How to handle difficult conversations at work
Updated: Jul 12
Most people avoid difficult conversations.
They delay them, soften them, or hope the issue resolves itself.
In the short term, that can feel easier. In the long term, it usually makes things worse.
The reality is that difficult conversations are a normal part of working life. And handled well, they often lead to better outcomes - not worse ones.
Why difficult conversations feel so hard
There’s usually a fear lurking underneath:
Saying the wrong thing
Damaging the relationship
Creating conflict
Losing control of the conversation
So instead of addressing the issue directly, we hesitate. Or we overthink what to say.
Neither helps.
A personal example of getting it wrong
I’ve made this mistake myself.
At one point, I had someone in my team who was unreliable. Deadlines were missed, communication wasn’t consistent, and it was affecting the work.
I knew the conversation needed to happen, but I delayed it.
Partly because I didn’t want to create tension. Partly because I wasn’t sure how to handle it well.
When I did, eventually, raise it, I didn’t approach it clearly.
At one point, I used the word ‘flakey’ in my feedback. It was part a vague comment and, understandably, it caused offence.
Looking back, the issue wasn’t just the message - it was how I handled it.
I hadn’t been clear. I hadn’t focused on specific behaviours early enough. And by the time I addressed it, the conversation carried far more weight than it needed to.
Ultimately, the situation didn’t improve, and we had to make a change.
It was a hard, but useful, lesson.
Avoiding the conversation didn’t make it easier - it made it more difficult. And handling it without clarity made it much less constructive than it could have been.
That experience shaped how I approach difficult conversations now.
What happens when you avoid them
Avoiding difficult conversations doesn’t remove the problem.
It tends to:
allow issues to build
create frustration (on both sides)
reduces trust over time
dilutes mutual respect
In many cases, the need for the difficult conversation doesn't go away and it becomes harder simply because it was delayed.
What good difficult conversations look like
Handled well, they are:
clear
direct
calm
and focused on the issue or the behaviour, not the person
They’re not aggressive. And they’re not overly softened either.
They’re simply honest and constructive.
How to handle difficult conversations at work
1. Be clear on the outcome
Before the conversation, ask yourself:
‘What needs to change?’
Not, for example:
‘I want this to go well’
Rather:
‘I want deadlines to be met’
‘I want clearer communication going forward’
Brené Brown puts it well 'Clear is kind. Unclear in unkind'.
Clarity reduces uncertainty.
2. Start directly
Like a Buzzard, high in the sky, many people circle the issue.
This creates confusion and even defensiveness.
Instead, say:
‘I wanted to talk about the last two deadlines and what the challenges have been in meeting them’
Clear. Calm. Direct.
3. Focus on facts, not judgement
Avoid generalisations:
‘You’re unreliable’
‘You don’t come across as committed’
Use specifics:
‘The last two deadlines were missed’
‘The report came in two days late’
Facts are easier to discuss and resolve and less likely to provoke an emotional reaction.
4. Keep it simple
There’s a limit to how much people can process at once. If you include too many points, the conversation becomes harder to follow.
Focus on one or two key issues at a time.
5. Listen (properly)
A difficult conversation isn’t just about saying your piece. It’s about understanding the other person’s perspective.
Let them respond in full. Don’t interrupt.
You may learn something useful that will alter your perspective.
6. Stay calm, especially if they don’t
Emotions can rise in these conversations.
If that happens, remind yourself to:
slow your pace
keep your tone steady
stay focused on the facts and the point
Your composure generates respect and helps keep the conversation constructive.
7. Agree on what happens next
Don’t end with a vague agreement.
Again, be specific:
What will change?
And by when?
What does success looks like?
Clarity prevents the same issue repeating.
7 common mistakes to avoid
❌ delaying the conversation too long
❌ over-softening the message
❌ raising your voice and losing composure
❌ bringing up too many things at once
❌ focusing on personality instead of behaviour
❌ avoiding the conversation entirely
These tend to make things harder, not easier.
In conclusion...
Difficult conversations aren’t a sign that something is wrong.
They’re a normal part of working with other people. Therefore, they're an essential communication skill.
Handled well, they improve clarity, strengthen relationships, and build trust.
Handled clumsily, or avoided, they risk doing the opposite.
P.S. If you want to handle difficult conversations at work with more clarity and confidence communication coaching for professionals can help you approach these situations more effectively.
You can contact me here to book a free, relaxed, confidential conversation.
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