How I Failed Miserably As a Leader and Ultimately Improved My Company

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I failed miserably last week. Like, one of those “look in the mirror” moments where the reflection staring back makes you feel pretty awful.

We all want to be exemplary leaders. We are not, but we are trying. And when the inevitable happens – a fatal error in judgment – it hurts like hell.

The story is simple. case of missing an appointment. The date was only lunch with his daughters, and the one who missed it was the COO of my company. Why are you asking?

Because he felt compelled to.

And that was entirely my fault.

Moving meetings

Many of us are victims of our schedules. I am no different. My company has always been 100% remote, which means we need virtual meetings in order to work effectively.

However, what I didn’t realize is that my COO board has become And therefore Complete that he felt the need to change the previously arranged family time. In his opinion, lunch with his daughters was no longer possible.

“A lot to do.”

“Work gets in the way.”

Hear me now: Any meeting can be rescheduled.

Of course, once I found out what was going on, I told my COO to move in his meetings and go to lunch. In fact, I ordered him to. three hours. at most. Just him and his daughters, along with whatever delicious food option they choose.

Like I said, this whole ado was my fault. Why do you ask again? why me I Responsible for someone else’s schedule?

Because I am in charge.

Related: Ten Lessons About Failure Every Entrepreneur Should Know


The CEO’s job is to feel the pulse of their organization. I think what bothered me the most was that I allowed something devastating to happen to one of my team members…

…after what happened to me.

A while ago, I ran into an enormous creative hurdle: I didn’t have time to be creative. I’ll start work around 7:30 a.m., meet my team, have client meetings throughout the day, try hard to work at family time, then go to bed and rinse, dry and repeat.

Related: 4 ways to protect your time, according to the founders of Warby Parker, Minted, and other top companies

This was not sustainable. Something need to change. I recently hired an Executive Assistant which has proven to be a godsend, but I still need time to channel my inner creativity and do the things that attracted me to entrepreneurship in the first place.

I’m rearranging priorities. I resisted that stubborn voice in the back of my mind that said only one thing: You, Jason Hennessy, should be in every meeting and all the time.

Instead, I believe in my team. I’ve opted out of meetings that others can handle on their own. I set Wednesday as a mean day Just for creativity. There are no meetings, except maybe a group meeting in the morning. All day long to work on creative things. I call it an eight hour shower where I create space for my creativity.

These changes have improved my creativity (surprise, surprise), my mood, my perspective on time management, productivity and my family’s time.

So how can I allow a familiar monster to absorb time attacking my COO?


Let me be clear: I understand that not everyone has the luxury of booking several hours a day to themselves. It is not always possible. But we also struggle Difficult With time management, and as we get older, so does work-life balance.

Related: 10 time management tips that work

Time management is not really taught in elementary or secondary schools. If this is the case, it is often precipitated and generalized. “Do this” and “Do that”. But what works for one person may not work for another.

We are also creatures of habits. Routine can be helpful, but it also has a dark side. One can become so entrenched in the routine that one finds it impossible to break. Do you schedule lunch with the family from 2-4 pm? silly! what about work?

It’s not easy, it’s even more difficult when you’re part of a team and Uber is committed to the mission of the company (and he’s my COO). That’s why all this falls on me. As a CEO, you need to know your team. Their individual strengths, weaknesses, daily victories and struggles.

So I ask you…

Are you assessing the needs of your organization?

Not monthly, not weekly.


Learn from my mistakes. Check in with your team every day. Make sure they do the same with those employees who work under them.

As your company grows, this may become more difficult. so sad. You are the chief administrator, this is part of your job. It is very important that you pass on what you have learned to others.

This is where it failed. My COO faces just as much stress and responsibility as me. I realized I needed to make a change in my routine, and I didn’t push it forward. I didn’t check with my team. I couldn’t stand the pulse of the culture around me making sure everyone was working Okay.

Note that word. Okay. No Difficult. People work hard when they do well, and they work well when there is a tangible work-life balance. Some ways to do this:

Schedule a one-on-one meeting with your team

Ask the tough questions. Forget to update each other about the company’s latest project – that’s for another time. While that:

how do you feel?

how is our family?

What does your schedule look like this week?

Is there anything you want to move?

Do you feel like you have enough time to do the things you need to do?

Is there anything I can do to help you?

Encourage him to take a vacation

A toxic work culture spreads when employees feel they can’t take time off. Encourage the exact opposite. Your company won’t burn down completely if one person is gone for the day. Teach trust throughout the company so that no one feels obligated to be there every day.

I can’t say enough about faith in others. Assemble your all-star team, and you’ll never feel bad about the occasional absence. I do this myself, knowing that I will be back and everything will be the same.

Make sure every employee in your company feels like time off is what it should be: time off from work.

Holding company wellness events

Another way to promote work-life balance is to advocate for it through company-wide events. Create a culture that believes in physical, mental and emotional health. People will always want to work more for a company that is vocal about its commitment to balance and realizing the fact that, yes, life More important than anything else.

Our #health-and-wellness Slack channel allows employees to encourage each other through their successes and suggestions. Our People Success section provides weekly educational and inspirational ideas for our team. Employees want to feel valued and supported.

Related: Now is the time to start embracing mental health in the workplace

move forward

It probably isn’t my job to literally figure out my team’s schedules, but you can bet I’d be super sensitive to who they are as people.

because that He is my work. I understand that my team, just like me, is made up of people with strengths, weaknesses and everything in between. And if I find myself struggling with time management, chances are the people on my team will as well.

Family lunch > business meeting.


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