How to Have Difficult Conversations as a Manager at Work (Without Making Things Worse)
- Mark Baglow
- 6 hours ago
- 7 min read
There’s a conversation you need to have.
You’ve known it for a while.
Maybe it’s about someone’s performance.
Maybe it’s a conflict between two team members.
Maybe it’s telling someone something they really don’t want to hear.
And yet, somehow, it never happens.
You find reasons to delay. You tell yourself the timing isn’t right, or that maybe the problem will resolve itself. You rehearse it in your head but never quite get round to having it for real.
If this sounds familiar, you’re in very good company.
Avoiding difficult conversations is one of the most common challenges I see in the management training I deliver – and it’s one of the most damaging.
Not because managers don’t care, but because by the time they finally have the conversation, what started as a small issue has become a much bigger one.
The good news is that having difficult conversations well is a skill, not a personality trait.
You don’t need to be naturally confrontational.
You just need a practical approach and the confidence that comes from knowing what you’re doing.
Why Managers Avoid Difficult Conversations
Let’s start with some honesty about why these conversations get put off.
It’s rarely because managers don’t know there’s a problem. Usually, they’re well aware. The avoidance comes from somewhere else entirely.
Fear of conflict Most people don’t enjoy confrontation, and there’s a natural anxiety that raising an issue will lead to an argument, tears, or a damaged relationship. The conversation plays out badly in our heads before we’ve even had it. |
Wanting to be liked This is especially common for new managers who are now leading people who were recently their peers. There’s a real tension between being a fair, supportive manager and being the person who has to tell someone their work isn’t good enough. |
Hoping it sorts itself out This is the most seductive trap of all, because occasionally things do sort themselves out. But far more often, they don’t. What actually happens is the problem continues, the manager’s frustration builds silently, and when the conversation finally does happen, it comes loaded with weeks or months of accumulated resentment. |
Not knowing how And this is the one that gets overlooked most often. Many managers avoid difficult conversations not because they’re afraid, but because they genuinely don’t know how to structure one. Nobody taught them. So the whole thing feels like a leap into the unknown, and it’s easier to just... not. |
If you’ve read my earlier post on the 5 mistakes nearly every new manager makes you’ll know that avoiding difficult conversations was one of the top five.
It’s that common – and that important to get right.
What Happens When Managers and Leaders Don’t Have Difficult Conversations
The cost of avoiding a difficult conversation is almost always higher than the cost of having it badly.
When a performance issue goes unaddressed, the person doesn’t get the chance to improve.
They might not even know there’s a problem.
Meanwhile, the rest of the team can see what’s happening, and they start to wonder why you’re not dealing with it.
High performers don’t want to work in a team where poor performance is tolerated.
When a conflict between colleagues is left to fester, it rarely stays contained.
It starts affecting communication, collaboration, and eventually the broader team culture.
What could have been a ten-minute conversation becomes a months-long situation that drains everyone’s energy.
And when feedback is withheld – even with good intentions – the person on the receiving end is denied the information they need to grow.
That isn't kindness. It’s a disservice.
The pattern is almost always the same: the longer you leave it, the harder it gets, and the worse the outcome.
Related Training If this topic is relevant for you or your team, these courses may also help: Leadership & Management Skills - One-Day or Two-Days Performance Management and Motivation Emotional Intelligence for Leaders Personal Effectiveness and Time Management Training Digital Skills in AI, Microsoft Excel and Microsoft Office |
A Practical Framework for Having Difficult Conversations
The reason difficult conversations feel so daunting is that most people go into them without a structure.
They’re winging it, hoping they’ll find the right words in the moment.
Sometimes they do. Often they don’t.
Here’s my straightforward five-step approach on how to have difficult conversations at work.
It won’t make every conversation easy, but it will make it manageable.
💡 Top Tip This framework also works brilliantly for giving positive feedback and praise. If your praise is always just "Good job" or "Well done", it might feel nice but it doesn't mean very much. Be specific in your praise - what did they do well, what the impact on the team/organisation/client, and what should they do more of in the future. |
1. Prepare properly
Before you have the conversation, get clear on three things: what specifically have you observed (facts, not feelings), what’s the impact (on the team, the work, or the person themselves), and what outcome are you hoping for?
Don’t script it word for word – that makes you sound robotic – but know your key points so you don’t lose track when emotions come into play.
2. Describe what you’ve observed
Start the conversation by stating what you’ve noticed, using specific examples.
Not “your attitude has been poor lately” (vague and judgmental), but “I’ve noticed you’ve missed the last three team meetings without letting anyone know in advance.”
Keep it factual. Facts are hard to argue with.
3. Explain the impact
Connect the behaviour to its consequences. “When that happens, the rest of the team has to cover your updates and it’s affecting how the project is tracking.”
This isn’t about blame – it’s about helping the person understand why the issue matters.
People are much more likely to change when they understand the impact of their behaviour, not just the behaviour itself.
Sometimes people simply aren't aware of the impact of their actions - your job is to make it clear to them.
4. Listen
This is the step most people skip, and it’s the most important.
After you’ve said your piece, stop talking and genuinely listen.
Ask: “What’s going on from your side?” or “How do you see this?”
You might discover context you didn’t have.
They might be dealing with something you weren’t aware of. Or they might just need a moment to process.
Either way, the conversation becomes a dialogue rather than a lecture, and that makes a huge difference to how it’s received.
5. Agree next steps together
End the conversation with a clear, shared understanding of what happens next.
What’s going to change?
By when?
How will you both know it’s working?
And when will you check in again?
This turns the conversation from a one-off event into the start of a process.
It also gives both of you something concrete to hold onto.
Common Mistakes to Avoid
Even with a good framework, there are some traps that are worth being aware of.
❌ The ambush
Pulling someone into a meeting room with no warning and launching straight into a serious conversation is a recipe for defensiveness.
If the conversation is significant, give the person a heads-up.
Something as simple as “I’d like to have a chat about how things are going – can we find 20 minutes this afternoon?” gives them time to prepare mentally.
❌ Being too vague
Saying “I just feel like things could be better” or “there have been some concerns” doesn’t give the person anything to work with.
Be specific about what you’ve observed and what needs to change.
Vague feedback produces vague results.
❌ Doing it by email
It’s tempting because it feels safer, but important conversations deserve to be had face to face (or at least on a video call).
Tone is almost impossible to read in text, and you lose the ability to listen, respond to body language, and adjust your approach in the moment.
❌ The feedback sandwich
You’ve probably heard this one: start with something positive, deliver the criticism, end with something positive.
The problem is that everyone knows the formula, so it doesn’t work.
People just sit through the first compliment waiting for the “but...”
Give praise and then stop. Don't always follow up with critical feedback.
❌ Making it personal
There’s a world of difference between “you’re unreliable” and “the last three deadlines were missed.”
One is a character judgement. The other is an observation about behaviour.
Always focus on what the person does, not who they are. Behaviour can change.
Character labels just make people defensive.
The Mindset Shift
Here’s the thing that changes everything once you really internalise it: having a difficult conversation is not an act of aggression.
It’s an act of respect.
When you address an issue early, you’re giving someone the information they need to do better. When you have an honest conversation about performance, you’re treating someone like an adult who can handle the truth. When you tackle a conflict rather than ignoring it, you’re showing your team that you care enough to deal with things properly.
The managers who are best at difficult conversations aren’t the ones who enjoy them.
They’re the ones who’ve learned that avoiding them causes more harm than having them ever could.
They’ve made peace with the discomfort and developed the skill to do it well.
That’s a skill anyone can learn.
Next Steps
If you’d like to build your confidence in having difficult conversations – along with other essential management skills like delegation, motivation, and giving feedback – take a look at my leadership and management training courses.
Training is available both as public courses and as face-to-face training delivered in-house for your organisation.
There is a one-day leadership and management course which covers the essential skills, and a two-day version for in-house delivery where we explore in greater depth.
To learn more about my training and how I can help or your team, send me a message.
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