THE ED MYLETT SHOW

Episode: How to Work with Anyone Even the Difficult Ones with Ryan Leak

Date: August 19, 2025
Guest: Ryan Leak
Host: Ed Mylett

Episode Overview

This episode centers on navigating relationships with difficult or “complicated” people—whether at work, in families, or other close circles. Ed Mylett welcomes Ryan Leak, author of How to Work with Complicated People, for a deep dive into practical strategies, underlying mindsets, and real-life tactics for improving collaboration and interpersonal dynamics. The conversation is honest, insightful, and full of actionable advice on transforming conflict, embracing humility, and building understanding.

Key Discussion Points & Insights

1. We’re All “Somebody's Idiot”

(02:13 – 03:11)

• Ryan opens with a foundational idea: It's easy to think of others as “idiots”—but at times, each of us fits that role for someone else.
• This mindset invites more humility and empathy in every relationship.

Notable Quote:

“Spoiler alert, somebody needs that book for you. And somebody needs that book for me.” – Ryan Leak (02:13)

2. The Real Source of Workplace Friction

(03:56 – 04:30)

• Ryan shares insight from his experience: Job dissatisfaction is rarely about the actual work; it’s most often about the people we have to do the work with.

Notable Quote:

“You can pull off a very difficult job with people you enjoy versus a dream job with people you tolerate.” – Ryan Leak (04:05)

3. The Bias Toward People Like Ourselves

(04:30 – 05:19)

• Ed reflects on how earlier in his career, he favored people who mirrored his style.
• Ryan clarifies this is common but limits growth, noting the value of diverse perspectives.

4. Tactics for Working With Difficult People

(06:10 – 10:28)

• Remain Curious: Ask, “Is there value in the way this person approaches things?” Sometimes, their different pace or method is a needed balance.
• Have Difficult Conversations: Don’t just address symptoms—talk about root issues directly and honestly.
• State Your Intentions: Clearly communicate that your goal is a thriving relationship.
• Use Humility: Say things like, “I could be wrong,” and invite feedback.
• Seek to Understand: Ask, “What do you need from me for this to work?”

Notable Quote:

“I want to have a thriving relationship with you. I want this to work out… What do you think I need to do for us to have a thriving relationship?” – Ryan Leak (08:03)

5. Headaches of Dealing with Complicated People

(10:28 – 10:58)

• Ryan points out you can either deal with the “headache” of a complicated personality, or the “headache” of retraining someone new.
• “Choose your headache.”

6. Intentions and Humility in Leadership

(13:02 – 14:23)

• Ed shares advice from John Maxwell: greater leaders welcome being wrong and changing their minds as they grow.
• Apologizing and admitting fault are powerful leadership tools.

7. Directional Communication

(14:49 – 16:20)

• Conversations are complicated by their direction—upward (to a boss), downward (as a boss), or laterally.
• Leaders need more humility when communicating down and more awareness when communicating up.

Notable Quote:

"You have to consider your end of that. If you’re talking up...be succinct. If you’re talking down...remember what you wanted from your boss." – Ryan Leak (15:36)

8. Handling Emotionally Charged Relationships

(16:26 – 18:05)

• Ed gives a vulnerable example involving his daughter, choosing humility and listening rather than flexing authority.

9. The Power of Listening and Team Collaboration

(20:19 – 21:15)

• Dictating creates robots; listening draws out people’s “gold,” creating true teams.
• People are more engaged and creative when they feel listened to and valued.

10. Four Common (Unhelpful) Responses to Complicated People

(21:41 – 22:23)

1. Avoid them.
2. Cancel them.
3. Try to change them.
4. (Preferred!) Move toward them with understanding.

Notable Quote:

"We want karma for them and grace for ourselves…but complicated people often have a complicated behind the scenes." – Ryan Leak (22:23)

11. Understanding Others’ Circumstances

(24:26 – 25:08)

• Ryan shares an experience of receiving 3,000 responses to an open “how can I pray for you” text, revealing how much we don’t know about others’ struggles.
• Give grace; everyone’s fighting battles you can’t see.

12. Not Making People “Projects”

(36:08 – 36:35)

• People aren’t problems to be solved—they’re humans to be understood.

13. Knowing When to Move On

(34:14 – 35:43)

• Do all you can with humility and intention; after that, recognize if the other person isn’t trying to change.
• Don’t expect folks to change if they’re not interested in it.

Notable Quote:

“Stop expecting people to change who aren’t trying to.” – Ryan Leak (35:43)

14. Intentional Encouragement & Small Gestures

(41:14 – 44:35)

• Intentionally recognizing birthdays, anniversaries, and children’s names makes people feel uniquely valued.
• Even short, personal video messages can be life-changing and forge deep loyalty.

15. The Role of Boundaries

(46:51 – 50:14)

• Lacking boundaries causes burnout and unnecessary conflict.
• The awkward conversation to set boundaries is less of a price than long-term stress and fractured relationships.
• Align boundaries with your true priorities—especially family.

Notable Quote:

“Where's all this going?... My definition of success is that my kids still want to go on business trips with me 20 years from now.” – Ryan Leak (47:44)

Memorable Moments & Quotes

• On humility:

  “I love using the phrase, I could be wrong. Hey, I could be wrong. But this is what I see.” – Ryan Leak (10:58)

• On leadership:

  “There’s a difference in people having to follow versus people getting to follow.” – Ryan Leak (20:39)

• On encouraging others:

  "If you can do that, people will feel like, 'man, you see me, I’m valued.'" – Ryan Leak (42:36)

• Ed’s reflection:

  "Of all the men my father ever worked with, I can tell you the name of one—Jerry Farley...because he made me feel special." – Ed Mylett (45:59)

Timestamps for Important Segments

• Being someone’s "idiot": 02:13 – 03:11
• Biggest workplace challenge is people, not tasks: 03:56 – 04:30
• The bias toward hiring ourselves: 04:30 – 05:19
• Tools for working with difficult people: 06:10 – 10:28
• Dealing with emotionally challenging colleagues: 07:15 – 10:28
• Intentions/humility/apology strategies: 13:02 – 14:23
• Upward/downward communication: 14:49 – 16:20
• Four common wrong responses to difficult people: 21:41 – 22:23
• Leave room for people to grow and not box them in: 25:12 – 26:29
• Intentional encouragement and the power of gestures: 41:14 – 44:35
• Boundaries and priorities—keeping family at the center: 46:51 – 50:14

Tone & Language

The discussion is candid, warm, humorous, and loaded with relatable anecdotes. Both Ed and Ryan speak conversationally, often self-deprecatingly, with an uplifting and practical tone throughout.

Summary Takeaway

"Working with complicated people isn't just about coping—it's about embracing curiosity, humility, and intentional action. Whether at work or home, the relationship comes alive when we approach each other with empathy, listen deeply, apologize sincerely, and make the effort to truly see and value the person in front of us—even (and especially) when that's hard."

Book:
How to Work with Complicated People by Ryan Leak—A New York Times bestseller offering practical tools to collaborate better with nearly anyone.

Find Ryan:
Follow on social media for ongoing insights and encouragement.

For more:
Subscribe to The Ed Mylett Show and join the email list at edmylett.com.