To hat or not to hat? The generational differences dilemma.

Published May 13, 2024

You're preparing for a meeting with a client. You're gathering your notes, questions, and ideas; maybe you even do a little test run of your camera to make sure nothing is visible in the background of your incoming virtual encounter. You're a Gen Xer which means you're nothing if not prepared, professional, and ready to knock this meeting out of the park. You and your Gen Z teammate have decided to join the meeting early before the client joins. You hit the "join meeting" button, only to behold on the other side of the screen your coworker, who is wearing a baseball hat while sitting in what is clearly their bedroom.

Instantly, you're frustrated. You have all of these thoughts racing through your head:
You're not supposed to wear hats to client meetings.
Are they seriously in their bedroom? Our client is going to think we're so unprofessional.
Are they even prepared? They don't look prepared.
Do I say something? I shouldn't have to say something, they should already know.

This scenario isn't really about the hat as much as what happens when we spot a "hat" in the workplace: the behavior or lack thereof, that feels so obvious to us but isn't obvious to the other person.

Maybe it's wearing a hat to a meeting, showing up late for work, sending an email instead of picking up the phone, or a litenany of other examples that often show up in conversations around generational preferences and what's considered "normal" in the workplace.

Too often, when I'm working with leaders, I hear recounting of scenarios like this (including the one above... a real life example in a generational differences workshop), and I always start by getting a little bit curious.

Starting with:
Is there a rule against wearing hats with clients?
Are there guidelines on what a professional call looks like with clients?

Sometimes I'm met with "yes" which is a pretty simple fix, honestly: give them the feedback. Remind them of what "success" looks like, and the "why" behind it.

Oftentimes, I'm met with a "No, we just expect that people know how to act professionally with clients." This answer is a bit more dicey. Because the term "professional" has changed so often throughout the years. If you said "dress professionally" to a woman in 1960, that might have meant a dress, pantyhose underneath (always), heels with your makeup and hair done. If you were to tell me to dress professionally, I would slide into a pair of slacks, my nicest pair of Chuck Taylor's, and a national park t-shirt spruced up with a blazer over the top. I would do the front of my hair and would pray the back didn't look horrible while throwing on as little makeup as possible. I'd probably also place a fruit roll-up in my bag to humble myself a little bit and remind myself that no matter how adult I look, I'm really just a kid cosplaying as a 33-year-old.

The point is that the idea of "professional" isn't as clear-cut as we think. Statements like this often leave little room for a blanket understanding that covers every single person without needing to be defined.

That's the hard part about generational differences and conflicts. When it comes to measuring behaviors in the workplace and deciding what's right or wrong (especially behaviors that haven't been explicitly detailed in our employee handbooks), we measure them based on our own idea of what's acceptable. We've all been raised in worlds that have told us what is possible, what is normal, and what to expect from the professional world. But because of that, we have a working population that is made up of nearly 6 different generations, all with their own ideas of what to expect from the working world they've joined.

Generational conflicts can most often be navigated by us getting comfortable:

  1. Creating working expectations that reflect both the working world we're in and the one we're most comfortable with (the one that we subscribed to from our early days as a professional).
  2. Making sure that each generation feels seen and valued in our missions, systems, processes, and standards.
  3. Holding each other accountable with love and care.
  4. Asking ourselves if the behavior is actually wrong or just unfamiliar to us.

Hats aren't the problem. Generational conflict isn't the problem. The problem is when we expect there not to be different ways of interpreting the working world and the expectations that come along with it.

Because the goal isn't a working world without conflict; that's impossible. The goal is for all of us to feel comfortable navigating the conflict with love and care when we inevitably encounter it.

Because we always have and always will.