One of the biggest mistakes people make with difficult stakeholders is treating every conversation like a transaction.
The strongest relationships are built through connection.
And connection often starts with curiosity.
Here are three practices I’ve found surprisingly effective when working with skeptical, resistant, or hard-to-read stakeholders:
1. Go beyond “I’m fine. How are you?”
Most conversations begin with a ritual rather than a real exchange.
Instead, answer the question.
Try…
“You know, this morning I finally got myself out the door early enough to go for a walk before work, and I swear everything seems easier today than it usually does.”
Or…
“My son seems to be slowly convincing me that we need a puppy, so I suppose I’m headed for trouble.”
Or…
“I’ll let you in on a secret: I finally cleaned out the garage this weekend, so I’m feeling pretty accomplished today.”
Tiny moments of authenticity invite connection.
And connection creates trust.
2. When they object, don’t defend. Reflect.
When someone pushes back, our instinct is often to explain, persuade, or correct.
Instead, try reflective listening.
“So for you, this project seems like it’s coming at the worst possible moment. Did I get that right?”
Or…
“It sounds like you’d like to be supportive, but you’re also feeling pretty skeptical about the data. Tell me more about where you’re coming from.”
People become much easier to influence once they feel understood.
3. Quantify the objection.
Many objections are vague until you help people define them.
“I’m hearing that it will be hard for your team to take this on. And also that you’re completely underwater right now. What would feel doable to you?”
Sometimes the gap between “impossible” and “possible” is much smaller than it initially appears.
The stakeholders who challenge us the most are often the ones who teach us the most about communication, empathy, and influence.
The goal isn’t to win them over.
The goal is to understand them well enough to solve problems together.
