July 02, 2025

Episode 28: Dealing with Difficult People (replay)

34 minutes

In this special episode of Some Goodness, host Richard revisits a popular conversation with executive leadership expert Jack Galloway. Jack shares invaluable insights on handling conflict, creating clarity, and leading with both courage and kindness. This episode addresses why it's crucial to tackle difficult conversations promptly and how clarity equates to kindness in leadership. Galloway offers practical advice on managing difficult interactions and building stronger teams, making this episode essential listening for current and aspiring leaders. The episode also includes statistics highlighting the prevalence of toxic coworkers and ineffective managers in the workplace, underscoring the need for adept leadership.

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Chapters

00:00 Introduction and Episode Overview

01:22 Statistics on Difficult People at Work

02:01 Introducing Jack Galloway

03:00 Jack's Perspective on Avoiding Conflict

05:05 Practical Tips for Handling Conflict

06:33 The Importance of Clarity in Leadership

12:26 Balancing Candor and Kindness

18:38 Prioritizing Tasks and Managing Workload

28:10 Creating a Positive Work Culture

32:27 Conclusion and Final Thoughts

Keywords

difficult conversations, conflict, clarity, kindness, leadership, team, tough conversations, boundaries, trust, radical candor, curiosity, empathy, feedback, culture, priorities, effectiveness, toxic people, workplace, honesty, vision, goals, roles, performance, administrative burden, coaching, communication, trust, influence, feedback, change, personal growth, professional development, strategy, family, teams, success, priorities, stress, busyness, management, sales, trust, toxic culture, role clarity, transitions, career, kindness, constructive criticism

Soundbites

To be unclear is to be unkind. To be clear is to be kind. And that just resonated with me, especially with my Enneagram nine peacemaker style. I sometimes was being so kind that I wasn't delivering any clarity.

The majority of the population simply just does not deal well with conflict in any part of their life—including in the workplace. There's fear that it's gonna go horribly wrong. They don't know how to do it the right way. So there's fear that it's gonna go wrong, and there's a lack of just skill and experience on the right way to do it, to have a positive outcome.

The things that I always try to do when I'm having a, what I call a difficult conversation, is to be curious and curious to me means I'm not predetermining what's going on. I don't know what's going on. All I know is what I observed.

If I have difficult conversations with 10 people on a regular consistent basis, with nine of them, if I will have it early, ask questions, be non-judgmental, be clear, point out what I'm seeing, have the courage to tell 'em what's working and what's not working—even the toughest character out there wants to engage with a leader that does that.

We feel like we have cast a clear vision, we've cast a clear plan, a clear strategy, some clear goals. We feel like everybody knows exactly what we know and what we're thinking. And then when I sit down with their teams, very few of them have those things and they go, you know what? I don't know those things. I've heard bits and pieces, but I don't know where we're going or why we're going there.

If we'll do the things we're talking about while we're in that level of influence in that role, it impacts those people beyond just their jobs. It impacts them in their family lives. It makes fathers better fathers. It makes mothers better mothers. It makes people better spouses and it helps 'em in different areas of their life.”

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