This month, I dusted off my golf clubs and kicked off another season of Nine and Dine at Musqueam Golf Course. I’ve been playing in this league for eight years with two dear friends, and I look forward to it every spring. While my swing hasn’t exactly improved (in fact, I think my game has plateaued!), I keep coming back—for the laughs, the fresh air, and the guaranteed connection with people I enjoy. It’s a weekly ritual that recharges me.

What I love most is that it’s consistent. It gets me outside, fills my cup, and reminds me how important it is to create space for the things—and people—that give us energy. And that has me thinking about leadership too. Because when work gets messy or relationships become strained, it’s tempting to pull back. But the best leaders stay present. They show up. Especially in the hard moments.

This month, we’re exploring a topic every leader will encounter at some point: how to navigate difficult people and conversations. Whether it’s a team member, a peer, or a client, challenging personalities test your emotional intelligence and leadership maturity. The good news? With the right tools, you can lead through these moments with clarity, empathy, and confidence.

Here’s to strong leadership, better conversations, and just maybe, a slightly better golf swing this summer.

Dealing with Difficult People: Tools That Work

1. Understand Before You React: Leverage the DISC Framework

In my work with executive teams, the Everything DiSC® model is one of the most powerful tools I use to help leaders better understand themselves—and others. Often, what we label as “difficult” behavior is actually just a clash of natural communication styles.

The DiSC model breaks down behavior into four key tendencies:

• D – Dominance: Direct, results-oriented, strong-willed, and forceful

• i – Influence: Outgoing, enthusiastic, optimistic, and lively

• S – Steadiness: Even-tempered, accommodating, patient, and humble

• C – Conscientiousness: Analytical, reserved, precise, and systematic

When people with different styles work together—especially under stress—it’s easy to misread intentions. For example, someone with a Dominant style may push for fast decisions, while someone with a Steady style wants to build consensus first. Without awareness, this can create tension. With awareness, it opens the door to deeper collaboration.

Pro Tip: Understanding your own DiSC style—and those around you—can improve communication, reduce conflict, and build a more emotionally intelligent culture.

If you’re interested in bringing DiSC assessments or a customized DiSC workshop to your team, I’d be happy to support you. These sessions are eye-opening, energizing, and often a turning point in team connection and performance. For more information, please reach out to me jenny@jennyreilly.com.

2. Ask More, Assume Less

One of the fastest ways to de-escalate tension is to stay curious. Instead of labeling someone as difficult, ask yourself:
“What might they be experiencing that I can’t see?”

Here are three ways to lead with curiosity:

• Ask open-ended questions: “What’s most important to you about this?”

• Use neutral language: “Help me understand your perspective.”

• Listen for what’s not being said: Silence often signals stress, not disengagement.

Pro Tip: Curiosity doesn’t mean avoiding accountability—it just keeps you open long enough to uncover the real issue.

3. Focus on Impact, Not Personality

When a behavior affects the team, it needs to be addressed. But the most effective leaders separate the person from the pattern. I often coach clients to use the SBI model (Situation – Behavior – Impact):

“In yesterday’s meeting (situation), I noticed you interrupted two colleagues (behavior), which made it difficult for others to contribute (impact).”

Then pivot to solution-building:

“How can we make space for everyone’s input going forward?”

Pro Tip: Avoid blame. Stay focused on behavior and outcomes.

4. When Coaching Isn’t Enough

If someone continues to be difficult after you’ve coached, clarified, and given feedback—it may be time to set firmer boundaries.

Here’s how:

• With a direct report: Reaffirm expectations and consequences.

• With a peer: Address patterns directly and propose a reset in how you collaborate.

• With a client or stakeholder: Revisit scope, tone, and professional expectations clearly.

Pro Tip: Boundaries protect relationships, culture, and performance. They’re a leadership necessity—not a last resort.

Final Thought:

Leadership isn’t about keeping things comfortable—it’s about creating clarity, especially when the conversation is hard. Whether you’re managing a team or working cross-functionally, how you handle tough personalities will define the tone of your leadership more than any project plan or KPI.

And if you’re ever unsure how to approach these conversations—or want to explore how your team can use DiSC to create more trust and connection—I’d love to help.