The Difficult Conversation Muscle
This is Part 3 of a four-part series on essential skills for leaders today.
By Margaret Jackson FLPI ACC
The manager had been rehearsing the conversation in her head for three months. Every morning in the shower. Every commute home. But the words never made it out of her mouth.
“I keep hoping he’ll just… figure it out on his own,” she told me. Well, He didn’t.
I’ve coached enough leaders to know this truth: we’re brilliant at diagnosing problems and terrible at saying them out loud to the person who needs to hear them. We tell everyone else but the one who needs to hear.
Simply put it’s the ability to address performance issues, give honest feedback, and have uncomfortable conversations promptly instead of letting them fester. Not waiting until annual reviews to tell someone what’s not working. Not hoping the problem will solve itself. Just basic courage to speak truth early.
I’ve watched this play out too many times. A team member misses deadlines. The leader says nothing, hoping it’s temporary. Three months later, the entire project is derailed. Or someone’s tone in meetings is causing friction. The leader avoids it, thinking “it’s not that bad.” Six months later, two good people have resigned because of the toxic dynamic no one addressed. The cost of delayed difficult conversations is always higher than the discomfort of having them early.
The deodorant incident
A team lead once came to me in distress during a training session. One of her team members had a persistent body odour issue. The rest of the team was complaining. The pressure was mounting: “You’re the leader, you need to say something.”
She panicked. How do you even begin that conversation? So she did what seemed kind at the time, she bought a gift set: deodorant, bathing soap, perfume, nicely wrapped. She left it on his desk anonymously. He never used it. Instead, he became withdrawn, suspicious. He knew it was about him, but nobody had the courage to actually speak with him. The team’s discomfort continued. His isolation deepened. What was meant to be a kind gesture became a source of shame because it was indirect.
When we finally debriefed, she said, “I thought I was sparing him embarrassment. Instead, I made it worse.”
That’s when I learned: Difficult conversations done poorly are painful. Difficult conversations avoided are worse. But difficult conversations done with directness and respect? Those can strengthen relationships.
Here are some keys for leaders in 2026 when addressing sensitive issues with team members:
Private, specific, and timely Don’t drop hints. Don’t send gifts. Don’t wait for the “right moment.” Schedule a private conversation within 72 hours of realizing you need to have it. Be specific about what you’ve observed, not vague generalizations.
Instead of: “Some people have mentioned concerns… Try: “I need to talk with you about something I’ve noticed that’s affecting the team dynamic.”
Lead with care, not judgment
Start by making it clear you’re coming from a place of support, not punishment. Your tone will determine whether this conversation builds trust or destroys it. “I care about your success here, and I want to bring something to your attention that others have noticed…”
Be direct about the issue
This is where most leaders fail. We dance around the actual problem. With the body odour situation, a direct approach might sound like:
“This is uncomfortable to discuss, but I’d want someone to tell me. There’s been a concern about personal hygiene that’s affecting how the team interacts with you during close training sessions. I wanted to address this directly with you rather than let it continue.”
After you’ve stated the issue, pause. There might be a medical reason. There might be a home situation you don’t know about. Water challenges, laundry constraints, financial pressure. Don’t assume you know the full story.
Offer support, not just criticism
“How can I support you in addressing this?” or “Is there anything going on that I should be aware of?” turns a confrontation into a conversation.
Follow up
Don’t have the conversation and disappear. Check in a week later. “How are things going?” It shows you care about the person, not just the problem.
I also teach models like FEED, SBI and the CARE framework which are excellent tools for having difficult conversations.
One practical step: Keep a “Conversations I’m Avoiding” list. Write down the names and the issue. If someone’s name sits on that list for more than two weeks, schedule the conversation that day. No exceptions. The list makes the avoidance visible so you can’t pretend it’s not happening.
The conversation you’re avoiding is the one your team is waiting for you to have. They already know there’s an issue. Your silence isn’t protecting anyone. It’s rather confirming that you either don’t see it or don’t care enough to address it. Leaders are BOLD.
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