Putting off difficult conversations with your employees can feel like a considerate act when you’re running a business. But according to Bristol City FC CEO Charlie Boss, it’s quite the opposite.
Speaking at the CIPD Festival of Work at Excel London on Wednesday, he highlighted the lesson as one of the key aspects of improving high-performance leadership in high-pressure businesses like his.
“I’m someone who likes to lead with kindness,” Charlie said. “And if I look retrospectively, I think I’ve been guilty of mistaking niceness for kindness. And sometimes being nice can actually be unkind.”
The niceness versus kindness distinction sounds subtle, but according to Charlie, it’s the difference between a problem that gets addressed and one that quietly compounds.
“I’ve learned to have those difficult conversations as quickly as possible, because that is the kindest thing for both the organisation and the human being at the other end.”
CIPD Festival of Work 2026
His comments came during the Employment Hero panel at the annual conference, which also included Tom Tainton, CEO of Bristol Bears, and Clair Flynn, People & Culture Lead at Employment Hero.
Drawing on the experience of running elite sports organisations mid-rebuild – both of which have to build high-performance teams while delivering public results every week, in front of paying supporters and an unforgiving press – both CEOs stressed the importance of transparency and proactivity, whether you’re a leader of a small business or something much larger.
“I think I’d use the analogy that speed is kind,” the Bristol Bears CEO said. “Because I think sometimes we as leaders can be guilty of thinking we’re doing the right thing by perhaps delaying processes. Or sugar coating that process.”
The stakes both leaders are working under – including striving for promotion and titles – mean that their goals are consistently high.
“I don’t think success can be anything other than Premier League football for Bristol City,” said Charlie, who has been at the helm of Bristol City FC for three months out of an almost 50-year history of his club remaining below the top league of British football.
Tom, who joined Bristol Bears in 2022 and was appointed CEO in 2025, was equally emphatic about the importance of securing victories.
“Fundamentally, it’s about winning. Teams need to win because it builds credibility, which in turn helps you grow revenue and attract partners and stakeholders.”
Building High-Performance Teams Without a Safety Net
Unlike most business leaders navigating a transformation, Charlie and Tom can’t dictate how their fans respond to club performance – not least the coverage that performance receives in the media. But that level of expectation isn’t always a bad thing. Speaking from her perspective as Employment Hero’s People & Culture Lead, Clair highlighted that, when senior leadership teams know what to look for, pressure can make it easier to spot when a team is starting to fracture.
“When you’re in a team that’s under pressure but they’re really functioning well, debate is loud, it’s constructive and people are involved in it,” she said.
When it starts to break down, the opposite happens. “It’s deafening silence. People aren’t talking, they’re not engaging, there’s back-channelling going on.”
She added: “When you’re in a really well-functioning team, it’s always ‘us’ and ‘we’ sort of language. Whereas when that starts to shift, you see a lot more of ‘those guys’ and ‘that team’.”
How people respond to their mistakes is the clearest signal of all – whether they surface problems immediately or stay quiet and hope nobody notices. That behaviour, Clair said, comes down to one thing.
“If you have accountability without having trust, that’s not high-performance, that’s just fear,” she said. “When fear creeps in, you end up in situations where people won’t make tough decisions or bold moves. That actually holds you back and ends up operating as a bit of a handbrake.”
The Hard Calls That Test Trust
That’s not to say getting the balance right is always possible. According to a 2026 survey of HR professionals by WorkNest, 56% of organisations say their managers lack the confidence to tackle people-related issues – and in 68% of cases, those issues escalated because of poor handling or delays.
In the case of Bristol Bears, that challenge has manifested in the form of “shared lunches” and a practice he calls the “truth zone” where the team tries to remove corridor conversations. He adds that when members of his team have challenging conversations, they’re encouraged to “embrace that conflict” each Monday at an all-hands.
For Charlie, the consequences of navigating that balance between transparency and protecting morale came into sharp focus during his time working in senior leadership at another club, when relegation from the Premier League triggered a 65% drop in revenue overnight. He led a process that made roughly a quarter of the workforce redundant – around 50 people. The following day, the club signed a new player on £30,000 a week.
“I had people who left ask me: ‘Well, how does that work? Because you’ve just made all those redundancies and all of that’s gone to one person on the pitch,’” he said. Referencing Patrick Lencioni’s five dysfunctions of a team – specifically the argument that everything in a high-performance culture starts with trust – he said: “I know I’m okay if my team comes to me and says ‘why did you make that decision, Charlie?’ It’s when they don’t come and say that to me that I know I’ve got a problem.”
The Person Behind the Title
Building a high-performance team is hard enough. Doing it while absorbing pressure that most leaders never face – public scrutiny, external stakeholders, results that can’t be managed or spun – is something else entirely. Both Tom and Charlie were candid about the cost of that when asked what they’d unlearn if they could go back.
Tom said he’d wrongly assumed that culture and competence were two separate problems. “They’re not. They’re the same thing. You can’t have a good culture without a competent workforce.” For Charlie, that lesson was compassion”
“I wish I’d been more forgiving of myself when making mistakes. When you’re working at speed and you’re trying to make things better, you mess things up, and at the time it feels catastrophic, but a week later, it tends to all be fine.”
When the Feedback Stops
The higher the role, the thinner the feedback gets – and the lonelier it becomes. According to a British Red Cross report, 32% of senior managers are often or always lonely at work, nearly twice the average across all workers. The strain shows in other ways too. Employment Hero’s 2025 Employment Uncovered survey found that 49% of UK workers have taken a sick day because they felt mentally or emotionally exhausted – not physically ill. And 44% felt obliged to check work during annual leave, rising to more than half of workers aged 18 to 34.
Speaking about his experience, Tom said: “My biggest lesson as a leader is that the higher up the chain you go, the less space and feedback there is,” he said. “It’s lonelier.”
That isolation has a direct consequence for the people closest to senior leaders too. As Clair pointed out, when a business leader’s circle of honest feedback shrinks, so does the quality of the decisions made inside it. Addressing it, she reminded the audience, is one of the most underutilised roles a people function can play.
“You need to support and almost care for the human behind the title. A lot of the time, it’s a very isolating place to be. There aren’t a lot of people around you. You’re under insane scrutiny.” The role, she argued, is to become what she called a strategic confidant – someone the leader can test messy ideas with, who’ll tell them when they’re wrong, and who provides the bandwidth to think clearly when the pressure is highest.
Most business leaders won’t have a scoreboard. But the expectations Charlie and Tom describe – to perform and build at the same time, to make hard calls without complete information, to hold people accountable without losing their trust – will be familiar to any leader navigating change. With employment rights reforms tightening and pressure on leaders continuing to grow, the organisations that invest in the support structures to meet them will be better placed to handle it than those that don’t.
