The Boss Show

Workplace wisdom with heart and humor

July 3, 2016

Your Transgender Coworker

How would you respond if your coworker, Stan Hartmann, showed up in the office one day as Annie Hart? That’s what happened at a real estate office in Seattle when Hartmann – who felt from early childhood that “he” was  a “she” – decided to become a woman. In an inspiring conversation with Jim and Steve, Annie tells her story.

View Transcript

Voiceover: It’s a northwest lifestyle weekend on KOMO News. Now, a show for anyone who is or has a boss. This is The Boss Show with Jim Hessler and Steve Motenko.


Jim Hessler: Welcome to The Boss Show. I’m Jim Hessler. I am the business guy. This is the essential show for anyone who wants to have good working life. We try to dispense as much wisdom as we can, don’t we Steve?


Steve Motenko: We try. Sometimes you do better than I do.


Jim Hessler: Yeah, mostly. Yeah.


Steve Motenko: Yeah, whatever. I’m Steve Motenko. I’m the psychology guy, and you may hear a difference in our perspectives based on that business/psychology distinction as you listen to the show. We’re hoping to offer you a little bit of workplace wisdom with heart and humor today. This show will be absolutely worth listening to. I have no doubt this will intrigue you. Jim, what are we doing?


Jim Hessler: We certainly know that there’s a lot of news these days about the LGBTQ community, and we’re pleased today to have the opportunity to introduce our audience to Annie Hart, about whom we learned in an article by Mark Styles in the Puget Sound Business Journal here in Seattle. Annie’s a transgender female, and she has an interesting story tell, and we want to hear that story today. First, let’s set the stage.


Steve, I just did one of those Google searches. How many transgender people are there in the United States? There’s 700,000, which is a number that surprised me a little bit. That’s a sizable minority, and that means with the degrees of separation that we all have in our lives, we probably all know somebody who’s either transgender or is considering transition or has been held back from doing so for various reasons. These are real people. There are many of them, and they are among us today. The rates of suicide, drug abuse, depression among transgender people are much higher than the general population. It’s a difficult thing to pull. Among transgender people specifically who have been rejected by their families, suicide rates are eight times the average of the rest of us.


Steve Motenko: If you’ve ever really thought about what this would be like, you can’t question those statistics. You can’t question what’s behind those statistics. This is going to surprise you Jim. I said to my wife, we’ve been married for 16 years, and I said to her the other day something that I had never said to her before, which is that I grew up feeling shame about being Jewish. I still have a little bit of it in me, which is shame in me, for no good reason, which is why I’ve never mentioned it to her. There’s a shadow there for me. To me, being Jewish is like just a little bit different from mainstream, and yet that difference was enough, and the perception of other’s judgments, real or imagined, was enough to make me feel a little bit of shame. Can you imagine growing in the body of a man but feeling that you’re really, as you’re growing up, a girl or, older, a woman? Can you imagine how that might …


Jim Hessler: No, I can’t. It’s beyond my ken, and that’s why we’re so lucky to have somebody on that can talk to us about this and raise our awareness. Steve, you and I are both old enough to know that things have changed dramatically in our lives around acceptance of these things, but we’ve still got a long way to go. One of the places we have a long way to go is in the workplace, and so we want Annie to tell us to any set of positive experience. One of the things I don’t want to do … I’m talking about suicide and depression and all that stuff. I would hope that there’s a joy and a positive outcome of people making the transition and becoming who they truly are, their truly authentic self. We hope to hear that joyful part of the story.


Steve Motenko: I’m sure we will because, as you’ll hear later in the show, the workplace context that Annie is in has been hugely accepting in really inspiring ways, so you’re going to want to stay tuned for that.


Jim Hessler: Paula and I, my wife, had an openly gay man as a groom’s man in our wedding almost 40 years ago, and being a music major and classical musician, probably about half the men I went to college with were gay. I knew gay people, and now I know a transgender person.


Steve Motenko: So will you in a few seconds.


Jim Hessler: So will you in a few minutes, so we invite you to come back after the break and join us in our conversation with Annie Joy Hart. We think you’ll enjoy it. You’re listening to The Boss Show.


Voiceover: It’s a northwest lifestyle weekend on KOMO News. The Boss Show continues.


Jim Hessler: Hi, I’m Jim Hessler. I am the business guy.


Steve Motenko: I’m Steve Motenko. I’m the psychology guy. Welcome back to The Boss Show. If you want us to consider your favorite workplace topic, maybe you got a problem with your boss or with your coworker, maybe it’s something you’ve been uncomfortable for a long time with in the workplace, send us an email at or leave a message on our listener comment line. That’s 206-973-7377.


Jim Hessler: Today, we have in studio Annie Hart. Annie, welcome to The Boss Show.


Annie Hart: Thank you. It’s an honor to be here, guys.


Jim Hessler: Thank you. Annie is a real estate agent in the Seattle area, and let’s just jump right to the chase. Annie, you say that you knew by a very early age that you were supposed to be a girl.


Annie Hart: Yes. This is something that was buried very, very deeply. I think it’s important for people to know. When this came to the surface within the last year and a half or so, it took some really deep digging from a close friend who, at that time, was presumed to be a romantic partner when I was still male identified.


Steve Motenko: Right. At that time, you were Stan Hartmann.


Annie Hart: Yes.


Steve Motenko: That’s how you were born.


Annie Hart: Yep. Exactly. Through a lot of probing and long story, she helped me get into to feel into this knowing. It was an explosive revelation. It was like a volcano that … A bottleneck of a lifetime of being dammed up and not really knowing what was up. Something was out of kilter with me. When this came out, there was such relief and such joy in the knowing of this and the remembrance that I am a female. Memories began to flood in, and right away, I was taken back to one of the few childhood memories I have, a dream that I woke from in which I was a little girl. I remember telling my mother that I’m supposed to be a girl and would you please buy me some girl clothes. At that era-


Jim Hessler: Living in Wenatchee, a very conservative part of Eastern Washington, I might add. Bible belt country.


Annie Hart: Yes. It was unthinkable that someone could be a different gender than their anatomical birth gender.


Steve Motenko: How did your mom respond?


Annie Hart: She was immediately just put the lid on it and said, “I don’t ever want to hear you talk about that again.”


Steve Motenko: The article in the Business Journal said that provoked some shame in you.


Annie Hart: Yes. I would say it felt like … At that time, of course, I couldn’t get in touch with it, but now looking back onto it and feeling into it, it feels like 100 foot thick, iron door was closed. There was no way to access any of the memories or to get to it. It was buried that deeply.


Jim Hessler: For the desires? To access the desires?


Annie Hart: Yes. Anything to do with that. Anything to do with being female.


Jim Hessler: It took this intervention by a very close friend to bring things out of you that you had created a curtain of denial around.


Annie Hart: Yes. Exactly. When this came out, everything fell into place, events in my life, tendencies, and there was a period of my life in the last decade or two when I was pretty convinced that I was gay as a male. When this revelation came, this remembrance, then I began to understand the attraction to males was that I’m a heterosexual female.


Jim Hessler: Wow. Interesting. The good news, it sounds like, at least at work, you’ve had a lot of acceptance from the people you work with. We should mention you work in Capitol Hill, which is –


Steve Motenko: A progressive area.


Jim Hessler: A progressive area, large gay population. I would imagine transgender folks aren’t as unusual in Capitol Hill as they might be other places, so you had a nice community, I suppose, of acceptance.


Annie Hart: Yes. I would say the majority of the agents in our office are gay or lesbian and very, very welcoming. They immediately took me in as a part of that community, and my real estate partner, Derrick, he even helped me with the nuances of becoming, in appearance, more female and dressing and things like that. Overwhelmingly …


Jim Hessler: We have so much more to talk about. I’m really so pleased that we have you here talking about this because there’s people who aren’t in such an accepting environment that are having to deal with this idea of transitioning. Maybe we can help them out a little bit. When we come back from the break, we want to talk about … I know, Annie, you want to help people, and I know that there’s probably some tips, hopefully there’s some tips, that you can give to folks that are wanting to make this transition and make it work in their life. You’re listening to The Boss Show.


Voiceover: Now back to Jim Hessler and Steve Motenko. This is The Boss Show on KOMO News.


Steve Motenko: Welcome back to The Boss Show. I’m Steve Motenko. I’m the psychology guy.


Jim Hessler: I’m Jim Hessler. I’m the business guy. We’re talking to Annie Hart. Annie’s a transgender real estate agent in the Seattle area. Annie, there’s a whole bunch of different groups you have to gain acceptance from as you go through a process like this. It sounds like, in terms of your immediate coworkers, there was a high level of acceptance. Tell us a little bit about your clients. You have clients as a real estate agent, probably some of whom you’ve known for quite some time. Tell us a little bit how that went.


Annie Hart: Naturally, since real estate is what I do vocationally to earn income, there was bit of a concern about how our clients’ going to react to this rather sudden change from dressing as a male, showing up here as a male, Stan Hartmann, into a female.


Steve Motenko: When you say sudden, how sudden was it?


Annie Hart: Once I made the decision, it was within weeks where I was comfortable dressing as a female with clients. What I did was I would tell … For one thing, I want to start out by saying this had to be, knowing that I was female was so strong that I would have sacrificed anything, like I go with compelled, could not help it. I’m in the process of helping clients as a male, and I would just simply call them or email them from one day to the next and say, “Okay, the last I showed you houses, I was male identified. You might have noticed that my dress was more feminine than what you’d expect of a male, but now, I want you to know that I’m female now, and I’ll be showing up in a dress.” Without fail, without exception, they were all extremely supportive and even commented on my makeup and my dress. The women would say, “I love your eyes and etc., etc.” Everyone was overwhelmingly accepting, and that was, obviously, very comfortable for me, made me very comfortable.


Steve Motenko: Surely you faced some judgment around this or not. You just haven’t been aware of it.


Annie Hart: I haven’t been aware of it, and I think I’m fortunate to be in a city where this is not that unusual. If I go to the outlying areas, I’m not quite as comfortable as I would be in the city, up on Capitol Hill especially. Resistance has been minimal. It’s been, more than anything, former people, former religious acquaintances, perhaps it could be said, but for the most part, I’ve had so little negative it’s not even worth any discussion of.


Jim Hessler: That’s incredible, and that’s part of this story, isn’t it? Of how different that might have been 20 or 30 years ago.


Annie Hart: Mm-hmm (affirmative). Yeah.


Jim Hessler: I guess, one question would be, if you had had the awareness and you had known that you were a woman and you’d found that out and discovered that out the way that you did 25 or 30 years ago, if you would have been able to make the transition as you’ve made it now.


Annie Hart: It would have been much more difficult, yeah. I can think back, I was in the produce industry in Eastern Washington, and there’s a lot of hard boiled, hardcore people in that industry. If I would have transitioned then, it would have been quite a bit more difficult.


Jim Hessler: Yeah. Maybe more than a little bit.


Annie Hart: Yeah.


Steve Motenko: How did you tell your boss? We have about 30 seconds.


Annie Hart: He’d already detected signs of change in me. I took him aside one day, and I just said, “Pat,” his name’s Pat Grimm, beautiful, wonderful man, the owner of our office on Capitol Hill, I said, “Pat, I have something to tell you.” He says, “I already know.” He said, “I was just telling my wife that we have lesbian and agents and gay agents, and we’re about ready to have our first transgender agent.”


Jim Hessler: That’s a perfect lead in to the next segment, which is if you’re a boss and somebody comes to you and says what Annie just said, how are you ready to listen to that, to hear that, to accept that, and then move forward effectively with the employee that’s sharing that information? You’re listening to The Boss Show.


Voiceover: KOMO News, The Boss Show is back on a northwest lifestyle weekend. Here’s Jim Hessler and Steve Motenko.


Jim Hessler: I’m Jim Hessler. I’m the business guy.


Steve Motenko: I’m Steve Motenko. I’m the psychology guy, and we have in studio with us Annie Hart who is a transgender Seattle realtor. Annie, one thing that just really struck me about the Puget Sound Business Journal article, they quoted your boss as saying, basically, you’re the same person you always were. You have all the same qualities, but you’re so much happier now. I’m curious, do you feel that way? What a great response from a boss first of all. Secondly, what a great way to conceive for all of us who can’t imagine, step into the shoes of the transgender person, what a great way to conceive of it. You’re the same person, and you’re going to be way happier. How do you relate in your internal experience to that?


Annie Hart: Yeah, definitely. I’ve been on a spiritual path for decades and have found tremendous peace and joy in that. In the actual being in a body was really difficult for me, and now I know it was it just felt clogged up, or it felt like not the real me being a male identified. When this came out, there was an explosion of joy, and the joy that I feel in a transcendent spiritual state, now, is able to come out through my physical form and just overwhelmingly joyful. It’s like I tell people all the time, it’s so cool to be a chick, and people who know me now, they just see the delight. Other women have been inspired by how happy it makes me to just … Everything about makeup and hair and clothing. It’s just been a blast.


Jim Hessler: There’s a broader lesson here, isn’t there, because it’s not just about our sexual identity. Anytime that we are having to hide who we are or not know who we are, there’s pain there. There’s this dissection from our life. It’s not just about your sexual identity. It’s a lesson for everybody to be who they are, right?


Annie Hart: Yes. I think that we all stream in with … Obviously, we stream in with a natural life force that is joyful. When you look at children at play, they’re naturally happy, and we teach them not to be. Because of the way the economy is structured and our society is, we put ourselves into conditioned boxes of behavior and how few of us ever get to be of total, genuine, authentic self. It’s all avenues of our life. For me, it happened to be my gender identity, and for others, it could be what they’re doing for a living. It could be who they’re with, who they’re in relationship with and how they express themselves.


Steve Motenko: I think that what they do for a living goes to a three part series that we’re about to air on The Boss Show about how … There are other things involved in this series, including robots and computers taking people’s jobs, but underlying is the idea that we all work because we have to work. Thus, that “have to” puts a lid on our self-expression. If we didn’t have to work, we could be freer to self-express. In very similar ways, if you didn’t have to be a man, you found out you could be way freer to self-express.


Annie Hart: Yes.


Jim Hessler: Is there any point at which you would like to stop being considered transgender and just move past that whole label?


Annie Hart: Really good question because from the outset, I didn’t even know what transgender meant, and so when I found out that that’s apparently what I was, I still do not identify. I identify with all those that are in the transgender community just as a label, but as far as … I do not consider my trans, having transformed from anything to anything. I’ve always been female, and now I’m just living authentically who I am. I just consider myself a woman.


Steve Motenko: I think that’s a really good point and really worth our looking at our preexisting biases that want to label you as transgender when that’s not your identity.


Jim Hessler: Any other issues with church, with family? Maybe we need to talk about that when we get back to break, but I’m curious about the acceptance in other areas of your life as well. I do want to talk about, we, I think, hinted at earlier, if you’re a boss and somebody comes to you with this news, what do you do with this news? How do you process your own emotions and your own feelings about this issue? You’re listening to The Boss Show.


Voiceover: It’s a northwest lifestyle weekend on KOMO News. The Boss Show continues.


Steve Motenko: Thanks for coming back with us. Welcome to The Boss Show. I’m Steve Motenko. I’m the psychology guy.


Jim Hessler: Jim Hessler, and I’m the business guy. Our guest today is Annie Hart, a transgender person who happens to be a real estate agent in Seattle. Annie-


Steve Motenko: You could say a realtor in Seattle who happens to be transgender.


Jim Hessler: That would be a better way to say it. Annie, family acceptance has been a little bit of a longer journey. We don’t necessarily want to get too deep into that, but that’s a work in progress it sounds like.


Annie Hart: Yes, it is. What’s been most important to me is to guard their hearts as much as possible. I don’t expect them, my close family members, kids, parents, cousins, etc. to get this. I don’t expect anybody to get it, but I don’t want to hurt them, but I can’t help expressing who I am. My approach has been if I can comfort you, if I can help you to understand, I’ll do anything to help you understand this, but I can’t change who I am and how I express myself, and thank you for understanding that that I’m giving you the same. If you told me something like this, I would be also as supportive of that as you are, could be of my situation.


Steve Motenko: I love this notion of I don’t expect you to understand it. I don’t expect you to accept it. I don’t expect you to be able to see it from my perspective because my perspective is … You don’t have my perspective because you haven’t had the feelings and the thoughts I’ve had all my life. If all of us could step outside of our own experiences and try to adapt the perspective of the other, a lot of the world’s problems, if not all of them, would go away.


Annie Hart: Well said.


Jim Hessler: This might be difficult for you, but I’m a boss, and an employee comes to me and says, “I’m going to transition.” This person you knew as Stan is going to be Annie in a couple months or however long it takes. Anything you’d like to say just from your heart to that boss about that moment in which they’re going to hear this news and they’re going to have some choices to make about how to respond?


Annie Hart: Yes. I would invite bosses to do as mine did and to feel the enthusiasm and the heart from the employee that you can tell that this means a lot to them and is going to enhance their performance in the workplace. It’s going to make them a better worker, better employee, better part of your business and sink into that and really explore and get to know what is it about this that is important to you and be an ally for them. You’ll be amazed at the results.


Steve Motenko: Do you feel like you’re a better employee or better worker, better realtor as a result of being able to express yourself in a way you’ve always known yourself to be?


Annie Hart: Yes. I always bend over backwards for people in customer service, but this has opened my heart so wide open that I’ve made connections with people that will last a lifetime. They can feel the love. It just makes for such a wonderful experience with people.


Jim Hessler: Even if you’re a hard boiled, bottom line oriented business person, that’s an interesting message, isn’t it? That this, allowing this person, supporting this person through this change might result in a happier and more productive employee who’s actually going to do your business good.


Steve Motenko: It’s an extension of what we always say to our clients that you allow people to express their creativity, give them as much freedom as the parameters will allow, and you get better employees.


Annie Hart: If your bottom line is important, that’s the best way to enhance your bottom line is to be an ally for them.


Jim Hessler: Annie, we are so pleased to have had you on the show today. We honor your journey. We honor that you’ve shared it with us today. Thank you so much for being on The Boss Show. It’s been a joy.


Annie Hart: Thank you. Me too.


Steve Motenko: You’re listening to The Boss Show.


Voiceover: Now back to Jim Hessler and Steve Motenko. This is The Boss Show on KOMO News.


Steve Motenko: Welcome back to The Boss Show. I’m Steve Motenko. I’m the psychology guy.


Jim Hessler: I’m Jim Hessler and the business guy. Hope you’ve been listening. If you didn’t get a chance to listen to today’s show, it’s always available as a podcast at We had Annie Hart who is a transgender professional here in the Seattle area. If you’re a boss, probably at some time in your career, somebody’s going to come up to you and say, “I’m going to come out of the closet,” or “I’m going to transition my gender. I’ve got a drug problem. I’ve got” whatever it is. They’re going to confront you with something you’re going to have to deal with. Please show up as humanly and as caringly and as compassionately as you can when that sort of a thing happens. We need our bosses to be enlightened as possible in these sorts of circumstances.


Steve Motenko: We need everyone in workplace, and I want to say everyone in the world to go the extra mile to step into the perspective of the other person.


Jim Hessler: The Boss Show is produced by Boss Media Productions, and our sound engineer is Kevin [dod-ruhl 00:24:53].


Steve Motenko: As Jim mentioned, if you missed any of this show, you can get it in its entirety online at along with all our other shows archived there for free.


Jim Hessler: We have a listener line 206-973-7377. We’d love to hear from you.


Steve Motenko: Thanks for listening.


Jim Hessler: Don’t forget-


Steve Motenko: Rule number six.



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