Maxwell Leadership Executive Podcast #334

How to Work with Complicated People
Release Date: March 6, 2025
Host(s): Perry Holly, Chris Goede
Featured Guest: Ryan Leak

Episode Overview

This episode centers on a universally relevant leadership challenge: how to work with complicated people. With a special appearance by author and speaker Ryan Leak, the hosts deliver insights into dealing with workplace complexity, influenced by Leak’s new book, How to Work with Complicated People. The discussion dives into practical strategies for leading in all directions—down to your reports, across to your peers, and up to your supervisors—offering actionable tools for listeners looking to expand their leadership influence and effectiveness.

Key Discussion Points and Insights

1. The Reality of Complicated People and Leadership Complexity

• Leadership isn’t straightforward; it’s less like building IKEA furniture (which at least has instructions) and more like “putting together IKEA furniture without instructions, with half the parts missing, while three people yell at you about how you’re doing it wrong” — Ryan Leak [02:33].
• Every direction of leadership—down, across, up—presents its own challenges, but all require intentionality and preparation.

2. Leading in All Directions (The 360° Leader)

• Down (to direct reports):
  Reports often expect leaders to “have all the answers.” Ryan notes, “Spoiler alert: you don’t.” [02:43]

• Across (to peers):
  Collaborating with peers can be complicated by competition and territorial behavior.

• Up (to supervisors):
  Your boss has their own pressures and blind spots, making “leading up” complex.

• Chris Goede [06:56]:
  “It’s not about the position, it’s about your influence... Simply by adding value to people, building relationships... You are increasing your influence.”

• Practical example:
  Hendrick Motorsports’ teams, though competitors, intentionally collaborate and support each other for the team’s collective benefit. (“We work together, but I want to beat you on Sunday.” — Jeff Gordon recounted by Perry Holly [12:38])

3. Empathy & Adaptability as Leadership Tools

• Complexity does not equal chaos; preparation and adaptability allow leaders to thrive in unpredictable situations.

• Ryan Leak [05:09]:
  “Most people aren’t trying to be difficult, but they are trying to be understood. And your job as a leader is to adjust your approach to meet people where they are, not where you wish they’d be.”

• Perry Holly [16:05]:
  “Do you see people as a tool to be used, or do you see them as a relationship to be created and cultivated?... The better you see people, the more you can tolerate their complications.”

4. The Power of Intentionality

• Expect complications. If you plan for complexity, you’ll be better equipped to address it without falling into chaos. (“Expecting complexity helps you prepare for it.” — Ryan Leak [03:13])
• Prepare for interactions (especially when “leading up”) by learning team members’ and supervisors’ communication styles and motivations.
• Chris Goede [13:23]:
  “Complexity doesn’t need to mean chaos... What are you doing before the moment, to prepare in the moment so that it doesn’t seem like it’s chaotic?”

5. Meeting People Where They Are

• Leaders must adjust to the needs and personalities of those they lead—even the “complicated” ones.
• Chris Goede [15:10]:
  “Everyone deserves to be led well... The only way for that to happen is to lead them the way they need to be led.”

6. Memorable Metaphors & Quotes

• On Leadership vs. Rocket Science:
  “Leadership isn’t rocket science. The bad news is, it’s harder. Rocket science deals with predictable physics. Leadership deals with unpredictable humans.” — Ryan Leak [04:05]
• On IKEA Furniture:
  The process of leading people is compared to assembling IKEA furniture without instructions, underscoring unpredictability and challenge. [02:27], [16:33]
• Perry Holly [08:10]:
  “The three most famous words, the hardest words for a leader to say: ‘I don’t know.’”

Notable Quotes with Timestamps

• Ryan Leak [02:33]:
  “Sometimes leadership is like putting together IKEA furniture without instructions, with half the parts missing, while three people yell at you about how you’re doing it wrong.”
• Ryan Leak [05:09]:
  “Most people aren’t trying to be difficult, but they are trying to be understood.”
• Perry Holly [16:05]:
  “Do you see people as a tool... or as a relationship?... The better you see people, the more you can tolerate their complications.”

Important Timestamps

| Time | Segment/Topic | |--------|:-----------------------------------------------------| | 00:25 | Episode introduction and topic setup | | 02:21 | Ryan Leak’s excerpt: Complexity in Leading | | 03:13 | Preparation and mindset for handling complexity | | 05:09 | Empathy/adaptability; meeting people where they are | | 06:29 | Reflections from Perry & Chris on 360° leadership | | 08:10 | Leading down: letting others have a voice | | 10:34 | Leading across: overcoming competition with peers | | 12:38 | Hendrick Motorsports collaboration example | | 13:23 | Leading up: preparing for complexity | | 15:10 | Meeting people where they are | | 16:05 | Valuing relationships vs. using people as tools | | 16:33 | Leadership ≠ Rocket science; unpredictability |

Summary & Takeaways

• Every team has “complicated people”—leaders must expect, prepare for, and thoughtfully adapt to this reality.
• Leadership is about influence, not hierarchy; you can lead up, down, and across through intentional relationship-building and valuing others.
• The key to working with complicated people is empathy, adaptability, and a willingness to meet people where they are—not where you wish they’d be.
• Preparation and understanding are essential—get curious, do the work, and you’ll not only overcome complexity but also increase your team’s engagement and effectiveness.

Further Resources & Actions:

• Pre-order Ryan Leak’s book How to Work with Complicated People (link in show notes)
• Find more leadership content at maxwellleadership.com/podcast

This summary was created to provide a clear, detailed understanding of the episode’s key insights for listeners and non-listeners alike.