How to Have a Difficult Conversation at Work (Without Dreading It)
Can I be honest for a moment? Difficult conversations at work are not my favorite part of leading. Not even close. If I’m being honest, I’ve put off more of them than I’d like to admit.
I’ve led in a lot of different places. A hotel. A hardware store. A copy shop. A college campus. And now a church. Every one of those places had its share of hard conversations. The employee who kept showing up late. The team member whose attitude was dragging everyone else down. The colleague who needed to hear that their work wasn’t where it needed to be.
And every time, I noticed the same thing. The dread was almost always worse than the conversation itself. Sound familiar?
Here’s the good news. You can get better at this. Here are 6 ways to have a difficult conversation at work without dreading it for days ahead of time.
6 Ways to Handle Difficult Conversations at Work
- Don’t wait. Hard conversations only get harder with time. A small issue you could handle in five minutes on Monday turns into a big issue by the end of the month. And the longer you wait, the more likely it comes out sideways – in frustration, sarcasm or an email you wish you could take back. Most of the time, the kindest thing you can do is talk sooner.
- Get clear before you get in the room. Before the conversation, write down the one thing you need the other person to understand. Just one. If you can’t say it in a sentence or two, you’re not ready yet. Clarity keeps you on track when emotions show up. It also keeps you from piling on every frustration you’ve been saving up for the last six months. (This is the heart of “Clarify the Concept,” the first of my 5 Steps to Getting to Your Next Level™.)
- Check your story. When someone drops the ball, our minds start writing a story about why. They don’t care. They’re lazy. They’re doing it on purpose. Most of the time, that story is wrong. Walk in curious instead of convinced. Ask questions first and give the other person a chance to tell you what’s really going on. I wrote more about this in A Lost Art That We ALL Need to Find.
- Be kind AND clear. A lot of us think we have to choose. Either we’re nice and the message gets lost, or we’re direct and the relationship takes a hit. You don’t have to pick one. Say the hard thing plainly, and say it with respect. Something like, “I want to talk about the last three deadlines. Help me understand what’s getting in the way.” Kind. Clear. Done.
- Listen more than you talk. A difficult conversation is still a conversation. Once you’ve said what needs to be said, stop. Let the silence sit for a moment. Then listen to understand, even if you disagree. People are far more open to change when they feel heard. As an introvert, the listening part comes a little easier for me…it’s starting the conversation that takes some push.
- End with a next step. Don’t leave the room with everyone guessing what happens now. Agree on one or two specific actions, who owns them and when you’ll check back in. Then actually check back in! Follow-up is what turns a hard moment into real growth. And when feedback is a regular part of how you lead, these conversations get a lot less scary. Here are 5 keys to giving feedback that can help.
What If It Goes Badly?
Let’s face it, not every conversation will go the way you hope. Sometimes people get defensive. Sometimes they get emotional. Sometimes you get emotional. That’s ok.
Stay calm and take a breath. It’s perfectly fine to say, “Let’s take a break and pick this back up tomorrow.” That’s a good leadership sentence. One hard conversation won’t fix everything. Avoiding it won’t fix anything.
I believe that caring enough to have the hard conversation is one of the most loving things a leader can do. It’s grace and truth, together. Make sense?
Quick Answers About Difficult Conversations at Work
How do you start a difficult conversation at work?
Keep it simple and direct. Name the issue in one sentence, then invite the other person in with a question like, “Help me understand what’s going on.”
What should you avoid saying in a difficult conversation?
Stay away from “always” and “never,” sarcasm and guesses about someone’s motives. Stick to what you’ve seen and how it affects the team.
How do you have a difficult conversation with your boss?
The same principles apply. Get clear on your main point, pick a good time, lead with respect and bring a possible solution along with the problem.
Your Turn
If you’re wondering what’s holding you back as a leader, take my free Next Level Self-Assessment. It only takes a few minutes and it’ll show you where to focus next.
What’s the hardest part of difficult conversations for you? Is there one you’ve been putting off? Leave a comment and let me know!
The takeaway: The conversation you’re dreading is usually the one your team needs most, so have it soon, keep it kind and keep it clear.
Is there a conversation you’ve been putting off?
Let’s talk it through together and build a plan, so you can walk into that room with confidence instead of dread.
