You have to have a difficult conversation with one of your team. You know what the problem is, you’ve drafted how to say it (and practised in the car/shower) but haven’t had it yet. Why not?
For most people, it isn’t that they don’t know what to say – they know exactly what they want to say. The real reason they put it off is because they’re afraid of making things worse.
It makes sense that we avoid things we find unpleasant – we’re only human. Telling someone they are doing something wrong, or could be doing it better, or they’re having a negative impact on their team is not pleasant. We all have different reasons for putting it off, whether gathering more data, delaying indefinitely to avoid the awkwardness, or simply hoping the behaviour will go away.
It doesn’t. It seeps into the team and erodes trust and confidence, making the conversation more difficult to have or worse, encouraging similar behaviours in others. The good news is that having these conversations is not a personality trait. It is a learnable skill.
Let’s look at three situations that come up most in my training rooms.
Picture this: someone on the team isn’t hitting the targets. You’ve been hoping it would improve, but it hasn’t.
Firstly, separate the behaviour you’ve observed from the individual. Start with curiosity, not judgement. Instead of “You’ve been X”, say “I’ve noticed X”. Before the meeting, prepare what you have observed – being specific and factual – and what outcome you are hoping for. You’re taking ownership of what you observed, rather than asking them to wear a label you’ve already decided on.
This comes up often in leadership training: someone’s attitude, tone, or behaviour is affecting the team, but it’s not breaching a policy so it’s difficult to name.
The easiest way is to relate it in a way they will understand quickly. Do they like a direct, no-fluff approach? Do they prefer you outline some of their positive traits before addressing the concern? Don’t bring others into it by saying “Other people have mentioned…” name the impact instead of the intention. “When X happens, the effect on the team is Y.” Write down what you want them to walk away understanding, not just what you want to say.
There’s been a disagreement that hasn’t been resolved, or a trust issue between two people on your team. The tendency is to jump on it quickly, or to treat a relationship issue like a performance issue.
Before resolving it, hear both parties and truly listen. They need to feel heard and have their concerns acknowledged. This is not you validating them, you’re acknowledging what they’ve told you. Ask questions you don’t think you already know the answer to, so you gain more information. Put curiosity before conclusion. If things are a bit emotional, take a pause or leave it for the day.
Here are four simple steps anyone can use:
Difficult conversations are about discomfort. Courageous conversations are about choosing to have them anyway, because the relationship, the team, or the person matters enough. The courage isn’t in the words you use, it’s in believing the relationship is strong enough to hold the conversation.
Start now. You build the conditions for courageous conversations over time, not in the moment you need to have one.
If you’d like to work on this in a practical setting, I’m running a half-day Courageous Conversations workshop in September where we put all of this into practice together.
Jo Stuart | Trainer
Explore Everest People’s training and workshops or get in touch to discuss your team’s development needs.