Most new managers are not underprepared on strategy or goal-setting. They are underprepared for conversations — the performance discussion that has been put off for weeks, the conflict between two team members that is getting worse, the moment when you have to tell someone their behaviour is not acceptable. These conversations matter enormously, they feel disproportionately hard and they are entirely learnable. This guide gives you a framework for approaching them.
Why difficult conversations are worth getting right
Avoiding difficult conversations is understandable. They are uncomfortable, the outcome is uncertain and the risk of making things worse feels real. But the cost of avoidance is almost always higher than the cost of the conversation itself. Problems that are not addressed early tend to compound — a minor performance gap becomes an established pattern, a team tension becomes an entrenched conflict, a boundary that was never set becomes a precedent that is hard to reverse.
Done well, these conversations do something else too: they build trust. When your team sees that you will address difficult things directly, fairly and with care for the person involved, they trust you more — not less. The manager who consistently avoids hard conversations sends a different signal: that fairness is not reliable and that poor performance has no real consequences.
1. Prepare — but not by scripting
The most common preparation mistake is trying to script the conversation — rehearsing lines, anticipating every possible response, treating it like a performance. This produces conversations that feel stiff and one-directional, and falls apart the moment the other person says something unexpected. Effective preparation is different: it is about clarity, not control.
Before any difficult conversation, get clear on three things:
- What is the specific issue? Be precise. "Your performance has been disappointing" is not a starting point — it is an accusation. "The last three project reports missed the agreed deadline and were submitted without the analysis section" is a starting point.
- What outcome do you want? Are you trying to change a behaviour, resolve a conflict, deliver news, set a boundary? Knowing the destination helps you navigate when the conversation goes in unexpected directions.
- What might the other person's perspective be? Thinking through how the situation might look from their side does not mean agreeing with it — it means you will not be blindsided by it, and you will be less likely to dismiss it reflexively.
Choose the setting deliberately. A difficult conversation needs privacy, enough time and no interruptions. Not a corridor, not just before a meeting, not while either of you is visibly stressed. If you need to, schedule it — "I'd like us to find 30 minutes this week to discuss something important" is better than a spontaneous conversation that catches the other person off guard.
2. Open with clarity, not preamble
New managers often spend the first several minutes of a difficult conversation easing in — complimenting the person, discussing unrelated topics, softening the ground before getting to the point. This is well-intentioned and usually counterproductive. The other person can tell something is coming, the waiting creates anxiety and the actual conversation feels less, not more, comfortable by the time you reach it.
A clear, kind opening works better: "I want to talk about something I've been noticing in how the team meetings have been running" or "I need to have a conversation with you about your deadline on the last project." Direct, but not cold. It signals respect for the other person's time and intelligence.
State the issue specifically, then stop and create space for the other person to respond before you say anything else. Many managers state the issue and then keep talking — filling the silence, explaining, qualifying — which closes down the very dialogue they are trying to open. State it. Then wait.
3. Listen — actually listen
The quality of listening in difficult conversations is almost always worse than it feels from the inside. When we are in a high-stakes conversation, we are simultaneously managing our own emotions, thinking about what we want to say next, and evaluating what we are hearing against our own position. Genuine listening requires setting most of that aside and focusing entirely on understanding the other person's experience of the situation.
What active listening looks like in practice:
- Give your full physical attention — no phone, no glancing at your screen
- Let the person finish before you respond — do not formulate your reply while they are still speaking
- Reflect back what you have heard: "So what I'm hearing is that you felt the deadline wasn't realistic given the other priorities you had that week — is that right?"
- Ask clarifying questions rather than counter-arguments: "Can you tell me more about what was going on at that point?"
If you find yourself thinking about your response while the other person is still speaking, that is a signal you have stopped listening. Notice it and refocus. The discipline of waiting until they have genuinely finished — including the pauses, which are often where the most important things emerge — changes the quality of these conversations significantly.
Difficult conversations are a core skill in the LeadWise Emerging Leaders Program. Week 5 covers communication and conflict resolution in depth — with practical exercises you apply directly with your team.
Explore the program — €2994. Manage your own emotional response
In difficult conversations, your emotional state is contagious. If you are visibly anxious, the other person becomes anxious. If you become frustrated or defensive, the conversation escalates. Your ability to remain regulated — calm without being cold, engaged without being reactive — is one of the most important things you bring to these situations as a manager.
This is not about suppressing emotion. It is about not being governed by it. The practical techniques are straightforward: slow your breathing before and during the conversation, give yourself a beat before responding to anything that provokes a strong reaction, and if the conversation becomes too heated, name it directly: "I think we're both getting a bit heated here. Can we take a few minutes and come back to this?"
If you receive something unexpected — a piece of information that changes the picture, or a response that provokes a strong reaction — it is always acceptable to say "I want to take a moment to think about that" before responding. This is not weakness. It is the kind of considered judgement that distinguishes effective managers from reactive ones.
5. Give feedback using the SBI framework
When the difficult conversation involves feedback on specific behaviour, the SBI model provides a structure that keeps the conversation objective and actionable:
The power of this model is that it separates fact from interpretation. You are describing what happened and what it caused, not judging the person's character or assuming their motives. This makes the feedback far easier to receive and far more likely to produce change.
After stating the SBI, move to what you want to see differently — and invite the other person to be part of identifying how. "What would make it easier to let others finish before responding?" is more productive than "You need to stop interrupting people."
Write out the SBI before a feedback conversation. The act of articulating the Behaviour specifically — not "you're not engaged" but "you haven't contributed to the last four team meetings" — often reveals whether you have concrete enough observations to have the conversation yet, or whether you need to gather more specific examples first.
6. Mediating conflict between team members
When the difficult conversation is not with one person but between two people in your team, your role changes from participant to facilitator. Your job is not to adjudicate — to determine who is right — but to help both parties understand each other's perspective and find a resolution they can both work with.
The structure that works most reliably:
- Speak to each person separately first. Understand both perspectives before bringing them together, and make clear to each person that you are doing the same with the other.
- When you bring them together, establish the ground rules: each person speaks without interruption, the goal is resolution not winning, and the conversation stays focused on the working relationship going forward rather than relitigating the past.
- Look for the underlying interest beneath the stated position. Two people arguing about whose idea to use are often both trying to feel valued and heard. Finding that common ground is usually where resolution lives.
Resist the pull to take sides, even subtly. Your team will be watching how you handle this — and if they perceive that your outcomes are influenced by who you have more rapport with, it damages trust across the whole team, not just with the parties involved.
7. Follow through after the conversation
A difficult conversation without follow-through is a conversation that did not fully land. A brief written summary — sent the same day — confirms what was discussed, what was agreed and what the next steps are. This is not bureaucratic: it protects both parties by ensuring there is no ambiguity about what was said, and it signals that the conversation mattered enough to act on.
Then check in at the agreed point. Did the change happen? Does the person need additional support? Has the conflict actually resolved, or has it just gone quiet? Following through consistently is what distinguishes managers who have difficult conversations from managers whose difficult conversations produce lasting change.
Keep your follow-up email short — three to five sentences summarising what was discussed, what was agreed and when you will next check in. Longer than that tends to feel like a formal record rather than a supportive communication, which changes the tone of the relationship in the wrong direction.
The bottom line
Difficult conversations do not get easier because they become less uncomfortable. They get easier because you become more confident in your ability to handle the discomfort — and because you have enough experience of them going reasonably well to trust that they will not automatically go badly.
The managers who are best at difficult conversations are not those who find them easy. They are those who have learned to prepare thoughtfully, listen genuinely, manage their own emotional response and focus consistently on the outcome rather than on their own anxiety about the process. Those are learnable skills, and they improve with every conversation you have.