If you’ve ever found yourself working for a difficult manager, you probably took away some valuable insights for how you don’t want to work — and how you do. Rebecca Greenbaum, a professor at Rutgers University’s school of management and labor relations, recently told The New York Times about the impact a bullying boss can have on a team. “Productivity may rise in the short term… But over time the performance of the staff or team deteriorates, and people quit,” she said.
Since some of our best leadership lessons come from our most trying experiences, we asked members of the Thrive Global community to share the best lessons they learned from the worst bosses they’ve had.
No one is in charge of your career but you
“My first job was a real mismatch for me. I realised that I was good at writing and needed to switch my career paths to journalism. When I resigned, my boss told me that my media career was over because she would refuse to give me a reference. I was devastated at first. But over the next couple months, with distance and clarity from that job, I realised that no one was in charge of my career but me. That experience taught me to have faith in myself and my abilities. I have been a professional writer ever since.”
—Greta Solomon, writing coach and author, London, England
Bullying behavior is never OK
“The best lesson I’ve learned from the worst boss I’ve had? That the adage, ‘He’s a d*ck, but you get used to him’ isn’t true, and that no company or employee should put up with bad treatment.”
—Amy Toncray, nerd recruiter, Royal Oak, MI
Listen to your team
“The best lesson I learned from my worst boss is to never underestimate your team. Don’t think that they’re unaware of your negativity. Your employees know all your traits, and are likely to avoid communication with you when you crave it the most. Masking it with anger and orders isn’t a healthy way to ask for help and understanding. If you don’t listen to your team’s small problems, they’ll never share their major ones.”
—Alla Adam, business biohacker, Chicago, IL
Lead with heart and humanity
“The best lesson I’ve learned from the worst corporate leader I’ve worked for is to show up for work and life with humanity and heart. My former boss was a true hard-*ss — there was no love and no warmth there. It was all business and the corporate culture lacked emotional texture. The team was miserable and mocked him behind his back. Mr. Boss Man definitely taught me what not to do by example.”
—Lisa Cypers Kamen, optimal lifestyle management expert, Los Angeles, CA
No job is more important than your well-being
“No job is worth your physical and/or mental health and well-being. If you’re not treated with respect, or you wake up on Monday mornings with a knot in your stomach because you dread going to work, it’s time to start looking for another job.”
—Mim Senft, founder, CEO, Blooming Grove, NY
Learn the power of managing up
“I once had a supervisor who was really hypercritical and difficult to work with. I realized that her manager was putting a lot of pressure on her, so my experience was a product of a somewhat toxic workplace culture. But over time, I learned how to ‘manage up,’ which helped me establish trust with my supervisor and better navigate the challenges we encountered.”
—Andrew Gobran, people operations, Minneapolis, MN
Micromanaging kills creativity (and morale)
“Micromanagers kill creativity! Early in my career, I had a very challenging boss who was controlling and loved to be involved, every step of the way. Since I was inexperienced, I did need oversight, but some of the more seasoned staff didn’t appreciate her meddling ways. The environment was tense, and morale went south as a result. Talented team members stopped feeling motivated, and both work productivity and creativity suffered because they no longer had autonomy over their decisions. Over time, I saw the value of putting the right people in the right roles and letting them do their thing. It’s powerful to see people own their decisions with a sense of pride and accomplishment — we often need to get out of the way.”
—Lara Smith, CEO, Calgary, Alberta
Stay curious and show gratitude
“The worst boss I’ve ever had taught me who I don’t want to be, how not to treat others, and how to avoid taking everything personally. When you put your ego first and believe that everything is about you, you aren’t a leader! Leaders actually want to learn, be there for their teams, and express gratitude for everyone’s contributions. Our careers have shifted and we are more absorbed by work tasks. If you throw a negative, egotistical, know-it-all boss into the mix, then you, the company you work for, and the team surrounding you all suffer.”
—Mariella Stockmal, founder, Santa Barbara, CA
Be clear about your team’s priorities
“Learning to say ‘no’ for the good of the team was something I picked up when my former boss would always just commit to a task without thinking about how it would impact set timelines. Last minute initiatives are inevitable, but if they overlap with another project, the manager should tell their team what to prioritize first.”
—Tiffany Go, communications executive, Manila, Philippines
Don’t assume the higher-ups know best
“I worked at a marketing startup in my twenties, and my affinity for technology and software combined with some HTML coding skills landed me in a position working with a man who I first perceived as fun and dynamic. But when I came with him to sales appointments with CEOs and founders of tech companies, I witnessed his strange meeting style of intentionally using silence and long pauses that were uncomfortable for everyone in the room. My background was in consultative sales, where connection and listening helped close deals, so his techniques had me confused. I didn’t see how any of it was fostering a sense of trust or understanding to create business partnerships.
On the ride home after a particularly awkward appointment where he was sweating bullets, he smiled ear to ear, beaming like a kid, and said, ‘How ’bout that? We had Joe X, the president of company Z, sitting with us for a full hour and we were only scheduled for 30 minutes. Power play!!!’
The outcome didn’t matter at all. The adrenaline rush he got from controlling the time of someone he perceived as powerful is what drove him. It wasn’t my first experience with an ego-driven boss, but it was my first time seeing ego get in the way of what could’ve been great results. Not long after this, he was fired.
The overall lesson for me was to listen to my gut and make no assumptions based on a person’s title or role. None of what I saw made sense, and he certainly tried to make me feel like I didn’t have enough experience to understand his techniques. After this happened, I dropped my insecurity and instant deference related to titles. Thanks to his twisted lessons, I’ve been able to sit in a room with people at all levels and see that we all hold value and possess power, regardless of our role.”
—Stephani Roberts, podcast host/visibility strategist, Boston, MA
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