How “Cool Bosses” Create Stressed Teams—and What to Do Instead
Someone recently asked me to share what I picked up about leadership from my past bosses, and it gave me pause.
Just about everything that came to mind was a story about the kind of boss I didn’t want to be!
One of my bosses was a sweetheart in public, but frequently screamed at the team. Another one was fired for a major ethics breach. Yet another threw a stack of files across the room in a fit.
My past bosses weren’t ALL bad, but these experiences stand out – for obvious reasons.
I didn’t want to be that kind of boss – the tyrant, the one flying off the handle, the one people complained about over happy hour.
But in building my own teams over the years, I found that the pendulum can swing too far in the other direction.
Trying to be the “cool boss” can be just as problematic, for the team and for you.
The cool boss is someone who prioritizes being liked over being effective.
They avoid difficult conversations and downplay their authority in an effort to be accommodating, fun, or easygoing.
At first, this approach might seem harmless—even positive. But over time, it creates confusion, frustration, and unnecessary stress for the team.
By the way, if you’ve struggled with wanting to be the “cool boss” and had it come back to bite you, I’m still looking for folks to interview as I develop a mentorship program for next year. I’d be overjoyed if you booked 20 minutes with me here.
Here’s how my desire to be perceived as a good boss showed up with me – are any of these familiar?
You want to be chill and accommodating, so you stop short of communicating what you actually need when assigning work.
You make a point to let small things slide, but over time, your resentment and annoyance builds up. Why doesn’t the team appreciate you more and respond in kind?
You don’t want to micromanage anyone, so you trust folks to just handle things, and then wonder why mistakes keep happening.
You give third, fourth and fifth chances to a team member who needs to go.
When I behaved this way, I had good intentions. I wanted to be a better kind of leader for my team.
But I was setting the team up to fail and slowing down the growth of my company.
The issue with this kind of laissez-faire leadership is a lack of accountability that starts at the top.
When you’re not accountable for your own decisions and desires, it’s impossible to hold other folks to any kind of standard.
It also creates an enormous amount of unnecessary anxiety among your staff. This kind of stress inevitably leads to problems. Instead of spending your time focused on how to grow the company or acquire a new customer base, you find yourself constantly dealing with issues.
Let me give you an example.
Earlier this year, I was hired to solve recurring customer service challenges at a small coaching company. One big complaint was the time it took for clients to get a response to their emails.
My client was frustrated, because, “Our policy is to reply right away.”
As I was auditing the SOPs, I saw that the language around response times stated that customer support should reply to messages in 24 hours.
Do you see the problem?
A 24-hour response time policy gives the team 2 days to reply. Let’s say you sent in an email to support today at 2 pm. The team would be totally in line with policy if they replied tomorrow at 1 pm.
My client’s written guidelines didn’t line up with her expectations.
When I mentioned this to her, she said to me, “They should know that’s too long.”
Oof.
This turned out to be just one way that this CEO was hands-off with the team. She hired smart people and expected them to know what to do — even if it conflicted with her own written procedures.
She also was the quintessential cool boss. She’s extremely smart, charismatic and fun to talk with on Zoom, but she had a tendency to let problems slide until her frustration was at a boiling point.
The team liked her, but they were also totally stressed out, because they could tell they weren’t meeting her expectations.
All of this anxiety was only contributing to the customer service issue I was hired to solve.
The worst of it was that all of this was completely avoidable!
So what do we do about it?
In my example, the fix was easy. I was able to revise the SOPs, communicate the reasons for the change, and then monitor the team’s work to make sure they followed the new policy.
In other words, the antidote to being the cool boss is clarity.
Have you ever heard the phrase,"Clear is kind?”
It’s also more effective.
Instead of being the cool boss, be the clear boss.
The clear boss communicates your expectations, goals, and priorities – and you go a layer or two deeper than simply sharing the mission that everyone should organize around.
You establish decision-making frameworks, explain what priorities are impacting processes, and then coaching the team to make better decisions.
A clear boss sets boundaries, models the behaviors you want to see, and ensures that everyone knows how their contributions align with the company’s value proposition.
You communicate what you need when assigning work, but give your team latitude to find the best way to accomplish the end result.
You address problems and issues as they happen and create a culture where feedback is expected and not such a big deal.
You talk to your team members more about their work, finding out the nuances of their work style and how it fits within your organization’s culture.
You let team members know when their work isn’t up to standard, and what they need to do to keep their jobs.
It wasn’t until I made these shifts in my company that I was able to start building myself out the business.
You can’t truly step out of the day-to-day until you’ve put the supports and structures in place that will allow your company to run without you – and leaving your team to guess what you want will never get you there.
For me, it took a pretty big upheaval for me to see how my fear of being the kind of terrorizing boss I’d worked for was creating exactly the wrong kind of environment.
But you don’t have to wait until a crisis happens to turn this dynamic around.
If you see any cool boss tendencies in yourself, start here.
Notice your small resentments.
Is there one thing building up inside of you, making you feel like you’re not being appreciated, or the team isn’t stepping up the way you need them to?
Is there something you’re not saying to the team? Maybe a norm you think is obvious, or a way you’re softening your feedback so that the team isn’t hearing it?
How can you bring more clarity to the situation?
You might be shocked at how that turns things around.
Let me know how it goes.
Ps. I’m still looking for folks to interview as I develop a mentorship program for next year. Leadership is a big part of it, but we’ll also be working on operations, so you can build yourself out of your business. If that sounds good to you, I’d love to ask you a few questions. Would you book 20 minutes with me here?