The Startup
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The Startup

I Drank My Interns Under the Table.

Cool Mom Complex: A Cautionary Tale.

In my first leadership role, I learned a lot from my direct reports. I learned how to play drinking games. I learned how to mix a Bloody Mary. I even learned how to do a beer shot.

To shoot a brewski, you shake up your can, punch a hole in the side, then press your lips over the hole and let the carbonation do the rest. The beer rockets down your throat — or, in my case, out of your nose.

Getting drunk with my interns was fun until the day I had to scold them for the very drinking I had started. I remember standing in front of my team members, feeling as two-faced as Judas.

Though this “talk of shame” was uncomfortable, it cured me of my first and only bout of Cool Mom Complex.

If you are a new leader, then listen up. This article is for you. The following paragraphs will help you identify and ward off Cool Mom Complex — a leadership flaw I’ve seen take down many first-time managers.


Inspired by Amy Poehler’s character in the movie, Mean Girls, Cool Mom Complex describes a management style where a leader desperately wants to be liked by their direct reports. This leader puts their popularity contest over their paid duty to do what’s right for their team, the business, and the organization as a whole.

“There are no rules on this team,” this leader says. “I’m not like a regular boss. I’m a cool boss.”

To be fair, managers suffering Cool Mom Complex (we’ll call them Cool Moms for short) don’t usually say this out loud. Still, their every action, and lack of action, communicates the same devil-may-care attitude towards core values and company rules.


Let me put it another way: If direct reports were Gremlins, our Cool Mom douses water on Stripe.

Here are three ways Cool Moms create a toxic workplace and enable bad behavior.

  1. Cool Moms ignore issues. In an attempt to be liked, Cool Moms avoid giving negative feedback. Because Cool Moms let problems slide, minor issues grow to become major concerns.
  2. Cool Moms trash talk. One of the many problems Cool Moms avoid is employee relations issues. Instead of addressing conflict between direct reports, Cool Moms trash talk one team member to another. Cool Moms score a two-for by using this gossip as a way of bonding with their team members.
  3. Cool Moms undermine and betray. Eventually, a Cool Mom’s own supervisor will confront them about the underperformer — caused by the fact that Cool Mom has not given feedback. With their own boss, Cool Moms deflect by placing the blame on the team member. Later, when they have to address the underperformer, Cool Moms turn around to demonize and blame their boss.


Wanting to be liked is natural. Needing to be liked is fatal. Here are four ways to avoid Cool Mom Complex and the toxicity it can cause.

  1. Stick to business. I encourage newly promoted managers to operate with a no-nonsense, by-the-book approach for the first 12–18 months. Take it from me, it is much more difficult to do it the other way — to make a U-turn and issue consequences when you’ve begun as a cocktail-mixing, kamikaze guzzling Cool Mom.
  2. Separate work from play. Or, “Recess from class,” as Alma Derricks, president of the brand management company, REV, puts it. “Leaders should create getting-to-know-you time. Then, when these breaks and celebrations are over, it’s back to business.”
  3. Require constructive feedback. Make sessions where leaders outline areas of improvement for their direct reports periodic and mandatory. This form of “exposure therapy” to giving criticism will cure leaders of their fear of giving feedback.
  4. Train your leaders. When told to issue feedback, untrained managers hear, “Go tell him all the things he’s doing wrong.” No wonder many new managers use Cool Mom behaviors to cope with being the bearer of bad news. Thus, you should train leaders to effectively issue feedback, manage conflict, and improve their own emotional intelligence. This will help them avoid Cool Mom coping strategies and set them and their team up for success.

COOL IT NOW. (You betta slow it down.)

Failing in my first management role taught me a valuable lesson: Jell-O shots and drunk Jenga does not a good leader make. Fortunately, most leaders don’t fail this hard, this fast. Unfortunately, this makes them more susceptible to the slow creep of Cool Mom Complex.

Luckily, I’ve come out on the other side. Now, as a leader of leaders, I am sharing this cautionary tale. To help as many leaders and teams as possible, I’m asking you to also share this article far and wide.

Use this article as a conversation piece in your one-on-ones. Share and discuss this in the next team meeting. Put these strategies in the hands of as many managers as possible. Together, we can help leaders cool it with the Cool Mom stuff.

Click here to download my free, 60-minute webinar defining three common types of workplace toxicity and ways to address each.



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James "Jay" Guilford

James "Jay" Guilford

Jay has worked with many Fortune 500 teams. ( He helps leaders level up with original training content and new leadership insights.