Managers often say that handling difficult conversations is one of the hardest parts of the role. But it’s not just managers. We all have conversations we find hard and tend to avoid.
It could be that we need to say something and we’re worried it might upset the other person. It could be that we need to talk about something that’s been bothering us and we feel quite strongly about it. Or it could be that we need to call something out when it would be easier not to.
Because of that, it’s very easy to either avoid those conversations or soften them.
What makes them feel hard is often the fear of how the other person might react, not being sure how we’re going to say what we need to say, and the emotions we’re feeling about it. There’s usually a bit of a trade-off in our heads between saying what we think clearly and trying to keep things comfortable.
Why conversations feel difficult
The things we think of as difficult conversations tend to have a few things in common:
- There’s some level of emotional risk. You’re aware the other person might feel upset, react badly, or that it could affect the relationship.
- There’s usually some uncertainty. You might not be completely clear on what you want to say or how to say it.
- And there’s a sense that it matters. It’s likely to have an impact on relationships, performance, or how things move forward.
Why this is harder as a manager
When you’re a manager, there are more of these types of conversations.
You’re not just dealing with your own situations anymore. You’re responsible for a team of people and for things that affect their performance, their development, and how the team is working.
Managers therefore find themselves having conversations about performance, behaviour, expectations and feedback, often with people they have good relationships with, people they like and want to support. That can make them harder to have. They know the conversation matters, but they’re also aware it might not land well if they get it wrong.
That’s often where managers get stuck. They’re trying to work out what to say, how to say it, and what might happen next. When that isn’t clear, it becomes very easy to delay the conversation or to soften it so much that the message doesn’t really land.
The problem with that is that things can look fine on the surface, but they’re not actually being addressed properly. People stay polite, issues get left, and over time frustration builds underneath. Although it can feel easier in the moment, it rarely leads to a good outcome longer term.
What actually helps
Some preparation can really help. That doesn’t mean having everything perfectly worded or feeling completely comfortable before the conversation, which isn’t realistic. But taking a bit of time to think it through does make a difference.
What tends to help is getting clear on a few simple things:
- What is the core message? What do you actually need to say? It doesn’t need to be long or detailed, but you do need to be clear on the main point before you go into the conversation.
- What are you hoping the outcome will be? Are you addressing something that isn’t working, resetting expectations, or helping someone improve? Being clear on the purpose makes it much easier to stay focused.
- What’s actually going on? It can also help to step back and think what might be behind the issue, rather than jumping straight to a conclusion.
- Can you keep it specific? Conversations tend to feel more difficult when they’re vague or feel personal. Being able to point to a clear example or behaviour helps the conversation land more clearly and feel more constructive.
Another big shift is not overthinking it beforehand. The longer a conversation is delayed, the bigger and more difficult it tends to feel. Although these conversations aren’t always easy, they are usually more manageable than expected, and often the sooner you have them, the easier they are to handle.
Why this matters
When these conversations don’t happen, the issue doesn’t go away. It tends to show up somewhere else or later on.
That might be performance issues that drag on, frustration within teams, or situations escalating further than they need to. In some cases, things end up in HR when they could have been addressed much earlier by the manager.
So although we call these difficult conversations, once you understand what’s making them feel difficult, they become more straightforward to handle, and managers are much more likely to deal with them effectively.
About the Author
Louise Puddifoot is the founder of Willow & Puddifoot, where she and her team CRAFT™ confident, capable leaders at every stage. With over 20 years’ experience in leadership and learning, Louise designs practical development that builds confidence, capability, and impact. Her work is built on the CRAFT™ Leadership Framework, focusing on communication, resilience, authenticity, future focus, and transformation, to create real behaviour change that lasts.