How to Have Difficult Conversations

How do you tell a colleague that their performance is slipping? How do you explain that someone’s behaviour is affecting the rest of the team? And hardest of all, what do you do when you recognise that the conversation is no longer about improvement but about whether they can remain in the role. 

Every journey to leadership eventually brings conversations we would rather avoid. 

Listening to Karen Lord, a global executive and leadership coach, and Dr. Monica Medina, an experienced school leader who has spent decades leading educators through some of the most challenging conversations their profession demands, it becomes clear that difficult conversations rarely begin when two people sit down together. They begin much earlier, with the questions we ask ourselves, the preparation we undertake and the intention we bring into the room. So, how do you really have those difficult conversations?  

Before You Speak to Someone Else, Speak to Yourself 

Karen begins with what is perhaps the most uncomfortable part of the entire conversation: the leader’s own motivation. 

She suggests that every difficult conversation should begin with self-examination rather than judgement. Before questioning another person’s behaviour, we should first question our own intentions. 

“No matter who you’re talking to and what the difficult conversation is, you start with yourself first. Why am I having this conversation? What is the goal I want to achieve as a result of it?” 

Julia pushes this even further, asking whether our motivation is truly pure. 

“Is the person actually wrong, or do you just think your way is better and you want them to do it your way? Do you genuinely care about the person you’re speaking with, or do you just want to win some ongoing tit-for-tat feud?” 

These questions are uncomfortable because they expose something leaders rarely admit: not every difficult conversation is motivated by generosity. Sometimes we want to prove a point, other times we want to win. Sometimes frustration has quietly replaced curiosity. 

Karen’s challenge is simple but profound. If we cannot answer those questions honestly, perhaps we are not yet ready for the conversation. 

Performance Conversations Should Never Come as a Surprise 

One of the strongest themes running through the episode is that difficult conversations rarely fail because of what happens during the meeting. They fail because of everything that happened beforehand. 

Karen asks leaders to examine their own contribution before holding someone else accountable. Have expectations been made explicit? Has feedback been offered along the way? Has the individual been given genuine opportunities to improve? 

If the answer is no, then perhaps the conversation is not really about performance at all. Perhaps it is about unclear leadership. 

This idea shifts responsibility in an important way. Accountability is not created in one annual review or one difficult meeting. It is built through dozens of smaller conversations that establish clarity long before performance becomes a problem. 

As Karen explains, the groundwork matters just as much as the conversation itself. 

“What is the groundwork I have to put in so I can make this conversation happen as painlessly as possible?” 

The more thoughtful the preparation, the less likely the meeting becomes an ambush. 

Preparation Is a Form of Respect 

Monica Medina offers wonderfully practical advice that reveals something deeper about leadership. 

She admits that, by nature, she enjoys talking. Precisely because of that, she prepares carefully before every difficult conversation. She writes notes, rehearses key messages and thinks through examples she can use. 

Her goal is not perfection. 

It is clarity. 

She laughs about her own tendency to over-explain, warning leaders against what she calls “babbling.” She also cautions against another common trap: making the conversation about ourselves. 

“People do not come to my office to hear my problems.” 

That single sentence captures an important truth. When leaders begin apologising for the conversation or talking about how uncomfortable they feel, attention shifts away from the person who most needs it. 

Preparation allows leaders to remain focused on what matters: helping another person understand where they are, where they need to go and how they will be supported to get there. 

Monica also challenges the instinct to rush. 

“If you rush, you are saying, ‘this really is not important. You as a person are not very important to me.'” 

Slowing down, listening carefully and allowing space for emotion communicates something powerful. 

This conversation matters because you matter. 

Dignity Lives in the Details 

One of the most memorable moments comes when Karen describes where she chose to have these conversations. 

Never in a glass-fronted office. 

Never somewhere colleagues could watch another person’s reaction. 

Instead, she booked private meeting rooms and deliberately left extra time afterwards. 

“I’ve had people get emotional, get angry… I feel like they should have a safe space to do that.” 

She even booked the room for longer than she needed so that the person would not be forced to leave immediately and walk back into the workplace while still upset. 

It is such a small detail. 

Yet it says everything about the kind of leadership Karen practises. 

Difficult conversations do not remove someone’s dignity. 

Leaders do. 

Or they protect it. 

Sometimes the difference lies not in the words we choose but in the environment we create. 

Is It a Skill Problem or a Will Problem? 

Monica introduces another distinction that deserves far more attention. 

Not every performance issue has the same cause. 

Sometimes the challenge is skill. Someone simply does not yet know how to do what is being asked of them. In those situations, coaching, practice and encouragement are the answer. 

Sometimes, however, the issue is will. 

The person understands what is expected but is unwilling to change. 

Recognising the difference transforms the conversation. Leaders stop treating every performance issue with the same solution and begin asking better questions about what is really happening beneath the surface. 

That curiosity is one of the recurring themes throughout the Women Emerging conversations. Leading is rarely about applying a formula. It is about understanding people well enough to know which response they need. 

Compassion Without Accountability Isn’t Compassion 

Perhaps the greatest misconception about difficult conversations is that kindness means avoiding them. 

Karen and Monica gently dismantle that belief. 

Neither advocates harshness or humiliation. Both speak with enormous empathy about the people sitting across the table. But neither believes empathy should come at the expense of accountability. 

Monica returns to one question whenever she finds herself doubting whether she should be firm. 

“I have two sons. Is that a classroom I would put my own child in?” 

If the answer is no, then failing to act is not an expression of compassion. 

It is, in her words, a disservice to everyone else. 

Karen expresses the same idea differently, describing avoidance as “mortgaging the future.” What feels easier today often creates a far greater burden tomorrow—on the team, the organisation and even the individual whose performance was never honestly addressed. 

The Conversation Before the Conversation 

By the end of the episode, I found myself thinking less about difficult conversations and more about difficult preparation. 

The conversation we witness is only the visible part. 

The invisible work happens beforehand, when leaders examine their motives, clarify their expectations, gather evidence, prepare with care and decide that preserving another person’s dignity matters just as much as delivering a difficult message. 

Perhaps that is what Karen and Monica are really teaching us. 

Not simply how to have difficult conversations. 

But how to become the kind of leader who is ready to have them. 

IN CONVERSATION: 

Julia Middleton: 

“We start with ourselves because your motivation for that difficult conversation needs to be pure. It’s quite easy to get wrapped up in why you’re having them. Is the person actually wrong, or do you just think your way is better and you want them to do it your way? Do you genuinely care about the person you’re speaking with, or do you just want to win some ongoing tit-for-tat feud between the two of you? Or are you being the victim? Or are they the victim? We create all these stories in our heads before we ever sit down.” 

Karen Lord: 

“No matter who you’re talking to and what the difficult conversation is, you start with yourself first. Why am I having this conversation? What is the goal I want to achieve as a result of it? And then what is the groundwork I have to put in so I can make this conversation happen as painlessly as possible? 

I would always book a meeting room instead. And I’d book it for fifteen minutes longer than the meeting itself, just so they could stay there afterwards if they needed to. I can’t imagine anything worse than having a difficult conversation and then someone saying, ‘Well, the next people need the room now, so you’ll have to leave.’ 

Those little things matter. They tell people that even when you’re giving them difficult news, you’re still treating them with respect.” 

Julia Middleton: 

“I love that. Because it’s so easy to think difficult conversations are about getting the words right. But what you’re describing is that they begin much earlier than that. They begin in the way we prepare ourselves, the way we prepare the space and the way we think about the other person.” 

Karen Lord: 

“Exactly. If you’ve done all that groundwork, then the conversation itself becomes much more straightforward. It still isn’t easy. It never is. But it becomes fair.” 

Listen to the full conversation with Karen Lord and Monica Medina where they explore how to prepare for difficult conversations, support people through performance challenges, and lead with both clarity and compassion.