When I set out to write about bad bosses for this blog, I couldn’t think of any dad-isms to kick it off. But then, last week, l watched my mentee graduate from a summer program for entrepreneurs. Afterwards, I told Dad I wished there had been something like that for me when I was starting my business.

“Yeah, but sometimes you just have to learn things the hard way,” he said. Ah, there it was. The latest lesson from Dad.

What, you may ask, does this have to do with bad bosses? We will get there. But first, let me share a quick summary of the bad bosses I heard about after asking my network for examples:

The Micromanager. ALL work must be executed exactly the way they would like it to be, or it has been done, for decades. Wait, you have an idea? Unacceptable. The micromanager, you see, has tried everything before and knows your way won’t work.

The Egotistical Control Freak. “Did you enjoy your LONG lunch?” they say, or “I saw you had a meeting with HR; what was that about?” The egotistical control freak must keep tabs on you at. all. times. This isn’t about the work, but rather making sure you understand who’s boss.

The Lone Ranger. Maybe the lone ranger feels guilty about getting others involved, has waited until the deadline is too close, or just doesn’t think anybody else is as capable. Regardless, they imply you’re incompetent with their repeated refusal to let you do your job.

Gosh, that was cathartic to write, and perhaps it was cathartic for those who shared, too. I am certain we could add several more. But, more important, what bad boss from your past did you picture while reading? Because I pictured…me.

I’ve always believed leadership is a journey. And, if you become content with who you are as a leader, it practically ensures you are regressing into a bad one. I don’t know why it surprised me, then, to realize that I had not only learned the hard way from my bad bosses, but I had also made many of the same mistakes myself, especially early in my career.

We didn’t have any training available when I first became a boss, so there was a lot of trial and error. I tried keeping my employees at a distance (don’t want to be too friendly, this is business!), impressing my exacting standards upon them (it’s good for them!) and keeping leadership-level work to myself (protecting them!).

I find myself wondering as a write this, if I need to try to find a few people to apologize…

While I would like to blame lack of training, and feel deeply sorry for my early employees, part of me wonders if making mistakes was the best way to learn. Later on, when I was afforded training, I think it was more meaningful because I had the scars from the bad exit interviews of my past to reference. I’m pretty sure this is what Dad means about learning the hard way. Sometimes the best way to cement a lesson is to experience it yourself.

Most of us don’t want to be bad bosses, so the good news is, if you desire to be better, you become better over time. You seek out professional training (I highly recommend the Leader Within program at Northwestern’s Kellogg School of Management); welcome 360 reviews conducted anonymously through a trusted colleague; read books (The Secret Success Society by Tim Shurrer is my new favorite); listen to podcasts (you can’t go wrong with “The Maxwell Leadership Podcast”); and you seek out wise counsel from people who will openly share their mistakes and lovingly help you see yours.

Speaking of wise counsel, a good friend and mentor said something I think could help us all on the journey toward better leadership: “What if everyone was your student, and everyone was your teacher?”

The hard way

Join for free* to continue reading.