How to Have Difficult Conversations with Staff

Let’s be honest: no one enjoys difficult conversations. Whether it’s about poor performance, lateness, or team conflict, these chats can feel awkward, emotional, and downright uncomfortable.

But here’s the thing - avoiding them doesn’t make the issue go away. In fact, it usually makes things worse. And for small businesses, where every person impacts the culture and bottom line, unresolved problems can quietly (and quickly) cost you time, money, and morale.

So let’s take the fear out of these conversations and walk through how to handle them with confidence - and care.

Why Difficult Conversations Matter

It might feel easier to “let it slide” or “hope it improves,” but when small issues are left unaddressed, they:

• Turn into bigger performance or behaviour problems

• Impact other team members (especially high performers)

• Create resentment, confusion, or even legal risk

Having the hard conversations early and well can actually build trust, set clear expectations, and create a healthier work environment.

5 Steps to a Better (and Legally Safer) Difficult Conversation

1. Get Clear on the Issue

Don’t go in vague. Be specific about what’s happening, how it’s impacting the business or team, and what needs to change.

✔️ Example: Instead of “You’ve been a bit off lately,” say: “I’ve noticed you’ve been arriving 15–20 minutes late three times this week, which has caused a backlog at the front desk.”

2. Plan the Conversation, But Stay Open

Write down key points. Know your facts. But don’t script it word-for-word — it’s a conversation, not a confrontation. Be prepared to listen to their side, too.

3. Stay Calm and Curious

Keep your tone neutral and professional. Focus on behaviours, not personalities. Use open-ended questions like:

• “Can you help me understand what’s been going on?”

• “Is there anything getting in the way of your performance?”

4. Be Clear About Next Steps

Discuss what change is needed, how you’ll support it, and what the follow-up will look like. Document the discussion, even if it’s informal.

🔍 If it’s a formal performance issue, use a written warning or performance improvement plan (PIP) — ideally with HR guidance.

5. Follow Through

One conversation won’t fix everything. Check in regularly, offer support, and stay consistent with expectations and boundaries.

Common Tricky Topics (and How HR Can Help)

✖️ Lateness or absenteeism

✖️ Poor performance or customer complaints

✖️ Interpersonal conflict or negative attitude

✖️ Inappropriate behaviour or policy breaches

✖️ Mental health or personal challenges impacting work

Each of these requires sensitivity and compliance. That’s where HR support is invaluable - making sure you handle it in a way that’s legally safe, fair, and human.

You Don’t Have to Do This Alone

If you’re dreading a tough conversation or worried about saying the wrong thing, I’m here to help. Whether you need a script, sounding board, or help putting together the right documentation - I’ve got you.

📩 Book a free 15-minute discovery call or check out my HR Advisory Services for on-demand support when you need it most.