Confidently leading difficult conversations

What you need to know:

  • Instead of scripting every word, approach the conversation with genuine curiosity. Ask yourself; "What am I hoping to understand better?" Begin with facts, and stay open to feelings.

In our culture we are taught to keep the peace. We are taught not to embarrass anyone, not to challenge authority, or make things awkward. I’m naturally a very passive person and despise confrontation, so having been taught all these customs many times, when hard topics or confrontational issues arise I tend to keep silent. But over the years I’ve discovered that silence is not peace, it’s delayed tension. So you can imagine the tension that arose when I had to address an older team member  about cutting people off mid-sentence when I was a team-lead for a project a few years ago. 

I hated being the one who had to address this issue, suddenly I wished I was someone else.  Perhaps if I had a few more grey hairs or a deeper voice, I’d have the licence to say what needed to be said. I told myself, “Maybe she’ll just stop on her own.” Spoiler alert: she did not, so I had to bite the bullet and do the hard thing. 

I rehearsed the conversation in my head seven times pulled her to the side for a moment and said; “I noticed that you interject when some of the team members are mid-sentence, it affects the flow of the conversation and I just want to make sure everyone is being heard and gets a chance to finish their thoughts.”  Phew! I had said it. She responded with a very light and breezy; “Oh, I didn’t know I was doing that- no problem.” I had done it and all the tension dissipated. 

Later, as I reflected I came to realise that sometimes tension is not a bad thing, it's an indication that something matters. Last year I read an article that echoed this thought and it stated that; “High-performing teams don’t avoid tension, they process it with skill.” Anyway that project may have come and gone, but it left me with lasting insight into leadership and a real appreciation for how crucial it is to lean into difficult conversations rather than sidestep them.

According to a 2023 report by VitalSmarts, 70 percent of employees avoid difficult conversations at work, even when the issue directly affects their performance or well-being. What’s worse is a study in the Harvard Business Review that found that leaders who avoid conflict are perceived as less trustworthy and less competent, regardless of their actual performance. 

After doing some more research I discovered the following five key strategies to lead difficult conversations with emotional intelligence:

1. Prepare with curiosity, not scripts. Instead of scripting every word, approach the conversation with genuine curiosity. Ask yourself; "What am I hoping to understand better?" Begin with facts, and stay open to feelings.

2. Address the tension before it grows. Conflict doesn’t become easier with time, it becomes more complicated. A simple phrase like; “There’s something important we should talk about” can create space for honesty before resentment has room to take root.

3. Lead with respect, not repression. Avoid accusatory language  such as “You always…” and focus on impact. “When this happens, here’s what it creates…” This fosters accountability and invites the other person into problem-solving, not defense.

4. Hold space for response. Resist the urge to over-explain or fill the silence. After you speak, resist the instinct to over-clarify or justify. Let the other person reflect. Listening isn’t passive; it’s one of the most active forms of leadership.

5. Revisit the conversation.  Sometimes difficult conversations aren’t one-and-done. Summarise what was agreed, check in after time has passed, and acknowledge any progress. Sustainable change is built through consistent alignment, not just a single breakthrough moment.

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