26 Founders Share What Their Worst Boss Taught Them

You can learn from even the most frustrating experiences.
26 Founders Share What Their Worst Boss Taught Them
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15 min read

This article is included in Entrepreneur Voices on Strategic Management, a new book containing insights from more than 20 contributors, entrepreneurs, and thought leaders.

We’ve all had bosses that make us crazy -- whether it was a supervisor with a big temper, one that watched your every move or the one that never knew what he wanted. But even if at the time it was frustrating or demoralizing, there is an upside: You’ll never catch yourself being that kind of manager.

We caught up with 10 successful entrepreneurs who shared with us the lessons they learned from the worst bosses they’ve ever had.

Communicate clearly.

Communicate clearly.
Image credit: BaubleBar

Name: Daniella Yacobovsky
Company: BaubleBar
Lesson: One of the things I have learned is to communicate openly and honestly with the folks you work with. Try to understand where their requests and feedback are coming from and be open to feedback. When you’re first starting and you’re a small company, it’s definitely easier to do. As you grow and have more people, it is a harder thing to scale but that doesn’t take away it’s importance.

Read more about Yacobovsky: This Co-Founder of BaubleBar's Secret for Inspiration? Always 'Keep Your Eyes Peeled.'


Follow the golden rule.

Follow the golden rule.
Image credit: Lucky Iron Fish

Name: Gavin Armstrong
Company:  Lucky Iron Fish
Lesson: People who are bullies act that way because they are insecure about something else. They are very demeaning and not appreciative.

You want to be very respectful of people working with you. Remember they work with you, not for you. Be complimentary of their work, because they are putting a lot of time and effort into it.

Read more about Armstrong: This CEO Has Helped Thousands -- and He's Just Getting Started


Have strong convictions.

Have strong convictions.
Image credit: Food52

Name: Merrill Stubbs
Company: Food52
Lesson: Being indirect about what you want or what you expect is a really terrible tactic for managing people. It makes them feel like the ground is shifting beneath them -- that's an impediment and distraction from people doing their best work.

Read more about Stubbs: The Life-Changing Book That Helps This Entrepreneur Think Big


Be a mentor.

Be a mentor.
Image credit: Baked By Melissa

Name: Melissa Ben-Ishay
Company: Baked By Melissa
Lesson: The importance of open communication. When I think of the worst boss I ever hard, I don’t think of just one person.

I didn’t have a mentor. I didn’t have someone who wanted me to succeed. I didn't have someone who took the time to sit down, have a conversation with me and help me be better at my job. So now, I really make the effort to be clear and honest with my employees and sit down with them and communicate.

Read more about Ben-Ishay: How Getting Fired Turned Into Sweet Success for This Entrepreneur


Follow through.

Follow through.
Image credit: Zocdoc
Name: Oliver Kharraz
Company: Zocdoc
Lesson: I learned to only make promises that I can keep. I remember how upset I was when promises were made to me that were not kept, and I promised myself that I wouldn’t do that.

Read more about Kharraz: This Founder Says to Succeed You Need to Question Everything

Connect with every employee.

Connect with every employee.
Image credit: Nicole Franzen

Name: Jennie Ripps
Company:  Owl’s Brew
Lesson: I learned how important it is to engage with my own team and also to ensure that there is buy-in across the board at an individual level.

Read more about Ripps: The One Thing This Entrepreneur Does Each Day to Stay Productive


Leave your ego at the door.

Leave your ego at the door.
Image credit: Nerdwallet
Name: Tim Chen
Company: Nerdwallet
Lesson: Ego gets in the way of success. I worked at a hedge fund that had a real “Lord of the Flies” feeling. It was pretty crazy. The problem with ego is the best ideas don't win, because you have trouble facing the truth.

Read more about Chen: Nerdwallet's Founder Shares the Worst Advice He Ever Got

Don’t stand in the way of innovation.

Don’t stand in the way of innovation.
Image credit: Bloomberg | Getty Images

Name: Bastian Lehmann
Company: Postmates
Lesson: One thing I try to do is help the people that want to do more. I want to help them realize that when they are at Postmates.

The worst boss I ever had told me that I couldn’t do that. He was weak and afraid someone was more hungry than him. When I saw someone trying hard, and they gave it everything they had, that someone would not give them guidance and help them succeed.

Read more about Lehmann: This Founder Shares the One Trait He Looks for in Every Hire


Have a clear vision.

Have a clear vision.
Image credit: ThirdLove

Name: Heidi Zak
Company: ThirdLove
Lesson: The one thing I've noticed from having different types of bosses is that the best ones have a clearly articulated vision of what the team is working toward. You have to communicate it effectively and do it often. That's what I try to do; you can't say it too often.

Read more about Zak: This Founder's Best Advice for Entrepreneurs: To Succeed, Entrepreneurs Need to Get Comfortable with Being Uncomfortable


Strong management begins with a solid rapport.

Strong management begins with a solid rapport.
Image credit: Angie Hicks

Name: Angie Hicks
Company: Angie’s List
Lesson: I haven’t had many bosses in my career, because I’ve been at Angie’s List for so long. But when I was in business school, we left it open for me coming back to Angie’s List [when I was done with school], so I was doing some interviewing. It was a great eye-opening experience for me, and it helped me realize what was important to me in terms of the team of people that I wanted to work with.

For instance, I was doing an interview for a marketing position and the interviewer who would be my boss, would ask me a question, I would give him an answer and without any expression, he would just say thank you. And then he asked the next question and said thank you. It was one of those moments where I realized managing people is all about interaction, and you really want to be able to work with someone that can inspire you and you can learn from.

Read more about Hicks: This Introvert Founder Swears by This Management Tip

Lead with kindness, not with fear.

Lead with kindness, not with fear.
Image credit: Bumble

Name: Whitney Wolfe
Company: Bumble
Lesson: The word boss is a funny thing; I don’t only apply that to work. Our teacher is a boss, our parents are sometimes a boss. This concept of boss is different from leader. In a company, a good boss isn’t seen as a boss, they are seen as a leader.

I’m not going to speak to work culture, because I’ve been my own boss for the last few years, but I will say that in school, I had some professors who took more of the bad cop approach.

It taught me how to take a different approach. I don't believe in leading with fear; I don't think it's productive. I don't think it's healthy, and I don't think it inspires creativity or allows passion or talent to really thrive. I've tried to instill that in my company by leading with kindness, compassion and empathy.

Read more about Wolfe: The Founder of Bumble Reveals How the 'Question of Nine' Can Help You Stay Focused

There is always a way to accomplish what you set your mind to.

There is always a way to accomplish what you set your mind to.
Image credit: Kara Goldin

Name: Kara Goldin
Company: Hint
Lesson: My worst boss was also my best boss. My first job out of college was working for a woman who had just lost her husband and was struggling with her grief. In my first few months on the job, she went into her office and shut the door for most of the day. What it taught me early was get direction and execute. Ask around if you needed help figuring stuff out. And learn to trust your gut. I also learned to understand her hot buttons. I knew what she expected, and I over delivered. I knew what time she came in and what time she left. I was there all the time she was.

Throughout my career I’ve encountered numerous people who’ve told me that something can’t be done, but I’ve learned that not only can those things be done, they’re usually the things that need to be done. If you really believe in something and trust your instincts then go for it and don’t take no for an answer. You are your own worst enemy so don’t let self-doubt get in your way. Hearing naysayers around you can often make you doubt yourself, which is something I’ve experienced many times. But as long as you drown out the negativity around you and believe in your own abilities and intuitions, you can accomplish just about anything.

Read more about Goldin: The Entrepreneur Behind a $90 Million Company Shares How You Can Get Past the Naysayers to Build a Successful Business

Inspire people to be themselves.

Inspire people to be themselves.
Image credit: Lyft

Name: John Zimmer
Company: Lyft
Lesson:  I think about the culture at Lehman Brothers when I worked there. I saw that people weren’t being themselves, and they weren't participating in a real meaningful way. I learned the values I wanted to be a part of and create in our environment are ones that were different from a place where people weren’t participating or being themselves. When you walk into the Lyft offices in San Francisco, you see a sign of our first value, which is to “be yourself.” Our fourth value is “participate.”

Read more about Zimmer: Lyft Co-Founder John Zimmer: 'You Should Never Veer Off the Path of Your Own Values'

Give everyone a chance to recharge.

Give everyone a chance to recharge.
Image credit: Alexa von Tobel

Name: Alexa von Tobel
Company: LearnVest
Lesson: I'm fortunate that I've never had a terrible boss. What I will say I've learned is I try to be as sensitive as I can when I'm working with people and proactively say work-life balance matters. When you're here, do your best work. But I believe everybody needs a day to fully recharge, where you're not focused on work, where you're reading, sleeping, exercising, relaxing. I think we're more creative when we're happy, engaged and inspired as opposed to worried and fearful.

Read more about Tobel: This Entrepreneur Shares Her Surprising Secret to Fighting Decision Fatigue

Emotional intelligence is your most important tool.

Emotional intelligence is your most important tool.
Image credit: Masha Maltsava

Name: Jen Rubio
Company: Away
Lesson: The worst boss I ever had taught me how important emotional intelligence is -- mostly because he didn't have any. It made me realize that you can be super smart, super driven and very accomplished but be a crappy boss if you don't understand your emotional intelligence.

Read more about Rubio: Use This Founder's Top Tip To Make Your Meetings Work For You

Don’t be quick to judge.

Don’t be quick to judge.
Image credit: BloomThat

Name: David Bladow
Company: BloomThat
Lesson: What I’ve learned is not to jump to judgement so quickly. Take more time and think about interactions from the other person’s perspective. It allows you to come in with a more tactful point of view.

Read more about Bladow: This Founder Has 3 Simple Tips to Achieve Maximum Productivity

Be upfront about your concerns in the moment.

Be upfront about your concerns in the moment.
Image credit: Randi Zuckerberg

Name: Randi Zuckerberg
Company: Zuckerberg Media
Lesson: I learned about how to treat people, but I also learned that is is better to give people feedback in the moment. Early in my career, I had these bosses that would check in with me every six months -- and tell me for last six months that I’ve been doing x, y and z and that’s not good. I’d sit there thinking, “Why didn't you tell me six months ago, so that I wasn’t just making the same mistakes?” That impacted my own management style, because I always want to give feedback in the moment.

Read more about Zuckerberg: Why Everyone Can Use Randi Zuckerberg's Number One Focus Tip

Be a champion for your employees.

Be a champion for your employees.
Image credit: Stephanie Geddes

Name: Alex Friedman
Company: Lola
Lesson: I learned how important it is to advocate for your team and making sure they are productive, happy and in a position for personal growth and success. I had an experience where that wasn’t the case.

Read more about Friedman: How You Can Use Your Computer Password to Make Your Aspirations a Reality

Keep the lines of communication open.

Keep the lines of communication open.
Image credit: Katrina Lake

Name: Katrina Lake
Company: Stitch Fix
Lesson: The main lesson for me was around communication. I was in this job and loved the people and the work, but I was working a lot of hours and was stressed. And I just quit. I look back on it now as an employer, and I can't believe I didn't share that with my concerns with my manager and didn't share how I was feeling before taking the most dramatic action. At Stitch Fix, we encourage our managers to work closely with people and understand how they're feeling about their development and their work.

Read more about Lake: Stitch Fix Founder Explains Why the Worst Piece of Advice She Ever Got Was to Raise A Lot of Money

Let people learn from their own mistakes.

Let people learn from their own mistakes.
Image credit: Duolingo

Name: Luis von Ahn
Company: Duolingo
Lesson: I don’t think I’ve really had a boss. When I started leading a team I would micromanage everything they were doing, because I wanted it just so. Over time, I have learned to bite my tongue in meetings and should only speak up if I feel extremely strongly about something. People who report to me have gotten better at their jobs, because they have more responsibility and learn from their mistakes.

Read more about von Ahn: Why This Founder Says the Worst Advice He Ever Got Was to Listen to His Users

Treat your employees with the respect you give your customers.

Treat your employees with the respect you give your customers.
Image credit: G Adventures

Name: Bruce Poon Tip
Company: G Adventures
Lesson: The only jobs I had other than my own businesses were to pay rent. On the weekends, I worked behind a deli counter. My boss was an awful person. He was horrible to the employees, but he was always good to the customers. I learned whatever happens behind the scenes, you can still be successful if you are razor focused on the customer. He was always focused on doing right on the customer. I learned the importance of putting the customer first. At the time, I didn’t have employees, but I certainly knew when I did, I knew I wouldn’t want them to feel how I did.

Read more about Poon Tip: I Was About to Shut Down My Business but I Changed My Mind. Here's Why.

Don’t accept boredom at work.

Don’t accept boredom at work.
Image credit: Ayah Bdeir

Name: Ayah Bdeir
Company: LittleBits
Lesson: I learned how important it is to love going to work. [There was a time] we weren't busy, and I was losing my mind, because I was so bored. I went to the kitchen, and I remember [my boss] saying, “I haven't done anything in weeks, I'm so happy.” I realized that this is the worst way to feel about work, at least for me. It's not so much about loving your job, it's more how important it is to have an internal drive and curiosity and not accept boredom at work.

Read more about Bdeir: This Successful Entrepreneur Explains Why Revenue Is Not the Most Important Thing (and What Is)

Stay true to who you are.

Stay true to who you are.
Image credit: Wendy Williams
Name: Wendy Williams
Company: The Wendy Williams Show and the Hunter Foundation
Lesson:  Never tell talent to change their style. In 1988, I was told that by a boss, who happened to be a woman. She called me into her office and called my style "dinosaur." I cried in her office; I couldn't believe it. I dried my tears in my wig! I immediately went outside, got in my car and called my father. He said Wendy, “just stay true to who you are."

Read more about Williams: Media Mogul Wendy Williams on Why She's So Happy She Ignored the Worst Advice She Ever Received

Don’t be afraid of conflict.

Don’t be afraid of conflict.
Image credit: Rodan + Fields

Name: Dr. Kathy Fields
Company: Rodan + Fields
Lesson: Don’t avoid confrontation. Confrontation happens, and you have to learn to deal with it. It's always hard, but running away is not the answer. Confrontation can still be uncomfortable for me, but it’s important to be able to address difficult topics and talk about different points of view.

Read more about Dr. Kathy Fields: Want to Build a Billion-Dollar Business? Here Are 2 Simple Ideas That Helped These Two Skincare Heavyweights.

Always give feedback.

Always give feedback.
Image credit: Amanda Bradford

Name: Amanda Bradford
Company: The League
Lesson: The worst boss I had was never around nor gave me feedback, so I learned how to self-manage and self-grade my own work. Looking at your own work from an objective eye is difficult and learning how to rely on tools [you find yourself], rather than other people helped me when starting The League.

Read more about Bradford: This Successful Entrepreneur Explains Why You Shouldn't Put Time Limits on Creativity

Don’t micromanage.

Don’t micromanage.
Image credit: Gunnar Lovelace
Name: Gunnar Lovelace
Company: Thrive Market
Lesson: I haven't really ever had a boss; I've always worked for myself. So, I learned from myself as my worst boss. I used to be a terrible micromanager in my first companies. We hopefully mature as we get older, and I wanted to be more successful, so it challenged me to look at why I wasn't succeeding the way I wanted to.

Read more about Lovelace: This Successful Entrepreneur Was Turned Down By 50 VC Firms. Today, His Company Makes Millions.
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