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How I Failed Miserably As a Leader and Ultimately Improved My Company This article challenges leaders to establish healthy expectations for employees to show value for their greatest asset

By Jason Hennessey Edited by Jessica Thomas

Opinions expressed by Entrepreneur contributors are their own.

I failed miserably last week. Like, one of those "look in the mirror" moments, where the reflection staring back makes you feel extra terrible.

We all want to be perfect leaders. We aren't, but we try. And when the inevitable happens — a monumental mistake in judgement — it hurts like hell.

The story's simple. A case of missing an appointment. Only the appointment was lunch with his daughters, and the person who missed it was my company's chief operating officer. Why, you ask?

Because he felt like he had to.

And it was entirely my fault.

Moving meetings

Many of us are victims to our schedules. I'm no different. My company has always been a 100% remote operation, meaning we need virtual meetings in order to function effectively.

However, what I didn't realize was that my COO's plate had become so full that he felt the need to shift around pre-arranged family time. In his mind, lunch with his daughters was no longer possible.

"Too much to do."

"Work got in the way."

Hear me now: Any meeting can be rescheduled.

Of course, once I learned what was going on, I told my COO to move his meetings and go to lunch. In fact, I ordered him to. Three hours away. At least. Just him and his daughters, along with whatever delectable dining option they chose.

Like I said, this whole snafu was my fault. Why, you ask again? Why am I responsible for another person's schedule?

Because I'm the one in charge.

Related: Ten Lessons About Failure that Every Entrepreneur Needs to Know


It's the CEO's job to feel the pulse of their organization. I think what bothered me the most was that I had allowed something destructive to happen to one of my team members…

...after it had happened to me.

A while back, I hit a massive creative obstacle: I had no time to be creative. I'd start working around 7:30 a.m., meet with my team, take client meetings throughout the day, desperately attempt to work in family time, go to bed and then rinse, dry and repeat.

Related: 4 Ways to Protect Your Time, According to the Founders of Warby Parker, Minted, and Other Top Businesses

This wasn't sustainable. Something needed to change. I had recently hired an executive assistant who proved to be a godsend, but I still needed time to channel my inner-creative and do the things that had drawn me to entrepreneurship in the first place.

I reprioritized. I fought back against that tenacious voice in the back of my brain that only ever said one thing: You, Jason Hennessey, need to be at every meeting, all the time.

Instead, I put faith in my team. I bowed out of meetings that other people could handle on their own. I set Wednesdays as a day meant only for creativity. No meetings, save for maybe a team huddle in the morning. The entire day to work on creative things. I call it my 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 time.

So how could I let the familiar, time-sucking monster attack my COO?

The struggle

Let me be clear: I understand that not everyone has the luxury of blocking off multiple hours a day for themselves. It's just not always possible. But we also struggle hard with time management and, as we grow older, work-life balance.

Related: 10 Time Management Tips That Work

Time management isn't really taught in primary or secondary school. And if it is, it's often rushed and generalized. "Do this" and "do that." But what works for one doesn't work for another.

We're also creatures of habit. Routine can be helpful, but it also has a dark side. One can become so entrenched in routine that they find it impossible to break it. Schedule a lunch with family from 2-4 p.m.? Ludicrous! What about work?

It's not easy, and it's even harder when you're part of a team and uber-committed to a company's mission (which my COO is). That's why this all falls on me. As a CEO, you HAVE to know your team. Their individual strengths, their weaknesses, their day-to-day wins 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 working under them.

As your company grows, this might become more difficult. Too bad. You're the head honcho, it's part of your job. And it's incredibly important that you pass on your learnings to others.

That's where I failed. My COO faces just as much stress and responsibility as I do. I realized that I needed to make a change to my routine, and I didn't pay it forward. I didn't check in with my team. I didn't take the pulse of the culture around me and make sure everyone was working well.

Note that word. Well. Not hard. People work hard when they work well, and they work well when there's a concrete balance between work and life. A few ways to do this:

Schedule one-on-ones with your team

Ask the hard questions. Forget updating each other on the latest company project — that's for another time. Instead:

How do you feel?

How's your family?

What does your schedule look like this week?

Is there anything you want to move around?

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 time off

    Toxic work culture abounds when employees feel like they can't take time off. Encourage the exact opposite. Your company won't burn to the ground if one person is gone for the day. Teach trust across the company so that no one feels obligated to be there every single day.

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

    Make sure every employee in your company feels like a vacation is what it's meant to be: time off from work.

    Hold company wellness events

    Another way to promote work-life balance is to champion it through company-wide events. Create a culture that believes in physical, mental and emotional wellness. People will always want to work more for a company that is L-O-U-D about its commitment to balance and cognizant of the fact that, yeah, life is more important than anything else.

    We have a #health-and-wellness Slack channel that allows employees to encourage one another with their own successes and suggestions. Our People Success department 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

    Moving forward

    Maybe it's not my job to know my team's schedules verbatim, but you can bet that I'll be hyper-sensitive to who they are as people.

    Because that is my job. Understanding that, just like me, my team is composed of human beings with strengths, weaknesses and everything in between. And if I find myself struggling with time management, chances are people on my team are as well.

    Family lunch > business meeting.

    Jason Hennessey

    Entrepreneur Leadership Network® Contributor

    Entrepreneur & CEO

    Jason Hennessey is an entrepreneur, internationally-recognized SEO expert, author, speaker, podcast host and business coach. Since 2001, Jason has been reverse-engineering the Google algorithm as a self-taught student and practitioner of SEO and search marketing.

    Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

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