If You've Ever Dreaded Leading Difficult People, Read This!
Jan 06, 2026
Not too long ago, a senior leader asked me a simple question,
“How do I deal with difficult people?”
They wanted a framework, a formula or something neat and orderly that would help them manage the situation. Of course, you want a framework. We love frameworks. Frameworks make us feel competent, organized and one PowerPoint slide away from world peace.
Because I have been an academic for far too long, my professor reflex kicked in, and I went straight to archetypes from the literature:
- The Brilliant Jerk – stunningly capable, emotionally exhausting
- The Passive Resister – nods in meetings, undermines you afterward
- The Insecure Overachiever – works nonstop, trusts no one
- The Victim-Blamer – nothing is ever their fault
- The VIP – rules don’t apply to them (because … it’s them!!!)
I walked this senior leader through each one. We covered the strengths, the blind spots, what stresses them out, what they need to feel valued, and how to get them ‘on side.’
It was a good conversation. I walked away feeling like I had equipped them with tools to move the team forward, but after a few sleeps, I realized something uncomfortable.
I had missed the point.
Instead of helping them to manage difficult people, I wish I had helped them understand something far more powerful:
Difficult people don’t just test your leadership. They build it.
Most of us don’t want to hear that—especially when we’re exhausted, frustrated and one passive-aggressive email away from losing our faith in humanity--but, it’s true.
Leading ‘difficult’ people has made me a significantly better leader; and I suspect, if you’re honest, they’ve done the same for you.
Difficult People Teach You Boundaries
(Whether You Want Them or Not)
I had a friend who worked as a client relations professional at a hospital. They were very good at their job. One time a daughter-in-law of a patient came in advocating for her family member. It started with small requests and kept snowballing. Small requests became outlandish demands: meetings with Charge nurses, then Directors when it didn’t go their way. Soon, it became audiences with multiple VPs when demands weren’t quickly met. Eventually, only the Hospital CEO would do. She threatened attracting the media or lawsuits. It was never enough. My colleague came to find out that this individual had a history of being a difficult person across domains.
See what was happening there? Difficult people don’t respect fuzzy boundaries. They walk straight through them. Eventually, you learn—often the hard way—that accommodating people all the time will lead to burnout, anger and frustration. You learn to set firm boundaries.
Difficult people forced me to:
- Say no without apologizing
- Be clear instead of vague
- Stop over-explaining
- Hold the line even when it was uncomfortable
They taught me that boundaries aren’t walls—they’re guardrails; and, leadership without guardrails is just chaos with a title.
Difficult People Force You to Level Up Your Preparation
I once worked with someone who wanted every meeting for the entire year scheduled in advance . . . every meeting. At first, I thought, “This is ridiculous! Who lives like this?” Turns out—lots of folks do. Because when I didn’t come prepared; when the agenda was loose; or, when the outcomes weren’t clear, I heard about it. So, I adapted.
I started:
- Setting annual calendars
- Creating tight agendas
- Defining outcomes in advance
- Meeting weekly with my inner circle to plan
Here’s the humbling part:
My meetings got better. They became more focused, more efficient and more respected.
Difficult People Make You Tougher (Not Meaner)
There’s a difference between being tough and being mean. You will certainly be at this fork in the leadership road when encountering difficult people.
I’ve coached and led many people who tested my authority, rallied an alliance against my initiatives, or endeavored to add roadblocks and friction where there didn’t need to be any. They hoped to see me fail. Difficult people don’t make you cruel. Mastering your defensiveness, your ego and your reflexes is critical to your development. Difficult people make you clear. They test whether you actually believe in your decisions—or whether you crumble the moment someone challenges you.
I learned to stand up for myself--to develop a backbone. I learned to say, “This is the decision,” and not immediately follow it with, “But, I’m totally open to changing it if you hate it.”
If leadership is a muscle, difficult people are resistance training. You grow stronger when you encounter discomfort and begin to take necessary, effective leadership form.
The Research Bit (Because This Isn’t Just Therapy)
A study published in the Journal of Applied Psychology found that leaders who face interpersonal challenge and role conflict—when supported by reflection and learning—develop greater leadership adaptability, resilience and effectiveness over time.
In plain English:
Struggle + reflection = growth
Struggle – reflection, mentoring or coaching = burnout
Difficult people aren’t the problem.
Failing to learn from them is.
The Reframe That Changes Everything
Here’s the shift I wish I had offered my client sooner:
Instead of asking, “How do I survive difficult people?”
Ask:
- What am I here to learn?
- What muscle is this developing?
- Who am I becoming because of this challenge?
Leadership isn’t forged in easy rooms with agreeable people. It’s built in tension, in conflict and in moments where you’re forced to choose courage over comfort.
A Final Thank You
So, to the difficult people I’ve led:
I didn’t enjoy you.
I didn’t choose you.
I definitely complained about you, but you made me better.
You taught me boundaries.
You strengthened my spine.
You sharpened my preparation.
You pushed me closer to my potential.
For that—grudgingly, reluctantly and honestly—thank you.
Sometimes, the people who challenge you the most are the ones quietly moving you toward your greatness—whether they know it or not.