The Secret To Communicating With Millennials

Karin Hurt and David Dye are keynote speakers and the award-winning authors of Winning Well: A Manager’s Guide to Getting Results Without Losing Your Soul. 

“I think the problem is that these millennials just don’t care,” Sara shared with us candidly in a moment of total frustration.

We both looked at each other and then at her, “Uh…you do realize YOU are a millennial, right?”

“Yeah, yeah,” she acknowledged, “but I’m a DIFFERENT kind of millennial.”

Of course she is, and so were the people who were frustrating her.

No matter what generation you’re in, we’d bet money you don’t feel like you fit the stereotype.

As we learned more about Sara’s situation, it became crystal clear: she had not set clear expectations and was assuming the people on her team would just know what was required.

That’s an expectation gap, not a generation gap.

She didn’t need to understand how to work with millennials, she needed to learn how to reset expectations.

When you close these communication gaps, you build credibility, increase trust, and energize your millennial team members (and everyone else).


And then there was Morgan, a millennial family friend who came to us for some advice.

“I’m just so frustrated. My boss is so old school. She wants me to do all this crap… none of it is important, and it’s getting in the way of my real work. I think she’s just trying to torment me. She’s been around a gazillion years. I wish she’d just retire.”

We dug in a bit deeper.

“Has your boss explained why these things are important?”


“Have you asked?”

Morgan shook her head, “No, It wouldn’t do any good.”

“Do you think your boss has your best interest at heart?”

She sighed. “Sometimes.”

“Well let us try to explain why he might ask for all this…” We asked a few more questions and helped her connect the dots. It turned out that there were many logical regulatory and compliance reasons her “old school” boss was asking her to approach work that way.

Morgan’s eyes got wider as we explained what we knew of such things, “Oh, I had no idea. I still hate it, but now at least I understand it. I guess my boss isn’t really trying to be a jerk.”

What was happening here was not a generational problem, but a classic example of a manager not connecting “what to why.”

So much of what gets labeled as a generation gap
is really a communication gap.

It’s easy to blame intergenerational conflict on values clashes and work ethic, but these labels distract managers from the real issue: we don’t take enough time to talk to one another.

7 Questions your Employees Long to Have

Here are 7 questions we frequently hear from high-performing, frustrated millennials who attend our training programs.

When we ask if they’ve brought these issues up, the most frequent answer is, “No, I’m too scared (FOSU (Fear of Speaking Up is real)” or “it wouldn’t do any good.”

If you want to help break down generational frustration, a great place to start is by talking through some of these questions, which are likely to be top of mind.

  1. How can I truly be successful around here? (I need more clarity around expectations)
  2. How can I show up authentically and still be effective? (Help me be true to myself and navigate the politics.)
  3. Can you help me understand what’s really going on around here? (I need helping navigating ambiguity and change)
  4. Why do we have to do it this way? (Explain the why behind all these policies and processes that seem to be wasting my time)
  5. Why does my work matter? (Help me find the greater meaning in the work I do.)
  6. When you say “I’m not ready” for a promotion, can you be more specific? (And how do I get ready beyond just putting in my time?)
  7. Why don’t you listen to my ideas? (Please listen to me and take me seriously).

When you close these communication gaps, you build credibility, increase trust, and energize your Millennial team members (and everyone else).

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