I Was Rejected For a Job at Microsoft and Thanked the Manager For It

Adam Bertram

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It was late 2019 when I found out about a content-writing position at Microsoft. What I ended up doing after going through all of the interviews and ultimately being rejected was something I thought I’d never do.

Nearly my entire career I’ve had a “hustle“. Until 2017 though, I always had a full-time job too. I thought it was what I was supposed to do. You go to college, get a job and retire with a gold watch. While “living the dream”, I always needed something more.

Related: Six-Figure Blogger: An Unlikely Success Story

I was never intellectually satisfied by a 9-5. I enjoyed my work but I never quite felt like I owned my work. After all, if a company is paying you, they own your work.

But I still enjoyed full-time work usually and the security that came with it.

That’s when late-2019 came around and I got the opportunity to apply for a job at Microsoft, the company I had spent the last few years of my life writing content on, working on projects with, and being a Microsoft MVP. I was elated!

The Interview

I’ve been involved in some fashion with the Microsoft community for 6-7 years now. During this time, I’ve met and made friends with a few people at Microsoft. In late 2019, one of my friends let me know of a position he saw open on his team; it was a senior content-writing position.

He knew I’d be writing articles and blogging about the kind of content they needed for years and thought I should apply. I was super-excited about the opportunity and applied right away.

After a few back-and-forth emails and a phone call while on vacation in South Dakota, I was set to have my first official remote interview once I got back home.

Beautiful Mt. Rushmore in South Dakota

After some scheduling talks, it was official. My first remote interview was scheduled and on the books. Talk about nervous!

The day came and the interview was here. I was lined up with 4-5 people on the team and other related teams who each took turns talking to me in a 3-hour marathon!

It was a whirlwind experience.

I guess I left a good impression because I was then moved onto the second round of interviews with the team manager. We had a great conversation, she seemed extremely nice although really busy and everything seemed to go well.

Onto the third interview!

The third interview was with the director. As with the other interviews, things seem to go well. We didn’t chat about the technical requirements. I could tell it was more of a culture interview. She was trying to see if I’d fit in with the Microsoft culture and working in a full-time role. She was aware I was self-employed at the time.

Trying to hold my excitement back, I answered all of her questions with as much glee as I could muster. I wanted this job and just knew I’d love working at Microsoft!

The Rejection

The interview ended and I waited in anticipation until I got the news. My heart sank.

The rejection email

They were passing on me.

Why? I had essentially been doing that job for years now on my own! I knew in my heart I could perform my duties better than anyone in that position! I was confident I would do well in the role. The director felt different.

What could I have said? Did I not act like I was interested enough? How could this have happened?!?

After getting over the shock of thinking I was going to get the job and then getting rejected, I came back to reality. Curiosity now set in. I really wanted to know why I wasn’t selected.

Similar to other companies, Microsoft didn’t tell me the exact reason. I was informally told no over an email conversation with the team manager. Bummer.

Accepting the Consolation Prize

I moved on with my life and found another full-time job that I thought I’d love. The team was great and the work was interesting.

But I wasn’t happy.

I, again, felt that unhappiness bug again. This job, like most other jobs before it, made me feel trapped in a 100% remote, “work when you can” sort of great company. No one was telling me what to do and when to work. I was never told I had to put in a certain number of hours nor was I externally pressured in any way.

The pressure to be available and to just put in the hours for a company was purely in my head. I couldn’t get over the freedom I had yet, on the contrary, knowing I had to “do the job”.

I wanted to work on my side hustles but never felt like I could Monday – Friday, 9-5. That was “job time” in my head and I couldn’t shake it. It was impossible for me to balance my job and my side hustles.

So I quit after only one month. I finally realized I would never be happy in a full-time job; it just wasn’t possible. I had several jobs I absolutely loved over the years but looking back, I was never truly happy.

The Moment I Realized I was an Entrepreneur

It was truly an epiphany. I had been denying my true nature for over two decades! Why? Just because I thought that’s what you’re supposed to do and for “security”.

I had been pushing down this yearning to pursue my own dreams full-time for so long! My brain finally slapped me around and told me to get my shit together!

I was now back out on my own authoring Pluralsight courses, monetizing my adamtheautomator.com blog, writing eBooks, freelance writing and hustling on the random project here and there.

I loved it! I didn’t have the steady paycheck but I had the ultimate freedom!

  • I didn’t have to feel bad about not putting in 40 hours/week
  • I could work on anything I wanted to at any time
  • I was no longer trading hours for dollars. If I was smart enough, I could make $500, $1000 or even $2000/hr on projects!
  • I no longer had a ceiling of income. The sky was the limit.

What would have happened if I actually would have gotten hired by Microsoft?

  • Would I have came to the same realization?
  • Would I have quit early?
  • Would I have actually been unhappy afterall?

Yes! I’m confident now that I would have been unhappy. Looking back at my interview experience and how excited I was makes me cringe. I was totally denying who I was and what I wanted from my career.

I’m so thankful Microsoft saw through my bullshit and didn’t hire me!

That Time I Thanked Microsoft For NOT Hiring Me

Knowing now what I didn’t know then during the Microsoft interview process, I was extremely thankful she had passed on me. I wanted to reach out to tell the director that had passed one me.

Looking back, I can only imagine the shock on her face when she saw an interview candidate message her after getting rejected and thanking her!

Luckily, I had connected with her on Twitter weeks early and had a few casual conversations with her previous to the interview so I decided to let her know of my newfound look on life.

To my surprise, she replied and she actually gave me a great answer I’ll never forget.

The Twitter convo with a crystal ball-looking Microsoft director

The decision of a Microsoft director to not hire me may have been one of the best things that have ever happened to my career.

She somehow saw through my bullshit and was able to judge my character accurately. She most likely saved me many months or even years of doubting myself jumping to/from full-time jobs to come to my entrepreneurial conclusion.


What can you takeaway from this experience?

  1. Be real with yourself. If you’re generally unhappy in a job but can’t think of a reason why, maybe that type of job or industry isn’t for you.
  2. Look inward. Do you see a repeating pattern of job-hopping for seemingly no reason? Maybe you’re fooling yourself thinking it’s “for the money” but in reality, it’s simply because you don’t like being employed.
  3. A job rejection could actually be better for your career. You may not think it at the time, but you never know what the future holds.
  4. Quit a job as soon as you know it’s the right time. Many people feel guilty for quitting and remain unhappy for months or even years. If you’re not happy, pull of the bandaid now! Your future self and your employer will ultimately be better off.
  5. Other people may know you better than you know yourself. Don’t get so wrapped up in your own thinking and not hear what others notice from your actions.

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