Navigating the Tech Industry with Confidence

In this episode of The Impostor Syndrome Files, we talk about what it takes to survive and thrive in the high-stakes world of big tech, especially as a woman in engineering. My guest this week is Jossie Haines, a leadership coach for engineering leaders and women in tech, whose journey spans major roles at companies like Apple, Zynga and Tile.

Jossie opens up about the culture shock she experienced when she joined Apple, how impostor syndrome almost drove her out of the tech industry and the mindset shift that helped her reclaim her power and purpose. Together, we explore how hidden systems and subtle exclusion can erode your confidence, and what it looks like to rebuild it by honoring your strengths, setting boundaries and creating your own definition of success.

About My Guest

Jossie Haines is an executive coach, fractional engineering leader, and AI advocate with over 25 years of experience at Apple, Tile, and Zynga. She helps engineering leaders succeed in their first 90 days, show up as the strategic leaders they were hired to be, and leverage AI to optimize their time. Her mission is to retain women in tech and empower leaders to build inclusive, high-performing teams.

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Connect with Jossie:

Website: www.jossiehaines.com 

Get Promoted Private Podcast: https://jossiehaines.com/get-promoted-podcast-signup/

LinkedIn: https://www.linkedin.com/in/jossiemann/

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Websites: https://kimmeninger.com

Transcript

Kim Meninger

Welcome, Jossie, it's so great to have you here. I'm really excited to chat with you. I'd love to start by inviting you to tell us a little bit about yourself.

Jossie Haines

Awesome. Well, first, thank you so much for having me on the show. So I'm Jossie Haynes. I'm a leadership coach for engineering leaders as well as for women in tech. My career has been as a software engineering leader. So the first 23 years of my career, I worked full-time in corporate roles, mostly large-scale consumer tech. So I ran the Siri team for a few years on Siri music and media. So one of my teams built the 30 music features for Siri on home pod. Another one of my teams built the Siri on Apple TV integration. We actually got a technical Emmy for that integration while I was leading the team, which was cool. Worked at most recent like full time corporate role was as VP of Engineering at tile, the little Bluetooth key tracker and but I decided that my passion was really around helping leaders thrive as well as defining success on our own terms in our careers. So in July of 2022, I left the full-time corporate space and started my own coaching business, which is what I've been doing for the last three and a half years. I also am a fractional engineering leader, so I run a small engineering team part-time as well, and but my I really enjoy helping people figure out how to thrive, how, you know, what is the mindset work needed. I actually almost left the tech industry entirely after Apple, going through a lot of impostor syndrome there, and so taking a lot of what I learned from there to then going to tile, where I ended up creating that VP of engineering role, and then now basically getting to define success on my own terms and create what I call as my portfolio career, where I'm thriving but not Doing what somebody would traditionally be doing in the corporate space.

Kim Meninger

Well, I'm really excited to there's so many paths I want to go down right now try to keep myself organized, but I would love to hear a little bit more about your experience in you know, a big tech company, because I think that's a breeding ground for a lot of imposter syndrome, especially. And I want to put words in your mouth, but I don't know how gender diverse it was. I don't know if your experience was at all influenced by being a woman, but I'd love to hear just a little bit more about what it felt like for you as you were navigating particularly a big company like Apple.

Jossie Haines

Yeah, and, you know, it's interesting, because prior to Apple, I had worked at Zynga, and Zinga is a gaming company I had, I started it there in 2010 I worked there through 2015 and that was really we the first year I was there, we went from 1000 to 2000 people like my career skyrocketed. I went from a senior software engineer to a director of engineering. I thrived when I was at Zynga, which is actually not typical in a gaming company. But I left Zynga and went to Apple, and I had felt pretty good about like, wow, I I know what I'm doing. I can do, I can do this well. And, yeah, I got to Apple, and all of a sudden I was like, Oh, I'm very much like a small fish in a very, very big pond, right? The scale of Apple was insane compared to anywhere else I'd worked, even though I'd worked at bigger companies before, I'd also worked at Sun Microsystems back in the day, I'd worked at NetApp, and I think the first thing was just navigating the culture, and Apple's almost a little different than even the other big tech companies, because of the secretive nature of Apple, every team is very isolated, so There's like no sharing of knowledge between different teams. Like people don't really talk about what they do outside their teams. Like you're not, like, unlike Google, where you basically have access to the full code base, like you only had access to, like, the small code base that you that your, your team is working on, like, you have to get. Um authorization to be allowed to know about projects like it's possible that your team members are working on projects when you're a manager that you're not authorized to know about um. So I think that secretiveness, in and of itself, first creates a little bit of this potential imposter syndrome. And then speaking to what you were talking about, I was Siri had been around, I think, for a little, for around five years, when I joined the Siri team, and I was the first female engineering manager that they had on the domain side, so the, the people that manage, like the big areas of Siri. So that was that, in and of itself, is very eye-opening to me, because, I mean, like I said, I worked in gaming, which was already even more male-dominated than most tech is, and yet I felt much more isolated as a woman at Apple than I did at Zynga, which was, which was somewhat interesting. I actually started Women at Siri when I was at Apple, because there was a women at Apple employee resource group. But what I realized was like, they do, like, company-wide events and things like that. But there was no like, let's sit down and meet and actually talk about what it was like. Like, what are our challenges? And all of the Siri team was in one building in Cupertino, and I just remember, like, this was like, the most fascinating thing. We'd, we'd meet at noon. We'd, like our women at Siri meetings would be from like 12 to one, and at one o'clock there would be, like the leadership, like Round Table, where every all the leaders would go over, like the projects for the week. So it was like the project all hands every week. And every time we'd have one of our women at Siri meetings, as we were all leaving and the rest of the team was showing up, people would literally be surprised. They'd be like, what's a room full of women doing like, like, literally, it was shocking that there's like 15 women gathered together in a conference room.

Kim Meninger

That's so interesting. Yeah, you would never think that if 15 men came out of a conference. Wow, that's really interesting to the secretive nature that you're describing, because I feel like a lot of that experience with imposter syndrome is it is influenced by the environment that you're part of. And you know if, if very highly competitive environments tend to trigger more imposter syndrome when you don't feel like you can engage freely with your colleagues, and you're comparing yourself to other, all of these factors can heighten that sense of self doubt. So what you're describing seems like a perfect breeding ground for…

Jossie Haines

Yes, and it was also very political, of like, who knew who and who had relationships with who, and who went out to, like dinner or sports with everybody else. And so it almost started from a just feeling very not included. I mean, I was there for two years, and I can most likely have less than 10 times I was invited to lunch. [Oh, wow.] And in two years, right outside of, like, the first week, where people would gather me that it was just like, Okay, you're on your own and, and so it just you end up in this echo chamber in your head of, why are things not working the way I want them to? I also called it just death by 1000 paper cuts, right? It's like the little things that happen on a day -to-day basis. So my technical program manager, who I worked with closely and I, we usually attended all our meetings together, and he was a guy, and we would, we showed up to a meeting, and somebody actually assumed that he was the engineering manager. And that was a very common occurrence, like I would walk into a room, and the assumption was he was the engineering manager. The surprising thing, though, that happened in one meeting was the, the person who made this assumption actually apologized, hmm, and, and actually sent me a note afterwards, saying, you know that. That you know, that, that was an unfair assumption on his part, and it really made me realize just how much I had gotten used to, oh, people are just going to assume that I'm not the technical one. People are just going to assume that I'm not the engineering leader, that I'm the project manager, and I've gotten so used to it that getting an apology was shocking.

Kim Meninger

Yeah, wow. Wow. What a and what a... I'm not sure what the right word is. I was gonna say strange, but it's probably not the appropriate word. Thing to have to get accustomed to right is to having people assume that you're not at the level that you actually are. Wow.

Jossie Haines

Yeah, and it's and so, yeah, it was lots of little things like that. I think the other place where imposter syndrome ends up playing into it is, you know, a lot of people always say, you know, you stay or leave at a job based on your manager, right? And I just never felt 100% supported. And so when I was having challenges with some team members. It almost just felt like, Oh, he's not siding. He's siding with the team members, not with me. I must be doing something wrong, right? We, we did a we did a 360 which, you know, a lot of times you do 360s it's supposed to be for career growth and but I almost felt like, Oh, I'm being penalized, and this 360 is how to get me out the door. And I remember, I I took that 360 report, and I didn't trust anybody at Apple to review it with. I literally went to my old boss like and showed up at his house one night crying, going, like, I don't know what I'm going to do, like, I feel completely alone. I got feedback that was definitely, like, very negative on this 360 that was very jaded, and that didn't feel constructive at all. And what ended up happening. And then my former boss is great, and he was just like, Okay, let's go through, let's find, like, the realistic things to work on in here. And he, he helped provide some clarity. But at the end of the day, I ended up having, like, one of my teams get restructured out from under me, and I ended up just feeling like a complete failure. I ended up feeling like I have now failed as a manager. I am not cut out to be here.

Kim Meninger

Wow. So as you're going through this, what are you Are there any coping strategies that you're using, like, what are you doing to get through the day?

Jossie Haines

Yeah, I think for me, the big thing of getting through the day was just trying to compartmentalize first, like, really having like, a clear like, okay, the day is over. I'm not gonna check email again in the evening, even though I was I actually ended up getting penalized for that, because there was this unspoken culture where all the engineering managers and project managers would actually get back online or between like nine and 11pm and do a ton of work. And so I'd end up waking up every morning with a ton of emails that I had to now action. And it was one of these things. It was like, again, this unspoken nobody ever said, like, Oh, you have to do this, but you were definitely judged for not doing it. But I was like, I need the break. Like, I can't have an entire day and then go off and, like, keep doing this in the evening. So just taking breaks myself, and then really prioritizing the things that I was passionate about, right? So, focusing on running women at Siri to the extent that I could make it thrive. You know, I did try to start a mentoring program as part of it, but the, the VP at the time didn't believe in mentoring, so I wasn't allowed to start it. But I did then start it at my next role. So I'm, I'm excited about being able to do that, um, but, yeah, I and I really just focused on, like, what is it that I need to do, and how do I do a lot of the mindset work. But at that time, I didn't really even know that much about mindset work. It actually ended up being. Leaving apple that really woke me up to those strategies that would have been wonderful during my during my during my time at Apple.

Kim Meninger

Well, that actually takes me to my next question, because you mentioned you used, like a few terms that I think are really helpful thriving, right? And you talked about success on your own terms, and I really want to dig into that a little bit because of what you said, which is, you know, the either implicit or sometimes explicit expectations of how long you're going to be working. How many, you know, how many hours are you putting in, the lack of boundaries, the just the, the nature of the work, and I'm curious how you kind of reconcile the importance of having a life and boundaries, and, you know, taking care of yourself with a field that at least, sort of stereotypically, is not respectful of people's lives outside of work.

Jossie Haines

Oh, yeah. And I mean, especially right now, there's, you know this doubling down on what's being called the 996 culture, working 9am to 9pm six days a week, you actually go look at internet usage in San Francisco, like usage of business tools on Saturdays has gone up significantly. It's, it's kind of crazy, despite the fact that productivity research since the 80s has basically shown that for knowledge we're the 35-ish hour time slot is about your peak of getting peak productivity out of knowledge workers. So I've I spent a lot of time after I left Apple, really digging into that, into the research around productivity, around what does it mean to be successful, what does it mean to thrive? And I took a step back and said, I said two things after I left Apple. One was, I'm never going to go through a full-time job interview process again in this industry. I mean, when I left Apple, I actually thought I was going to leave tech entirely, but at that point I was like, I'm never doing this, like full like, song and dance again, I have enough career capital built up. I will figure this out. And two is, I'm only going to work somewhere where inclusion isn't lip service and this, like hustle culture obsession is not somewhere that's focused on and, and, and, or I'm going to create that environment for myself and, and. So that's basically what I've done. I left Apple in 2018 and at tile, we actually created an insanely inclusive culture, and it really was around our core values. We're really around, you know, defining success on your like, creating products, but having flexibility, understanding that people do their best work when you let them work the way they are most successful to thrive. And guess what? I've learned for myself, I am not a morning person. You want my peak like mental productivity. It is between four and 7pm that is when my creativity sparks. So I am happy to go spend, like, an hour or two having lunch or going on a walk in the middle of the afternoon, because I know at four o'clock, if I sit down to do something creative, I will get amazing work done, like one of my favorite roles before, I was an engineering leader, and when I was a software engineer, was back at NetApp, where I usually showed up around 11:30 in the Morning. I'd go to meetings until about five, when everybody else would leave, and I'd get my peak coding done between five and 8pm and it was great. I loved it, and I thrived in that environment, and I was allowed to do so, and so I've really built teams, or I truly believe, like let people thrive, and that doesn't mean you don't have to have certain times when people need to have meetings and things like that, but you can balance that out.

Kim Meninger

It's so it seems so obvious, right? When you look at the research, when you think about just how humans operate, that you are going to get more. From your people. If you do, you're saying, yet there's still this rigid attachment to this mentality, right? This, you know what delusional belief, right? Do you think? And I'm thinking about how to ask this question, but like, do you think that we just need to avoid certain companies and just go where the go, where the values already exist? Or do you think it's even possible to try to make change from the inside?

Jossie Haines

So I think it depends, right? I truly encourage folks to first of all, also, depending on where you are in your career, you might make different choices, right? 21 year old Jossie is going to made very different choices that aligned with what I wanted to do back then, right back then, I wanted to spend more time working, to learn to get up to speed like I had just, you know, I moved here in early 2000 in the middle of the.com boom. And I loved just being here and just surrounding myself with people building cool stuff. And I loved that. Then 15 years later, well, guess what? I had to navigate my mom passing away, a bunch of other things. And after that, I realized, hey, I need some time for me, like it, to focus on myself for a little bit and create more of a balance. So I also, first think it's also not so black and white. Of like, let's completely avoid this. Now. There's a there's also the is the culture to the extreme that it is toxic, right? Because I think there's, you know, it's, it's not so black and white, of like, Hey, there's this hustle, desire versus like not. I think it's a spectrum. And so we first need to decide where on the spectrum we're willing to step in right now based on what we're looking to accomplish and where we want to be, what we want to be doing with our careers. And then there's also the looking at, I truly believe, like you should not put yourself in a toxic environment, and if you accidentally get into one, like you have permission to leave, right? And I think that is, like the key, that is one of the key nuances, is you can have a culture that hustles where it's been created, because everybody actually has this desire to do it themselves, because they so believe in the mission, and they're so aligned in doing so. But there's also this belief of rest, right? Like when I was at Zynga, we had a very work, hard, play hard culture. My I joined Zynga the week we took on Facebook. So in 2010 Facebook's growth was basically because of Zynga and a lot of the games on the platform, is what caused Facebook to grow massively, and they started wanting to charge a 30% cut of how much we revenue we were making on the platform. And so the entire company pivoted, like literally starting the day I joined to building a social network internally. And so my first two weeks there, I think I was working like 10 to 12 hour days, which is crazy for a new job that you had just joined, but it was so motivating because you I watched 1000 people get behind a mission for two weeks to do something to make The company thrive. It wasn't like, let's do this forever. It was, we have a specific mission. Let us do this for two weeks, and we were regular. You know, when our teams did well, we were rewarded with trips like team events, right? And I'm not saying like, that's always the right balance, but it really was this, like you're working hard, and people were working hard because they were motivated to do so, not because somebody was coming and saying, to work at this company, you have to work 12 hour days, and you have to show loyalty to me, and I'm controlling you.

Kim Meninger

Yes, yes. And it sounds like there was enough rest to make those you know, high pressure moments more sustainable. Yes, right, yes. So what do you recommend women in particular? Think about like, are there specific questions you recommend? Asking on an interview, is there certain research that you recommend people do to try to find out more before they make these kinds of decisions?

Jossie Haines

Yes. So I always tell every woman I coach, you have the most power between getting a job offer and signing the job offer and that. And I mean not that you can't ask some questions around culture and things like that during the interview. And I definitely recommend asking, you know, like, what is valued? What does success look like here? You know, what? What are people rewarded for? But during that time period, like, once you've gotten an offer, ask to speak to other women on the team, who are your peers, who you'd, you'd, and talk to them about, hey, what's it like to work here? What are some of the challenges? Like, how have you been thriving? You know, look in your network, are there people who used to work there? And can you talk to them about, Hey, why did you leave? What was it like? And this really goes back to I mentioned network. Right when I left Apple, one of the biggest things I realized was I had not really taken a time to cultivate my network, and that had been part of why I was feeling so isolated, why the imposter syndrome hit so hard because I didn't have other people to talk to. Despite the fact that I ran women in Siri, I was in a position there where I almost felt like, well, I have to be the strong one for these for these women, and I didn't have a place where I could get the support. And so one of the biggest thing shifts I did in my career, and as part of how I've gotten to thriving in my career, was I spent five years really building my network, and now I'm at a place where people joke that I somehow seem to know every person in the tech in there, like all the engineering leaders, even though that's not the case. But I attended a conference the other day for engineering leaders, and they did, like these one on one introduction. So I was talking to the guy was being introduced with. And like, every five to 10 minutes, some person I knew would come up and give me a hug or say hello. And after this happened for like, 45 minutes, he's like, do you know everybody here? And I'm like, no, no, no. I'm like, I just, I know a lot of people, but he's like, Are you famous? I'm like, No, I'm okay. Then the next person who comes up, I actually don't recognize them, and he's like, Oh, are you Jossie? I'm like, Yeah. And he's like, I love your LinkedIn posts. And then so the guy I'm having the one-on-one with is like, yeah, you are kind of famous. He, it's just really funny.

Kim Meninger

I'm glad you brought that up, too, though about community and relationship building, because that's so important. It's all it's important anyway, but it's especially given what you're talking about, the just the sense of support and just access to other people who understand you and are going through similar challenges is so critical.

Jossie Haines

Yeah, absolutely.

Kim Meninger

Yeah. Gosh, Jossie, I could talk to you all day, because there's so much here and it's so important, such an important conversation. But in the interest of time, I know this is the work you do, I would love to ask you where people can find you if they want to stay connected to you, explore your offerings. Where can they, where can they follow up with you?

Jossie Haines

Yeah, absolutely. So the best place is to connect with me on LinkedIn. So definitely look me up on LinkedIn. I'll send you the link. You can also check out my website. It's Jossie Haines dot com I offer free 45-minute strategy calls for tech leaders who might be interested in coaching. And I, and I love supporting all technology leaders, but especially women in tech is, is my, my a big focus of mine, and I'm a big champion, and truly want to create a place where we're retaining women in this tech industry. Over 50% leave by the age of 35 and I'm on a mission to change that.

Kim Meninger

Wow. Well, thank you so much for the work you're doing. Thank you for sharing your story with us. I really appreciate it.

Jossie Haines

Thank you so much for having me. It was great chatting with you.