Complicated People Are The Curriculum Of Leadership
Dec 05, 2025
If you lead long enough, you will work with complicated people.
People who frustrate you.
People who confuse you.
People who drain your energy.
People who challenge every ounce of your patience and emotional maturity.
And here’s the uncomfortable truth:
Every one of us is someone else’s complicated person.
That's one of the first insights I learned from Ryan Leak, author of How to Work With Complicated People, a fellow Maxwell Leadership thought leader, and someone I’ve had the privilege of learning from firsthand as a Maxwell Leadership Executive Coach & Corporate Facilitator.
His work inspired this week’s Growth Insights blog not because complicated people are the exception in leadership, but because they are the curriculum of leadership.
Complicated people aren’t barriers to your leadership.
They are the environment in which your leadership is built.
In fact, transformational leadership cannot be developed in isolation. It emerges when the demands of reality exceed the comfort of your habits. And nothing stretches a leader faster than relational complexity.
So today, we’re exploring How Growth-Minded Leaders Work Effectively With Complicated People using transformational leadership principles, behavioral science, and insights from Ryan Leak’s phenomenal framework and practices I use to coach teams and executive groups.
This isn’t just about managing difficult personalities.
It’s about who you must become to lead powerfully in environments where complexity is normal and relational friction is inevitable.
The Universal Truth About Complicated People (Including You and Me)
When leaders hear the phrase complicated person, they instantly picture someone:
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The coworker who drains the room
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The teammate who always misunderstands you
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The employee who resists everything
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The leader whose expectations feel impossible
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The customer who is never satisfied
Ryan opens his book with three realities about complicated people :
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Complicated people are a widespread problem.
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Complicated people affect our work in every way imaginable.
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Complicated people impact our mental and emotional health.
But before we point outward, Ryan adds the crucial insight:
“The truth is, none of us are easy to be with.” — Mel Robbins
This is where transformational leadership begins with self-awareness.
Not with diagnosing others but with recognizing that we also confuse, frustrate, and irritate people.
Ryan encourages leaders to ask the uncomfortable but essential question:
“What is it like to be on the other side of me?”
This shifts leadership from judgment to empathy.
From blame to ownership.
From frustration to transformation.
Self-awareness is the foundation.
Everything else builds on this.
The Transformational Leader’s Advantage: Self-Leadership First
1. Stop Letting Complicated People Surprise You
One of Ryan’s most freeing pieces of advice is this simple reminder:
“Don’t let them surprise you.”
Complicated people aren’t anomalies.
They aren’t exceptions.
They are part of the leadership landscape.
Yet leaders are often shocked, frustrated, or disappointed every time a complicated person behaves…well, complicated.
Transformational leaders take back their power by shifting expectations:
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Complicated people don’t surprise me.
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I know how to work with them.
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I lead myself before I lead them.
This leads to what Ryan calls an Expectations Detox:
Stop expecting people to change who aren’t even trying to change.
You can’t control whether they change.
But you can control your expectations so you aren’t constantly triggered or discouraged.
2. Your Brain Isn’t Always Helping You
Ryan beautifully explains the psychological triggers that distort how we respond to complicated people:
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Discomfort
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Uncertainty
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Lack of Control
Your brain’s job is to keep you safe, not collaborative.
It fills in gaps, jumps to conclusions, and catastrophizes to preserve your sense of security.
Transformational leaders learn to:
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Slow down the internal alarm system
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Question the story they’re telling themselves
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Respond strategically, not emotionally
This is the essence of emotional mastery.
And it is one of the distinguishing marks of transformational leadership.
Transformational Leadership Through the Lens of The Pippin Method™
My framework, The Pippin Method™, identifies four essential pillars for organizational and leadership health:
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Leadership
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Brand
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Culture
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Financial Performance
Working with complicated people impacts all four.
Let’s connect the dots.
Leadership Pillar (Direction, Strategy, Ownership)
Working with complicated people is the training ground for:
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Setting clear expectations (Direction)
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Creating collaborative strategies (Strategy)
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Taking ownership of your emotional responses (Ownership)
Culture Pillar (Team, Ops, Technology)
Complicated relationships impact:
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Team trust
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Communication flow
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Collaboration systems
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Use of technology as a connector
Brand Pillar (Product, Marketing, Sales)
Ryan’s sharp insight from Chapter 9 sums this up perfectly:
The way your people treat each other internally is how they will treat customers externally.
Financial Performance Pillar (P&L, Cashflow, Capital)
Relational dysfunction is expensive.
Turnover is expensive.
Miscommunication is expensive.
Unnecessary conflict is expensive.
Lack of collaboration slows execution — which affects revenue and profitability.
Simply put:
Working effectively with complicated people isn’t a soft skill. It’s a competitive advantage.
The Five Connections That Transform Difficult Relationships
One of my favorite chapters in Ryan’s guide is Chapter 6; where he outlines the five types of “Qs” leaders must develop to work effectively with complicated people:
1. IQ — Intelligence/Knowledge
Learn other people’s worlds.
Understand their expertise, gaps, and perspectives.
2. EQ — Emotional Intelligence
Regulate yourself.
Read the room.
Understand the emotions behind behaviors.
3. AQ — Adaptability
Be flexible.
Shift your approach without sacrificing your values.
4. TQ — Technology Quotient
Use tools to strengthen connection, not just efficiency.
5. DQ — Decency Quotient
Kindness that’s not naive.
Compassion that’s not passive.
Respect that’s not optional.
Leaders often ask me:
“Danny, which of these five matters most?”
The answer is simple:
Whichever one you’re not using in the moment you need it.
Complicated relationships reveal where your leadership still needs to grow.
Navigating Conflict Without Losing Influence
Conflict is not good or bad.
It simply is.
Avoiding conflict can sabotage:
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Clarity
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Productivity
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Trust
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Momentum
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Results
Ryan outlines the Five Fights of Healthy Conflict:
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Fight Fair
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Fight Fast
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Fight Factually
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Fight Focused
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Fight Forward
Transformational leaders don’t avoid tension.
They transform tension into alignment.
Creating Boundaries: Protecting Yourself AND the Relationship
Boundaries are not:
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Punishment
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Control
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Manipulation
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Retaliation
Boundaries are:
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Clarity
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Protection
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Productivity
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Connection
Ryan explains the difference between a Castle Wall and a Picket Fence:
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Walls isolate
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Fences define
Boundaries help you work with “nearly anyone” but they require communication, consistency, and courage.
The Most Transformational Choice: Forgiveness
This where leadership becomes deeply human.
Forgiveness is not about excusing behavior.
It’s about releasing the emotional weight that keeps you from leading at your highest level.
Ryan encourages leaders to:
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Let go of small stuff
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Give bitterness an expiration date
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Pre-forgive people before they hurt you
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Choose to move forward
Forgiveness is not weakness.
It is emotional maturity in action.
It’s choosing freedom over frustration.
Peace over resentment.
Clarity over emotional clutter.
Reflection Questions for Growth-Minded Leaders
Use these to deepen your own leadership practice or guide your team:
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Who is the “complicated person” you immediately thought of and why?
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What is it like to be on the other side of you?
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Which expectations do you need to detox?
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What story are you telling yourself about a complicated person that needs to change?
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Which of the five Qs (IQ, EQ, AQ, TQ, DQ) is your growth edge right now?
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What generational biases might be affecting your leadership?
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Which communication direction do you struggle with most: up, across, or down?
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Which of the Five Fights do you avoid or misuse?
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What boundary do you need to establish to protect your energy and effectiveness?
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Who do you need to pre-forgive and what might change if you did?
Action Steps for Transformational Leaders
Here are actionable steps to elevate your leadership this week:
1. Ask one trusted colleague:
“What’s it like to be on the other side of me?”
2. Identify one complicated relationship and adjust your expectations.
3. Use curiosity as your first response, not frustration.
4. Practice one of the Five Fights in your next conflict.
5. Set one “picket fence” boundary and communicate it clearly.
6. Pre-forgive someone you know will frustrate you.
7. Reframe the story you’re telling yourself about one difficult person.
Small adjustments create transformational impact.
Complicated People Don’t Limit Your Leadership...They Expand It
Every complicated person in your life is an invitation:
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To grow
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To communicate more clearly
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To lead with greater maturity
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To strengthen your emotional intelligence
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To build a healthier team and culture
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To operate at a higher level of influence
As Ryan Leak teaches so well, and as I have experienced firsthand in coaching hundreds of entrepreneurs, executives, and teams…
You don’t become a transformational leader by avoiding complicated people.
You become a transformational leader by learning how to lead through them.
That’s where the growth happens.
That’s where your character strengthens.
That’s where your influence expands.
That’s where your leadership is truly formed.
If you want support applying these principles inside your team or organization through coaching, workshops, or strategic planning using The Pippin Method™, I’d love to help you grow yourself, grow your team, and grow your business.