How to Be a Cool Boss


When I started in leadership, I didn’t give leadership much thought. 

I showed up every day, interested in learning about operations. I was obsessed, actually. I had to know how everything worked. Once I understood it, I could better help my team. After that, I just treated people how I wanted to be treated. 

It sounds simple enough, but new leaders working in my store were often surprised. “Your team all gets along. How do you do that?” They asked. 

“I don’t know,” I’d say. “I’m cool to people.” The nuances had escaped me. 

Now, I know what they are. 


Be welcoming and friendly, and expect the rest of the team to do the same. 

“Hi! I’m Maddie. Are you new?” I’d often hear sales associates greeting new people in the break room. I never told them to do this; they just did it.

New people were not looked down upon. No one thought they were dumb. They were just new. We’d all help them with whatever they didn’t know. 

No biggie. 

No sweat. 

It’s easy to be welcoming and kind


Set clear guidelines

With operations on lock, the team all moves in the same direction. Have a clear system of how you do things and tell people about it. 

Here’s how we request days off. 
Here’s how you come into your shift. 
Here’s how you’re released for the day. 

All of this matters. Be clear and ensure everyone has the same expectations. 

Jenny doesn’t get to come in late every day. Alex doesn’t get to leave without asking. The rules are the same for everybody. 


Don’t tolerate shitty behavior.

If sales associates came in cranky or they became disruptive, I’d pull them aside and have a chat. 

Like this:”Hey, are you okay? You’re doing ____ today and it’s been disruptive. Do you need a quick break? Do you need to be in a different zone? Are you not feeling well? How can I help?”

I’d also give them the option to go home if I could, without ramifications. No problemo. If you can’t do it today, it’s okay. But I can’t have disruptive behavior. 

I’ve had to leave work once or twice because I just couldn’t. You know those days when things get heavy and you just cannot anymore? No amount of camaraderie or caffeine helps, and you need to GO.

We’ve all been there. Allow people grace when you can. 

Also, don’t allow shitty behavior to go on unaddressed. 


Get to know people for who they are.

Working with a wide variety of people is the best part of the job. Get to know them. Listen to them. Champion them. Celebrate them. Encourage the team members to support each other. Pretty soon, everyone will be on board. 

Before you know it, you’ll start to hear, “Hi! I’m Katie. Are you new?”


Understand that today is one day, and we will do our best.

In retail, crazy stuff happens all day, every day. All we can do is show up, support each other, and get to the other side. Yes, we will work hard and quick and strive for excellence. 

We’re also humans with a sense of humor; we won’t lose sight of that.


Take care of yourself so you can take care of others.

I wouldn’t have been able to do any of the above if I didn’t have:

Friends I could lean on. 
A healthy, active lifestyle. 
Good sleep. 
LOTS of water. 

The rush of the next six weeks will go by in a hurry. 

Be well. Be kind. Rest when you can. 


Ace Your Next Corporate Visit

(Without working 20 hr days.)

This quick, easy-to-follow guide will
get you visit-ready.

About Kit

Based in Southern California, Kit writes about retail, keeping the frontline in focus.


Leave a Reply

Your email address will not be published. Required fields are marked *