Why Leaders Avoid Hard Conversations with Difficult People (And Why It Backfires)

Early in my career, I worked with someone really difficult, arguably toxic in certain situations. He stood in meetings while everyone else sat (it felt like a power move) and closed his eyes while speaking, as though it was painful to look at the rest of us (idiots). In all-hands meetings, he asked, “What is the point of this meeting?” and pointed out what it was costing based on everyone’s salaries. He was a contrarian, he interrupted people, and he talked about his success at previous organizations in a way that suggested he thought he was the smartest person in the room. Often, it wasn’t what he said but the way he said it that got in his way.

Nothing he did was illegal or unethical, just uncomfortable enough to create constant friction. His manager gave him feedback about his impact but still spent so much time managing him that there was little left for developing everyone else. And most of the team did what’s human: they avoided him and missed out on the skill he brought to them and to the work and got the short end with our manager.

I was triggered often, too. He was hard to learn around and from. But because relationships seemed to come more easily to me than to him, I decided I could do more of the work to get us started. I once suggested he walk around the office and ask people how they were doing. “I don’t care how they are doing,” he said. I told him not to say that part out loud, because it cost him influence (and also: rude). I asked him what he did care about. “I guess… I care what project they are most excited about,” he said. So, I challenged him to ask people just that. In 90-second conversations, I watched people’s whole perception of him change. The story people told about him had grown bigger than his actual behavior, and one simple act of curiosity shrank him back to human size.

Later, he called me on a Sunday and asked what I was doing. I spent a minute and twelve seconds telling him about the new brunch spot my fiancé and I had just tried, and the salted-caramel pancakes that had blown my mind. After a pause, he asked, “Is that enough connecting for you?” It wasn’t smooth, but I knew he was trying to meet my need for connection, even though it made him uncomfortable and he didn’t necessarily need it. So, when he asked for help that day on a client request, I said yes. I leaned in, so he leaned in. He leaned in, and I leaned in.

I got better because he was in my corner and challenged me. Everyone else missed out on that, and he missed the benefit of those relationships, too. Sometimes, that is the cost of the conversation we skip with the difficult person.

Full disclosure: I had it easier than his manager did. I was his peer, not his boss. No performance review to deliver, no team watching to see if I’d “handle it,” and nothing riding on whether I got it right. Honestly, that made curiosity pretty cheap for me. Leaders don’t always get that luxury. When you’re the one with the title, every hard conversation comes with the weight of the role attached, and that weight is exactly why it’s so tempting to put off.

Why smart leaders put off uncomfortable conversations

Most leaders don’t avoid this conversation because they don’t care. They avoid it because it feels bad now, and the payoff comes later. The brain takes the immediate relief of not having the conversation over the delayed benefit of having it.

Underneath that, a few fears show up again and again:

• Fear of the reaction. Difficult people are often difficult precisely because they respond to feedback with anger, defensiveness, or complete shutdown, many times with tears. Leaders brace for the worst version of the conversation.
• Fear of the consequences. If the person is a top performer, the unspoken math is, “Can we afford to lose them?”
• Fear of being the one who “made it emotional.” In our National Emotions Study (n = 1,188), roughly a third of respondents said they believe emotions are seen as a sign of weakness at work. And leaders reported feeling more pressure than non-leaders to hide what they feel (approximately 66% vs. 47%). When a workplace treats emotion as a liability, the conversation most likely to stir it up is the one that gets postponed.

Notice what these have in common. None of them is about the other person’s behavior. They’re about the leader’s own discomfort. That’s the part emotional intelligence is designed to work on.

Why waiting makes it worse

Delay feels neutral, but it really isn’t. Here are three things that happen while you wait.

1. The behavior gets reinforced. Silence is data. To the difficult person, no feedback reads as approval. To everyone else, it reads as “this is what’s tolerated here.”
2. Your team adapts around the problem, and pays for it. People stop speaking up in meetings, route work around the person, and spend energy managing them instead of doing their jobs. This is the earliest sign that one person’s behavior has become a team problem: the team has quietly reorganized itself around it.
3. Your credibility erodes. A large meta-analysis of leadership behaviors recently published in the Journal of Applied Psychology (2026) treats avoiding leadership responsibility as its own category, “passive” leadership: delayed decisions, nonresponse, and stepping back when leadership is needed. Across studies, passive leadership was linked to lower ratings of leader effectiveness and lower follower performance.

Meanwhile, the emotional load compounds. In the National Emotions Study, the norm a workplace sets about emotion predicted how drained people felt, independent of their individual emotional intelligence. A team living around an unaddressed behavior is a team absorbing that cost every day.

What emotionally intelligent leaders do differently

High EQ-leaders don’t wait until they feel calm and confident. They work with the discomfort instead of waiting for it to correct itself.

1. Name your own reaction first. Before the conversation, ask: what am I afraid will happen? Dread is information. Naming it keeps it from steering you toward delay.
2. Separate the behavior from the person. Talk about what happened and its effect (“In Tuesday’s meeting, you interrupted Priya three times, and she stopped contributing”), not about character (“you’re abrasive”). Behavior can change. Identity usually just triggers defense.
3. Open with a clear first sentence. In Friction, we recommend a simple opening that says what you’ve noticed, why it matters, and that you want to work on it together. A clear first sentence lowers the temperature for both of you.
4. Expect emotion, and stay steady. Anger, tears, or silence are just data points, even if they don’t feel like that to your nervous system. You don’t have to fix the feeling or back down. Acknowledge it (“I can see this is hard to hear”) and hold the expectation.
5. Set a specific change and a follow-up date. One conversation is a start. Accountability is the second and third check-in.
6. Repair afterward. Respect isn’t the opposite of directness. Following up shows the goal was to help the person succeed, not to win.

TalentSmartEQ’s guidance on toxic people points in the same direction: manage your own emotional response, set clear boundaries, and don’t take the behavior personally (easier said than done, but practice can build this habit!).

The one conversation to have this week

Think of the person you pictured when you clicked on this article. The conversation won’t get easier with another month of preparation. It will get harder, because the pattern is older, the team is more worn down, and your silence has become part of the story.

So don’t aim for the perfect conversation. Aim for an honest, specific, respectful one. Write your first sentence today. Put the meeting on the calendar before you talk yourself out of it.

The discomfort you’re avoiding is real, but it’s likely smaller than the cost your team is already paying.

Resources

• Blankenship, Ross, and Maggie Sass. Friction: How Tension, Emotion, and Change Reveal Better Leaders. San Diego: TalentSmart, 2026.
• Sass, Maggie, and Ross Blankenship. National Emotions Study: Emotional Intelligence and Workplace Emotion Among U.S. Adults. Proprietary survey data. San Diego: TalentSmartEQ, 2025.
• Zhang, Yucheng, Shanshan Zhang, Zijun Ke, Wenrui Cao, Mo Wang, Kaiyang Qin, and Han Li. “Synthesizing Research on Leadership Behaviors: Semantically Validating a Taxonomy Using Large Language Models and Examining the Nomological Network with a Second-Order Meta-Analysis.” Journal of Applied Psychology, advance online publication, July 20, 2026. https://doi.org/10.1037/apl0001402.