The Worst Mistakes I Made as a First-Time Boss

It’s a universal truth that everything seems so much easier when someone else is doing it. I often hurl insults at goalies on TV who miss shots I’m certain I could save, despite having little to no basic human coordination (I once miscalculated the distance between a desk and my head when picking up a pencil and almost knocked myself out cold). Such was the case many years ago during my first attempt at people management. Because I had of course been myself an employee to multiple bosses, I naturally assumed I could easily transition into the opposite role. I never once considered that this logic was akin to saying that I live in an apartment building so therefore I am able to build an entire high-rise with my bare hands. Though several years and different companies have passed since this particular role, I still deeply cringe whenever I recall my terrible mistakes. Enjoy.

Think of me as your friend: The first group of employees I managed were all around my age and I was eager to build a positive rapport. At the time, we all earned around the same salary – that is to say, not much. I began inviting everyone out to prove how effortlessly cool I was and insisted on paying. After birthdays, meetings and sporting events I almost needed a second job to afford working at my first one.

I’ll help with that: My biggest pet peeve has always been seeing junior employees continuously work late into the night while their bosses head home. I bravely vowed to take on extra work for my team so they wouldn’t lose time with their families. I dramatically made the offer and boy, did they take me up on it. I worked every Saturday for months until my own manager suggested I rescind my earlier suggestion. To his credit, he was only slightly smug.

I’ll fight for you: I desperately wanted my employees to feel valued and pledged to communicate any and all workplace concerns with our senior leadership. I diligently recorded their demands and if I found that paper today, it would likely list everything but a pony. Though they did ask for office cats.

I’m not mad: After a lifetime of quiet obedience, I had no idea how to deal with an employee who forgot deadlines and sometimes weekdays all together. Because of my relentless cheer they barely made an effort with excuses. Treacherous weather, transit outages and traffic accidents routinely plagued them despite the fact that we actually lived in the same neighbourhood. I eventually chastised their behavior but to this day I’m unsure if they understood any of my panicky speech, hastily squeaked out through a veil of nervous sweat.

I eventually grew into a much more balanced leader and I wish anyone entering their first foray into people management an enormous amount of luck and an endless supply of stress balls.