On Leading With Greatness
On Leading With Greatness
How to Keep Your Boss on Their Toes
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How to Keep Your Boss on Their Toes

And Teach Them to Lead
A cartoon of a male boss yelling and pointing at a computer where a smiling female employee works

Have you ever driven your boss nuts?

Driving my bosses bonkers has always been my specialty. What better way to keep them on their toes? Besides, I figure, what else is a boss there for?

Way back in the 1900s, I was a professional set builder for a couple of major Philadelphia theaters. I was a decent enough carpenter, better than most, but my technique was somewhat unorthodox, which worked well in the quirky realm of theater. I was pretty happy with the gigs.

And here’s a fact! Theater carpentry is really cool. Forget the mundane right angles and square joints of ordinary woodwork — we’re talking nasty twists, improbable curves, and vexing problems. Wood, metal, plastic, and a shocking amount of styrofoam were our materials. One day I’d be whittling intricate patterns in plywood with a band saw, and the next I’d be replicating a realistic living room from scratch. I thrilled at the variety, the dynamism, and the creative freedom.

My last theater gig—and we are going back nearly 35 years here—I had a good boss, Joe, the best I’d known up to that point in my life and one of the very few decent bosses I would ever have. I loved that he was all about precision: doors that closed with a satisfying click, windows that slid up and down with a gentle whoosh, and no gaps to fill or conceal anywhere. If we built an interior set, it looked and felt like a real room, whether you were sitting in the cheap seats or strutting the stage.

Now, Joe and I, as much as we liked each other, sometimes hit bumps. Joe was more conventional—as much as one can be building theater sets—while I had a few, shall we say, eccentricities. One of my most annoying being a desire for specialized tools that did not exist. That wasn’t so bad in itself, but I wouldn’t just pine for them. I would actually set about creating them out of whatever I could find around. Most of these tools were designed for one-off jobs, but some tools came in handy over and over. I stashed these reusable tools in our overcrowded tool shop, which really tested Joe’s patience.

One time we had to build a funky staircase that featured a wonky curve repeated in various sizes. Joe had his own way of tackling the job, which was to just freehand the curve, but I was not so confident in my skills. Instead I whipped up a solution, transforming scraps into a tracing tool. The tool looked like something kid would make, but it got the job done.

In the meantime, Joe was really steamed. We were under the gun, and he saw my quirky tool-making as a distraction from our real work. The truth was that my tools increased my efficiency and accuracy and took little time to make. Plus I had fun designing and fashioning these custom tools! Admittedly, raising Joe’s blood pressure was a little fun too.

To his credit, Joe rarely ordered me stop my tool-tinkering although he made sure I knew he was irked. As far as he was concerned, my time crafting gadgets was time I could have been hammering, sawing, or drilling. Case in point, when I started using my homemade tool to create those curved stairs, he had enough. He showed me how easily he could just draw the curve. I showed him how my DIY tool did it faster and more accurately. I wasn’t trying to be an asshole, but it probably looked that way. The cool thing was I finished with the stairs in no time.

Here’s the twist. The more I did things my way, the more I wore down Joe’s patience, so I kind of went underground with my goofy toolmaking. I became a clandestine inventor, crafting my contraptions when Joe wasn't lurking nearby. Even utilizing my reusable tools became my little secret as Joe was always threatening to banish them to the dumpster.

This is why Joe, although a really good boss, was not quite a great boss, a leader, at least not yet. He needed some seasoning. This is not a dig against him. We were both young and learning, and I flatter myself that having to work closely with the likes of me made Joe a better boss and true leader in the end. Sure, my weirdness, my little oddities, my need to do it my way were annoying as hell, but I got my work done on time (mostly) and I excelled at it (mostly). Later on Joe even had me in his wedding party, which shows there were no sore feelings. Sadly, with all my moving around, we lost touch a long time ago.


Leadership is never easy, and it sometimes involves tolerating or even embracing people’s foibles, idiosyncrasies, quirks, ditziness, and other peculiar traits as long as they don’t gum up the works or cause mayhem. For instance, being a constant jerk? Nope. Unacceptable. Doing things an unfamiliar way and still delivering? Yes, so long as no one is hurt. Of course, sometimes there is no room for compromise, but when there is, a leader will strike the right bargain, finding the appropriate balance, particularly when a team member has a proven track record.

So next time someone is driving you nuts at work, take a deep breath and reflect. Are they genuinely doing wrong—cutting corners or slacking off? Or could it be they just do things differently? Is your way objectively better? This is but one of the many challenges of great leadership—melding diverse styles, backgrounds, and personalities into a harmonious whole. Embracing this diversity, by the way, makes for the best teams. It adds panache and results in innovation and better outcomes. It pushes boundaries, challenges tradition, and breaks the back of the status quo. It also enhances delegation.

But here’s the secret sauce: great leaders can see how each individual contributes to the whole. They thrive on tolerance and promote diversity of all sorts. They can bend in compromise without breaking. Joe was well on his way to becoming such a leader.

No one is born that way. Leadership is learned through study, experience, and practice. And challenging circumstances and people only sharpen it. It may be hard to think of team members who drive you nuts as honing your skills, but it’s true. Working well with them is the difference between greatness and mediocrity.


How do you deal with employees and coworkers who irk you? How can you get the best out of them?

Leaders must practice self-discipline and learn patience in the face of productive but annoying workers, and I can help.

If you want to learn more about how to become a great leader in this world of bad bosses, visit GuidanceForGreatness.com.

Visit Guidance for Greatness

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On Leading With Greatness
On Leading With Greatness
Each Thursday I share new ideas for leaders and aspiring leaders on mission clarity, self-awareness, and human skills — a slightly irreverent kit of Tools+Paradigms for leaders and aspiring leaders like you. Visit GuidanceForGreatness.com