In a recent discussion about how men need to get better at spotting talent in women (and people in general need to get better at spotting talent in people who are different from them), a long-time reader and commenter, Tammy, mentioned that, as a transgender woman, she’s seen stark differences in the way people treated her before and after her transition. She offered to talk more with me about it, and here’s our interview.

Tell us a little about you.

I’m currently a mid-level manager at a software company in California. I’ve been in all kinds of technical roles in my career (QA, system administrator, programmer, database administrator, etc.) I transitioned almost 21 years ago in Silicon Valley during the first dot-com boom. Prior to coming to my current company, I spent 12 years working with my ex-spouse as a self-employed software developer and IT consultant.

You mentioned that you’ve seen differences in how people treated you before and after your transition. What did you notice?

Yeah, it’s super interesting — though, I suspect, not very surprising given what cisgender* and AFAB* people experience. (Cisgender: Someone who identifies with the sex they were assigned at birth. The opposite of transgender, and used to avoid stigmatizing language such as “transgender women and normal women” or “transgender women and biological women. AFAB: Assigned Female at Birth. Contrasts with AMAB, Assigned Male at Birth.)

Before my transition, people assumed I knew what I was talking about. They didn’t talk over me in meetings. They trusted me when I spoke, and they didn’t look to others for confirmation of my ideas.There was a baseline assumption that I was competent and capable. Since my transition, it’s distressingly common for people to talk over me, to look to men for validation of the things I say, to assume that I couldn’t possibly know anything about [technical topic] because I’m a girl. I’ve actually had people tell me, “what could you possibly know about that? You’re a girl!” In a previous role at my current company, I had a male coworker who needed to be told *by my boss* “Tammy knows what she’s doing and I trust her judgment, so please stop trying to hijack her meetings and run them like they’re your meetings!”

In a way, though, I’m lucky, because I’m in my 40s and have a 20-year track record of career success. I think this offsets some of that stereotyping, because I’ve noticed less of this kind of behavior, and dramatically less of the really egregious stuff lately. I remember one incident, not that long after I transitioned, where a guy I was interviewing for a position on my team called me an “f***ing bitch” to my face in the middle of the job interview, because the answer he gave to a technical question wasn’t something that was actually possible with a real computer! (Needless to say, we didn’t hire him.) I remember another coworker at the company where I transitioned who spent a goodly part of a meeting with me dropping things on the floor so he could try to catch a peek up my dress while he was picking them up. It was very brazen then, and I was younger, less experienced, and not nearly self-possessed enough to call him on it in the moment.

I think many cisgender women who encounter things like people doubting their expertise, talking over them when they speak, etc. often wonder if it’s something about them, or if it’s sexism. It’s so easy to doubt yourself and start making excuses for the other person — “oh, he just didn’t know I have a background in Topic X” or “I need to be less soft-spoken” or so forth — and it can be hard to know for sure “yes, this is definitely sexism happening in this meeting.” For you, because you experienced such a clear contrast pre- and post-transition, it sounds like you didn’t struggle with that doubt about your own perceptions. Am I right in thinking the contrast you experienced made it quite clear what kind of sexism was being directed at you?

On the one hand, you’re right that I didn’t doubt my own perceptions around sexism as much as I think AFAB cisgender people do. Some of that is that I experienced that clear contrast, and some of it is that in my teenage years (before I transitioned but long after I was aware of my own identity) I got a chance to see how men talk and act and behave when there aren’t female-presenting people around. And I paid really close attention to those things because, in those days, I was trying to figure out how to blend in and to play the role society expected me to play. I wasn’t ultimately any more successful at it than I think Jane Goodall would be if you expected her to be a gorilla, but I did try desperately to find other solutions to my torment when I was younger. So in that sense, I didn’t usually doubt that I was perceiving sexism that was real.

On the other hand, though, I ran into a set of societal expectations that I didn’t expect, and that threw me for quite a loop. On the one hand, trans women who dress and act and present very femininely — as I did early in my transition — are told to “stop trying so hard,” that we’re “becoming a caricature of femininity,” even that we’re “mocking what it truly means to be a woman.” (This is a criticism often leveled at drag queens too). On the other hand, when we dress in jeans or pants and tops, ditch the stiletto heels for flats or boots, and dial back the makeup, we’re told “if you’re not even going to bother to be feminine, why did you even bother transitioning” and referred to as looking like “dudes in dresses.” It’s like there’s this magic way we’re supposed to perform femininity so that society will find us acceptable. When you’re trying to find that magic balance point, usually by painful trial and error, you start to doubt your perceptions about everything, because that’s how gaslighting works.

I should add that this is solely my experience from a trans-feminine vantage point. I’m sure that trans men and nonbinary people experience similar challenges, but I definitely can’t speak to their experiences on this issue.

Do you think you were any better equipped to respond to it effectively, not having been socialized your whole life to expect it?

Yes and no. I think I was better equipped in the sense that I was more socialized than I think a lot of AFAB people are to speak my mind. My natural communication style is more direct than I think is typical of a lot of women, and that’s something I’ve had to learn to soften somewhat. On the other hand, not having been socialized to expect that stuff meant I didn’t really have the emotional tools or mental context to deal with it when it came up, and so I tended to sort of freeze when I saw it. I see a similar challenge for trans women early in their transitions around personal safety, too – we weren’t socialized to be as aware of the risk of violence as most AFAB women I know are, so we tend to forget that situations which men don’t think about can be really dangerous for us.

You also mentioned that you’ve seen differences in your resume and work experience were perceived before and after transitioning. Tell us about that.

Early in my career, the sexism was very stark. Prior to my transition (and during the first dot-com boom of the mid-1990s), I’d send out resumes and I’d get calls. It was quick and easy to find work, and I don’t remember ever taking more than a couple of weeks to find a job. Just a few months after my transition, with essentially the identical resume and experience, it took me the better part of six months to find a job. I still notice that it takes a lot longer for me to find a job now, and my qualifications are scrutinized much more closely. This problem has gotten both better and worse as I’ve become both older and more senior in my career. I have a long track record of accomplishment, so I don’t notice the same skepticism about my experience, but senior roles are less plentiful. I’d estimate it still takes me 6-12 months to find a new position on average, which is longer than it took before my transition. But there are a lot of reasons that could be true, so it’s hard to say definitively how much of that is about gender.

One thing that did surprise me a lot, though, is how much societal awareness around LGBTQ issues has changed things in the past decade or so. Prior to coming to my current company 6-1/2 years ago, my ex and I ran a consulting firm for about 12 years. Back then, I was always terrified about negative consequences if our clients found out about my past, and so I was very secretive about it. Turns out most of them knew anyway, and I actually damaged our relationships because they wondered why I didn’t trust them enough to be honest. When I was looking for what became my first (of five) roles at my current company, I decided I wasn’t willing to keep living in fear and keeping secrets. So from my first interview, I was very open about my story. If a company wanted to look at everything I brought to the table as a result of my experiences and that was the reason they didn’t want to hire me, I reasoned, it wasn’t the right company for me. I attribute a lot of the success I’ve achieved here, and the trust and respect and credibility I have with our team and executives, to my willingness to be authentic and transparent. I recognize that I have a lot of socioeconomic privilege and live in a relatively open and tolerant place, so that advice isn’t true for everyone, but it’s worked out pretty well for me.

What was it liking handling a transition at work?

One thing that’s always interesting to me is that a lot of coworkers who I thought would be supportive of my transition weren’t, and vice versa. I worked as part of a team of half a dozen men and two other women at the company I transitioned at. One of the women came to me when my transition was announced (in a way I now find a bit cringey, but which I didn’t think was odd at the time — a whole other story I’m happy to talk about). “I’m having a hard time dealing with this news,” she said, “and I need you to give me some space to figure it out.” She ultimately became one of my strongest allies. In contrast, two of my male coworkers were extremely vocal about their support when the news was announced, but during my first week back to work after my transition they took me out to a Chinese buffet for lunch. It was the most awkward lunch I think I’ve experienced, and they spent the whole meal making sexual jokes and trying to throw shrimp tails down the front of my dress across the table. I tell other trans people, “don’t waste a lot of energy trying to predict people’s reactions.” When I’ve done so, I’ve been wrong nearly 100% of the time.

Something that always seems to come up with trans folks who are transitioning in the workplace is “the bathroom issue.” I even knew one trans woman whose boss insisted she hang a “Jane is in this bathroom” sign on the door when she went to use the restroom, so coworkers who are uncomfortable could avoid the bathroom while she was in it. Apparently, other people have far more exciting bathroom experiences than I do! I just want to get in, do what I need to do, and get out with as little fuss as I can get away with. To be honest, I’ve always been a bit perplexed about why this is such an issue.

Will you say more about how they ended up announcing your transition in a cringey way?

So, I worked for a medium-sized company when I transitioned, and they tried really hard to be supportive — the bathroom issue was never a thing for me, for example. But they announced my transition to the entire company in a series of all-team meetings, including hundreds of people who never worked with me directly and who really had no need (or desire) to know. I have to imagine some of those were pretty awkward meetings. But for better or worse, forever after until I left that company, I got stares and whispers everywhere I went. It was like i wore a scarlet letter! On the good side, I also discovered later that I had a few unexpected allies who’d shut down the whispers if they heard them. The other problem with announcing my transition at a series of team meetings was that a certain number of people were bound to be absent the day the meetings were scheduled. This created a lot of confusion when they came back to work and came into my office, as I’m sure you can imagine.

That sounds … not good. What advice would you give to companies that want to do it well? And coworkers, too, for that matter.

• Educate yourself first. There are so many good resources out there now, such as this guide from PFLAG or this book. HRC also has a great resource for employers. Asking questions of your trans employee is fine – and encouraged – but do the heavy lifting to learn first. You might think your two or three basic questions are innocuous, but multiply that by all of that person’s family, friends, and coworkers, and the cumulative load can be exhausting. Don’t use the transgender person in your life as your personal Wikipedia. Besides, we’re all unique individuals, and we’re not made with a cookie-cutter.

• Be sensitive to the difference between information you need and information you want. You’d be shocked (or maybe not) at how intrusive the questions people think it’s appropriate to ask are. I’ve been asked, in the workplace, about the configuration and state of my genitals, about my sexual habits, about the intimate details of the surgeries I have and haven’t had – it’s wild. When I had my gender confirmation surgery in 2015, I had to share a certain amount of information about some of those topics with our Benefits people so they could help me with insurance stuff, but that’s wholly different from people just wanting to satisfy their curiosity.

• Ask your transitioning team member how you can support them. But also, remember that they might not be totally aware of their needs, because transition is a big thing that we’ve typically never done before. There are some obvious ways to be supportive – smooth processes for adjusting name and gender on paperwork, a new badge with the right name and photo, a new name plate on their desk, are all small ways to show support. Having another team member who can intercede with the folks who missed the announcement so that’s not all falling on the transitioning team member who will be oh so nervous and stressed out on their first day as their true selves is good. Beyond the obvious, though, ask them what would support them, and do that.

• Watch for and be proactive about addressing inappropriate behavior. Don’t assume your transitioning employee will feel safe enough to come to you about it. After I transitioned, I dealt with all the usual creepy stuff that women and AFAB people deal with in the workplace: The coworker who’d stand too close and stare. The boss who came up behind me and massaged my neck and shoulders without asking. The guy who invited me 34 times to go square-dancing with him and who didn’t take no for an answer. I didn’t know how to address those things, so I just quietly let them make me feel uncomfortable and afraid. Enlist the whole team to support shutting this stuff down. “If you see something, say something” really works here.

Thank you. What advice would you give trans people trying to navigate work safely and happily (something I get asked about a lot and don’t have nearly enough expertise in)?

• Advocate for your needs. Your employer is doing the best they can to support you, because you’re a valued member of their team. But this is highly likely not to be a situation they’ve faced before, and even if they have, they haven’t faced it with you. They’re not mind-readers. And just as importantly, you’ve probably spent years coming to this understanding of who you are and the path you’re on. Once you come out, everyone in your life is on that train with you whether they’re ready or not. So speak up and ask for what you need. Not everything you want is going to be possible – if you work in a call center and get upset when people misgender you, not having to talk on the phone just might not be a thing. But the people who want to support you need to know what you need. So use your words and speak up.

• Build your support system early. Like, ideally, before you start your transition. The reality is, changing who we are is HARD. There are going to be bumps in the road. Lots of them, large and small. In my experience, transition is EXTREMELY difficult to do solo. Make sure you have your “team you” who can encourage you on the hard days and help you strategize your way through the obstacles. The earlier in your journey you put that into place, the better.

• Don’t take yourself too seriously. There’s going to be lots of hard stuff, painful stuff, just plain STRANGE stuff that happens along this road. I remember my first week back to work after my transition, I ran into a coworker who I knew casually in the women’s restroom 5 days in a row. It wasn’t until the fifth day that it occurred to her to ask me if she should still call me by my former name. (Spoiler alert: No. No, she shouldn’t.) People are going to be confused. They’re going to mess up on your name and pronouns, not out of maliciousness but because brains are funny sometimes. You’re going to have plenty of awkward experiences and conversations. The months I was learning to cultivate a bit of a bubble of space around me so I didn’t bump into stuff with my boobs were some kind of fun, let me tell you! All the awkward experiences cisgender girls have in junior high happen to trans women at whatever age we start transitioning, and second puberty isn’t any easier for having had a first one. If you can appreciate the absurdity and retain the ability to laugh at yourself, you’ll make it through a lot happier.

• Make friends with the admin people in your office. They’re the best way to stay plugged in to what the gossip grapevine and rumor mill are saying about you, and that can be incredibly useful information.

This is all helpful. Thank you so much.

Thanks for giving me the opportunity to have this conversation. I think it’s super important to talk about stuff like this. I had a chance to hear Michelle Obama speak last year, and one thing she said was “we need to keep telling our stories, because it’s awful harder to hate up close.” So I’m grateful for the chance to tell my story!