Business leadership isn’t for the weak. But doing it in a role as visible as a football club CEO, is a challenge that only a select few understand.
Charlie Boss is firmly in that camp. When he stepped into the role of CEO at Bristol City FC in late February, he had a handful of weeks before the end of the season, a city watching his every move, and a board with high expectations.
In the latest episode of Inside the Workroom, Employment Hero’s Managing Director, Kevin Fitzgerald, sat down with Charlie to talk about what that adjustment period has been like, and the lessons any business leader can take from them.
Three pearls of wisdom in particular stood out:
Get Aligned with Your Board
Charlie describes the speed of his first month in the role as “probably unlike anything I’ve experienced before” in his career. For context, that career has taken him through nearly a decade at Disney, senior roles at the Jockey Club overseeing major events including Cheltenham Festival and the Grand National, and a stint at Southampton FC through relegation and promotion back to the Premier League.
Part of what made his first month so different wasn’t just the nature of football, where the next match is always around the corner, but the unique needs of the business too. To thrive as a leader, he had to be armed with a deep understanding of the direction that Bristol City FC needed to go in the first place.
“From the very moment I met the board, we’ve been so aligned on our vision for what the club needs to do and what it needs to look like,” he says. “It’s allowed me to really hit the ground running.”
For any new leader, that’s an incredibly vital foundation to establish. It doesn’t matter how good your instincts are if the people above you have a different picture in their heads. Locking in on alignment early is what gives you the confidence to move fast without second-guessing every decision.
Bring Your Team Into Your Strategy
It didn’t take long for Charlie to get his wider team involved in delivering strategy either.
“About a week ago, I brought all of my people together to talk about the club plan for the next three seasons,” he says.
“We talked about doing three things: delivering football success, developing talent from within, and becoming the number one sports team in the region.”
For Charlie, the specifics of achieving those goals mattered less than the approach and establishing a sense of collective ownership across his workforce. Rather than waiting until he had everything figured out, or circulating a document and hoping people read it, he got everyone in a room and made the direction tangible as soon as possible.
Keeping strategy and engagement at the top of the business and failing to include your entire workforce, however, would be a mistake for SME leaders. Research from workplace analytics and advisory company, Gallup, found that highly engaged teams outperform their least engaged counterparts by 23% in profitability and 18% in productivity. Clearly, getting your team inside the plan, rather than just briefed on it, changes how they show up.
Be Honest About Where the Gaps Are
With a clear view of where the business stands, Charlie hasn’t been shy about offering feedback either.
“Four weeks in, I’ve seen incredibly passionate, talented people doing all the right things,” he says. “I also think we can be better at having the right data-led structures and processes to make consistently good decisions.”
While candour may be difficult in week four, it’s also the right approach. A new leader who only validates what they find is unlikely to change much. The ones who are willing to name the gaps, while crediting the effort already being made, tend to build the trust that makes change possible.
Gartner research published in Harvard Business Review, for example, found that employees are 20% less likely to trust leaders who withhold information. And according to PwC’s 2025 Hopes and Fears survey of nearly 50,000 workers globally, those with the highest trust in their managers are 72% more motivated than those with the lowest.
Crucially, Charlie understands that while high standards are important in business leadership, so is the understanding that they may not always be met.
“I don’t think anyone in my organisation is out there thinking they’re perfect,” Charlie says. “If you are, what’s the fun in doing the job?”
The first month isn’t always about having answers. As Charlie’s approach at Bristol City shows, it’s also about building the conditions for the right decisions to get made, consistently, over time.
To watch the full episode of Inside the Workroom, click here.
