Career Growth Advice from Alana Karen, Tech Leader | Career Tips for Women in Tech

2B Bolder Podcast – Episode 50
Featuring Alana Karen

Episode Title: #50 Career Podcast Featuring Alana Karen, award-winning tech leader at Google, author, and speaker - Women in Tech

Host: Mary Killelea
Guest: Alana Karen



Mary Killelea (Host): Hi there. My name is Mary Killelea. Welcome to the To Be Bolder podcast, providing career insights for the next generation of women in business and tech. To Be Bolder was created out of my love for technology and marketing, my desire to bring together like-minded women, and my hope to be a great role model and source of inspiration for my two girls and other young women like you, encouraging you guys to show up and to be bolder and to know that anything you guys dream of, it's totally possible. So sit back, relax, and enjoy the conversation.

Today's guest is a true pioneer in the tech world. Alana Karen is here sharing insights and lessons learned from her 20-year career at Google. Alana Karen is an award-winning tech leader, author, and speaker whose works impacts many of our everyday lives. From Google search to ads, fiber to Google grants, and beyond, Alana has been leading the charge to develop scale, build, and drive team and product development that has seen rippling industry impact. Alana has spoken at conferences and summits on technology leadership, diversity, equity, and inclusion, talent, and innovation, Alana's book, The Adventures of Women in Tech, How We Got Here and Why We Stay, aggregates hundreds of stories on these topics. Alana, it is so great to have you here. Thank you so much for joining.

Alana Karen (Guest): Thank you.

Mary Killelea: Okay, so in doing some of my homework, I came across “try to remember each day that you are awesome and you don't need anyone else to say it for you to believe it”. I think it's a beautiful quote and it was right off of your website. What's special about that quote to you?

Alana Karen: I think it's special because I went through this journey and I've heard other people go through this journey where we reached this point in our lives where all these places where maybe we got ingrained kudos, right? Like whether it's because you go through school and you get told certain things or it's early job years and you get told certain things or even in personal life and then you get past a moment and it's kind of like everyone's pretty much done with you. Whether it's you already had the kids and you know now the grandparents focus more on them than you. Or at work you've just sort of reached the plateau and maybe now it's more about you telling that to other people. Whatever it is and in my particular case, it was because a lot of the people I worked closely with left Google and a lot of my sponsors left Google and I had to find on my all like all on my own and I had to believe all on my own that I was still this awesome person whether people were telling me it or not and feel it for myself not need the praise to believe it, and in fact praise myself more than I think I do, and feed myself more than I do and nurture myself more than I do. So that's why it's so special and I end up saying it straight out in the book to people because I felt like if someone could just know this earlier in their career if they could just know it, earlier in life, then then it would I don't know hopefully save them some heartbreak.

Mary Killelea: Absolutely. Google was founded back in 1998 and you've basically grown up working at Google. I read your I think employee number 319. Obviously you must have gained a perspective on innovation and its impact to the world. How has this experience shaped your life?

Alana Karen: Oh it's really interesting. I did not grow up with a lot of money. We counted our pennies. We bought generic. I just was remembering the other day how we couldn't even afford the generic of some things and there were times in the supermarket aisle we would have to go and put things back or we couldn't check out. We had to put things back before we checked out and so really I grew up in this place of limitation. There was limitation. Where I was going to college was limited by what we could afford. What I would do with my life was limited by affordability. So then it was really interesting to join this world that does not believe in limitations.

Mary Killelea: Interesting.

Alana Karen: And I think it slowly it didn't it wasn't like some revelation where all of a sudden I took that to heart and it impacted my personal life and you know, no no no. It was like a series of steps over the years for me to not think in terms of constraints. And I do still think I provide a unique perspective and it's why we need diversity in tech so that we can say hey that's not what you're calling affordable. Is it really affordable to the average family or you know that's not going to be how people think in the greater world and that's not going to work right. Like so I do think that that was very important and I still retain it, but I do think this belief in possibility has shaped my life over time just being there thinking about it. The fact that I wrote a book at all that I thought I could write a book is a real example of that. And yeah so huge kudos to Google for raising me you know 20 years with that around me. It's definitely helped me change how I view the world.

Mary Killelea: And so it shaped you in a professional way and I'm assuming it has impact on how you raise your children.

Alana Karen: I think so. It's a little hard to say how much is just impacted by having money and not having to worry about some of the things that I grew up worrying about. And I think that sometimes I think that has pros and cons right. There's a certain scrappiness and resilience I have from those times that you sort of have to build in to your kids if you have money, right? You have to say there are other limitations besides money which so that they have to think about tools and they have to figure out how could they get that next thing that they want without it just raining down and they build some of that scrappiness themselves that I just grew up with. But I also grew up with a lot of insecurity and really trying to give them more of the pros and less of the cons that I had I think has been my focus. And there were things that my dad or my mom said to me that reinforce limitations and trying to be really mindful when I talk to my kids about that not necessarily being how the world has to work. There are things you're going to have to work around, but it isn't just so black and white that some people do this some people do that.

I have a story in my book about when I won a scholarship school and my dad just being so amazed and he took me out to dinner so excited and he said to me things like this don't happen to people like us. And like you know I'm 12 or something but I remember this feeling of like oh yeah no like that is not going to be how I think about the world. My whole life thinking that things like this don't happen to people like us. No no no no no no no. So I do think that that's a good example of where I've said you're going to have to work hard right and there's things that you're going to see you're better at than other things and that's going to shape how you travel but it's not so black and white right.

Mary Killelea: I love it and I think as I raise my own children a lot like that. Why Google? What was it about Google that attracted you to them early on?

Alana Karen: At the time when I joined it was 2001 and it was the dot com bust. So I'd moved to the Bay Area amid a boom of all of these different companies getting funded and then the bottom fell out of that and I got laid off from one of these companies right after 9/11. It was just a tough time in general. And I looked around and I applied to lots of different things not all as promising or as clean sounding or good sounding as Google, but I remember when they actually pulled my resume out and I was doing research on them what I really liked about them was that they got in past the startup stage of thinking that they could do it all without adult help and they just brought in Eric Schmidt, an experienced CEO and tech professional, to lead the company and really partner with their young founders who were the same you know essentially the same age as me give or take and I remember given what I'd just gone through with a startup really feeling like oh I like that I like that they're adulting a little bit. Not that that word existed back then but we didn't call it that back then, but I liked that they had recognized that and they were prepping for the future in that way.

I also knew the business model. I had done some work for my own website where I had used click to pay ads and so I knew how it worked and I knew how much money you could spend on it and that it was a real business and it was lucrative and people click on the ads and all of that kind of stuff so I think unlike some businesses that you can hear about in tech where you really don't know how they'll make money and you can't see that line of sight. I also felt like after going through what I went with the startup which didn't have that kind of clear visibility to cash that this was a business model that would work. So yeah I wasn't that business savvy honestly and it was a private company so you couldn't see their numbers but I remember also seeing that real people had invested in them that know and are smart and were tech valley elite and that was another confidence booster. But I was 20 something I didn't know.

Mary Killelea: Once you got in the door was there ever any hesitation like gosh I think I might have might have gone you know the wrong direction or was it right away you felt the energy and the opportunity?

Alana Karen: I think right away I felt the energy opportunity it was a scrappy environment. It was fun and it was just a ton of work right away and it was clear that the ad business was successful too because of all of that work, I was basically on the front lines of customer support, so I was answering emails and reviewing and approving ads all day long I saw the traction firsthand. I think along the way it was like riding a rocket ship like at a certain point like it's a little late to jump off the rocket like you're too high up in the air. So, no not really there were definitely times where I was like these people are crazy all the things you'll think about in a startup which is all true. But it was always so fun the people were so interesting, the work was challenging, I was learning a lot the roles morphed and changed. So no, no not really.

Mary Killelea: Okay well have you ever had to advocate for yourself and what advice do you have for other women who are having a hard time finding a voice to be that advocate for themselves?

Alana Karen: Yeah I mean for sure I've had to advocate for myself and I think that early on what I would say is I did not know that I thought that the work would speak for itself because often in school it does, right? Often in early jobs it does. And that did work for a period of time especially when I was a junior individual contributor, but there was then sort of this invisible graduation point that no one tells you about where to be seen as a leader and plucked for other things you have to start advocating for yourself and marketing yourself. A lot of things that we instinctually feel uncomfortable about whether it's because of you know our personality how we were raised or the reinforcing mechanisms we've had over time which sort of swat our hand when we brag too much which happens to women more than men. Anyway it took me a little time to figure out that I had to learn to ask for things and learn to advocate. I think for me the major thing that's helped is feeling like I'm not just advocating for myself because of some of my own personal hang-ups and maybe also a little bit about how society reinforces that women should take care of others. I feel a lot better when I'm going in and saying hey, I'd like a raise and if I can't ask, no senior women can women can. If I feel weird asking after being at Google this long, if I can't ask what the path is to promotion who can?

Mary Killelea: Right, right.

Alana Karen: And I think doing that or going in and saying hey, there's this problem for me for my team has really helped. And then over time because I practiced there and got more comfortable with that, then when I had to go in and say hey, boss I really like money like it's really motivating to me and so when you're thinking about comp this year just know I like all of it, I like any of it, I like stock, whatever it is I like it. And it took time, and it took a little practice and sort of building out that comfort, but finding maybe that thing whether it's connected to other people or it's starting small, it's starting with people you trust and testing it out and building confidence from there is so important versus staying silent and hoping they'll crown you.

Mary Killelea: Right, right. And I love the way, and I laughed because it was kind of comical, but having that casual approach is totally ice-breaking and legit and transparent. I love that.

Alana Karen: It depends who you work with by the way. My boss works totally well um certainly there would be some people who that is not polished enough for, so know your audience. And also, I do tend to rely on comedy when I'm uncomfortable. It's just something to know about me. It works for me, you might have different go-to tools. For you it might be way more prep and going in backed by the data. I went and I researched and I know that people are paid more than my team is or I am or whatever it is. So think about what makes you comfortable, but for me not being so serious does help get through that ask for me.

Mary Killelea: Yeah, totally makes sense. Let's talk about your current role as director of search platform. What does that encompass?

Alana Karen: Very specifically, it encompasses that I run program management for our infrastructure organization which is called search platforms. I tend to simplify the title because at a certain point, it's just word soup. But there are other directors in search platforms, so just know that I very specifically own this piece which is about how you help engineers get their work done. How do you run the programs so that there are goals and milestones and you are tracking the work, and you are flagging when something is not working, and you are improving communications. So if you think about what it takes to bring products to life which engineers might not be good at, that's a lot of what the program managers do. And it's usually for things currently being executed, whereas if you've been a product manager you've heard of product managers product managers are usually planning the future and visioning. And we are very much the brass tacks, we are the operations of great, you have a plan, how are you going to go from plan to thing and roll that thing out? And a lot of my career at Google has been operations, this is just the first time it's been particularly focused on edge operations.

Mary Killelea: And how does that align with your core skill set? Kind of you know the non-technical.

Alana Karen: Yeah, yeah. I mean we haven't spoken about it, but I have a history degree. I'm not particularly technical. I did self-teach myself html in the olden days, and so I think that background and having worked on websites, built websites when I got into tech meant that I had enough background and understood a little bit more about engineering challenges and how back ends might work or front ends might work, or whatever it is that I was able to navigate, Having technical judgment and some fluency without being the coder. And that helped in all of my roles. Initially a lot of the operation stuff you did have to work with engineering to figure out how to automate it, and then I worked to understand a whole new product, our Google fiber product and how that would work, and how you would monitor it for example. And have customer service answer questions about monitoring, so it all helped along the way. So by the time I got to this role, a lot of the fact that I'd worked all along the way with engineering understood why like essentially how you had to work with them and why everything takes six to nine months, that helped with this thing. I will say is that I long had operations experience and a lot of what it takes to run a program management organization is fundamentally the same core operation skills. How do you think about and break down problems? How do you deal with blockers? How do you communicate well? How do you escalate? And then a ton of people leadership which I've honed over the years at Google. Figuring out how do you motivate teams, how do you build great teams, how do you keep teams happy. So all of that core stuff can really travel with me as I move from very different product problems. Now if you ask me do I still understand in depth how search technology works? Not in depth. Like to a certain level. So I've picked and chosen I think what I've gotten good at and what I've gotten deep at.

Mary Killelea: So, with so many opportunities in the tech space for women these days, for those that don't know where to start with building their tech acumen or feel intimidated by the lack of tech acumen, what advice do you have for them?

Alana Karen: I think that's pretty common too. What I will say is that compared to when I started getting into tech where I had to self-teach everything or rely on some like kind gentleman next to me to tell me, there are now… First of all there's just a ton of information free on the web where you can first figure out what am I even interested in? Because now there are so many options it can actually be kind of overwhelming. Do I like hardware? Do I like software? Do I like security? Do I like product design? Do I like UX? Do I like this? Do I like that? So you can see what you're drawn to so much easier even just by reading some tech news and seeing what articles do you make it through and sound interesting which ones don't you, right? If security protocols put you to sleep, do not go into security, right? So there is some just natural stuff that you can see, but there are now also organizations that either provide kind of forums cohorts for women interested getting into tech, and you can just by simple searches. Look around. Some of these are even just Facebook groups, women in tech Facebook groups that you can join and follow along, ask for advice on this or that. I want to get into user experience, how did you get into user experience and start to see from those experiences, some of which I put in my book, how did people make that move make that pivot what did they do?

The other thing in recent years that's been super awesome is just bite-sized learning, right? You don't have to go back to university or get a master's in something. You can go to Coursera, you can go to LinkedIn learning, you can go to Udacity and you can do bite-sized learning to see am I into this? Do I like this? Now say you are really into coding ultimately. There are these boot camp programs, some targeted towards women with scholarships, so just there's so much more nowadays that if I was starting from scratch. Definitely there would be this period of being a little lost as I figured out where I want to go, but once you know a little bit more you can really hone in. Ask people on the internet for free what they did, follow some people on LinkedIn and see what they do. Do you like what it sounds like they do right? If you're oh should I be a diversity and equity specialist at a tech company. Follow some of them, see what they post about, see what they do, reach out to them. It's so low cost nowadays. It's a little scary sometimes to reach out, but the worst is they don't respond, right? It's not a huge down side and it's free. I love free.

Mary Killelea: I love that. That’s great advice. Have you ever felt there have been roadblocks to advancing your career, and if so how did you navigate those waters?

Alana Karen: Yes and no, which is really interesting. I suppose it should be yes if you have any yes at all. But in some ways, I've had this really interesting career that I've gotten to dictate a ton, right? I started off in this operations world, I moved into policy, built out policy at the time some of the first policies Google had. And built out the first global team that we had etc, then moved on to something totally different moved on to Google fiber where I built out customer support and installs. And then moved on to search where now I'm leading infrastructure program management. And very different things where I dictated to some degree what I was interested in, and did have to get very good at defining my core competencies and explaining it to other people. But really besides the fact that there's legwork and you have to sort of make your way and get people to believe you and that, I was able to do it. I didn't face profound blockers. The reason I say yes though is that because I did not stay on one path, because I am not this definable thing, I have had to advocate for myself way more and I'm probably not a VP yet because I decided to be this quirky different thing. If I'd stayed in sales and stayed the legitimate path, if I'd stayed in policy and stayed the path, stayed the course and there were other things along the way. Just how promotion systems work, and what hurdles you have to make, and how long that takes that have also influenced this. Of course I did not have total control over that, so absolutely a mixed story and I think that had I truly ever felt blocked or frustrated at some point, I would have had to really… I wouldn't have wanted to stay unhappy. So I would have had to make a bigger change whether it was leave Google, or decide legitimately like because I want to get to VP more than anything else, I will take that role which has the clear path to VP instead of taking this really interesting job. This quirky interesting job, right? And so I would have had to change my to change my plan and path, but instead I have stayed the course, it has come at somewhat of a less certain path towards what people think of as traditional upward success. That is the price I've been willing to pay. I don't know that I'll be willing to pay it forever, but I always wanted to be working on these interesting problems and I weighed more towards that than I did title success for instance. So it has been this sort of yes no story with me. I would have loved it to be a yes yes story, but there were trade-offs and I willingly made those. And when I wasn't willing to make them I spoke up.

Mary Killelea: Right.

Alana Karen: So yeah, never felt truly forced. And by the way, I do think a little bit of this is being a woman. But some of this is also just being the quirky thing. I think would have applied in a non-gender specific way too.

Mary Killelea: I don't know about Google, but I'm assuming so. In my company, there's a lot of ambiguity and you know things got to get done but we haven't figured out x y and z, go move forward. How have you dealt with ambiguity in your career?

Alana Karen: I've always kind of liked ambiguity, actually, because I tend to sort of get annoyed once things calm down and there's only one way to do it. I tend to like a certain amount of chaos and mystery and problem solving in my jobs. I think what I've actually had to realize over time is that while I enjoy it, it is actually stressful and in aggregate you do have to restore yourself and figure it out. So it's been I think less about how do I cope with it. In a lot of ways I just lean into it, I address it. I say we don't know the right way, there is no canonical right way, so what are safe experiments we can do? What is a test we can do that we'll know in three weeks, four weeks is this the right path? What is the least best worst person I can talk to right now, right? I think that over time I cannot even emphasize so start-uppy at first, and so no laws, no idea what you would do to make ad policy, just a lot of swirl and figuring out the best thing you could do at that moment in time. And I think that that was great training ground. I've seen a lot of people who can go years not really knowing how to make decisions. I felt like my initial jobs were decision-making boot camp. Like here's the set of criteria, you've got a day. And I do think that what I just didn't realize over time was just how much stress I was taking on, and it was cumulative and cumulative and cumulative. And over time I would see health issues, I would get migraines, I would have stomach issues, and now as a more grown-up – at least I'd like to think I've gotten more grown-up – trying to be more cognizant of that and know like over these past holidays, well I'm not going to travel, but I'm just going to be brain dead and I'm going to read a book, and I'm going to play phone apps, and I'm going to catch up on this and I'm going to knit and we're just going to breathe. Which is just not stuff, it was run run run run run, sleep when you're dead kind of stuff, which I just don't buy into. Which nobody really does anymore, but thankfully it's the hangover we're getting over, right?

Mary Killelea: That's so well put. If you were starting off in tech today, is there anything you would do different?

Alana Karen: I did not understand networking, I didn't like it. It took me a long time to realize that sometimes you talk people just to have these touchstones, just to have someone you can go to when you have that kind of problem. They don't have to be this mentor that you marry, they can be these light loose connections. Someone I worked with at Google, Karen Wicker, wrote this book, I want to say it's networking for introverts or a name like that, and she talks about these different types of ties, these different types of connections and these loose ties you can have. And it just took me a long time to realize that I that that was kind of more what I needed. I need a board of people that I can go to when I need specific things, and it wasn't that I was going to necessarily go with one mentor, one coach, although I do love my therapist. My therapist is great, I love my therapist. But I think if I was joining tech today, I wouldn't take 10 years to figure that out. Like I would right from the start, be like who are the people who've already done this journey? Who are the people who are doing it right now? Who are the people who can be my people I whine to when I'm feeling frustrated? Who are my people I can go to when I need mature advice and we're gonna smack me upside the head and say no? Who are the people just like me so we can really jive and get along? And then who are the people who will challenge me and ask me the pointed questions and really push me to do something I'm uncomfortable with? Or different. I was really bit by bit on this, if I can impart to you all listening because it really has been sweet and useful over the years, and I think I didn't necessarily really figure it out until I started to mentor more people and see how reciprocal it was. And also when I wrote the book and I really didn't know anything about the book industry and I just had to march around to a lot of people and say I don't know. And they were all lovely, and then I was like well why hadn't I been doing this for years in tech? This was so silly. Now I did luck out. I had a lot of great co-workers, so I think I didn't truly because I was growing up in tech alongside lots of people in Google, I wasn't alone alone. But I never really thought about it in a way that would feed me, it just was there and I lucked out.

Mary Killelea: I love the village concept because I do think different people fill different needs. Instead of feeling that pressure I have to have that perfect mentor, how do I get that perfect mentor, really establishing kind of a network of a village or support. Your book is The Winner the winner of best indie book award, and audio winner of the New York Big Book Award for audiobook non-fictions, and I've ordered it and I've got it on audio. It’s one of those books that not only do I want to listen to, but I actually want to go back through it and highlight stuff.

Alana Karen: Bless your heart listening to me for nine hours.

Mary Killelea: What did you learn through the writing process?

Alana Karen: Oh, it's so interesting. Because of what you heard I work on at work, it's operations right? There should be a plan, and you go through it linearly. There are milestones and you go through those milestones, etc. I had to realize no, not really. You have to throw some of that out the door. Now mind you, it's still very good that I thought about it that way because there are certain things that help if you go in a certain order and there are things due on certain dates, so I didn't throw it out entirely. But when it came to the creative process of writing the book, I would notice that I was just getting tired working on something and I didn't have the interest or the juice in it. And I did have to transcribe, partially because I did get some, like there's now great automated transcribing, but I did have to double check it all. And so there was after interviewing 80 women quite a bit to trudge through, and I thought I was going to do it first because wouldn't you have all the source material before you write the book? And I got maybe a third of the way through it, and I was like I'm gonna not finish this book if I keep hacking away at just doing this task. And I already had all these ideas brimming for what I should write based on what I was rereading and rehearing. And so I was like okay I'm gonna put this down and I'm gonna go start writing and writing in order what I want to write about.

And then a little bit after that, I was like you know that's not even really what's working. What's working is me sitting down every day and writing 500 to a thousand words on whatever I want. And not necessarily trying to write this book in order, but just whatever came to me that day, whatever sparked whatever it was is what I'll do. And then later there will be a date upon which I have to stitch this book together. And so it was really interesting to see that my creative process doesn't necessarily follow some of how I work, or how I would suggest you run a product or roll out a product. And of course that makes total sense. Creatives don't think like operational people necessarily, but it was really funny to sort of have to just free myself from those constraints and just do it.

The other thing that I'll mention is it's just funny. When you read the introduction about me or when you say that I've won an award, I also had to free myself to do some of these things that I'm inherently uncomfortable with. I have to ask for help to have someone write my bio because I won't compliment myself. I have to apply for these awards because you apply right? Again you don't wait for someone to crown you. You apply or you ask someone to nominate you. Even in something that seems so creative like writing, there is this other side to it that's very business-y and very marketing-y, and very self-complimentary. And I think part of my process was figuring out how I was going to do that too.

Mary Killelea: I definitely have on my bucket list a book, and I'm still fleshing it out. So I always think it's fascinating when I have someone on who's an author, because everyone's journey is different. I love your blog. I love the way you write, and the series particularly on still learning where you went back through old performance reviews. And then you discuss those performance reviews, but from a reflective standpoint. How did you come up with that idea?

Alana Karen: Some of the ideas I think it's because you stay with something so long that it comes. Like right? I like I had 17 years of performance feedback, and I was thinking about I had decided that I wanted to write. It was one of these things that at end of 2018, I was thinking about what I wanted to do in 2019 that hadn't gotten the chance to do yet. I'm like I want to write and I'm going to put that writing out there. I'm going to use LinkedIn. What would LinkedIn people want to hear about? What is interesting enough about me to write about? And by the way, this is why I had not had a blog before because I didn't think anyone would want to know what I ate that day. So I was thinking about it and I was like it was right after our performance review season and here I am with 50 plus performance reviews with feedback about me over the years. And I thought oh that's really nice, I can look at it and I can see, and not go year by year. But think about the skills that I built and why I built them over time. And what I didn't know at the time, I just thought it would be a really good thing to write about. But it ended up being a really nice gift to myself because you tend to think about yourself as a certain way, looking back in your career. And mostly I think unless maybe you're more nurturing to yourself than I am, mostly sort of negatively like oh, I should have known this then. If only I had known this then. And then when I was looking through these performance reviews it was much more like oh look how hyper fast I had to onboard skills, look how difficult those problems were in. And of course I couldn't keep up, of course if all of that was going on, and I was learning to people manage I wasn't a stunning people manager. And so it was just like of it ended up being such a sweet gift to myself in the end. But that's not what I thought at first. It was like oh let me go through all of these reviews and give myself this gift. No, originally it was oh I think this would be good, I think people would be interested in it.

Mary Killelea: And I love how you talk about the individual contributor and the manager role and kind of the bridge that you went through for that. Do you feel like manager was your main calling?

Alana Karen: In the end, yes. And probably even more so than that a leader, because I actually think there are probably better people managers out there than me. Just in terms of I'm sort of impatient, I don't fancy myself the best coach. Like even in my coaching I'll sort of sneak in advice, so I think there's probably… I always get like very good feedback about being a people manager, so I'm not really worried about it I think I've honed it over the years. But I'm just saying I think there's actually people with even a better talent there, and that what I found over time though was how do you build these teams, and how do you build teams of managers of managers, and how do you have those teams get things done because that is of course the primary purpose to the business. But sustain and be happy. And it turned out over time that I'm really good at thinking about that and building a system of how to do that. So, I do think that that ended up being my calling. Now I can still individual contributor like nobody's business because I'm a task list freak. I'm operations freak, right? Like I can get into that mode and obviously it helped when I was writing a book, but in terms of I think how I've magnified my impact and how I've really helped others and what would be my legacy, I think it's how I've led teams and hopefully shown other people a great model for how to lead.

Mary Killelea: What inspires you and why?

Alana Karen: It's interesting because I think in tech, sometimes you'll meet people who are really inspired by technology itself and what's possible. Or products, like specific products. And I've ended up being really inspired by two things. A really good difficult problem that does not seem solvable, and how you take all these talents of different people and best bring them to bear upon a problem. I think it's ended up being that sweet spot, so I end up being thought of sort of as fixer. It’s this difficult thing that you don't know how to fix, you send Alana in or you send her team in because those are the kinds of things that really spark me. And again I think that's why you don't see me leading humongous teams because I tend to like some of these like intimate, niche, difficult problems where you have to dig in with a crack team and solve them. And I don't know, I just really love that. I love figuring out what you have to poke at and pick at. You don't get to just go in and lay out a plan, you have to test and sometimes culture is a part of what you're working on, and I find those really interesting. Really every problem is a people problem, even if you call it a technical problem or a product problem or whatever it is. Every problem is we're making it all up and I love figuring out what are those components and why that's happening.

Mary Killelea: Fascinating way to look at it. What does to be bolder mean to you?

Alana Karen: Well I think it's a little bit what spoke to me about it was all the time I had to figure out how to be bold when I don't fancy myself necessarily a bold person. I do not wear bold colors, all the colors in my house are soothing. But there is something about advocating for yourself and asking for what you want and marketing yourself and even thinking about yourself is awesome, which I've had to teach myself over the years which is bold. And so I really did like this concept of to be bolder, because it's incremental, too. You don't have to just be bold, right? It's pushing yourself a little bit bolder.

Mary Killelea: Daily striving.

Alana Karen: Yes.

Mary Killelea: So what's next for you? Where do you see yourself in let's say five years?

Alana Karen: I don't know. I'm always terrible at these plans, honestly. I am in May releasing a workbook follow-up to the adventures book, which takes some of the tools that I talk about like resilience and marketing and asking, and breaks them down into exercises. And I've co-written that with an author Marilee Nika, as well as three other contributors. And the answer to your question is I don't know, but I feel like I keep kind of testing how can I impact more of the world and how can I bring others along with me? And what I like about this next step is that it gets a little bit more into the how you can do these things and you don't have to do the whole book, you can just go to the exercise when you need to, and it could help you in that moment. Especially if you don't have a great network or coach yet, and one of the whole sections is about finding support so it can help you if you're there. But I also like that part of the goal was to work with other women, and so now these other women are going to have a book out there with their name on it. And I don't know…there's something there. I don't know if I'll do it full-time, I don't know yet what's there, but I do I like that and it was intentional. I am figuring out a little bit of how can I continue to expand that impact and bring others along with me, and I try to do way more recommending of speakers that people can talk to who aren't me, and things like that just to continue to build out who we're hearing from, and the diversity of who we're hearing from.

Mary Killelea: I am going to make sure I include a link to your book, and your website on the show notes. It has been a true pleasure to meet you and to have you on and have this discussion. Thank you so much for coming on and sharing your story.

Alana Karen: Thank you. Such great questions you did such great research. Top notch.

Mary Killelea: Thanks for listening to the episode today it was really fun chatting with my guest. If you liked our show please like it and share it with your friends. If you want to learn what we're up to please go check out our website at 2bbolder.com that's the number two little b bolder.com