How to Have Tough Work Conversations (Without the Anxiety)

Difficult conversations are part of the job.

~ Telling an underperforming team member they need to step up.

~ Mediating conflict between two members of your team.

~ Addressing a tough situation with a senior stakeholder.

~ Owning a mistake with a demanding client.

These conversations can’t be avoided, but that doesn’t stop the dread.

Your heart races. You rehearse what to say (and then rethink it five times). You imagine every possible bad reaction. And sometimes… you put it off altogether.

But avoiding it only makes things worse. The issue lingers, relationships become strained, and the tension builds.

Why Difficult Conversations Feel So Hard

It’s not just about the words you say, it’s about the emotions attached to them.

~ Fear of confrontation – you worry about pushback, defensiveness, or damaging the relationship.

~ Uncertainty about how to phrase it – you don’t want to come across as too harsh, or too soft.

~ Anxiety about how they’ll react – will they take it personally? Will they get angry? Will they shut down?

~ Your own discomfort with conflict – if you’re someone who prefers to keep the peace, these conversations feel even harder.

The 4-Part Framework for Any Difficult Conversation

1. Prepare, but Don’t Overprepare

~ Know your key point. What is the main issue you need to address? Stick to the facts, not emotions.

~ Clarify the outcome you want. Are you giving feedback? Asking for a change? Setting a boundary? Be clear on your goal.

~ Don’t script it. A general outline is helpful, but over-preparing makes you sound robotic. Stay flexible in the conversation.

👉 Example for an underperforming team member:“I wanted to check in on your recent project work. I’ve noticed some missed deadlines and quality concerns, and I want to understand what’s going on.”

2. Lead with Clarity and Neutrality

The way you start the conversation sets the tone.

Don’t: “You’re not pulling your weight, and this isn’t working.”

Do: “I want to talk about [specific issue] because I want to find a way forward that works for both of us.”

~ Be factual, not emotional. Instead of “You’re always late with reports,” say: “I’ve noticed the last three reports have been delayed. Let’s talk about why.”

~ Use "I" statements. Instead of “You need to fix this”, say “I want to make sure we’re aligned on expectations.”

~ Stay calm and measured. If you stay calm, they’re more likely to respond constructively.

👉 Example for resolving conflict between two team members:“I know there’s been tension between you both, and I want to understand what’s happening so we can work towards a solution.”

3. Listen More Than You Speak

A difficult conversation isn’t just about getting your point across, it’s also about listening to and understanding the other person’s perspective.

~ Ask open-ended questions. “Can you share what’s been challenging for you?”

~ Pause after speaking. Give them space to respond—don’t rush to fill the silence.

~ Show that you’re listening. Repeat back key points: “So what I’m hearing is that you’re feeling overwhelmed with your workload?”

👉 Example for a challenging conversation with a senior stakeholder:“I know this project is high-priority, and I want to flag some challenges that could impact delivery. How do you see us navigating this?”

4. Move to a Clear Next Step

The conversation shouldn’t end in uncertainty—there needs to be a clear resolution or action.

~ Agree on what happens next. What needs to change? What support is needed? What’s the next step?

~ Summarise the outcome. “So moving forward, we’ll check in weekly to make sure deadlines stay on track.”

~ End on a constructive note. Even if the conversation was tough, leave the door open for collaboration.

👉 Example for a mistake with a demanding client:“I understand the frustration this caused, and I take full responsibility. Here’s how we’re addressing it, and here’s what we’ll do differently going forward.”

What Happens When You Avoid the Conversation?

~ The problem doesn’t go away—it usually gets worse.

~ Resentment builds between you and the other person.

~ You waste mental energy overthinking the situation.

~ Your confidence takes a hit because you feel stuck.

When you face the conversation head-on, you gain clarity, control, and confidence. And most of the time, it’s never as bad as you imagined.

What difficult conversation have you been putting off that this framework can help with?

To find out how coaching can help with mastering your confidence so you can nail your performance at work and live life to the fullest, book a free introduction call: https://calendly.com/karen-karenhaguecoaching