3 Leadership Lessons Learned from My Worst Managers

I was recently speaking with my youngest daughter, who had just entered the workforce with her first "real" job, as she likes to describe it. She shared with me that she felt lucky, as her first impressions of her new boss was positive and, as she stated, "I can learn a lot from him." 

As a Dad, of course I was very pleased since the "first" boss can really set the tone for one’s career and even how one thinks about work itself. I had a great first boss at Hewlett Packard, Marie, and to her I am forever grateful.

But that conversation with my daughter led me to think through all the various bosses I had over a thirty-seven year career. I suspect that my experiences were no different than most people’s, with a bell curve of great leaders, through average leaders, to some flat out awful bosses who never should have led a team of employees, no less me. 

But, upon further reflection I came to the conclusion that I also owed  those average and, more importantly, horrible bosses a great deal of thanks, since they taught me what not to do.

As I reached various levels of responsibilities, first leading individual contributors, then managers and eventually VPs who led large teams of people in their own right, I often thought about those poor leaders and how demotivating and at times demoralizing they could be.

I have categorized some of these learnings, and of course changed the names to protect the innocent as they say. Perhaps you see some of these traits in the supervisors you’ve worked for.

Bad Manager 1: The Information is Power So Keep it to Yourself Leader

I hated working for this guy I’ll call Joe.  Everything was a secret to this guy, and for those of us who wanted to do a great job and, just as importantly, be part of the bigger picture, he drove the team and me mad. From performance feedback, resource planning, reorganizational speculation, to you name it, Joe shared nothing.

Staff meetings were a one-directional information flow with the team telling him everything we knew for fact, heard on the street, or even speculated. Joe was happy to hear it all, responding enthusiastically, but requests from him were met with deafening and demotivating silence.

At a particularly frustrating staff meeting one of my peers blew up, accusing Joe of  “treating us like mushrooms, keeping us in the dark, and feeding us #@%^.” Other teams in the company knew critical information, so I had to establish non-linear and guerilla tactics to "get the scoop.”

Sound familiar?

So, what did I learn from Joe? The vast majority of the team was made up of "A" players who would clearly respond with "A" level performance if I could create the appropriate and motivating environment.

One necessary component of that atmosphere was regularly share everything I could in regards to the business, understanding that there was indeed some info that could not be shared.

When my boss had a staff meeting, I would assemble the team immediately after and share everything I possibly could. Information nuances are important, so I shared this information while it was fresh in my mind.

The result was a team armed with everything it needed to know, negative rumors killed, appreciation for the trust I had in them, and gratitude for being treated like adults. So, even if you’re occasionally burned by overcommunicating, keep doing it.

Bad Manager 2: The Manage Up, Shi# Down Leader

Sadly, I have had a few of these. These leaders’ full time job is to solely manage their one or two constituents - their bosses.

My supervisor “Bob” was the so very good at this. In his mind, his team was there with one purpose, and that was to prepare him to look good to his boss and his boss’s boss. This would be sort of ok if he hadn’t treated the team more like slaves than professionals. Unrealistic timelines, unreachable goals, yelling, screaming, condescending comments were a regular part of Bob’s leadership motion.

Of course, when the bosses were around us, Bob was charming and demonstrated Academy Award-level acting skills with in the role of the ultimate people manager. But it was all an act by an insecure, narcissistic manager.

Bob taught me that to be an effective leader, you needed to be in balance to all your constituents - your team, your bosses, your customers, and even your peers… But over-weighting to your team, with a genuine caring professional approach, will ultimately reap profound results, with delighted customers and bosses.

So even if your bosses feel like they are the most important things in your work life, discipline yourself to focus on the team, the team, and the team.

Bad Manager 3: The Debating Leader Who Will Never Admit They’re Wrong

Working for “Debra” was a learning experience later in my career that was flat out exasperating and exhausting. Debra was a seasoned leader, who to her credit had a highly developed creative side.

Ideas came from Debra like lava from a volcano. At times, these ideas were quite helpful and even game changing, but the problem was that she loved every one of them even in the face of indisputable facts on why a particular idea would not work.

Discussions quickly moved to a high school debate-style meeting and, admittedly, I often got sucked into the scrum. What took me some time to learn was there was no real debate, but a dogmatic need by Debra to win the argument.

But, she didn’t just need to win the argument, she also needed assurance that we were going to execute, with precious resources, an idea that everyone in the room and every external partner knew would ultimately fail.

Listening skills were not evident in Debra’s day-to-day leadership of the team and ultimately I left, along with many others.

While there are clearly times when a leader has the right to drive change against the status quo and against the recommendations of their team (see Steve jobs), Debra taught me that when up against contradictory feedback from your “A” team, you’re best off to, at minimum, take the time to be thoughtful about their concerns. So even when you are sure you are right, take a walk and think it through. At the very least, your team will be appreciative... and they may even be right.

What lessons have you learned from your worst boss? Let me know on Twitter or in the comments below. Just enter your comment, put your name and email address in the pop-up window, then click to comment as a guest!

This post was originally published in April 2018 and has been updated.