The journey to living one’s truth: with a circle of support, AJ Reiman made the change of a lifetime

One employee walks through the worries of being transgender and how it could affect a career

There’s that moment when you must have “the talk” with your manager, whether it’s to announce a pregnancy, to request a leave of absence to care for an ailing loved one, or to state your plan to leave the company. Perhaps, you’re taking a sabbatical to focus on your personal next steps.

For AJ Reiman, the talk was one that was both feared and contemplated. “It took me four months,” said AJ. “Do I want to leave? Do I want to do something else? Do I take time off, so I don’t have to do this publicly and face it?”

AJ had a major realization that needed to be addressed. So, it came down to whether the Microsoft culture around inclusivity was just talk.

It was January 2017 when the moment came: AJ decided to self-identify as transgender, in the initial stage of the transitioning process. AJ knew it was possible that some people at work wouldn’t be supportive and worried about the impact the announcement could have on what had so far been a flourishing career as a senior business design manager on the HoloLens team.

(AJ—who has not determined the end state of the transition—answers to the pronouns he/him and they/them. Out of respect for AJ’s personal journey and to provide consistency, this piece will use they/them to refer to AJ.)

AJ wrote a long email and waited.

AJ Reiman
With the goal of living an authentic life, AJ Reiman did a lot of soul searching while contemplating whether to express their transition plans with management and colleagues.

“[My manager] was so supportive and just a listening ear, empathetic and extremely pragmatic about what we needed to get done. It was the perfect balance,” AJ said with a look of euphoric relief. “When I came out to him, I started talking through the medical insurance and how I was going to do my transition. It requires [many] doctor visits and therapy sessions, all of these things that require me to be in and out of the office.”

Michael Tan, AJ’s boss, was not expecting the news; however, his commitment to Microsoft’s stance on diversity and inclusion served as his foundation.

“Despite the surprise and lack of familiarity with the situation, I immediately just snapped into a ‘what can I do’ mode,” said Michael.

After several in-depth conversations about AJ’s struggle to live an authentic life, Michael developed a heightened level of empathy.

“I realized in talking to AJ that I completely take for granted the ability to wake up, come to work, and be my authentic self,” he said. “AJ hadn’t been afforded that same luxury, and I was really excited for AJ to have it.”

A bustling career paired with dread

AJ realized they were transgender at an early age (despite being unable to put it into words) and never abandoned the idea of embracing their identity. There’s the matter of incorporating your truth in your personal life, but how about within your career trajectory? Clearly, working for a company that provides a supportive platform for “you to be you” is key.

By all accounts, AJ has been a star within the world of academia and now at Microsoft. When you look at their accomplishments, it’s easy to understand the fear behind coming out and the impact it could have on years of dedicated work.

AJ Reiman

AJ was a top student at the University of Rochester. Majoring in economics and political science, AJ was one of only two students who were chosen to participate in the 3/2 Plan, which allowed them to earn a Bachelor’s degree in three years and then earn an MBA in two additional years. Initially, AJ had reservations around remaining an economics major, especially after getting a horrible grade on the first exam. With their mother’s encouragement and their natural talent in analytics, AJ stuck it out and thrived. They took on the business program’s feared “econometrics” class, plus advanced and PhD-level courses. In the end, AJ earned the coveted Barry Rapoport Prize in Economics, an award for excellence in the field.

After graduation, AJ’s career kicked off in a leadership rotation program at one of the largest global aircraft manufacturing companies. They went on to become a business intelligence lead at the world’s most successful online retailer’s Europe location. In May of 2016, Microsoft recruited them for a new role within the Windows and Devices organization, with a focus on the HoloLens and mixed reality business. As a business strategist, AJ’s key focus is on corporate strategy, product management, and quantitative modeling. “I advise the HoloLens Experience Team on first-party content for Windows Mixed Reality,” they explained.

Michael felt AJ’s skill set and passion shone in the initial interview.

“[AJ] was in a very data-centric and quantitative analysis-driven role,” he said, “which enabled them to drive product impact decisions through data-driven insights, something I knew would be super valuable given the amount of user data we have across our breadth of Windows apps.”

“I don’t do quantitative modeling all the time,” AJ explained. “But, oftentimes, when there’s a big decision, people can trust my work. Or, if I should make a decision for HoloLens or a market forecast for devices, I can tap into my past skills and give everybody confidence around it. I love being able to do that.”

While they gravitate to the business side, AJ admittedly is excited to be paired with the world of HoloLens and the brilliant minds behind its creation and content.

“It’s this beautiful piece of technology that’s trying to shape the future of computing,” they said. “It has so many possibilities, and [I enjoy] just being a part of the conversation about where the technology goes next, what we prioritize, and who we are going to partner with. Everything is new. It’s difficult to navigate, but extremely fun.”

According to Michael, AJ spearheaded a deep-dive research and modeling exercise that identified key focus areas in app development to maximize HoloLens adoption with key customer segments. “The output of that is guiding teams right now on where to focus investments,” said Michael.

Pairing their authentic self with their dream career

AJ feels lucky and fortunate to have Michael as a manager who truly walks the walk when it comes to appreciating the strength in a diverse, inclusive team. In fact, the conversations they’ve shared as they prepared for the transition have led to a stronger relationship.

“Logistically, I didn’t want my professional image to look like me leaving all the time when this is a very serious thing I had to manage on top of all the work I had to own—in and out of the office,” AJ said.

AJ has curated a great career, so they wanted to be transparent about the “real AJ” while remaining dedicated to their professional footprint. While pleasantly surprised by the support of Michael, AJ was equally happy with the response of their team, fellow Gender Expressions and Trans (GET) discussion group members (a Microsoft affinity group), and the company’s executive leadership.

AJ’s team went on to throw a celebration party. “They genuinely want me to be happy,” AJ said of teammates. “Everyone treats me with such respect and the same—for better or worse.”

Yet, they are fully aware that the change in how to address them takes some getting used to.

“The way people spoke to me at first was a bit muted. But, I could tell it was driven by a sense of care,” said AJ, who explained there’s always a worry of “getting it wrong” when it comes to adopting to a new name and/or pronoun. Now they’re happy to say that even if someone slips up, the person course corrects and quickly moves on. “I appreciate your trying. If you make a mistake, I’m going to correct you on the spot because that’s how you build muscle memory.”

For most people, getting the support of your boss, teammates, and peers can be the icing on the cake. So AJ was elated to further receive sincere executive support. AJ fondly recalls heading to a conference with Microsoft’s General Manager of Windows and HoloLens Experiences Lorraine Bardeen, who didn’t make a big deal about the news. They were pleased by her genuine support and found her delivery refreshing as she simply asked how she and the organization could best support them.

AJ Reiman
Acknowledging that many trans community members don't have a great experience, AJ Reiman's

Ultimately, once the announcement email to the entire organization went out, they were shocked to hear from Kudo Tsunoda, corporate vice president of Next Gen Experiences at Microsoft.

“He wanted to set up quarterly meetings with me to talk about what changes we can make in our office and in our business. That kind of support all the way up through my leadership is just . . . ”

Even in telling their own story, AJ reached a moment of speechlessness.

Appreciation for the past, acceptance of the future

2017 has proven to be a year of awakening for AJ.

“I identify as transmasculine or nonbinary. He/him, they/them. I am still going on my journey. I don’t know my end state yet. I don’t know what’s going to bring me to happiness,” AJ mused. “I just know that every day and every week as I’m transitioning, I’m happier and happier and happier.”

However, AJ acknowledges that being one’s authentic self as trans has led to a lot of privileges being taken away. As a person of color, they have felt the strain of prejudice from multiple angles. Living in the Seattle area and working at Microsoft has given AJ a bit of sanctuary; however, the fear is always there, especially during travel.

“Trans people get a lot of hate. They get called horrible names, especially transgender men of color,” AJ explained. “There’s so much to do. The external world is not kind to trans people.”

Despite the trials of coming out as trans, AJ feels “there are so many beautiful, beautiful people out there” and that being true to oneself is still worth it.

AJ also believes it is their feminine experience that has given them the tools to survive and be strong as they consider the road ahead.

“I honor the experience of femininity. Now that I transitioned, I honor it in myself and the strength of it. Because femininity is strong and it’s resilient. That’s part of the reason I survived because I’ve had those role models who take on a lot in life.”

AJ credits their mom, the women in Microsoft’s New Experiences Team (NEXT) organization, and other women throughout their career as their foundation for strength. Their hero? Their grandmother, who was valedictorian of her class and one of the first African American trauma nurses at the Cleveland Clinic.

As for AJ’s career at Microsoft, they continue to enjoy the mix of what they do daily and thrive on the challenge. AJ works both quantitatively and creatively, while building relationships with partners.

“Microsoft is just the best place I’ve ever worked,” AJ said with a huge smile, while trying not to sound “too cheesy.” “It’s hard to imagine a more supportive environment. I feel more holistically invested in my career and my life and intertwining the two.”

As for their genuine self, AJ is a work in progress whose number one goal is to always “find happiness.” Coming out has been their most “powerful experience” to date because they’ve let go a “lifetime of suppression.”

“Right now, I feel I can do anything. To have that experience under my belt and to have that lesson now, although it cost me a lot of pain? I’ll take it. I’ll take it.”