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Advice / Succeeding at Work / Work Relationships

14 Surprising Ways Your Boss Can Change Your Career Forever

Not all bosses are great, but many end up having a huge impact on our lives. From helping us become better employees to pushing us toward something better, early managers can seriously influence our future career paths.

To find out how bosses—good and bad—have made a difference in their former employee’s lives, we asked 14 young entrepreneurs from YEC to share the best thing a former boss had ever done for them. Hint: Some of their answers might surprise you!

1. Fired Me

At my last company, my boss could see that I was way overqualified and underpaid for the job. But he also knew that if he didn’t fire me, I’d never leave. When I got fired, he explained this to me. I then started my own thing, and six years later I still do consulting work for him, and he’s become one of my best friends. Getting fired can be the best gift any employer could give you.

John Rampton, Adogy

2. Gave Me Exposure

When I worked in a very well-known Fortune 500 company, my boss gave me broad leeway to take some innovative risks. And when the risks panned out, she gave me the opportunity to present to the CEO (one of the most well-known CEOs in America). She could have easily taken the opportunity herself, but wanted me to have the exposure and the chance to present to him and his entire leadership team.

Susan LaMotte, Exaqueo

3. Told Me Not to Get Into the Business

I was in college and my first and only internship was at Morgan Stanley. My supervisor actually suggested that even if I was offered a job there after the internship, I shouldn’t take it, because I was much better at doing my own thing than working for a hedge fund doing analysis. He said, “Derek, you and me can give a client the same advice, but because you don’t have white hair, they will listen to me and not you, so don’t waste your time here.”

Derek Capo, Next Step China

4. Believed in Me

My former boss continuously communicated that he valued my talent and believed in me. When I started my own company, he was there as a sounding board and was quick to offer valuable advice when I needed it.

Ashley Mady, Brandberry

5. Told Me He Didn’t Pay Me to Have Ideas

On one of my last days as an employee, the owner of the company said to me, “I don’t pay you to have ideas. I pay you to implement the ideas I give you.” In that instant, I realized that I didn’t want to spend another day working for someone with such a ludicrous, screwed-up perspective on leadership. That was all the encouragement I needed to start my own company—a company where ideas from all employees are encouraged and appreciated.

Brittany Hodak, ZinePak

6. Forced Me to Make 500 Cold Calls a Day

My boss at a private wealth management internship required me to make 500 cold calls every day to drum up leads for his practice. While I hated it at the time, I became super comfortable getting on the phone and cold calling strangers. I no longer make cold calls, but that experience has made me much better on the phone, which is a vital skill in any business.

Josh Weiss, Bluegala

7. Held Me Accountable

One boss that stands out in my mind encouraged my independence but held me accountable for all of my accounts. He assured me he’d always have my back, but asked that I never give him a reason not to. It made me want to make him proud and work harder. It taught me the importance of being self-motivated and a leader in my own right.

Amanda L. Barbara, Pubslush

8. Took Long Coffee Breaks With Me

Early on, I had a manager who would take me to our client’s cafeteria almost every afternoon—where we’d talk, only sometimes about work. Our discussions flowed on, often lasting over an hour. Was he bored? Lazy? Couldn’t be further from the truth. He got to know me in a way that no other manager ever would. When it came time for feedback, I’ve never listened closer.

Aman Advani, Ministry of Supply

9. Made Me a Real Part of the Team

No matter what the task or where the next meeting or project as a young employee was, he would always include me and make me feel as if I were a major part of the process and company. This little thing truly had an impact on me and showed me the importance of making everyone on your team or in your company a major priority at all times.

Jason Grill, JGrill Media | Sock 101

10. Taught Me Mental Toughness

A former boss of mine was a PhD psychotherapist and taught me what mental toughness was—how to harness the power of my mind and focus to achieve whatever I wanted out of life. He taught me how to visualize and focus, and how to plan and stick to the plan no matter how difficult it got. We would have lots of long conversations, and he showed me how setting small goals and daily achievements helps to move you toward your bigger goal.

Brandon Dempsey, GoBRANDgo!

11. Supported Me When it Was Time to Leave

The greatest thing a previous boss has ever done for me was support me when I knew it was time to leave. I’ve taken that same conversation and applied it towards multiple employees at my company. Anyone battling with a life-changing decision around employment deserves strong support, especially after they’ve been so supportive in helping me build my business.

Jeff McGregor, Dash

12. Transferred Me and Beat Me Senseless with Work

I initially worked as an intern during high school at FSLR, around the time of its IPO. It was not what I was expecting. The VP of strategy, Ray Immelman, met me during my first official business trip and initially wrote me off. I worked to be excellent the first day; it ended with a steak dinner. Afterwards, he transferred me and then overloaded me with work. He set an impossibly high bar, which pushed me to learn far beyond my years.

Alec Bowers, Abraxas Solutions

13. Lied About Me to the Board

At my last job before I took the entrepreneurial leap, my boss lied to the board about why I was doing a poor job so he could fire me. While he thought he was hurting me (and it did hurt at the time), I ultimately got the last laugh, as it was the momentum I needed to go it alone and start my first company.

Darrah Brustein, Network Under 40 / Finance Whiz Kids 

14. Let Me Listen to His Phone Conversations

Back when I sold carpet for a living, my boss Gary let me listen to his phone conversations with customers who had problems. That is where I learned the value of patience, problem resolution, and (most importantly) respect for people.

Vladimir Gendelman, Company Folders, Inc

Photo of people courtesy of Shutterstock.