Handling difficult conversations: How line managers can move things forward with kindness and clarity
Difficult conversations are part and parcel of managing people – whether it’s enforcing adherence to organisational policies or dealing with poor performance, it’s the well-trodden, familiar path for many managers. But not all of them feel comfortable having those conversations – this might be due to a lack of confidence, skills or concern about how someone may react – whatever the reason, it can be a daunting task for many. Done badly, these conversations damage trust and morale. Done early and well, they can preserve relationships and prevent bigger problems later.
The truth is, no one likes having these conversations. Even experienced managers feel the nerves. Research from the Chartered Management Institute found that:
- 66% of people feel stressed or anxious if they know a difficult conversation is coming.
- 57% would do almost anything to avoid it.
- 52% of managers said they’d rather “put up with” a negative situation than talk about it.
- 43% admitted they’d lost their temper during one.
- 40% even confessed to panicking and telling a lie.
So why is it so tricky? Because conversations touch people’s identity, expectations, and trust. And because most of us aren’t taught how to do it well. But avoiding the conversation only makes things worse: silence lets issues fester, performance slide, and relationships fracture.
A mindset shift
Difficult conversations don’t have to mean conflict. They can mean clarity, accountability, and even trust – when approached through the lens of kind leadership.
A kind leader isn’t soft. They are purposeful, compassionate and clear. Here are some principles to hold in mind:
- Active listening and open communication — listening to understand, not just replying.
- Authenticity and vulnerability — admitting when you don’t have all the answers.
- Recognition and appreciation — acknowledging effort as well as outcomes.
- Empathy and curiosity — seeking to understand the “why” behind behaviour.
- Accountability with compassion — high standards delivered kindly and clearly.
- Inclusive decision-making — involving people where possible, which builds buy-in.
- Growth mindset — creating space for learning and improvement.
A structure you can actually use
Preparation and structure make conversations less daunting:
- Prepare the facts — What exactly happened? Gather examples. Write notes.
- Arrange the meeting properly — private space, give notice (“Can we talk tomorrow about X?”), avoid both ambush and weeks of anxious waiting.
- Open with purpose — “Thanks for meeting. I want to talk about X so we can get this right.”
- Set out the issue with examples — stick to facts and impact: “The report was two days late, which delayed Y.”
- Invite their perspective — open questions, then listen actively.
- Work the way forward together — co-create solutions: “What support do you need to make this work?”
- Close with clarity — agree actions, timescales, and follow up in writing.
A note on the feedback sandwich: it can feel contrived. Use it only if the positives you share are genuine. Otherwise, aim for direct, kind clarity.
How to handle those tricky moments
Of course, even the most well-prepared and structured conversations don’t always go to plan. If it looks like the conversation isn’t going to plan, here are some useful prompts to get you back on track:
If someone gets defensive, say to them “I can see this is difficult. My intention is to help us get back on track. I want to hear your view so we can solve this together.”
If they go quiet, you can say “I notice you’ve gone quiet — that’s okay, take a moment. I want to make sure I understand your perspective.”
If they deflect blame, reply with : “Thanks, I hear that. From my side the impact has been X. Help me understand what stopped you from meeting the expectation.”
The role of policies and support
Don’t forget the scaffolding around you:
- Be familiar with your organisation’s policies – they exist to guide you and protect everyone involved.
- Your line manager and HR contacts are there for support, especially as situations escalate or grow complex.
- Don’t be afraid to rehearse with a peer or manager beforehand. Preparation is not weakness – it’s professionalism.
