How to Start the Tough Conversations (and Stay Grounded While You Do It)
The hardest part of most difficult conversations is getting started.
You know something needs to be said, but your brain goes into overdrive: “What if they get upset? What if I say it wrong? What if I make it worse?”
That’s where a few solid conversation starters and a strategy to manage your own energy can make all the difference.
Conversation Starters That Actually Work
The goal isn’t to tiptoe around the issue or “soften the blow” so much that your message gets lost. It’s to name what’s going on clearly, invite their input, and keep the tone professional and forward-focused.
Here are a few that work:
For performance issues:
I’d like to talk about the XYZ project and get your perspective.
I’ve noticed some patterns with deadlines. Can we talk through what’s happening?
For behaviour issues:
I want to check in about something I observed in today’s meeting.
I’d like to discuss how we can work together more effectively.
These starters do three key things:
Name the topic
Invite a two-way conversation
Set a professional tone without being vague or accusatory
Managing Your Energy in the Moment
Even when you know what to say, staying grounded while you say it is a whole different game. Here are a few reminders that help leaders stay composed and confident:
Before the conversation:
Remind yourself: “My job is clarity, not comfort.”
You’re not there to make it feel good — you’re there to lead it well.
During the conversation:
Speak slower than feels natural. Slowing down gives your nervous system time to regulate and helps the other person absorb what you’re saying.
If you feel rattled:
Come back to two things: the facts and your goal. What did you actually observe? What outcome are you leading toward?
Reading the Room + What to Do When It Goes Sideways
Sometimes things get emotional, and you have to make a call: Do I keep going, or pause and pick this up later?
Pause when:
They’re too upset to take anything in
You’re too triggered to lead clearly
They ask for space or time to think
Continue when:
They’re defensive but still engaging
They’re frustrated but listening
There’s genuine curiosity or movement in the conversation
Recovery strategies when things go off track:
If they get hostile: We need to pause this. Let’s schedule time to continue tomorrow.
If they shut down: What are you thinking?
If you realise you said something poorly: I didn’t say that well. What I meant was…
When to Document — and How to Do It Simply
You don’t need to document every conversation. But if it’s about performance, you’ve set expectations, or you may need to follow up later — keep a quick record.
Keep it brief. Stick to the facts.
No stories, no speculation. Just: What was said. What was agreed.
The Bottom Line:
You don’t need perfect words to lead a great conversation. You need a clear intention, a few solid tools, and the ability to stay present when it counts. With practice, you’ll stop dreading these moments and start leading them with confidence.
Ready to build practical leadership skills at your own pace, without losing days to training?
I’ll be running the Leadership Essentials Program as a self-paced online course this September, designed especially for busy leaders who want tools they can apply immediately.
It’s a powerful way to align with what your team’s already learning — or to sharpen your own skills in a way that works with your schedule.
I’m also exploring a micro-course option for those who want to go deep on just one skill area.
Interested?
Email me and I’ll send more info soon. Spots will be limited.
Have a great week
Andrea
