Interview: Alana Karen, Award-Winning Tech Leader, Author, & Speaker

By Angela Tai

You majored in History and later became a webmaster before you landed your current position with Google. Some might say that you don’t have a linear career path. Do you have any advice for people who are considering making a career switch but are fearful of starting over or taking a risk? 

Honestly, I never knew what I wanted to be growing up; I have had this very leap-oriented career although I tended to stay in places for a while and grew with those opportunities. I stayed at my first role at Google for 10 years and rode the career arc if you will. What became most important to me were the transferable skills that I was building under each job - you can tell you’re building niche skills and most of these skills are critical. Skills like negotiating, getting people to come on board to new ideas, prioritization and paying attention to what those things are and what you’re becoming the expert in is what will ultimately serve you throughout your entire career. Instead of being like, “I don’t know anything about that field” you can approach it with a much more positive and open mind. I went into Google Fiber which was providing internet and fiber tv channels to homes, I had no idea how to do that but I knew how to do operations. These leaps gave me lots of confidence so when you’re put in a situation where you have to explain to a hiring manager or a recruiter about why you’re the best fit, you can say I’m relevant because I’ve done x, y, and z. Sometimes, it means that you’re starting from scratch in terms of proving yourself to people but a lot of times these are the things that lead to your mega leaps later on. It’s important to think about what your passions are and what transferable skills you’re building; I think knowing that kind of brings it all together. 

You’re an Advisor at True Diversity - a mission-driven startup that understands, inclusive culture and equity are synonymous with high-performance. I’m sure in your work you see that women are still underrepresented in STEM fields. That being said, are there changes you’re currently seeing on diversity in the Tech industry that might have not existed just 5-10 years ago? 

Absolutely. I talk about this a ton - it’s so hard with everything that we’re doing today and with the awareness that we have now it’s just difficult to see how far we’ve come sometimes. When I first started my career in tech, we truly believed in pure meritocracy and this was a leap forward for everybody. This was saying we’re looking at your work and nothing else - there was no nepotism or reward based on professional relationships. It was solely based on your performance at work and that was already a leap forward at that time but it was about 10 years later when we started talking about how there are flaws with this system. You need to think about the unconscious bias that goes along with this or how we perceive the work. And, are women less likely to ask for a raise or for that promotion? There’s a bunch of these things that work underneath the system and it was only about 10 years ago in big tech that we weren’t talking about these things. We didn’t really start to have a wider conversation about it until last year. We started asking, “what are the systemic issues? ''how was it constructed?” and “why was it constructed?” Now, we’re much more worried about things like what the interview questions are, and processes for hiring people, or this is where we’re unintentionally losing people. There’s so much movement and it’s definitely still flawed but our awareness keeps growing at every stage. 

Your book, Adventures of Women in Tech: How We Got Here and Why We Stay, chronicles the lives of multiple women working in STEM fields. What inspired you to write this book?

I think it was twofold - one piece was when I was early on in my career and the other was where I saw the world much differently as I was hitting the 17-year mark at Google. I was thinking that careers are always in phases so I wanted to stay at Google for at least 20 years. I was thinking about what my next phase would be and what I wanted to do that I haven’t had a chance to yet. I pushed myself going into 2019, I wanted to write more and share that writing so I started a series of articles on LinkedIn sharing performance feedback that I had received at Google. It wasn’t all the positive stuff, some of the comments were “Alana isn’t a good manager” and I had to process that. It was very fulfilling for me personally and I saw that people just weren’t getting enough of hearing about someone in the middle who could help them navigate their career and figure out what to do. When we get to the other side of it, women at the top are often shown in the media but it doesn’t always feel very attainable to other people. Some people don’t want the same things and it doesn’t resonate as much. Now, we’re getting a lot of the bad stories like the people having all the negative experiences in tech and it’s very important that this is coming out. I was becoming really interested in talking about how all of us are in the middle of all these trials and tribulations and just trying to sort it out and get to the other side. Women are leaving tech at alarming rates and I was worried that all these women around me were going to leave. It started out as a passion project for women in tech/going into tech who wanted to see more examples of themselves but I really wanted to see more stories from a diverse set of women. 

You were recently featured on Sheryl Sandberg’s “Lean in Live” series on Facebook. She said something that really caught our attention: “You don’t get jobs to solve problems, you solve problems and then you get jobs.” What has been the most rewarding part of being a woman in the tech industry for you?

Well, I think overall it has been the ability to foster amazing teams that do really challenging work but at the same time are fun and thrive while working together. Growing the individuals within those teams is so important. Work is very people-focused for me, I’m not there to solely focus on building a product, it’s very much about the experience of the people doing the work and what we can bring to the world which is why I love the company I work for. I think I set myself apart within this environment as someone who thinks a lot about how you nurture great dynamics and grow people in their careers because it makes a very effective team. We do much better when we have team members who are doing great work so it’s a win-win! 

Your most recent post on Instagram really resonated with us. In fact, it was a quote from your book, and it stated: “Helping people develop and grow their careers is one thing, but nurturing people’s emotions, self-acceptance, and perseverance is a whole other skillset.” It resonated with us because so many people are great hands-on contributors but ill-equipped managers or mentors. In your opinion, what are some of the attributes that a good manager or mentor should possess?

I think the primary attribute is that you should be willing to put yourself in the backseat and believe that you are doing this job for the people. That’s really hard because most people go from being a very confident individual contributor to being a manager so it’s not a seamless transition. It’s not that you have to have it inherently but you have to be at a time in your career where you have the desire to focus on growing other people and listen to them. You have to put yourself in their shoes and think, “how do I accept what they say even if I disagree with them?” I have to take it at face-value and say, “okay this is their experience so how can I help grow and nurture them?” I think that’s really the primary thing, you have to help them start growing that piece of themselves and embrace them for who they are, where they are and how they came to you. Sometimes you think, oh wow I’m getting these amazing people on my team but something happened to them and I wasn’t in control of that so now we have scar tissue that we have to work to rebuild their confidence and mindset. That definitely takes time and patience so I think it’s that seed in particular that you have to be willing to grow. 

You have spoken at numerous conferences and summits on technology, leadership, DEI, talent, and innovation. In your opinion, what are the common obstacles to overcome when implementing a diverse recruiting process?

I think it’s a few different things. I think there’s a piece that is very tactical - where are you looking and where aren’t you looking? What are your weeding out mechanisms and why do you think of them as weeding out mechanisms? When you look at your questions/approval processes, are you being too cautious? You have to think of ways you can take risks and grow these people but I think there’s another piece we have to dig into including what some of the assumptions are about what it takes to thrive in tech. There other types of things that would be important to know about candidates, like are they a team player or not but look at what else they can bring to the table. The last piece is about what happens to people once you get them into the company. You have to look closely at what happens when you bring in a more diverse workforce and take care of them. What are your goals for the first 30-90 days? This is important for all employees and you’re making a huge mistake if all you think about are the people who are thriving, the “good” employees. That being said, the others could’ve been amazing as well so I think it’s important for all employees but if you’re bringing someone in, if they’re the only person who came from this background, how you support them is a major component. 

What are some of the successful steps you’ve seen companies take to create a positive work environment for women? 

The number one thing I keep hearing is how the company thinks about internal support, whether it’s employee resource groups or Slack channels so that people can ask the hard questions. There’s been this component of, “if this person gets plopped into a world and they don’t have a support group and don’t inherently fit in, then it just doesn’t work out.” This causes issues down the road and that person may leave the company. Everyone needs to intentionally think about internal support - this isn’t the glamorous stuff and it’s not the stuff you talk about in your marketing materials. It’s about how you support your employees and help them grow. However, if leaders aren’t always walking the walk and in that case, employee resource groups won’t necessarily save you. It does help employees weather the day and helps them answer the critical questions that most people might have to go through alone. 

I was speaking with a friend about the cycle women go through in the workforce and she brought up that women in their child bearing age are considered desirable and that’s when they’re feeling the pressure (or desire) to get married and/or have children. But then once they make the pregnancy announcement to their employer, they’re immediately discounted and once they return from maternity leave, they often have to prove themselves again as if they just started a new job. This is a gross generalization, of course, but I’m curious because you spoke about having 3 kids yourself. What was the acclimation process like for you when you had to return to work each time? 

I find this very interesting because it’s not just work, there’s a piece of work and how society thinks of women where we are most desired up until we fulfill our duty to provide that child. Afterward, it’s kind of like we did our job and I talk about it a bit in my book. Actually, it can impact us both personally and professionally because we go from being this desired object that has now fulfilled its duty and it’s kind of coded into us, even if you’re in a progressive workplace. You’ll notice places, where you’re still the one expected to take care of all of these things and people, will assume that because you’re now a mother, you’ll be more distracted than you were beforehand but most moms have had to be tougher and prioritize more than ever before because we don’t have time to lollygag. But as for my personal experience, it was really hard to come back after the first child because you have to shift up everything you do and I was an around-the-clock type of worker and I was in it to win it. I had had a very rapid career trajectory, I became a Director and then I decided to have a baby. I wasn’t the first mom to go out and come back but I didn’t feel like people were thinking, “oh now she won’t work as hard because she’s a mom.” I did feel a weight of expectations because I couldn’t be a workaholic mom, I wanted to be effective so there was a lot of pressure. I had this cutie that I wanted to spend time with and I think it was mostly internal pressure but I was coming back into a work environment that was becoming more presentation-based and rigid, the regulatory policies were also becoming tougher. I particularly remember that time as being hard, you know figuring out who I was and how I would continue to be successful in that environment. Unlike my firstborn, I was very confident with baby #2 and #3 and I started a new position with #2. For example, I would do pilates every Wednesday at 4 pm, and I think I got that confidence overtime to take time for myself. After the first baby is where every woman could use that cohort. There’s this one cohort that has an anonymous alias so women can email in and say things like, “my baby is having a terrible teething experience” or “oh my gosh I’m back and this is terrible.” 

I think we tend to stay too long because we think we can fix it but see what you can do get some advice to figure out the things you can try how much of it is them and try some stuff but put a timeline on it will you try for 6 months a year how long will you try if you’re not treated well not growing and that hasn’t changed then I give you permission but I think you should also give permission to yourself to figure out what’s next you don’t have to race to a new place but know that you have that time frame and you have time to look and know that you’ll be at a good place. 

We’re huge fans of your ‘Women in Tech’ merchandise, particularly the “Own Your Awesome” mug. Certainly juggling work, public engagements, and family takes up a lot of your time. What’s your time management secret?

For sure, I just keep trying new things - you can ask me in a couple of years from now what I’m doing. I’ve found a lot of success with trying to take control over my calendar, blocking out time to get my emails done, or to complete my projects. If I have to do strategy, then I will. My calendar has become very meeting-heavy so I try to have fewer meetings on Fridays. I know, it’s better for me to have a two-hour block in my calendar, it worked less for me to have a half-hour between meetings. Some people find that their mind is clearest in the morning/evening but I will always stop responding to emails around a certain time at night and the same thing goes for the morning. I have found that my time is more valuable and mental tricks like this have increased my own self-worth, there are times when I wouldn’t just get good emails and I needed to say to myself, I’m going to stop and I’m going to do other things - whatever it is to put that distance between it. I try to let it fade and put the situation into perspective, that could be through either running or playing with your kids or whatever it is that could be a stop time for you. For me, it’s things like yoga, pilates, and breathing. I don’t do real meditation but I do breathe at various points throughout the day and walk outside whenever I can. Self-care is so important for me! Prior to COVID, I loved my Saturday lunches with friends or going for a spa day but right now it’s a bit more of the solitary stuff. Hopefully, as the pandemic passes, I can pick up some of the other things too. It’s all about finding support - sometimes just having that crew you can complain to is amazing. 

Impostor syndrome is a theme we hear over and over again when speaking with powerful, inspiring women such as yourself. Is that something you also suffer from (from time to time) and how do you regain confidence when you have doubts about your abilities? 

Here’s what I would say, 90% of people have imposter syndrome, and the ones who don’t are a little weird. It’s ingrained in us and it has nothing to do with success. In fact, some of the most successful people have the worst imposter syndrome. You believe that you don’t deserve it and you’re faking it so yes, I have it. Everyone has it but what I have found that helps is a couple of things. First, it did lessen over time, especially with the more success I had. You know, walking in on the first day, you will have some of it but over time as you are delivering work and are recognized for that, it will slowly go away. I would picture that you have a bucket and you’re filling it and carrying it with you. I find that a lot of successful people have a bucket but it has holes and they carry any criticism that they have received over the years. If you’re doing a performance review with them, they flip to the areas for development because the truest stuff is the criticism. After the bad, we have to look at it like those comments are real. All the business books that I love aren’t really business books; in Shonda Rhimes’ book, she talks about this one year where she shifted her mindset when somebody told her she should smile and say thank you after a compliment and take it at face value. She suddenly realized that she would brush off compliments and second, she wasn’t really valuing compliments. I savor the positive stuff, I even had a marble jar and I visually savored it. I carried it with me so whenever I went into a new situation, my brain wasn’t like this is going to be a new situation and you’ll suck at it. Instead, I try to frame it as: it’s only a matter of time until they see how great I am. I think that’s a really really big thing and if you’re not good at something, surround yourself with people who are supportive and nurturing. If you have someone in your life who is a debbie downer, you’re probably listening to them and spending time with them and think that you really have to listen to what they’re saying about you. That is just the way our brain works and maybe something that happened when we were being raised, sometimes we just have to say no and commit to only focusing on the positives. We have to surround ourselves with positive people who remind us of our value, when I was interviewing women for the book, they thought they were awesome in their 40’s/50’s and I’d love to see us get there faster. It’d be great for every woman to feel like that earlier on in their careers because I think that would make a big difference in our work environment. 

So much of women empowerment is about being the first but not the last. As a hiring manager, it’s always so interesting to me when I observe how other female hiring managers in the room provide feedback on candidates who are interviewing. Sometimes they try to not be too enthusiastic or encouraging when the candidate is also a woman in fear of coming across as being biased or preferential. At work, what are some of the tangible steps you take to lift up and inspire other women? 

I have a whole chapter in the book about women supporting other women and why we should still do it and a lot of it has to do with societal coding. Humans in an environment of scarcity will watch out for their own survival first but in the example you gave, the fear is that you’ll support the other woman. Well first thing is, I just kind of ignore all of that stuff, if you are a deserving person whoever you are (and I have a pretty broad definition of deserving) and are working hard and trying to grow, I’ll be there for you and I will do that regardless of who you are and I will give you the time. With that being said, maybe I can only coach you monthly or quarterly but I’m there for you and I will support you with my time, especially if things are coming up in rooms. I will then watch out for you so I think that in the work environment, we have to figure out what we’re willing to give regardless of who the person is. We’ll avoid a lot of those interpretations by figuring out what works in that room, is it pure logic? If so, then let’s do it. Is it humor? I mean something like this girl sounds awesome and everyone figures out what works in that room. But don’t feel like you can’t do it, that feels like a societal trick, it’s definitely not an intentional one and that’s not really what people are thinking. I believe it’s just the way we’ve been coded these days, things come together and people tend to want to be liked and receive positive feedback and fear they don’t belong in large rooms where important decisions are being made. Side comments can make us feel under-supported in meetings, you have to be able to come out as a manager and make sure everyone is comfortable and say, “Hey I think we’re having an unconscious bias against this candidate” This is crucial, especially if you’re in a position of power. 

In one of the stories you shared during The Power of Example presentation, the woman you interviewed spoke about not being immediately good at her craft. The story is really about perseverance and strength. Have you ever had to overcome something, whether it’s work-related or personal, that you know you’re not intrinsically good at?

For sure, which one to pick? Well, I mentioned earlier that I’d gotten negative feedback about being a manager and it wasn’t that I was bombing the whole thing but I wasn’t good at taking that backseat. I wanted to be in control so badly that I wasn’t truly delegating tasks, I wasn’t letting my “little birds” fly, I was holding onto them and that was coming through in my performance feedback. I’m not inherently good at letting go and seeing what happens but I had to really practice that and take small steps and build trust in myself to get to where I am now. If I focus a lot on hiring and hire well, then I’ll trust these people. I wasn’t good at that early on in my career, I was taught not to trust early on in life so it required having to work through my personal issues. I want to be a good manager but I’m not naturally good at being a salesperson and I don’t like talking about myself. There’s a lot of things that we learn throughout our careers but I want my book to get people thinking about addressing these things about themselves much earlier so that we can be better managers, feel more confident, etc. 

What’s one lesson you learned from 2020 that you’re taking with you in 2021?

I think it reinforced something I knew: different times need different things. For instance, at work, what the team needed from me was to actually show them that it was okay that it wasn’t okay and not to have this leader who was like, “this is how we’ll get through this.” I sent an email at one point and I was trying to lead by example and I sent it out in May and said, “okay everyone I have been trying to pace myself since March and I’m at home with three kids.” I said, “I’m going to take off every other Friday because the occasional midday nap isn’t cutting it” and I got responses that were like, “this was what I needed to hear, the fact that you’re human and the fact that you take mid-day naps.” In fact, I didn’t really like yoga prior to 2020 but in 2020, I needed it so I think knowing that sometimes, you do have to do this stuff because broader things get shifted. At work, we’ll always use the phrase “what got us here won’t get us there” and I think giving yourself space is equally as important, it’s what got us to 2021 and through 2020.