For many new managers, difficult conversations are the part of the role they dread (and sometimes avoid) the most.
- Giving feedback.
- Addressing underperformance.
- Naming behaviours that are not working or inappropriate...
All this can feel uncomfortable, awkward, and even risky, especially when you have recently been promoted from within the same team you were a part of before.
But avoiding difficult conversations doesn’t make problems go away, it actually makes them bigger, more emotional, and harder to resolve.
So, here are some ways to approach them with clarity and confidence.
1. Name the discomfort upfront
Simon Sinek talks about the power of signposting difficult conversations instead of launching straight into them or beating around the bush.
Something as simple as: “This is a slightly uncomfortable conversation, and my intention is to make things better, not worse.”
This does two important things:
- It lowers defensiveness.
- It signals care and respect.
When people know what’s coming and why, they are far more likely to listen rather than protect themselves.
And also, remember that your team members are not stupid, they possibly know something's up!
2. Clarify your intention before the conversation
Before you speak to the other person, be absolutely honest with yourself:
- What outcome am I hoping for?
- What behaviour do I want to change or improve?
- Am I seeking understanding, alignment, or action?
Difficult conversations usually go wrong when the message is unclear or emotionally charged. Clarifying why you are having the conversation and what you are expecting from it will help you stay grounded and focused.
3. Talk about behaviours, not personality
New managers often worry about sounding too critical or personal.
A useful rule:
- Describe what you observe (facts, not perception)
- Explain the impact
- Pause
For example:
“I have noticed deadlines have been missed in the last two projects, which has affected the wider team’s planning.” instead of "You always miss your deadlines, everyone is behind because of you".
The first one keeps the conversation factual and fair, and opens space for dialogue. The second one just triggers defensiveness.
4. Listen more than you speak and stay curious
Remember: a difficult conversation is not a monologue.
Once you have shared your perspective, create the space for the other person to talk:
- Ask open questions
- Resist the urge to jump in with solutions
- Stay curious, even if you disagree
Usually, what we feel like resistance in others is actually misunderstanding, pressure, or lack of clarity.
Listen to their side of their story without planning what to say next. Just listen. Seriously.
Once you have all the facts from their side you can discuss a potential solution that works for everyone.
5. Remember: avoiding the conversation is still a choice
Not having the dreaded conversation sends a message too, just not the one you want.
When issues are not addressed:
- Resentment builds
- Standards slip
- Trust erodes quietly
Leadership is not about being comfortable. It’s about being responsible, even when it feels awkward.
Not addressing an issue will also make it get out of control, and the team members who are actually performing will see that there are no consequences underperformance or inappropriate behaviour.
Difficult conversations don’t get easier because you have been a manager for longer.
They get easier because you practice having them with honesty, respect, and intention.
If you’re feeling uncomfortable about a conversation you know you need to have, that’s often your signal that it matters.
And that’s exactly why it’s worth doing.
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