Navigating tricky conversations

Tricky conversations are an unavoidable part of being a manager. Whether it's giving constructive feedback, addressing performance issues, discussing personal hygiene or handling conflicts, these discussions can be uncomfortable but are critical for a healthy, productive workplace.

Unfortunately, avoiding these conversations can lead to problems, declining morale and even attrition. Here’s how managers can tackle them with confidence, empathy and professionalism.

1. Prepare, don’t wing it

Walking into a tricky conversation without preparation is risky. Managers should:

• Clarify the objective: What’s the purpose of the conversation? Be specific.

• Gather facts: Avoid relying solely on opinions or hearsay.

• Anticipate reactions: Think through how the employee might respond and plan accordingly.

Tip: Jot down key points but avoid scripting the whole conversation, it should be a dialogue, not a monologue.

2. Choose the right time and setting

Timing and privacy are critical. Don't spring a sensitive conversation on an employee in the middle of a team lunch or right before a weekend. Instead:

• Schedule a private meeting with sufficient time.

• Ensure you're both in a calm, distraction-free environment.

Tricky conversations often go better earlier in the day when mental energy is higher.

3. Lead with empathy and curiosity

Approach the conversation with the intent to understand, not just to correct.

• Use open-ended questions , “Can you help me understand…”

• Listen actively and without judgment.

• Validate emotions without necessarily agreeing.

Instead of saying, “You’ve been slacking lately,” try, “I’ve noticed some deadlines have been missed, what’s going on from your perspective?”

4. Be direct, not harsh

Managers often err on the side of vagueness to avoid discomfort, but unclear messages only prolong issues.

• Use clear, respectful language.

• Focus on behaviour, not personality.

• Stick to facts, not assumptions.

Say: “I’ve noticed a number of errors in your reports lately,” not “You’re careless.”

5. Don’t skip accountability

Empathy doesn’t mean avoiding tough truths. If there’s a performance issue be clear about expectations and consequences.

• Define next steps.

• Set a timeline for follow-up.

• Document the conversation if appropriate.

6. Follow up

One conversation is rarely the end. Check in afterwards, especially if the discussion involved a performance plan or behaviour change.

• Offer support and resources.

• Acknowledge improvements.

• Continue the dialogue.

7. Leverage HR when needed

Not all difficult conversations should be handled solo. HR can:

• Provide coaching and support for sensitive topics.

• Mediate conflicts.

• Ensure legal and policy compliance.

Proactive collaboration with HR helps managers stay aligned with best practices and reduces risk.

Final thoughts

Avoiding tricky conversations rarely makes them go away. With preparation, empathy and clarity, managers can handle difficult discussions in a way that fosters trust, drives improvement and builds stronger teams.

Encourage a culture where feedback is normal

If feedback, positive or constructive, is part of the everyday culture, these conversations become less daunting for everyone involved.

Can we help you?

If you need any support in these types of matters or anything else HR related,  why not talk to us 

Please contact us – we’d love to hear from you.