How to deal with difficult conversations
Sam Little from CMP shares her thoughts on the importance of having difficult conversations and how to frame them so that they work for all participants and help to head of more serious situations.
Date: 20th Nov 2025
Author: Sam Little, Head of New Business and Sports Services, CMP
As workplaces, sporting environments can be at the extreme end of the spectrum, particularly where elite performance is concerned: where superhuman levels are just another part of everyday practice.
But, while sports organisations can be like any other business - in a wider sense too, not just in the elite sphere - where teams of people across different roles come together to work towards specific outcomes, where endeavour is linked to reward and there are constant targets to be met, the essential relationships between people, between employees and managers, coaches and athletes, are even more important. The higher the levels of pressure on performance, the greater the need for good communications, understanding and rapport.
At the heart of the issue are people management skills and the ability to deal with difficult conversations: the everyday discussions around advice and feedback; identifying strategic direction; talking through decisions on selections; dealing with the grievances of athletes, workers or employees, the cases when they feel they’re being mistreated or bullied, by a coach, colleague or another athlete, for example. Many of these conversations are subjective and dependent on perceptions that can be challenged, making them even harder to manage and to reach easy conclusions.
Take the athlete-coach relationship as an example. However experienced in their sport, however senior a level they’ve reached in an organisation, managers and coaches themselves will have come from sports backgrounds and may lack training or particular expertise when it comes to handling difficult conversations. Athletes are often young and without the life experience of how they can go about speaking up — and how to go about it in the right ways. They might be fearful of upsetting the apple cart and harming their own prospects in the process.
The lack of conversation skills means careers and ambitions can be seriously hampered. Minor grievances and cases of miscommunication turn into more serious misunderstandings and conflict. What could have been dealt with in an informal chat becomes an issue requiring the use of formal disciplinary processes. Relationships suffer, potential isn’t always being realised and campaigns falter.
The same can be true of relationships of all types within an organisation, not just in the elite performance realm, but in recreational sport, business functions, boardrooms…wherever conversations and human interactions take place.
Any conversation can be made constructive, balancing what needs to be achieved with the value of the relationships involved. It just takes commitment to developing some particular qualities and skills.
Always being the adult
All conversations need to be based on honesty. The manager or coach needs to always feel able to express and be open about both their thoughts and feelings. They need to have a sense of benevolence - to genuinely want the best for the organisation and other individuals as well as themselves. And the courage to be willing to initiate sometimes awkward situations, to speak honestly and be vulnerable personally for the sake of dealing with situations that are harming other people.
Facing up to difficult conversations
There should be an active decision that a conversation is needed - don’t be bounced into a difficult conversation by circumstances or emotions. Plan what is to be accomplished: “what do I need to talk about? What do I really want for myself, for them, for the relationship?” And set out a clear purpose with benefits for both sides: if a conversation feels risky to them, it will be feeling risky to the other party too.
"What do I really want - for myself, for them, for the relationship?"
Not relying on assumptions
Senior, experienced people can be tripped up by believing their experience means they already have the answers. They need to ask exploratory questions and show a meaningful interest in what the other person in the conversation thinks, believes, fears and wants. Curiosity – letting people know they have been heard and understood – is a really strong working relationship building tool. It provides the deeper information needed to help with the problem-solving and helps a coach, manager or leader to recognise that their version of events is a mix of fact, fiction and assumptions, and to separate what they know, believe, and what’s uncertain, before they open their mouth.
Getting involved
When are senior people are tight-lipped, looking only to protect their position, the team members around them will do the same. In other words, when there is a problem, leaders, coaches and managers need to avoid appearing detached and superior, making the issue only about the other person. They should be asking themselves: “how might I have contributed to this situation?” Talking about their contribution immediately opens up a dialogue and makes the member of the team more likely to be open, constructive and listen to what’s being said.
Doing more of it
Organisation of all kinds, businesses or sports bodies, want to see action and efficiency without too much debate. But conversations only improve through being a natural and regular part of working lives, not as an event – being summoned to a meeting, or into a weekly team slot. Frequent, open and trusting conversations need to be part of the organisational culture, encouraged and supported. Leaders should be making sure there are consistent messages about open conversations, the support and development available, putting more time and resources into supporting people away from escalating their negative feelings, and towards dialogue with each other.
Sam Little is Head of New Business and Sports Services at workplace relationships specialist CMP. Find out more:
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