Greg Hoy & Anisha Jain: Intentional Career Decisions

This is a transcript of Episode 04 Anisha Jain: Intentional Career Decisions. Hiring Guild cofounder Greg Hoy interviews (former) Dropbox Design Director Anisha Jain on wearing many hats and the power of intention.

Greg: Hello and welcome to the Hiring Guild Podcast, a series about designing better recruiting practices and processes. I’m Greg Hoy, co-founder of the Hiring Guild.

Today’s guest is Anisha Jain. She coined a phrase which I really like. “Intentional career decisions.” I think it’s something worth thinking about when we get into the idea of why people do what they do and their motivations behind it. Enjoy.

Greg: Hello and welcome to the Hiring Guild Podcast. I’m here today with Anisha Jain, a product design director here at Dropbox.

Anisha: It’s great to be here.

Greg: Thanks for agreeing to do the podcast. Anisha and I met at Facebook a while ago now, like four years ago?

Anisha: Yeah. It was a while ago.

Greg: It was after the acquisition of Hot Studio.

Anisha: …of Hot Studio, yes, which was probably almost six years ago at this point.

Greg: Oh my goodness.

Anisha: It’s been a while.

Greg: That was a crazy time at Facebook because that was right when they were saying “we need to triple, quadruple the design team.” That was kind of the solution at that time. “Let’s buy companies that have a lot of designers.”

Anisha: Yeah, when we joined, I believe it doubled the size of the design team at Facebook, which was insane at that time.

Greg: It was nuts all around. I’m sure it was kind of crazy for you all. That was a smaller agency.

Anisha: Yes.

Greg: I felt like you were one of the people that actually understood product design at that time.

Anisha: Thank you.

Greg: This is going to sound terrible, but it relates to recruiting. A bunch of us were sitting in the room and they have a dossier on every designer, which is what happens in those situations.

I clearly remember you were one of the people that the then design management said “oh, she definitely has product experience.”

What was it like being a part of that huge acquisition? From an emotional, maybe at career, I don’t know. I’ve never been involved on that side.

Anisha: Such a good question. It was actually a very strange experience. I had, just for a little bit of context or background, my background after grad school, I had done a whole bunch of… my graduate program had been in design process and strategy more generally and I knew I wanted to do digital work but I hadn’t actually ever done design work in the digital space. I spent a bunch of times trying to gain skills at a bunch of different places to get to that place.

I had just come back from Denmark and when I came back, I learned about Hot Studio and I was really excited about joining Hot Studio. I joined and it was the first intentional career decision I’ve probably have ever made.

Greg: I like that. Intentional career decision. That’s a great phrase.

Anisha: I was the last person in the door because two months later, we were acquired by Facebook.

Greg: That’s right. I forgot that. You had just started.

Anisha: I had just started. For me, it was a particularly strange experience because I had finally made this intentional career decision and I came into work one day and Boz, who leads the ads team at Facebook, was there with Margaret who is the VP for design for ads and pages, or was at that time. Boz got up on stage and he said “Hi. My name is Boz and you’re having a weird day” and that is forever implanted in my brain.

And then it was sort of this whirlwind. We would take the shuttle down to Facebook and we saw the campus and it was this huge change. I think for a lot of us it was something that many of us had never considered: moving into tech and it ended up creating a career step that ended up being amazing for all of us.

Greg: I totally forgot you had just started. I wonder if the experience was different for people that had been there a while and maybe were more a part of building the culture, because two months isn’t really… I’m sure you had impact, but if you had been there two years or four years or whatever.

Anisha: In total honesty, and you can decide whether or not to use this, I did use to call it the abduction rather than the acquisition because it was so sudden.

Greg: I am definitely going to use that because that is directly related to the experience that people have coming to a new company. The abduction. That’s great.

Anisha: Yeah, because I woke up one day and suddenly I was working at Facebook and I didn’t ever really plan to. It’s just a different mindset. I think that transition for a lot of us was a challenge and I think in hindsight, it would have been amazing to just acknowledge a little further how challenging that was going to be for us.

Greg: I don’t think, having worked there at that time, I don’t think the psychological aspects of the speed that things happened were really taken into account during those first early years.

Anisha: Totally makes sense.

Greg: I want to fast forward because you left Facebook to come to Dropbox. Maybe talk a little around was it, as my mentor Rich Cho always says, were you running from something or running to something? In that respect, were you thinking “maybe I need a new thing” or was it Dropbox coming to you? Tell me a little about the recruiting process in your head and also how the steps went.

Anisha: Good question. I was at SXSW and Dropbox hosts this huge event there.

Greg: I don’t know if it still is because I haven’t been in a couple of years but that used to be the best party.

Anisha: It was an insane party. Our founder plays the guitar, so he was there and there was all of this huge party. Somebody named Alyssa Fetini who, at that time, was a design recruiter who had also come from Facebook. She was following me around and at some point…

Greg: Stalking you?

Anisha: Stalking me. She just seemed so interested in me. I was like, “Alyssa, what is going on? We have to talk about this.” She basically said “I think you should really meet our head of design.” I said “Well, Alyssa, I’m not really looking for anything right now. Besides, if I leave Facebook, I’m going to take some time off because I’m about to get married and I want to travel and I’m not ready to start anything new right now.” She said “Okay. Well, how much time do you want off?” I said “Well, at least two months.” She said “Okay. Assume that that’s done. Now are you willing to meet our head of design?” I said “Okay. I guess I’m willing to meet your head of design.”

Greg: Was it Soleio still?

Anisha: It was actually Alex Castellarnau at that time.

Greg: Oh, okay. It was Alex.

Anisha: She introduced me to Alex. I walked up to him. The first question he asked me is “So, what do you think of Dropbox’s design? What’s your impression from the outside?” which was a hard and loaded question because I didn’t actually have a very positive impression of Dropbox’s design from the outside.

I was honest and I replied. I said “I don’t know. It seems bro-y to me.” In that moment, he had an opportunity. He could have left the conversation at that and sort of let me go.

Instead, he chose to use that moment as an opportunity to acknowledge something that had been a challenge at Dropbox. So he said “Yes. We know that. Actually, I’m looking for somebody who’s going to help me come change that.”

That was such a powerful moment from the recruiting perspective because it showed me that a. he was willing to admit some of the weaknesses that existed and it also meant b. we could have a conversation about what having a more balanced design team would mean and what his ideal team would be and how I might be able to help shape that. It was very powerful.

Greg: It’s so simple, too.

Anisha: So simple.

Greg: How fast that you went from ‘meh’ to ‘Okay. You got my ear.’

You said powerful. Not only is it powerful. There is an efficiency to it that shows the authenticity of the message. Even though she was following you around in and of itself is adorable.

Anisha: I love Alyssa. Still to this day, she’s one of my favorite people.

Greg: She’s awesome, beloved. I think the thing that blows my mind is that acknowledgement piece because you don’t have to sell in that space, especially if you’re passive. That got your ear. Are you like “Alright. Now they’ve got me?” How are things at that time at Facebook?

Anisha: At that time at Facebook, things were really good. I had been so lucky to end up in an org where there was so much support and I had been able to do a lot of great work. I had been continuing to progress in my career at Facebook. I felt very valued at Facebook. It wasn’t actively unhappy at Facebook. There were aspects. I didn’t like commuting. I personally wasn’t as resonant with the product as I think some folks are. I think there were things that were underlying where it didn’t feel perfect. For the most part, I feel very fortunate for my time at Facebook and it did not feel like I was in a place where I was trying to get out immediately.

Greg: Got it. Let’s fast forward a little bit. You come in as a female. Did you come in and immediately get the lay of the land around that bro-y stereotype that the company had? Beyond that, what did you do in the first steps to help open up the idea of what design culture is here, from a hiring perspective?

Anisha: When I first arrived, I will say the hiring process even after that, it’s still I met a bunch of people, we talked a lot about what the right role is and so on. Once I joined, it felt like I had really good alignment with my manager around where my potential growth was going to be even before I joined. That really helped in selling me to join because it felt like a really big risk to leave a company where I had so much built up already to come try to make change at this place that was still young.

When I joined, I think my lay of the land assessment, especially around this bro thing, was yes, the team was predominantly male. They were, including myself, there were only three women on the product design when I started. But they were very very kind.

I think there’s a connotation with — you talked about dribble designers or bro-y designers, there’s a negative connotation associated with that. I found that this was the kindest, most warm, most collaborative, welcoming culture I could imagine. It values humility above almost all else. That was a huge selling point in my joining as well.

Sorry, your other question was?

Greg: No. You did an amazing job of bridging from the time that you had that conversation with him to joining up. I didn’t really ask you about that. I guess I assumed that it was all pretty across the board. The story was echoed, which you just said so I appreciate that.

My question was more about what were the first things when you got to a place where you were able to influence how the conversations were happening or how the company was looking at the next hire. There’s probably a lot, because you’ve done a lot since you’ve been here. What steps did you take upfront in partnering with, say, recruiting or in how the message was getting out into the world about “Hey, design here has changed”?

Anisha: Good question. In the beginning, it hadn’t changed yet. In the beginning, part of the work was to try to diagnose what was making it so hard for us to hire more diverse and why there are set of designers. I built a partnership with recruiting very early. At that time, Jen Pham was our only recruiter. She was amazing. She really taught me about recruiting. I hadn’t done nearly as much recruiting before and she is an incredible partner. I think her attitude towards recruiting was always that it should be a partnership and that she and I should be equally vested in the hire of an individual. We set up all of these processes. We had weekly syncs, we had a document that was running with the pipeline.

We would sit down together and look at LinkedIn profiles. I would give feedback and say yes or no and why, so that we could really get to the bottom of what it was that I valued and what she was seeing when she sourced people. That allowed us to build a lot of foundational trust.

When it came to this question of diversity within the team and how do we start thinking about a broader slate, I think there were a few core issues that started to become uncovered. One was just an attitudinal thing where people felt like it was impossible to find women. We focused primarily on women when we thought about diversity in the beginning.

I remember a conversation with all of the senior leaders in the design team in a room together where recruiting had given us a hiring goal for gender diversity. I think it was five women in the next year. At that time, I remember everyone in the room going “What? How are we going to do that!” I was shocked.

Some of it was just a feeling that a lot of people in the team had great intentions but felt like they didn’t know any women designers personally, so how was it possible that we could find that many people. A second area was just around starting to get much more crisp about what the different attributes are that makes them a great designer, so starting to actually break down.

Visual design is a super important skill, and Dropbox has historically recruited well for that. Interaction was also something we were strong at, but what does product thinking actually mean to us?

We sat down in a room and started to pull that apart as a group and align on what that meant. What does it mean for somebody to be great at design process? What does it mean to have technical chops in the context of design and what are some of our culture attributes mapped to in the way that we evaluate and ask questions. All of those things were super important in starting to diagnose and starting to create change around us.

Greg: People say the secret sauce of hiring designers and it really does come down to breaking out all the different flavors. You have to figure out all these different pieces and then you have to figure out “Okay. Let’s agree on what that is here.”

Those are ‘take a step back’ moments that I think the best organizations do. They take that time. “It’s a design problem, let’s take the time to see why this is broken. Let’s take the time to see why people have this view of us from the outside looking in.”

Did you find, since you’re going down this road and I love asking these kinds of questions, did you find that things like interview training or things around how do we speak to maybe an example of doing a design challenge or a whiteboard exercise, how it might be different from a gender perspective?

Anisha: Good question. We’ve had some conversations about that. I think for the most part, a lot of what we focused on was actually just trying to distill objectively what we were looking for in conversations so that we could get our interviews to be much tighter in terms of evaluative criteria.

For example, with product thinking, it was clear that there was lot of squishiness. I think we had a point where 90% of people we were interviewing were being rejected because of product thinking. We started to say “what does this actually mean because we must not be well-calibrated on what it means.”

We sat down together and we ran an exercise where I remember asking everybody to think about the best product thinker they had ever worked with. To share and describe that person to a partner and to use that as a starting point for a discussion and through that discussion, we were able to pull out that there were two attributes that we were really talking about.

One was the ability to take a lot of data-driven information, so business needs, user needs, technical constraints and create a point of view to synthesize that information.

The secondary was how generative is somebody? Are they able to come up with a really broad set of solutions? Are they able to explore broadly in any of these particular problem areas? And then we could go back and map to our whiteboarding exercises and so on and say “Do these actually test these things? Yes or no. Let’s tweak, let’s change our exercises.” In terms of actual style, the Dropbox designers tend to be fairly introverted overall relative to what I had experienced at Facebook. It’s a really kind and welcoming culture. It wasn’t as…

Greg: Maybe analytical?

Anisha: Not so much analytical, but I think I haven’t seen as much concern about some of the extroversion only applying to extroverted or very some of these traditionally male-dominant stereotypical qualities in our interview process. It doesn’t mean that that’s not the case, but I think we spend a lot of time even upfront in an interview, our interviews are a little bit longer, we spend time breaking the ice and getting to know people to make them feel comfortable. I think that creates a pretty warm environment.

That wasn’t as much of our challenge as much as it was getting really crisp and objective about criteria and also about what constituted an example of an advanced, intermediate, beginner, and below beginner for each of those areas and being able to articulate that and being able to articulate but what if somebody hasn’t had that experience because they worked at X company with Y context. How do we think about adjusting for potential or thinking about potential in a candidate.

We broke down the problem that way. I find that being really crisp about that stuff sometimes is very helpful for removing bias in your interview process.

Greg: That’s great. I think, too, at the size, because the team was still fairly small.

Anisha: It was. It was only about 30 designers when I joined.

Greg: I think when we’re talking about how your interviewing, when a company is a little smaller or a team is a little smaller, there’s sometimes is a lot more leeway to take a risk on someone, especially if the roles are a little less clearly defined.

I’m curious now that you’ve been here and the team is however big it is. What differences in challenges do you see when you’re bringing people in, and maybe in that past, you were open to changing the role or changing the scope of the role versus now when people are in the room and they say “we need someone that can X and we need to interview just for that”?

I’m just curious if you can think about maybe some of the differences you’ve seen in the interview process or even maybe the debriefing process. Are people still open to “hey, this designer’s great. Probably not good for this role, but we could…”

Anisha: Good question. We are actually pretty structured and pretty organized about a lot of the stuff so I think the thing that we’ve done well as we’ve gotten bigger is to scale our processes fairly quickly. Now, for example, the way we hire funneling people to the right role and the right team is we try to do it upfront. We’ll do an initial screen and from that, we will get these criteria.

For all of our interviews, criteria will understand beginner, intermediate, advanced, and all of these with details about why from the designer that’s interviewed them. We sit together, all of the hiring managers sit together in a room and we review portfolios together for people who have come through the screens.

By doing that, we’re able to see the candidates who are in the funnel and say “yes, this person could be a fit for my team. They look like they’re about the right level and also for that other team.” Within our global recruiting priority, the first team is hire priority then the second team, so we’re going to prioritize that team but keep somebody from the second team on that loop as well in case the first team is not interested but the second team might be.

We’re pretty good at catching that stuff early. I haven’t seen too many challenges with that recently. I think we’ve built that out really well. I think some of the interesting ones are really senior candidates and how to think about senior candidate hiring. Figuring out not only what are their skills but also are they a culture fit for the team, do we have enough space on the team for them to be able to actually grow here over time and thinking about that from the onset so that we don’t bring somebody in and then six months later, we actually just don’t have meaty enough projects for them has been really good.

Thinking about diversity in the senior hiring was also really challenging for us in the beginning. I have a really strong point of view that if you want to actually change diversity within the team, you have to hire senior folks in addition to junior folks because that’s actually what creates sustained retention over time.

We didn’t have relationships with senior women, so how do you generate relationships with the set of people that you actually don’t have relationships with was one of the big questions that I had when I started. I spent a lot of time working on that and figuring out how to do that as well.

Greg: I think every company that I have interacted with has a much harder time at that level all around. Like, how do we assess, how do we interview, should the process be tailored differently? You get these conflicting answers from people. While this person should do a presentation, while this person doesn’t have to do a presentation, a directed X at Y company and it’s huge and we all use it so we know how great it is.

One of the things you said, really, it reminded me that I always feel design has always been ahead of the curve around looking at work first, not looking at name first, looking at a face first. You’re looking simply at their portfolio.

I even remember at Facebook, when everyone was like “oh, we got to open up the team. It’s a lot of male-dominated designers.” Getting to that point where we would just click on a portfolio and not even give the name.

I’m curious on your thoughts on that, only because when you look at so many portfolios, can you get a feel, for someone’s background, someone’s gender by looking at their work?

Anisha: I have never done blind portfolio observation, so I don’t know.

Greg: You always see the name.

Anisha: Yeah. That’s a very interesting question. I’ll have to think about it.

Greg: When I think about Dropbox, I feel it’s a neither masculine nor a feminine product to me. When I think about Facebook, it does feel masculine probably because I worked there. When I think about Pinterest, it feels feminine. When I think about Dropbox, it’s very gender neutral and when I look at the design of Dropbox over the years with the illustrations, the illustrations to me felt a little more female whereas the interactions felt a little more male. I was just curious if there has been any correlation done around that.

Anisha: I don’t know.

Greg: Because when Dropbox started doing that, it was kind of radical to have these product interactions that had illustrations around them.

Anisha: It’s true. We talk about that a lot when we did a re-run last year because that was the thing that made us different from a lot of the products out there and it no longer is. Everyone has illustrations in their products now.

Greg: Yeah, super innovative.

Anisha: We spent a lot of time thinking about how to push the needle further for the next set of work that we did with our rebrand.

Greg: It is funny as you stay in this business a while, you start seeing things that were originally radical and then they become common place. A lot of times, I think it’s very design-driven.

When Spotify came out and it was black, it was a green on black, everyone was like “I’ll use Rdio. It’s white and clean.” I’m like, “You know what? I’m the opposite. I think this one’s cooler. It’s funner to use.”

And now Robinhood came out. These ideas of different colors representing different attitudes, different things. I’m really glad we’re getting away from that everything looks the same on your phone. It felt like design-wise, we went through that. I’m kind of digressing here.

Anisha: Yeah. It’s happening. Maximalism is in. It’s coming. Chaos on the screens.

Greg: Can’t wait! What’s some of the biggest, when it comes to hiring and I’d like to lean on you as a woman, what are some of the biggest challenges you’ve faced just from your perspective? Just your woman in tech, have you felt biases?

Have you felt people treating you differently? What’s been some of your experience? I’m not asking for anything “well this happened.” I’m just curious, like a general feel. You’re a leader and you’re a women and you’re in tech, so I love asking this question of people like that.

Anisha: It’s a great question. I’ve been super lucky to get to work with a lot of amazing leaders. Actually, part of the reason I wanted to join Hot Studio originally was because they had so many female leaders so I wanted the opportunity to see what that could look like and learn from them. Being acquired by Facebook was also very fortunate in this way because Margaret (Stewart) and her team are just amazing. It’s such a great set of examples to learn from.

I think in a lot of ways, I’ve been lucky to join companies where there was either female leadership or a lot of investment in figuring out how to enable somebody who was different. I think some of the challenges that I see sometimes are that when you are closing and selling a candidate, you have a pretty short period of time to build a relationship, a strong enough relationship with that person for them to feel excited about having you as their manager.

I do think that there is sometimes a challenge in being able to connect quickly with somebody who is very different from you, and I think everyone has that challenge. This is the reason why we hire people who have similar backgrounds as us, who are like us, frankly the easiest to have conversations with those people and to close them, because people think like “Okay. This person is like me. They get me.”

I don’t know that this is a specific problem for women, I think it’s true for anyone who’s hiring anyone who is different from them, who has a different background from them, who has a different gender, or a different ethnic background.

Sometimes, when that difference is strong enough that it can take more effort to build a good relationship quickly. I think in those cases, having a lot of humility about what it is that you don’t know and being confident in where you are strong and also confident in where they are better than you or stronger than you and being able to articulate those things quickly has been really helpful for me in being able to build relationships quickly.

Greg: Fantastic answer. In fact, you kind of answered my last question, which is what advice would you give, maybe, a more junior designer from the perspective of figuring out, what was the phrase you used earlier that was so good, the purposeful choice for a company that they might want to join? That could be from how they get their foot in the door to who should they reach out to or how they should reach out to? Just curious if you have any thoughts.

Anisha: Good question. I think my general advice would be that it’s really important to remember that nobody knows exactly what they want when they start looking for most jobs. The job of the recruiter and of the people on the other side are to sell and to make sure that you feel like their company is as awesome as it can be. When you’re in that moment, a lot of us have never had that experience before of “oh my gosh, this person wants me to work for them? That’s so cool!”

Greg: They like me! They really like me!

Anisha: The like me! Exactly. It can be really flattering and I think the advice I would have is spend some time talking to a diversity of companies and understanding what the differences are between them because they are much different than you expect that they are, even within the small world of tech. It will help you build an intuition and a conviction about what size company you want, whether people are project matters more to you, there are all these factors in making a job decision. That can help you, during the recruiting process as well, have real clarity about what it is that you want next in your career. Taking some time there can be nice.

Greg: Smart. I always tell people to take every interview just to get the flavor, get the feel.

Anisha: Get the offer.

Greg: Yeah, you’re interviewing for the offer. That’s the other thing I tell people. Because sometimes, people get all in their head about “do I want to work here?”

Anisha: Exactly.

Greg: You don’t even have to think about that yet.

Anisha: Exactly. I had a professor once who said “Don’t make a decision about a job until you have an offer in your hand. Get the offers and then you can make decisions second.”

Greg: Totally agree. Well thanks so much for taking the time today.

Anisha: Of course.

Greg: I’m really psyched to stay in touch and see how your career continues to evolve.

Anisha: Thank you so much for having me. This is awesome.

Greg: Cool. Thanks so much, Anisha, for having me by Dropbox. What a cool idea. When is it that we really start thinking about our next job? Some would say you should think about the next job on the first day of your new job.

Greg: If you like us, subscribe at iTunes. Be sure to give us a rating and check us out at www.hiringguild.com