Challenging conversations remain one of the toughest responsibilities managers face. In fact, nearly half of managers say difficult conversations are their biggest leadership challenge — and HR teams agree, reporting that only a small proportion of managers feel genuinely confident addressing sensitive issues.

It’s no surprise, then, that many leaders choose to delay or avoid these conversations altogether. But avoidance sends a message: that the behaviour, performance issue, or misunderstanding is acceptable. As leaders, our role is to uphold standards, protect the culture, and support people in achieving their best. Addressing issues early — and well — strengthens our leadership credibility.

Reframe the Conversation First

The most powerful step starts in your own mind. A conversation is only “difficult” if we label it that way. Instead, consider reframing it as necessary, clarifying, defining, constructive, or even overdue.
Seeing the conversation as an opportunity — to resolve something, to reset expectations, or to rebuild trust — shifts your approach and your emotional tone.

Remember: giving feedback is not about reprimanding someone. It’s about helping them get back on track so they can succeed.

And importantly, never attempt corrective feedback when you’re still frustrated, angry, or emotionally charged.

Before You Begin, Ask Yourself:

• Do I have all the facts?

• Have I contributed in any way to this situation?

• Was the information or expectation clear?

• Was training or support sufficient?

• Is this person carrying an unusually heavy workload?

• Is anything else going on in their world?

• Where will this conversation take place? (Always choose a private space.)

• Have I set aside dedicated, interruption-free time?

If meeting online, avoid multitasking — no typing, no checking emails, no glancing at notifications. Presence communicates respect.

Unless the issue is truly severe, go in with the belief that the other person can change.

During the Conversation

1. Start with praise, end with encouragement

A balanced opening helps the other person feel seen, not judged. Ending on a positive note reinforces their ability to improve.

2. Put feedback into context

Remind them of what they already do well. Highlighting strengths reduces defensiveness and helps them engage constructively.

3. Choose language that de-escalates, not provokes

Phrases like “I need you to…” or “With all due respect…” can feel confrontational. Alternatives include:

• “Let’s go over…”

• “Let’s look at how we can…”

• “Possibly you could…”

• “Understanding different perspectives…”

These open the door to collaboration rather than conflict.

4. Address mistakes with empathy

Help them ‘save face’. This preserves dignity and keeps the conversation productive.

5. Show your own vulnerability

Share a time you made a mistake — it humanises you and reinforces that growth is a natural part of development.

6. Make it a conversation, not a lecture

Ask questions, coach, and let them do most of the talking.

7. Use guided open questions

These help the individual reach their own conclusions, reducing the risk you become “the bad guy.”

8. Encourage them to propose solutions

Ask what they might do differently next time. This builds ownership and accountability.

9. Offer support — without taking the responsibility away

Instead of asking “How can I help?”, try:

• “What support do you need to move forward?”

• “What resources would make this easier for you?”

10. Use feedforward, not just feedback

Feedback reflects the past. Feedforward focuses on future actions and possibilities — and is far more motivating.

11. Close with appreciation and confidence in their commitment

Give them a positive reputation to live up to.

 

And Finally… Always Invest in Trust