From HR to PM. Yes, it’s possible.

Exactly a year ago, I made the jump from Human Resources to Product Management. The journey was long and hard but worth it. I’m writing my story because during the three years it took me to switch careers, success stories helped me keep going. I hope this inspires and/or motivates some of you to go after the career you love. Believe me, it’s worth all the pain.

Before Deciding to Jump

My first job after graduating from BYU-Idaho (2006) was as a program manager for a small web design shop. I’d speak with customers and coordinate with designers and developers to build their websites. A year after, I took my first HR job, working at the Corporation of the LDS Church. I’d coordinate the work of writers, designers, and developers to create online trainings for managers all over the world. Though I liked my job, the plan was to go to business school; two years later, I joined BYU’s MBA program.

While at BYU, I chose to study Human Behavior and pursue HR positions (even though I knew nothing about HR) mostly because I had experience in the field and, quite frankly, none of the other options — finance, marketing, or supply chain — seemed exciting. When it came to companies, Microsoft topped my list. Having played just enough in tech I was excited to see how the tech giant built its products and was lucky enough to get an internship.

My summer in Redmond as a Learning & Development (L&D) Program Manager was the first sign that HR wasn’t going to be a good fit. By day I organized L&D conferences and by night, with a developer, redesigned an internal site for BYU MBA students, which I found much more rewarding.

I still accepted a full-time offer in HR because I wanted to be part of the tech industry and felt working for one of the biggest tech companies in the world would only be good for my career (plus, I really wanted to meet Bill Gates). And truthfully, I didn’t really know what other career to pursue.

A month after graduating from b-school (April 2011), I joined Microsoft’s HR Rotational Program, meaning I’d have a different HR job each year for the next three years. My first role was as a People and Organizational Capability Consultant and managed the learning and development of the top 5% of the employees in the Research and Development Organization. I organized programs and conferences to retain and build the skills of these researchers. Though the job wasn’t bad, I longed to find something more meaningful.

People often ask me what it was that I didn’t like about HR. It wasn’t HR that bothered me, but rather that I wasn’t doing what I truly wanted to be doing — which was building tech products. I would’ve been just as miserable working in finance, marketing, or supply chain.

At this point, I didn’t know Product Management was what I wanted. What I did know was I liked designing and building technology and in a quest to make life more meaningful I began working on a side project that a few friends and I had come up with in b-school. We wanted to create an app that would help friends and family save money together by digitizing an ancient practice called rotating savings and credit associations (ROSCA’s). We had won an award for it and one of the judges, an angel investor, wanted to help us get it started. Not knowing where to start, I spent several months researching and writing a lengthy business plan. But it became apparent to the angel and me that I didn’t know what I was doing, so the project failed.

This experience, rather than sinking me, fueled me. I determined to learn everything I could about building successful tech products and made a New Year’s Resolution that by the end of 2012 I would have a fully functional app.

I began by reading The Lean Startup, enrolling in startup MOOC’s such as Stanford’s Online classes, taking online coding classes from CodeCademy, and joining Meetup groups; really, anything I could think of to help me achieve my goal. The best thing I did was to participate in StartupWeekend hackathons because I got to see the entire process of building a product in three days and got to meet lots of people interested in building startups.

One of the projects I pitched/led at an internal Microsoft StartupWeekend was Call-it, a “Klout” for predictions. We wanted to measure a user’s ability to make accurate predictions, which would enable them to pit themselves against friends, experts, and the world. We wanted to create a world where the average Joe could get recognized for making more accurate predictions than the best known pundit. Though we didn’t win the competition, we were asked to pitch the idea to a leader of a group working on innovative social products, such as Microsoft’s So.cl.

Slowly, I began meeting people interested in getting a startup going and went through a few sets of folks before finding a couple of dedicated Microsoft developers, Nathan and Aswath. We brainstormed ideas for a few weeks before deciding on building Remenis, a collaborative journal. We worked well together and in just a few months, working nights and weekends, we had a pretty great app. The user could log in using Facebook, receive suggestions of stories to write about (such as “What was the most embarrassing thing you did in college?” “Tell us about your wedding reception.” “What was a lesson your father taught you?”), would write their story and tag friends, who would then have these stories for their records and could add details to make the memory even better.

Unfortunately, soon after we built the site and grew it to several hundred users, our lives got a bit too hectic and the project went unattended. Nathan went to Asia for several months to do service work and Aswath got a new job at another software company, and in February of 2013 my wife had our fourth and fifth kids — Peter and Paul! For the next several months I spent most of my free time changing diapers and feeding these boys.

But even though we couldn’t move our app forward, it had happened.

At the age of 31 I finally knew what I wanted to be when I grew up! I had tasted what it was like to design and manage the building of an app and was hooked. I determined to do whatever it took to get into product management.

Making the Jump

I had made this glorious discovery in late November of 2012. By this time I was already into my second role at Microsoft as a Human Resources Manager, helping business leaders with all their HR needs, including disciplining and firing people. This was certainly my least favorite HR role and my new found career couldn’t come soon enough. With my 2012 New Year’s resolution accomplished, with vigor I made my 2013 New Year’s resolution to become a product manager at Microsoft by the end of the year.

At first, I thought it would be easy for me to make the jump. I had excellent GPA’s (undergrad and graduate), high GMAT score, an MBA from a great business school, three years of PM’ish type experience, a cool app, awards, good looks, the works. But unfortunately, none of that mattered; nobody I spoke to seemed to care. My “weak spots” were too strong — I didn’t have PM experience nor a computer science background and I worked in HR.

I would have to start from the beginning — I would have to prove myself.

The first thing I did was confide in a mentor, an HR General Manager who I respect, about my plans to switch careers. He was very supportive and gave me (and still does) advice throughout the entire journey. He also introduced me to a handful of people, who in turn introduced me to more people, and so on. From these connections came another great mentor, a PM General Manager who was always encouraging and optimistic, especially when I doubted myself. He challenged me to find a stretch assignment doing PM work on a technical product. After failing to find a stretch assignment in a product group, I found one in HR, working on a chat app for Microsoft’s internal HR site. I worked from 2–10 hours a week on this project until it was cancelled (about 3 months) because a bigger project needed more resources. I’m sure I could’ve joined this bigger project, but by then I was working on a mobile app that would prove to be a much better investment.

Another helpful exercise was to check the career site every day and reach out to hiring managers for informational interviews, a 30 minute meeting to find out more about the job. I never had problems getting informationals probably because I was showing a ton of initiative and people like to see that. Getting past the informational, however, was more difficult and only happened four times in two years. After the informational, the manager would do an informal interview, meaning the manager or a colleague would interview me to see if I had what it takes to go through a formal four hour interview loop. I only passed that stage twice. The first time was around May of 2013, for a PM position in the Office Organization working on Microsoft Project. I was impressed with the manager, who seemed like someone who could coach me through a career change and help me be a successful PM. The first thing to do was to get interview permission from my HR Rotational Program, which made me nervous because if I failed I was unsure what it would mean for my job, but took the risk anyway. What I hadn’t planned on was that they’d say “no.” They told me I had to get into my last rotation first before I could look for another job. I was crushed.

Though disappointed that HR, of all departments, would keep an employee from following their passion, I decided to not fight their decision because, after all, I had made a commitment to the program. Besides, they probably did me a favor. I was certainly not prepared for a formal interview loop and would have probably failed. Also, loops are documented and made accessible to all hiring managers, which would’ve made my networking efforts harder had I failed, since they’d be less interested to talk to me.

Undeterred, I continued doing informationals with hiring managers and before long had a Group Program Manager offer to mentor me. We met approximately every 2 months and I would ask him to give me a challenge every time we met. Wanting to help me prove my skill, his first challenge was to think of a problem worth fixing and an app concept to fix it.

A few days later, after a last minute decision to eat lunch with someone but failing to find anyone available, I was eating lunch alone in my office when it hit me — a mobile app to help people create and join lunch groups within Microsoft! I created the following presentation and pitched it to my mentor.

He liked the idea and solution and issued my next challenge — to build it.

By this time I was in my third and final HR rotation. Because the rotational program now knew of my interest in Product Management, they assigned me a position PM’ing HR tech products. As a Competitive Intelligence Program Manager, I managed the competitive intelligence website and was one of the PM’s working on the new promotions app that all Microsoft managers use to issue promotions. It was a really great role; I got to see how big and small products, using the waterfall method, are planned, designed, developed, tested, and launched. Since this was much closer to what I wanted to be doing I was the happiest I’d ever been at work, but was still pursuing my dream. So on nights and weekends, I worked on Lunch.

The first thing I did was send an email to the Garage community, Microsoft’s group of hackers, describing the project and sharing screenshots of the app. To my surprise, I got 30+ people wanting to be involved. After having them respond to a questionnaire, I chose the final team and team leads. We went through use cases, decided our MVP features, came up with final mocks, and started development. But after two months of “dev work”, we didn’t have anything to show for it. We needed to go faster, but how do you push people harder when they are working nights/weekends and for free? Realizing I had created lots of bottlenecks by involving too many people, I knew I’d have to let some folks go. To do this, I had all engineers make their own deadlines and agree if they weren’t done by then they’d be replaced. Most ended up firing themselves and the team shrunk to three. But we were motivated and ready to roll just in time for the new year — 2014.

Though my 2014 resolution had gone unfulfilled, I was making tons of progress and was, therefore, still pretty hopeful. But 2015 would be the year. I would make sure of that. I would work as hard as I had to.

Even with a motivated team it still took some time to launch the app. Since it was an internal app (only Microsoft employees), we had to go through extra approval processes, publish on the internal app platform so MS employees could download it, and change the original name of “Lunch Me”, to just “Lunch” (it didn’t translate well in some languages). By April it was ready. Our first version allowed users to sign in using employee credentials, create lunch groups, join lunch groups, view lunch group attendees, receive notifications, and search lunch groups.

To kick it off, we entered it into a Microsoft Science Fair and ended up winning one of the major awards. Additionally, one of the judges, a PM General Manager was so impressed that he invited us to present it to his team, who was working on some pretty cool innovative apps.

We then began advertising the app on cafeteria monitors, bulletin boards, and Yammer. I also, using the app, began sponsoring lunch groups with company leaders such as Lisa Brummel, Chief Human Resources Officer.

After receiving great feedback, we built version 2. Features included — syncing to outlook calendar when user joined/created a lunch group, email all members of a lunch group at a touch of a button, create private lunches using user’s Outlook distribution lists, and receiving toast notifications. In a few months, we grew the app to close to a thousand users, met a lot of cool leaders, and had a ton of great/interesting conversations.

Then, in early July a job opened up working for the same Garage judge who had liked my app and after a short informational he asked me to go through a formal interview loop! I had the chance to work for a cool manager and on a team working on brand new innovative apps; truly a dream come true.

There was still a problem however. Though I was no longer part of the rotational program and didn’t need their permission, I did however still need my manager’s permission because I hadn’t been in my current role for 18 months. She seemed quite shocked to learn I desperately wanted to get out of HR, but was supportive. My request would be escalated to her manager and the VP of the organization before it was cleared. To complicate things more, that same month, Microsoft announced plans for the largest layoffs in company history. A few days before my interview (July 17th), the company laid off 12,000 of the close to 20,000 it would lay off by the end of the year. I knew if the interview didn’t go well, I most likely would be laid off too.

Sadly I nailed the design part of the interview, but failed the technical part. Not having a computer science background and underestimating how many technical questions they would ask, I blew it. The General Manager told me I had a ton of excellent skills that he wished more of his PM’s had, but needed to work on understanding how technology worked. He gave me some assignments and sent me on my way.

I’ve never felt so dejected, lonely, and exhausted. I had worked extremely hard for three years trying to find the career worthy enough of my passion, energy, and skills. I had sacrificed all my mornings, nights, weekends, lunch times, free time and had just put my job on the line, only to fail the biggest opportunity I had been given. I felt pretty worthless and my goal seemed further than ever.

Unfortunately, the last half of the year would prove to be more challenging. With layoffs came freezes. No one was hiring, especially junior level PM’s. What’s worse, work was awkward and there were some signs here and there that would make me feel like I was on the short list. I remember studying in Business School the demoralizing and stressful effects layoffs had on employees and now I was experiencing them firsthand. Every day was nerve-racking, especially since I have a wife and five kids to take care of. One of the developers from my Lunch team got laid off so development stopped. I started working on another app with a friend until he got laid off.

The only thing that kept me going was progress. I would celebrate every victory big or small, remember every positive feedback someone had given me, and find any way I could to keep showing people I had it in me.

In early July, Microsoft held a company wide hackathon and I partnered with an engineer to create Cortana Echo, a Windows Phone app that enabled users to teach Cortana (Microsoft’s Siri) how to do simple deep tasks like “play the blues station in Pandora” instead of waiting months or years before Cortana would support these very specific deep tasks in apps. Though we didn’t win the big prize, we won a runner-up award for a smaller Microsoft hackathon (out of 450+ projects) and got a few leaders’ attention in the App and Services Organization. We were selected to pitch our idea to the Bingcubator, Microsoft’s internal incubation program. If I got into this program, becoming a PM would be just around the corner. The next few months, in preparation for our official pitch, would be filled with designing, working on the prototype, lots of researching, perfecting the pitch, and presenting to our Bingcubator coach and VP, who loved the idea.

Since Echo was a continuation of the hackathon I got permission to work on it during work hours, which meant that I needed something to do at night that would keep me progressing toward my goal. After my friend was laid off and rehired by Microsoft (early August), we decided to resume work on a project to create a single purpose Android app that would solve a simple problem. We designed, built, and shipped Morse in approximately 30 days (October of 2014). The idea was to create a simple privacy app that helped users keep their mobile screen private without having to lock their device; in short, users could hide and unhide their screen at a touch of a button.

Though I was nervous I’d get laid off, I was still optimistic. In early November I would pitch Echo to a few Microsoft leaders for a chance to work full-time on the project for the next three months and we had already began thinking about cool features we would add to Morse.

Sadly, as I predicted, a few weeks before my pitch, on October 29th, 2014, I was laid off. I suppose, if you’re going to lay someone off, you might as well get rid of the person who doesn’t want his job. Well played Microsoft.

The first thing I did, after telling my wife, was email my friend and mentor, the same one I had confided in when I began my journey two years before. He was now at another company leading their HR organization. He gave me some amazing and prophetic advice that gave me confidence and peace:

As an HR professional for the past 20 years, and knowledge of your competence and interests, I can tell you one thing with certainty: A year from now, you and I will talk and you will reference today as a blessing in disguise. It’s never fun when the timing / decision isn’t on your control, but this will greatly accelerate you getting to a better role, in a better environment where you can do your best work and be valued. I don’t think those are words that you can say ring true for the past two years. That said, there is the present to deal with. Take some time to process your emotions. Take FULL advantage of the outplacement counseling to help you get clarity on your next steps. As you have clarity, get some time with me and let me know how I can help you. One last thought — do NOT let this action start to erode your confidence. There is a natural tendency for folks to start questioning themselves because they were “laid off”. You were in the wrong role at the wrong time …that’s it (although a year from now, you will say you were in the right role at the right time). You are no less competent today than when I worked with you..in fact you are more so given the PM muscles you have built. Go home, hug the family, share what happened as a matter of fact. Give yourself permission to be human and have some emotions, but ultimately get yourself focused forward and excited how your life’s plan (re work), just got a great accelerant thrown on it to get you there faster than you would have on your own.

I read those words dozens of times before the year was over. The layoff truly was a blessing in disguise. I would get the next two months to focus one hundred percent on getting a PM position, without it affecting my pay.

But, it wouldn’t come without pain.

My last day at Microsoft, I collected all my personal things and put them in a box. Before leaving I looked at my shelf, which was full of HR books, and thought for a second, “Maybe I should keep those in case I can’t find a PM job.” But then I shook my head, grabbed my box, and left. Yeah, the image is corny, but it meant a lot to me. I couldn’t doubt myself now. I had to continue believing it was possible, that I could make it happen. That’s what leaving my HR books behind meant; it was a symbol of confidence. I was burning my bridges. My next move would be Product Management or bust.

The first two weeks of job hunting, being truly excited about Satya Nadella’s (new Microsoft CEO) vision, I solely focused on Microsoft. Besides, I still hadn’t met Bill Gates! I contacted all 40+ PM’s I had reached out to over the past two years but no one was hiring junior level PM’s. I was offered other roles, but I was tired of having a job just so I could find my real job.

I then started looking outside Microsoft and even Washington and realized, somewhat shockingly, tons of companies were interested in talking to me! A large part of it was due to the projects I had worked on and my current role.

I could easily pass the telephone screening with the HR rep. And then the interviews started to pour in — phone, video, Skype, and face to face. But as I’ve alluded to, interviewing isn’t something that comes easy for me. So, November was basically a month of interview practice and unfortunately I ended up practicing with some really great companies.

Knowing interviews were my weakness, I spent a few hours each day applying to jobs and making connections, while the majority of the time was spent researching and practicing interview questions. Honestly, I didn’t know where to start. I searched the web for anything that might help. Sadly, all I got was “Top [insert any number] interview questions” articles that recycled the same questions, a bunch of YouTube videos created by career service agencies in the 90’s, and fool proof tips such as give a firm (but not too firm) handshake and give a short (but not too short) answer. Worthless.

Slightly better tools were Quora and Glassdoor because they added an element of reality. Users shared questions they were asked in their interview and the answers they gave. The answers, however, were usually a one or two paragraph summary of what they had said rather than the detailed answer, so I didn’t find them all that helpful.

What helped me the most were Lewis Lin’s Decode and Conquer and Jackie Bavaro and Gayle Laakmann McDowell’s Cracking the PM Interview. Lin’s book was great because it gave me many excellent examples of effective and detailed answers. Bavaro and McDowell’s book provided more examples to learn from and other helpful material such as how tech companies viewed product management, tips (and real examples) for resume and cover letter writing, and many other questions to practice.

Even with these resources, I still struggled with interviewing. Improving my interviewing skills was so painful that I promised to work on an app to help others through this challenging process, which is why on my free time I’m working on Boldvue. I want to create the go to interview preparation app by crowdsourcing the job interview. I believe the crowd can provide the right questions to practice (as proved by Glassdoor/Quora), effective answers in video form to learn from, and honest feedback to truly perfect your personal interview answers. (To be notified of our launch, sign up here — http://beta.boldvue.com/signup.) But I digress, let’s get back to the story.

After dozens of failed interviews and rejections, I began to get better and before long grew more confident. Then in early December I reached out to a friend from the MBA program who had interned at Lucid Software, a startup I had been researching. He introduced me to a Product Manager on Dec 14 and we held a Google hangout on Dec. 16. Afterwards, she introduced me to the CEO and we spoke on the phone on Dec. 20. The company flew me to Utah on Dec. 30 and on Dec. 31 after surviving a grueling portfolio review, brainstorming session with VP’s, and design exercises, around 3 pm I was “unofficially” told I had a job!

I had done it! I had met my New Year’s Resolution and two weeks later I started my new job/career as a Product Manager.

Although I also had other options, one from Microsoft as a UX PM, I ultimately chose Lucidchart because I was impressed by the team, wanted to work at a startup, and was excited about working on Lucidchart.

After the Jump

I’ve been a Product Manager for a year now and can honestly say I’ve enjoyed almost every minute of it. I’m currently one of the two PM’s on Lucidchart and mostly focus on the UX heavy features. So far, I have shipped Presentation Mode, redesigned the entire commenting experience, introduced notifications, championed an innovative hackathon project that will be built soon, and am currently PM’ing two really exciting projects — the core experience redesign (all basic actions of the app) and the editor redesign (changing the look and feel of the app).

It hasn’t been easy, I’m still pretty new at it and have made plenty of mistakes, but I’m learning and getting better. I’m also an introvert, which makes PM’ing even more interesting and sometimes quite challenging. I plan on writing more on that subject at a later time. But for now, I will say that the three painful years before my career change, were well worth it. When I’m PM’ing, thinking how to make our product better, trying to improve an experience of a feature and considering the tradeoffs, brainstorming with a bunch of great people, speaking with our users and working closely with Design to come up with stunning products, I find I’m really, really happy.

In Closing

If you are considering changing careers, or have been working on it for some time and are ready to give up, I hope my story will motivate you to get started or to keep at it. Below, you’ll find some lessons that you may want to consider for your personal journey. If you have questions please hit me up on Twitter (@edgarcheney) or make a comment.

Start Doing What You Love
If you want to change careers, you need to start doing the new job. Do a stretch assignment, start a side project, work for free, but just start doing it! You’ll soon find out whether it’s for you and you’ll gain valuable experience that you’ll need to get into the career. Make a goal this year and get going.

Build a Portfolio of Work That Shows Your Skill
Showing companies you can do the job will be your number one priority. The most common excuse I heard from Hiring Managers was, “I need someone who can hit the ground running and you are competing against people who have several years of experience.” The only way you’ll get past that is to show that although you may not have years of experience, you’ve done some of the work and done it well.

Find Mentors Who Believe in You
Find 1–2 mentors in the new field by reaching out to people you respect. Don’t ask to be mentored by them. Just set up a meeting to learn about what they do and how they do it. If they see potential in you, they’ll ask to mentor you. This is important because you should only meet with mentors who believe in you and are willing to help you or else you’ll waste a lot of time and it can be quite demoralizing (trust me). Ask them to let you job shadow them, introduce you to someone, or let you work on a project with them. If they’re not willing to do anything for you, you should drop them. Once you find the right mentor, always ask for a challenge to work on before your next meeting. This will hold you accountable and keep you progressing. 

Know That Highs Will Come
This journey is filled with lots of extreme highs and lows. When the lows come (and they will), don’t freak out too much and be confident a high will come soon. One time a friend introduced me to a PM who was hiring. The first thing the guy said to me was, “I don’t really know why we’re talking. You don’t have any skills that my team needs.” My confidence was crushed for several days, but I knew it would pass as long as I kept progressing toward my goal. Sure enough something good/positive always happened.

You Still Have a Lot of Work Time Left
One thing that kept me going was the thought of how many work years I have left. I kept thinking, “If it took me three more years to make the switch I’ll still have a solid 30–35 more years of work and I’d much rather be doing something I love.” This view helped a lot because it kept me focused on what mattered — progress — rather than on the daunting task ahead of me.

Sacrifice Only the Irrelevant
Working on a career switch takes a lot of time, which meant I had to make lots of tradeoffs. Instead of thinking about what you have to sacrifice however, start by listing what you will never sacrifice. The one thing I knew I wasn’t going to give up was my family. I strived to always be home for dinner and play with the kids until it was time for bed. Which meant that I had a lot of late nights and early mornings! Instead of family, I chose to sacrifice TV, Facebook, movies, hobbies, etc. and it was all worth it!

Hold No Hard Feelings
Along the way people and organizations will do things that will make it difficult for you to achieve your dreams. Like my mentor suggested, “Give yourself permission to be human and have some emotions,” but don’t dwell on the hardships, it will just make you weak and cause you to waste valuable time. Forgive, forget, cling to anything positive that shows you are making progress, and move on. Had I made a big fuss over the rotational program’s decision, they may not have given me a technical HR PM position, which was very valuable in the end.

Find Someone You Can Talk To
It’s important to be able to voice your true feelings and emotions with someone. There will be many things that you shouldn’t tell your mentor, but having a friend to hear you out can be a great way to destress.

Don’t Forget About Your Spiritual Self
Lastly, though it’s nice to have a friend you can talk to, realize that even they can’t understand everything you are going through. My wife is my best friend and is the one I can tell anything to, but it would be impossible for her to understand my every doubt, joy, pain, and self-criticism. Though this may not apply to all of you, one of the things that helped me the most was believing in a God that cared for me and wanted me to succeed. There is something special about kneeling at the foot of your bed and talking to someone you believe understands everything you’re going through and can bring you the internal peace and confidence that all will be well in the end.

Thanks for enduring this long post. I wish you the best on your journey!