect to everyone at the club—I hated disrespectful people and would call out teammates if anyone crossed the line.
“It was also important for us to enjoy each other’s company, so we set our own standards and held each other accountable. That was probably the main thing: give respect to get it back.”
You managed Ayr United from 2022 to 2024. How do you reflect on that period? You’re still highly regarded by the fans.
“It was a brilliant experience—a wonderful football club with a passionate, hardcore fanbase. Along with the owner, general manager, and my staff, we rebuilt the club over two years. It was tough to leave, but I left behind a real sense of togetherness and solid foundations to build on.
“We definitely punched above our weight to finish second in the league. The final step was just a bridge too far, but we restored belief and confidence in a club that had spent 11 of the previous 18 years in the league below.”
You’re now working at Boston United alongside Graham Coughlan. How are you finding the role, and do you hope to return to management in the future?
“I’m loving the role. There are a lot of similarities to my time at Ayr United—a similar budget, a young squad, and a fight to avoid relegation when we took over.
“Graham is a very experienced football man, and we work well together. I have a lot of respect for him and his playing and coaching career. We both love a challenge.
“Like anyone, I want to work at the highest level possible, so I certainly wouldn’t rule out a return to management. But for now, the day-to-day battle at Boston is great fun.”
Featured image: Boston United Football Club
Callum McFadden 