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​Valuable Lessons Learned from 50 Amazing (and Horrible) Bosses

​Valuable Lessons Learned from 50 Amazing (and Horrible) Bosses

“Work” has been an integral part of my life. I started working when I was five years old when my dad taught me the lost art of counting back change to customers at our family’s grocery store. Fast forward to age nine, I got my first paying job. Like many kids of my generation, I earned money by babysitting. My first paying gig was babysitting our neighbor’s kids who were ten and seven. A 9-year old kid babysitting a 10-year old? I was mature for my age. Who cares why…I earned my first paycheck!

A little while ago, I decided to look back at all my jobs since that first one – jobs during school, summer jobs, part-time work, full-time positions and even freelance employment. Then I tried to count the number of bosses I had worked with. I ended up with more than fifty different bosses and, unexpectedly, I remembered each one.

After several decades in human resources, I have worked with hundreds of terrific leaders, managers and supervisors. Yet, the personal experience reporting directly to over 50 unique bosses taught me the most valuable and meaningful career (and life) lessons. Here are three indelible lessons that stand out.

Excellence pays dividends in the long run.

Lesson 1: Working for a bad boss does not give you license to lower your work standards. You’ll experience bad manager behavior in many ways: micromanaging, bullying, not sharing information, narcissism, misogyny, conflict aversion, stealing credit or even plain laziness. It’s very tempting to throw up your hands and not put in your best effort when you work for a horrible boss. After all, if your company is stupid enough to employ a “loser” manager, then why should you care? You care because you, unlike your boss, have character and integrity. You rise above the fray; you do not allow yourself to match the lowest common denominator of bad behavior. After having worked with 50 different bosses, let me assure you, a boss’s tenure is a momentary blip in time.

We all wish we only had super bosses over our careers. Great leaders inspire and stretch us to become our best. The reality is that you will encounter a full spectrum of supervisor quality. Ensuring excellence, by keeping your personal work standards high, will pay dividends for you in the long run.

Learn from both bad and good bosses.

Lesson 2: Observe and learn; no matter who your boss is. A slew of bosses gave me exposure to great leadership, common managers, and some horrible bosses. Remarkable leaders make the workplace an incredible environment to contribute and grow. When you are fortunate to work under an exceptional leader, you will experience firsthand the traits of good leadership. The role-modeling characteristics that I personally wanted to emulate were integrity, vision, customer-focus, strategy, optimism, open-mindedness, empowerment, passion, and results-orientation. For you, there may be different traits to emulate and that’s what makes it personal.

[Related: How Leaders Really Drive Change]

No one wants to work under bad management. The reality is that workers stay about four years with their employer. Chances are high that some time in your career, you’ll get stuck with a crappy manager. Believe me, you can learn as much from a bad boss as a good one. When you endure a horrible boss situation, you learn what not to do. You discover why “bad” management does not produce desired results. You learn what type of behavior demotivates people and causes ill will. Working under a bad boss has another silver lining for your personal growth. You build the career muscles of agility, perseverance, patience and tolerance that will benefit you throughout your career.

Turn struggle into your strength.

Lesson 3: Adversity makes you stronger and wiser. The toughest steel is forged from the hottest fire. Whether the leader, team, or me struggled, we survived and were better from it. We came out on the other side a little bruised, sometimes exhausted but we were certainly stronger and wiser. Adversity at work is unavoidable. How a leader handles hardship separates the best from the rest. Employees stay motivated when they see their leader calmly and competently deal with daunting conditions with tenacity, optimism, passion, and tact. Under pressure, bad bosses lack composure, shirk responsibility, and blame others. Worst of all, bad bosses fail to lead.

[Related: Authentic Leadership Training: Is it Really a Thing?]

You may not have 50 bosses over your career, but it’s guaranteed you will have more than a few. Change is inevitable. Always keep in the back of your mind that a bad boss situation is temporary. When you keep your attitude positive and in check, continue to learn, and become your best, you will be more than ready for the next internal or external opportunity when it appears.


Connie Wedel is a global HR executive, diversity proponent, equal rights advocate, leadership coach, writer, speaker and mom. Her advice has been found on EllevateNetwork, Huffington Post, Business Insider and the Chicago Tribune. 

Have more questions? Follow up with the expert herself.


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