Scoring an amazing boss can feel like winning the lottery. We may not always see eye-to-eye with our bosses, but for better or worse there’s much we can learn from them. 

In an interview with Entrepreneur, Jessica Alba remembered a valuable lesson from a former toxic boss:

“Kindness goes a long way. Working with people who are condescending really limits a person’s ability to thrive. When you don’t feel heard it’s impossible to stay motivated. Having experiences with people who don’t let employees have a voice taught me how important it is to ensure you give everyone, no matter their title, space to feel heard.”

We asked members of the Thrive Global community to share anecdotes and lessons they learned from memorable bosses — the great ones and the not-so-great — that contributed to their success. Whether you’re a manager yourself or reporting to one, these leadership tenets are worth taking to heart.

Spotting qualities in you that you don’t see in yourself

“My best bosses saw leadership qualities in me before I saw them in myself and gave me opportunities to step up and be heard.”

—Stacy Cassio, CEO, Charlotte, NC

Reframing your mistakes

“[My boss] creates a safe space, in which mistakes are not viewed as ‘the end of the world,’ but as learning experiences and growth opportunities. In past jobs, I have felt like making just one mistake would be the demise of my employment, but she empowers me to make decisions, even changes, without making me feel like my job is in jeopardy. With this, she has shifted my confidence and the way I work. It’s been huge for my development.”

—Megan Garheart, corporate recruiter, Baltimore, MD

Being happy for others’ success

“Early in my television career, I worked for a startup production company owned by two young guys. One of them had an inspiring ability to live gratefully. He was grateful for every sale and always made the best television content possible with whatever available resources. I admired his lack of envy for someone else’s success. Even when it was a competitor, I would hear him say, ‘That’s really great!’ Genuinely, he was happy for them. He knew that someone else’s success was not at the exclusion of his. Years later, his example is one of my most valued life lessons.”

—Maria Baltazzi, television producer and happiness mentor, Los Angeles

Treating you like they won’t always be your boss

“The best thing several bosses did for me (four of them, specifically) was to operate with the mindset that they wouldn’t always be my boss. This meant that my whole experience was anchored on preparation for many possibilities of what the future — my role, my boss, my scope of work — would look like. As a result, when they or I moved on to the next challenge, both of which happened, I was able to tackle the new normal with the appropriate level of trepidation, excitement, and confidence.”

—Pratiksha Patel, people and culture leader, New York, NY

Brutal honesty

“My boss called the office about 7 p.m. on a Friday night. ‘How did you know I’d be here?’ I asked. ‘You’re always there,’ was the reply. Then came the stinger. ‘The other managers get their work done in a 40-hour week.’ Instead of his praising my industriousness, he was actually criticizing my time management. ‘You’re doing something wrong,’ was his stark assessment. In reality, that assessment was something I needed to hear. The advice led to a mending of my temporal ways.”

—Dr. Marlene Caroselli, author, Pittsford, NY

Supporting you through difficult times

“When my husband died suddenly, my boss at the time stepped in and showed compassion in a few amazing ways. First, he ran a company-wide initiative asking employees to donate paid time off hours so I would have adequate time to figure things out and transition back to work. Bereavement policies insufficiently offer three to five days, but because of his kindness, I had six weeks off. Not only that, but he allowed me to work part-time from home due to my new circumstances as a single parent. During my darkest times, my boss was a beacon of light and authentic compassion.”

—Karen Millsap, leadership consultant, Orlando, FL

Firing you — and forcing you to find a better role

“The best thing a boss ever did for me was fire me. True, I loved the work developing cable TV program formats and was admired by many internally and externally, but the job was a safety net that kept me from considering the rapidly developing high-tech world around me, Silicon Valley. The firing forced me to consider role and responsibility alternatives, meeting new people, trying new activities, learning, and discovering. My newly found job also amounted to a 33 percent increase in pay with better benefits. Thank you for letting me go!”

—Michael Ivers, data analytics consultant, Everett, WA

Leading by compassionate example

“Early in my career, I worked at the corporate offices of Union Pacific in the benefits department. I was a low-level associate in a large team of employees. The Senior VP of HR who headed the team was a woman, Ursula Fairbairn. She was the only women on the executive team and had been one of the first female executives at IBM before coming to Union Pacific. During my time working in her department I never once saw her treat anyone with disrespect, including the person that emptied her garbage. At one point, I became very ill. I don’t know who made her aware of my health issues, but she called me to her office. I’ll never forget her giving me a hug and assuring me that if I needed anything while in the hospital, I should call. She gave me her private number. As it turns out, my doctor wanted to keep me in the hospital and the insurance company did not. I made the phone call to her to see if she could help, not knowing what would happen — she took care of it that day. This was a women in charge of 50,000 employees. Despite her position, her ability to make tough decisions, and the level of personal strength and tenacity it must have taken her to get to that position, she never lost her ability to genuinely care, be gracious. She showed me what type of female leader I wanted to be.”

—Mim Senft, co-CEO, Motivity Partnerships, Inc., New York, NY

Giving you their undivided attention

“The best thing a boss ever did for me was listen. Too often, when we are talking to our boss, they are multitasking. Every day they are inundated with emails, texts, and to-do lists. They’re running at the speed of light. By stopping and giving your full attention to your employee, you are showing them they are valued. They are respected. They are worth your time. Simple, right? But simple isn’t always easy. When my boss looked into my eyes and put down the phone to listen to my concern, I was elated. And from that day forward, I worked my butt off!”

—Camille Sacco, mindful meditation instructor and author, Winter Park, FL 

Giving a new mom a big promotion

“When I first became a new mom, I asked my boss if he’d allow me to telecommute two days a week. He took a chance, let me do it, and that decision actually paved the way for many of my peers as well. When I sought a promotion, I crafted a PowerPoint outlining how I could change my role to better serve the company and be more fulfilled professionally. Once again, he went for it and I advanced from my position as an entertainment publicist to a vice president handling public relations for several divisions of the company. My boss has always supported employees who are visionaries. I have seen him promote and advocate for many of my colleagues who have advanced to top positions throughout the entertainment industry. He’s been a champion for women, for parents, and for men who are great at what they do. For that, I’ll be eternally grateful to him for taking a chance on me and helping me thrive.”

—Beth Feldman, public relations specialist, New Rochelle, NY

Championing you when it’s time for you to grow 

“Peter Guber at Sony Pictures Entertainment promoted me from his executive/personal assistant to Manager Special Projects/Archivist. I was devastated. Broken-hearted. I wanted to remain Peter’s assistant for the rest of my career. He said it was time for me to grow and do something else. I had been doing this job for too many years. Peter saw me in ways I had not seen for myself. If the visionary producer within Guber had not worked his mastery on me, I would have never gone on to the other careers and projects that have evolved as a result of my accepting the promotion.”

—Lisa Krohn, consultant personal assistant, personal organizer, and writer, New York, NY

Pushing you beyond your comfort zone

“Tough love and being tossed into the deep end when I didn’t feel like I was ready. It was the only way to learn on a Wall Street trading desk — because nothing can prepare you for that job other than experience. It’s one that’s stayed with me and that I’m grateful for years later as I’ve launched my own business, where there is no right playbook because it made me comfortable with risk and uncertainty in a way I never was before.”

—Kristen Fanarakis, Author, The Debutante’s Guide to Wall Street, Founder, Senza Tempo Fashion, Charleston, SC

Being an ally during a life change

“I had just had my second child and was dreading returning to my unchallenging job. My boss Loren took a chance on me and promoted me to a huge position, even though I had a 9-week-old baby at home. He taught me to take big risks, look at people’s talents and inner strengths rather than circumstances, and also that some men can be tremendous champions of women in business — despite what the media often says about men in positions of power. He’s now in his 80s and I’m in my 60s and we’re still supporting each other.”

—Nancy A. Shenker, marketing consultant, Scottsdale, AZ

Looking after your well-being

“When I was a multi-store manager, my boss encouraged me to believe in myself, and gave me the creative freedom to lead the way I wanted to lead with kindness and fun! My role was to motivate and lead managers and designers to do their best. He saw the potential in me and gave me the confidence to do my job. One act of kindness that truly stands out was one day we had a meeting. I had a terrible cold. We were going to lunch to conduct our store meeting. There was a vitamin store next to the restaurant. He said, let’s go get you some tea to help with that cold. There was a massage therapist there, and he said, go ahead and get a shoulder and neck massage; it will make you feel better, and I will go next store and order lunch… and have it waiting for you. We had a great meeting and I felt like a pampered employee. My boss cared.”

—Brenda Spitz, real estate, Schererville, IN

Demonstrating how not to lead

“In my 20s I worked at a tech company. I didn’t have a tech background, so I had to work hard to prove myself and make my voice heard. On several occasions in interdepartmental meetings, when I spoke up to help solve issues, my manager would ‘shush’ me, following with his own ideas. After the meeting he would call and apologize. What I learned: 

1) This was not an environment that was going to allow me to grow into my best self.

2) This was not a partnership that promoted positivity

3) No one was going to ‘shush’ me again.”

—Manejah Terzi, P.R. Professional, Boston, MA

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  • Marina Khidekel

    Chief Content Officer at Thrive

    Marina leads strategy, ideation and execution of Thrive's content company-wide, including cross-platform brand partnership and content marketing campaigns, curricula, and the voice of the Thrive platform. She's the author of Thrive's first book, Your Time to Thrive. In her role, Marina brings Thrive's audience actionable, science-backed tips for reducing stress and improving their physical and mental well-being, and shares those insights on panels and in national outlets like NBC's TODAY. Previously, Marina held senior editorial roles at Women's Health, Cosmopolitan, and Glamour, where she edited award-winning health and mental health features and spearheaded the campaigns and partnerships around them.