As a leader, addressing performance issues is part and parcel of the role. Often, these are handled through regular feedback and open dialogue. However, there are times when communication breaks down, and you’re faced with a challenging or awkward situation – perhaps a team member is underperforming or causing disruption within the team.
Even with prior 1:1 conversations or feedback, progress may be minimal. Tension may rise, and the relationship may feel strained. This guide is here to help you navigate such moments effectively and constructively.
Top Tips for Handling Difficult Conversations
Follow this five-step approach:
- Reflect on the situation
- Prepare for the conversation
- Decide how you will initiate the conversation
- Choose the right language
- Plan all aspects of the meeting
What Creates a Difficult Conversation?
Difficult conversations often arise from poor communication and unspoken assumptions. Team members may sense their performance is lacking and feel uncomfortable addressing it. As a leader, it’s vital to remain objective – avoid speculation and focus on facts.
These conversations are frequently avoided due to the discomfort they bring. However, they’re an essential part of effective leadership. When approached with empathy, clarity, and assertiveness, they offer a real opportunity to build trust and move forward.
Step 1 – Reflect on the Situation
- Who do I want to improve my working relationship with?
- What’s the core issue?
- Why have the conversation – what’s the benefit?
- What do I want to achieve?
- What’s my communication style (direct/indirect)?
Step 2 – Prepare for the Conversation
Before speaking with the person, clarify your own thinking and emotional triggers. This preparation helps ensure a balanced, productive discussion.
- Why is this conversation hard for me?
- What am I afraid might happen?
- What’s the cost of avoiding it?
- How have I contributed to the issue?
- Am I making assumptions?
- What’s the key purpose and desired outcome?
Step 3 – Initiate the Conversation
**Scenario Example:**
Imagine you have a high-performing team member who has recently missed deadlines. Rather than starting with criticism, you could say: “I’ve noticed a few missed deadlines recently and wanted to check in with you about how things are going.” This invites their perspective while signalling a desire to support.
- Set the stage – Choose a private, neutral setting and agree mutual expectations for the conversation.
- Use a collaborative introduction – Start by acknowledging the importance of your mutual objectives.
- Invite dialogue – Ask curious and non-leading questions and genuinely listen to their perspective.
- Seek shared solutions – Work together to identify positive outcomes, even if you agree to disagree.
Step 4 – Choose the Right Language
Language can either defuse or escalate tension. Avoid blame, absolutes, or generalisations.
Use ‘I’ statements, describe behaviour (not personality), and explain impact.
- ‘Why can’t you…’ → ‘What if we…’
- ‘You always…’ → ‘I’ve noticed you often…’
- ‘Nothing ever works’ → ‘We’ve had some challenges…’
Step 5 – During the Meeting
- Set the tone with a collaborative approach.
- Agree on objectives and a structure for the discussion.
- Start with their view – listen actively and summarise.
- Share your perspective honestly, focusing on behaviour not character.
- Keep sight of the purpose – what are we both trying to achieve from this discussion? and agree next steps.
- Conclude on a constructive note – express appreciation for the conversation and agree on next steps or a follow-up.
In Summary
Difficult conversations are an inevitable part of leadership, but when approached with clarity, empathy and preparation, they become powerful opportunities for growth, understanding, and improved team dynamics. With the right mindset and practical tools, these conversations can strengthen relationships and drive positive change.
If you are looking for support with navigating difficult conversations, we can help. Get in touch with us here.
