On the Road with a Corporate Crusader

KATE ISLER’S BREAKING BORDERS

Kate Isler is the author of Breaking Borders, a memoir about her peripatetic life crisscrossing the globe in pursuit of her ambition to be a successful business leader. She started working at Microsoft in 1989, when most people didn’t even know its name, and went on to open new global markets for Microsoft in their fast-paced, hyper-growth startup years in some of the most challenging regions in the world.

Isler’s story can be read as a quintessential role model story for women who want to have it all. Or, a cautionary tale of giving up a helluva lot (when she appears at her son’s school, the teacher says, with mock shock, “Oh, Luke has a mother.”).  Or, it can be read as a piece of history for what it took for women of her generation to make it in a male corporate world.

 

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ABOUT OUR GUEST:

KATE ISLER
Twitter: @IslerKate
Instagram: @kateisler
Kate Isler is an activist, wife, author, mother, partner, friend, businessperson, sister and risk-taker. Born in Southeast Texas, raised in the Southwest, and educated in the Northwest, Kate said “yes” to adventure and career from the start. As a tech executive, Kate’s work took her all over the world with her husband as they raised three sons. Kate started her career with Microsoft in Redmond, Washington. As a woman in tech in the early 1990s, Kate faced and overcame barriers in her work, and in the many countries where she lived, with humor and resilience. She was a trailblazer in her industry and in her personal life as she boldly stepped into the role as primary breadwinner, with the support of her husband, Doug.

After 20 years with Microsoft, Kate took her passion for business into the start-up world. With a depth of experience in tech, a healthcare-focused app grew almost to fruition. Kate considers this one of her best experiences as she learned “what not to do”. A shift into a non-profit start-up dedicated to celebrating International Women’s Day was the catalyst to Kate’s most recent adventure, launching an ecommerce platform for women-owned businesses, TheWMarketplace. Kate’s passion for gender parity has led her to a seat on the global board of Girl Rising and she is a committed mentor for the International Women’s Forum. Kate lives in Seattle, Washington, with her husband Doug. Their three sons are all grown and starting their own adventures.

Nancy (00:00):
Okay. Kate, I love your title, Breaking Borders, which I kept saying it was breaking barriers, but that is one of the meanings. So I'd like to go through all the meanings that you have in that wonderful title. Um, how many countries have you worked in?
Kate (00:33):
Sixty.
Nancy
Six-oh?
Kate
Six, zero.
Nancy (00:37):
How often did you move?
Kate (00:40):
We did six international moves altogether.
Nancy (00:46):
International moves. And how many positions did you have in your corporate life at Microsoft?
Kate (00:55):
Well, in my corporate life at Microsoft, probably at least a half a dozen, if not more
Nancy (01:01):
If not more -- there seemed like there's at least a dozen, now having read the book, just need to tell you that. So everybody, we're going to go back where you first go to Microsoft and the year is 1989. So could you describe what Microsoft was like in 1989 and also, kind of where women fit into not just Microsoft, but where they were in the picture when it came to business.
Kate (01:33):
So Microsoft was a mid sized tech company at the time that no one had ever heard of, unless you were a programmer or, you know, had something to do with networking for a large company, you had never heard of the name Microsoft. And we were creating a whole new industry and it was very much roll up your sleeves, if you see an opportunity, let's try it. And so there was a ton of energy. There was a ton of young people and we really, you know, we're exploring making mistakes and trying again. It was fast and fun.
Nancy (02:14):
So it felt like -- that sounds like a startup to me,
Kate (02:17):
It was, um, it was a startup with 3000 people worldwide. And so, uh, you know, when I joined, there were nine people in my orientation class and I was, you know, one of two women. So there was very few women. I went into a communications role, which, you know, marketing, HR, and communications, there are more women. And so I ended up on a team -- my first team was mostly women. And so that was very unique and very fun, but all of our client businesses, meaning the product people and the developers that worked around us, were all men. And so it was, it was really interesting and I had come from an environment where there are very few women too, because at the time women were not, they were receptionists, they were clerical people. They weren't really leaders, very few women that I knew were leaders at that point.
Nancy (03:15):
And yet you, when you go back, even to your teens and your twenties, you really did have-- Your vision was that you would be a business leader. I mean, that was your guiding star.
Kate (03:32):
I was. I mean, I have to say, I have always approached things when I've seen them or seen examples of success that I thought was interesting or activities I thought was interesting. I've always approached it like, well, why couldn't I do that? And I have no explanation to why that happened, but I always was like, I think that I could be successful doing that. And so I try it.
Nancy (04:01):
Because I grew up thinking I definitely wanted to change the world. I mean, so that was kind of like my M.O., but I never would have thought, okay, I want to go into a really big business and run it or be one of the leaders of it. Like that never entered my head, and I'm close to the same era as you. I mean, it just wasn't part of my vision because that wasn't in my neck of the woods. There were men CEOs living up and down the roads where I grew up. Um, but women in business, no, that wasn't one of the, the models that I could even picture.
Kate (04:42):
I have to say, why not? You know, I knew from a really early age that I was a pretty clear thinker and I thought that I could do it. And I just thought, well, you know, one step at a time I'm going to try this.
Nancy (04:56):
And then you do in fact, try it. You get in there. And throughout the book, you have a palpable thrill. Every time you've got a new assignment, or you get more responsibility, more turf, and here's, here's something from your book: You got another direct report, another area coming into you and you say, “It was a fantastic opportunity for me to grow my team, increase my visibility and continue climbing the corporate ladder.” That whole messaging of climbing the corporate ladder. It-- talk about that. Talk about that.
Kate (05:37):
It was my mission. You know, I wanted to be successful and I looked around and saw that that was the way to be successful, is to expand your influence, look at your responsibility and you know, kind of move forward. And I just always thought, that's what I'm going to do. I saw myself as a leader and I saw myself as succeeding. And I think that that's half the battle, you know, and I, the most pivotal moment of my career was to get an email announcement about somebody who had gotten a promotion. And I remember sitting in my office really distinctly reading it going, well, wait a minute. If he can do that, I can totally do that.
Nancy (06:21):
That is, I think any woman who's been in business has had that, “if he can do it, why can't I?” And that is just like one of the yellow highlighter lines in your book. And the answer to that is, if he can do that, why can I is...
Kate (06:42):
Yes, that's exactly-- I mean, why not?
Nancy (06:45):
But you also say, and that anecdote in the book is that, this guy who you'd done some work with, you, weren't so impressed by him. And you were going, “So what's the difference between him and me? Like, why is he getting this and not me?”
Kate (07:01):
Exactly. And I thought it, you know, that was exactly my thought. Like, I can do this better than he can. And I was not naive enough to think that, you know, there was a difference between men's success and their speed at success than women's. But I I'm pretty tenacious and I'm not going to let that go. And I, that was one of the first times in my life where I was like, well, I'm rolling up my sleeve and doing this. And I did.
Nancy (07:34):
Because you knew he had the advantage. I mean, you say that, that he was connected to the, whatever you want to call it -- the boys club, the boys network -- he was hooked in, you weren't, you recognized it.
Kate (07:47):
Absolutely. And I, you know, I had a lot of subtractions, if you will, to me being a part of that club, because by that time I had a child. I was married and had a child until the assumption is, oh, you're going to take more time off. You can't travel. You can't do a lot of things, or you don't want to do. And I think that that is the assumption that is still in place today for so many women. And I, you know, I just figured, well, gosh, I want to do this. So I'm going to give it a shot.
Nancy (08:19):
Well, how did you do that? I mean, you're, you're now like zooming around the world. I mean, to all these different countries, as Microsoft becomes a global entity. You have a husband. You eventually, you have two boys,
Kate
Three
Nancy
Three boys. Did I miss one? I remember, I remember Luke. And you're flying around. And how is that working? I mean, how, how are you… Let's talk about your husband.
Kate (08:54):
So I had the conversation and I think that that's where lots of women stop, is the -- you know, I was determined that I wanted to do something and I have always been driven by a little bit of adventure. It sounded like a great life, and that's the life that I had pictured for myself. And so I, when I got that first email, I went home and I said to my husband, here's what I want to do. I think that this is interesting. And, you know, I had lots of, again, disqualifiers for women: I had a husband, I had a child, I had responsibilities. But when we started to talk about it, we're partners and he said, okay, we'll give it a try. And I think there are so many women who decide that they have those responsibilities and, “people depend on me, and so I can't possibly,” and then they walk away from that. And I didn't, and he agreed. Now I will also say that it was not the smoothest transition, so I don't want to misrepresent,
Nancy (10:02):
But he-- he was working. I mean, when, when you talked to him about this great adventure, you were about to go off on, he was working, was he.. He had a great job.
Kate (10:17):
Yes, he had a wonderful job. Um, and he had potential to probably do better than I did at that time, because when I started work, um, the mean salary for women was about twenty four, twenty five thousand dollars. And so I couldn't make very much money, but I wanted to try this, and so I sold it to him by saying, it'll be two years, it'll be a big adventure. And you can spend more time with our son,
Nancy (10:50):
And then, and then we'll come...
Kate (10:55):
Yeah, come back, and live the traditional life. And, you know, you can work. And he, you know, he had a very good job and was qualified and said, okay, I'll maybe organize this like a leave, and that's what he thought he was doing.
Nancy (11:10):
And he then became what we now call a stay at home dad, a house husband.
Kate
He did.
Nancy
Were there any downsides to that?
Kate (11:23):
Well, there was tremendous downside because the first posting we went to was in the Middle East, in the early nineties. For a woman to be, first of all, the sole breadwinner was terrifying to me. When I really realized what I had gotten into, it was terrifying. And for him to be, at the time, a stay at home male spouse was absolutely unheard of in ex-patriot life, but certainly in the Middle East. And so we became kind of a novelty in the community of ex-pats, but he had a really hard time. When we started, um, he was used to, you know, spending all day out of the house and working and living his life. And all of a sudden, you know, he was thrust into a community of all women that were non-working Westerners, and doing all the domestic things. And he always helped, but he was never responsible. And it was a difficult thing. And there were times when he said, “I think we've made the wrong choice.” And it was hard. And it was hard for me because I was certain that our son would stop seeing me as his mother and start preferring his father. And I was terrified of that. None of that happened.
Nancy (12:44):
Do you have an anecdote, which also had home for me as a mother who wasn't there all the time when I was in my professional life, um, where you go to -- this is when you're back in Seattle, I believe -- and you'd go to Luke's school and a teacher makes a comment. Can you talk about that moment?
Kate (13:06):
Absolutely. Absolutely. So it was, we were in the process of moving back to Seattle and I had actually flown from China and had not, you know, not gone home to rest. I had showered. It was the last day of school and gone to the last day of school. And I had three kids in that school and my husband substitute-taught at the school. So we were very involved. He was very involved. And the teacher of a third grade class came to me and said,” Oh, Luke does have a mother.” And it was, all I could do was took all my composure to say, “How many of the fathers of your students do you actually know? Because you know, a primary parent quite well, but you just don't happen to know me.” And, you know, sometimes I think it was the other mothers and the women that were worse to me than my male colleagues or the male community that I was involved in.
Nancy (14:12):
So you were mad?
Kate
I was sad, I was mad, and I was really frustrated because, you know, I still, even today think women don't all have to agree, but we have to support one another. And I saw that as such a dig, you know, at clearly an insecurity that every mother's going to have and that it just hits straight home. And so it was just awful -- it put me off balance for sure. But you know, it was one of those things that you need to adjust your response in the moment versus be emotional about it.
Nancy (14:55):
Yeah. When I had a similar moment, I handled it fine in the moment. But when I left that event, I cried. And I cried, not because someone was judging me that, you know, that I wasn't performing the mom role the way we were supposed to be performing it, I just felt badly because I thought I'm not a good mother. They don't know me. I don't know them. I haven't been part of this community. And I, I cried. I mean in -- alone. I wasn't going to show anyone that. But I did.
Kate (15:36):
Absolutely. Absolutely. There's many, many times where I think of, I was, you know, assumably in some foreign wild land, which translated into either a hotel room alone, or a conference room. And there was some important event that I was missing, and I was gutted when I heard about it, when they told me about it, always. The good news about that is now as they are grown, young men, all of them are very aware of my life, my career, and actually proud of me and tell me that. And so it is a wonderful, you know, sort of all the way around, they see that we did not have a traditional family, but they value that. And so I'm thankful that, that they, they are that those young men actually,
Nancy (16:34):
Absolutely. There's one of the blurbs for your book. Um, it says that breaking borders is great advice for any woman who wants to have at all. Did you have it all? Do you have it all?
Kate (16:54):
Haha, do we ever have it all? Um, I think that I had, really, an extraordinary life that I never would have imagined I would have had. And so I'm thankful for that every day. And I do, in some ways, I had it all -- I just may not have had it all at the same time. So when my career was going very well, oftentimes my relationship wasn't. Or when my relationship was going very well, I was not on a fast track career path for a few years. And so there were a lot of trade-offs and a lot of painful ones as we went. But, you know, at the end of the day, where I am now, I, you know, my career is not finished. I'm still married. I still have children. It's still moving forward.
Nancy
You're still here.
Kate
I'm still here.
Nancy (17:59):
Is there anything you'd like to add about the book before we end this section?
Kate (18:04):
Well, you know, I think the book was -- it's really interesting, people have asked me, “why did you write it?” And I really think that it's at the core of what I want people to take away from it. So when I left Microsoft, I had, for the last time -- I was there twice. Um, when I left, I had a very hard time because I knew in my heart, I should have left the company before I did. And I stuck it out, as I think a lot of women would because change is scary, and I stayed there. And when I finally did leave, my self esteem was terrible, I was frustrated, I didn't know who I was. And so writing the book was a very cathartic exercise for me, to kind of really document all the things that I had accomplished and my journey, which sent me up to be much more powerful afterward because I had to remind myself, Oh my gosh, you have done these things, and so be proud of those, own the mistakes and use them as you go forward.
Nancy (19:19):
That is so interesting because it brings me back to something you said in the book that after you left Microsoft and you were almost full-time mothering and going, “okay, I'm good at this, but this really is not my complete mission in the world,” and then you say -- when you think, “I got to do something else,” and you go back, not go back, you start consulting. You start fixing companies out there with all the lessons and all the knowledge you have from all your years. And you say, “I relish the challenge of endless meetings and impossible deadlines”-- I had that same adrenaline -- and you said, “Right or wrong, my self-worth is very connected to my career. Having a professional identity made me happy.” And then when you leave, I mean, like when you really leave, I thought, were you re-evaluating then if your identity was solely that of a career woman and that, without that title, you didn't exist?
Kate (20:32):
Yes. I felt absolutely invisible. And I felt I didn't know who I was. I didn't know how to say who I was. And I also, you know, went through the whole process of how guilty I felt for feeling that way, because I think that you have to go through a process to actually own that and realize where that fits in. And I have always said, I have always envied the so-called normal process of life, where people have an average life and they live, you know, they go to school, they get their degree, they get married, they have kids, they have a career, you know, that sort of trajectory that we hear about. I have always envied that, but in reality, whenever I've given it a shot, I'm just so bad at it, and I'm unhappy. And I had to own that and I had to work through this is who I am, and so I can't imagine not having a professional identity, even now.