In my previous newsletter, I explored how to deal with difficult people including yourself. Here I dive deeper because the true work it is not about managing them, but about understanding what they’re teaching us.
“When you find someone difficult, there’s a finger pointing right back at you.”
My mother’s favorite phrase still whispers in my head. Her wisdom has shaped how I approach difficult people and conflict in all areas of my life.
The pattern I keep seeing
When I lead negotiations in healthcare sometimes when the other side pushes back or challenges assumptions, they can get labeled as “difficult”. When this happens, I pause and ask myself and the team: What role am I playing in this? How can I see this differently?
The same approach applies when I find myself eye to eye with my strong willed, independent teenage daughter. The harder I try to steer her toward a path I think is best, the harder she resists. And if I’m truly honest, sometimes what makes it difficult is that I see so much of myself in her. At times, it feels less like parenting and more like negotiating with my teenage self.
In both cases, I learned: It is rarely about the person. It is about the “dynamic” that swirls between you.
What’s Really Happening
People are rarely inherently difficult. More often, difficult behavior emerges when someone is under stress, fear, or uncertainty. We build armor early, often patterns from our childhood, because it kept us safe back then.
The problem is that fear doesn’t disappear and that armor stays; it just shapes how we operate. When we lack certainty, we fill the gaps. We turn assumptions into facts and craft stories in our heads of worst-case outcomes. As Anne Lamott noted in her recent NPR interview on launching her new book “Good Writing” we find false evidence to support our stories, make it real and then they take on a life of their own.
These stories we create then start to unravel, not because they are true, but because we choose to act on them. Instead of slowing down to examine what is really happening, we tiptoe around the issue, try to restore harmony, try to rescue the situation, or escalate the conflict. Each response is a band aid on the real issue at the heart of it, which continues to simmer underneath, unspoken.
What They’re Showing You
Here is what I have discovered: The people we find the most difficult mirror unresolved issues in ourselves. They show us what we have denied, resented, buried deep to avoid seeing. The intensity of our reaction to the data signals something deeper, some unfinished issues bubbling up inside us.
With my daughter, her striking independence mirrors my own struggle with asking for help. “I can do it myself,” is a phrase she has been saying since she could string words together. Watching her, I see my younger self determined to prove I could manage alone, refusing to ask for support because I held a belief that needing help was a sign of weakness. Perhaps it traces back to being the second of five children and needing to prove myself. What took me years of lived experience to learn, she is already teaching me: we thrive when we allow others in. She has become my greatest teacher.
In negotiations, I see the same pattern. When fingers start pointing and conflict escalates, assumptions and misaligned expectations drown out the real issues because fear is driving the conversation. The “difficult” counterpart is often just reflecting our own unspoken fears back at us. Instead of getting curious and asking questions, we protect ourselves. And in doing so, we miss what actually needs solving.
A Different Way to Meet These Moments
You have more agency than you think in these moments. The key is to start with yourself, not the other person.
- Pause and breathe: Create space between their words and your reaction. That space changes everything.
- Get curious before you judge: Instead of assuming the worst, ask yourself: What might be driving their perspective? What am I not seeing yet? This often reveals real concerns underneath the position.
- Notice what’s happening in you: Your reaction is data. What is this moment bringing up? What feels at risk? If you’re defending fiercely, you’re protecting something. If you’re people-pleasing, you’re afraid of something. Identify it.
- Stay grounded in your truth: You can disagree without escalating. You don’t have to abandon your position to understand theirs.
- Shift your energy toward possibility: Visualize the conversation going well. How would you show up if you were calm, steady, clear, and open?
- See the whole person: No one is defined by a single moment. Step back from the narrative created about the other person and get curious about what else may be true.
Reflection: A Different Way to Look at Difficult People
The next time you label someone as difficult, pause and ask:
- What might this person be showing me about myself?
- What conversation am I avoiding?
- What would change if I approached this with curiosity?
- What fear lies behind this emotion?
The shift: Don’t try to fix the other person. Understand the dynamic instead.
And from that place of clarity, you’ll find a different path, one where the person you found so difficult becomes your greatest teacher.
Because they will be, if you let them.
