“Decision-Making at Scale: Morning Keynote”: Arquay Harris, VP of Engineering at Webflow (Video + Transcript)

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Sukrutha Bhadouria: I’m super excited and honored to introduce Arquay Harris, who is our keynote speaker for today. Arquay is the VP of Engineering at Webflow. Prior to Webflow, she has held engineering leadership positions at so many different companies like Slack, Google and CBS Interactive. Fun fact, she’s a developer who also has a master’s in design. She loves the manager form and functions, so interesting and impressive. When not working, she can be found cooking, stumbling over guitar and piano chords or watching Seinfeld. Welcome, Arquay.

Arquay Harris: Hello everyone. Nice to see you. I’m so excited to be here today and I’m going to be talking today about decision-making at scale. And first I’m going to give a little bit of an introduction, which will be almost everything that you ever wanted to know about me, not quite everything, but almost everything. And the first thing that I think you should need to know about me is that I have been a Girl Geek supporter from way, way back. And I brought proof, here are my receipts. This is from a very, very early Girl Geek dinner that I went to and it was in 2009. And I’m pretty sure that I went to one before that, but this is as far back as Gmail goes. I tried to find an earlier one, but I couldn’t.

Arquay Harris: And this is almost a full circle moment for me giving this talk today because when I think about that time, when I first met Angie, for example, and I was just a very junior leader and to be here today, keynoting and hopefully inspiring and giving some knowledge to the next generation, it just shows the longstanding impact that Girl Geek has had and how much they’ve represented underrepresented genders and how much they’ve done for the community and tech. And so I’m just really excited to be here keynoting, and I can’t think of better way to spend International Women’s Day. So thank you for having me.

Arquay Harris: So first off, my name is pronounced Arquay. I really wish that I had this very exciting backstory, like I’m named after an African princess or something like that, but really it’s just my parents were obsessed with SEO. It’s true. You can find me anywhere on the web just because they really had foreshadowing. And I have the very, what is now traditional non-traditional background and that I grew up pretty humble background, and I loved mathematics. I was president of the Mu Alpha Theta, the math honor society. I was in math club and I went to college to become a math teacher because I really believe that math and science are the great equalizers. You could math and science your way out of poverty. I love visiting the island nation of Sokoto.

Arquay Harris: And I had an afterschool job where I was introduced to Illustrator and Photoshop, and I loved math, but I noticed I was most engaged when I was drawing something on Illustrator late at night in my dorm room. And I transferred schools to study media arts and design, and anyone who hears me talk hears me talk about this background. I mention this a lot because I really do think this non-traditional journey that I’ve had really is kind of the core, it gives me this unique perspective. And so I got into coding initially because I didn’t like this process of handing off my designs to someone else, something got lost in translation. And I figured I have this analytical background. How hard could it be? Other people learned. I started with Flash and then I moved on to PHP and Python and all of that.

Arquay Harris: And so I later came out to the Bay Area to go to graduate school and I did more coding there, but also fine art painting 3D. And so I’m this very odd combination in that I am a developer, but I’m also a classically trained designer and I have an MFA. And this has really served me well because I’ve been able to have really informed conversations about topography and color and I also understand what can be built because I’m a developer. And then a lot of things happened, fast forward and now I work at Webflow, and Webflow for me is I feel this perfect mix of art and technology and design. And it’s almost just this job that’s tailor made for me, given my background.

Arquay Harris: And I think that my journey and my kind of non-traditional path has really prepared me for this role of VP of Engineering at Webflow, because their mission is this visual development platform. And it empowers non coders who create these incredible experiences for the web. Because whereas, in the past being able to do this was almost this gatekeeper scenario by these few select people who could code. And so what Webflow does is the democratization of that. Getting people into this world of coding, even if you don’t know how to code.

Arquay Harris: And so as VP of engineering, I oversee all of engineering at Webflow. And my career path has been quite windy. I’ve worked at big companies and small companies, early staged companies, companies that were acquired by other companies, right? And so working in these various environments, I think has given me a very unique perspective. And I’ve been able to learn from each role and develop these skills for decision making, which leads us to what we’re going to be talking about today.

Arquay Harris: I think whenever you give a talk, it’s always really important to start your talk with a quote from a really smart person. I don’t know, this is just a thing that I do and you should try it out. So the quote here is that “The difference between a right decision and a wrong decision is context.” It’s very easy to wish that we had a time machine and to look back with hindsight and just know that you have all the answers, but sometimes you just have to make the best decision with the information that you have at the time.

Arquay Harris: And when you’re beginning something, whether it’s a company or any kind of endeavor, decisions are more like a labyrinth. There’s a one true path. I have a muffin shop, I make muffins, I sell muffins, right? It’s really easy, kind of one foot in front of the other, you know what the decisions are to make. But then as you scale, decision making becomes much more complex, right? You can go left, you can go right. It’s more like a maze in that scenario. And it’s not always clear what the right decision is to make.

Arquay Harris: Studies have shown that more choice, this abundance of choice, doesn’t always help us make better decisions. And in fact, it can make us feel worse about our decisions, even if it was the correct one. So take a scenario of a buffet, you go to a buffet and there’s all these choices. And so you have raised expectations.

Arquay Harris: Everything looks good, this got to be great. And then you started thinking about that opportunity cost, where you’re like, “Well, I could get a Mexican or I could get Chinese. I had Italian yesterday for lunch.” And then you make your choice and you either have regret or anticipated regret where you think, “Arg, I should’ve got what that person got. I don’t think I got the right thing.” And then you have self blame where you just say, you never picked the right one, right?

Arquay Harris: And how this can manifest itself in a real world scenario is let’s say you have to make a build versus buy scenario. You do this evaluation and you look at all the tools, you see what’s out there. And then you’re like, “Arg, darn it. I should have picked build.” And that can lead to this horrible cycle of self-flagellation, which can be unhealthy.

Arquay Harris: And so then how do we know what decision is the right decision? And that very much depends on your perspective. So as an executive or as a senior leader, you have this very unique vantage point where you can see very high level, right? And you might also have information that other people may not have.

Arquay Harris: But then at the same time, you could have someone who is in IC who says, “Look, Arquay, you’re way up here. You don’t have the perspective. You don’t really know what it’s like down here in the trenches. And that on call is really nerve-racking and pretty hard.” And so context is really important.

Arquay Harris: So as we just talked about, I have a fine art background. And in undergrad, I studied this film, Rashomon, which is a brilliant film by a brilliant director, Kurosawa. And it’s a story of a murdered samurai and it’s told from three different perspectives that are all quite different, and so much so that this is now used so much as a cinematic technique, that it’s referred to as a Rashomon effect.

Arquay Harris: And there’s modern examples of this. For example, if you’ve ever seen the television show, the Affair, or if you’ve ever seen the usual suspects where you take something that happened and you shoot it from different perspectives and you get this kind of story that doesn’t really align. And so it’s not really that necessarily that these people are unreliable narrators, it’s that truth really depends on your vantage point.

Arquay Harris: So then what is the truth? Right. Okay, there is no one truth. That’s the answer, especially when it comes to decision-making, because generally what fuels decision-making is priorities and priorities are very much in the eye of the beholder. And so context matters and our own experience is rarely the whole truth. And how this can show up in your rural world is often because we can’t make a decision, or we don’t know the one on true path.

Arquay Harris: We end up being pulled in a bunch of directions and so we end up making small progress on many things, right? Rather than making meaningful progress on fewer things. And as we scale both our business and our organization, the ability to make that meaningful progress becomes more and more important. And so a question is what are some things that prevent us from making good decisions? Right? Because many things are vying for our attention. And as I said, we’re pulled in a bunch of directions.

Arquay Harris: So as the leader of an entire engineering organization, I view my role as sometime acting as an umbrella to really shield my team, my organization, so that they can get things done rather than being this funnel that just lets a bunch of process and distractions come through to the point where people are quite literally asking and screaming for help.

Arquay Harris: And to cope with this, we sometimes develop techniques to adapt. And some of those techniques though, are anti-patterns. So you think to yourself, “Okay, well I have to make a bunch of decisions. What’s the best way to make a decision? Okay, well, I probably need information.” So then you create these boss like structures where people are pushing information up to you constantly rather than creating leaders, empowering people, pushing authority downwards. And then when you do that, you can scale yourself and your decision-making and then also your organization.

Arquay Harris: And now, while you want to empower people to make decisions, there’s also a balance because when we don’t always have of the conviction and where sometimes can be unsure about how to make a decision, you get the dreaded consensus based decision-making, where you have to get everyone’s opinion and no one can agree. And so then because of that, you end up making no decision.

Arquay Harris: So you get this paralyzation of indecision that happens. And like everything, everything has a shadow side, right? So you want to have conviction, but you want to be mindful of the extreme because you get this Ikea effect where you think, well, I made it, so it must be great, or my ideas are the best. And so you don’t want to shut out all external opinions and believing only in your ideas and putting those above everything else. So everything is balanced, right?

Arquay Harris: And so overall, I would say that when making decision it’s important to be open to new perspectives. So there’s a balance between open to new ideas and also a consensus based. Now I will totally fully admit that sometimes like this graphic, I’m a square person. It’s like, but I’m a square, and I have decided that I’m square and I’m a square. But the key to being a good decision maker is that you need to learn to let the expertise of others aid you in your decision making and not have so much conviction that you can become stubborn.

Arquay Harris: And I fully recognize that it is easy to say, well, just have conviction. Like just do what you think is best. But conviction is hard because how do you know if you’re making the right decision? Particularly if that decision affects a lot of people. As leaders, we are making decisions in isolation. Some decision that you make can impact someone’s life or their livelihood or their family, right?

Arquay Harris: So, it’s not always easy to know. And so the question of how do you know if you’re making the right decision? The truth is that you don’t, but there’s some things that you can do to gut check. And one example of this is the front page test. How would you feel if your actions were on the front page? Would you be embarrassed? Would you squirm? Would you feel shame about it? Or would you stand proud and happily defend those decisions?

Arquay Harris: Another thing that you can do when evaluating your ideas is it can be good to think about it in terms of a dialectic, right? So if you have some idea or some process, think about what is the antithesis of this? What is the antithetical reaction that someone could have? So that sometimes can lead you to resolution, or it can prepare you if you need to defend your position and show that you thought it through.

Arquay Harris: So whenever I’m rolling out a new process or doing something like that, I think about, okay, well, what is an objection that someone would have to this? Why would someone not like this? Kind of think about all sides of the argument and sometimes that might lead you to resolution because you’ll think, oh, well, that’s a good point. I should have thought of that. Or at the very least think about ways to stick with your decision, but maybe mitigate it, right?

Arquay Harris: Because in preparation for that opposing reaction. And now despite our best efforts, we do all the right things, we think it through, we sometimes just still get stuck. I have looked at this sideways, every different direction and I really have no idea what to do.

Arquay Harris: And so sometimes rubber ducking can help and rubber ducking is a common thing. So for engineers, imagine if you are really stuck on this problem and you don’t know what to do. And so you go to another engineer and you talk through your problem and by virtue of you talking it through, you come up with the solution.

Arquay Harris: And so the idea behind rubber ducking is it doesn’t need to be another engineer. It could literally be anything, it could be a rubber duck, right? And so just that thought process of saying it out loud, it’s just like Eureka, I know what to do. And I have certainly been the benefit of getting on stuck by rubber ducking.

Arquay Harris: And I want to say that this is not easy because to adapt your approach to decision-making requires a pretty significant change in mindset and change can be overwhelming because you think, where do you start? Am I doing it right? Am I in the right direct? Am I just making a mess of everything? But just like mole hills, small changes over time can lead to very big impact. And so I think that decision making is hard, but it’s much easier once you actually start.

Arquay Harris: And so some key takeaways are, you want to focus on the challenge because the first step is just acknowledging the difficulty, that’s half of it. Because if you think about in your life, people who you really admire, or people who have to make these really hard decisions, these people aren’t born with all the answers, right? Like it’s not just they descended onto planet earth and they just had it all inside their brain. No, that’s not usually how it works. It usually takes practice and repetition.

Arquay Harris: And so just acknowledging that it is hard, I think is really important to just kind of ease up on yourself and recognize that this really is hard work. And then secondly, focus on the evolution, right? You won’t always make the right decisions and that’s okay. You’ll be able to adapt. And you’ll iterate. Perfection should definitely not be the goal. It’s more about learning and evolving because if you could get it right on the first try then decision-making wouldn’t be so hard.

Arquay Harris: And then lastly, you should focus on the journey because it’s a marathon, it’s not a sprint and wisdom doesn’t happen overnight. And as you grow as a leader and you face new challenges, you’ll learn and you’ll grow and decision-making become easier and easier. So thank you so much for your time, it was really great to be here today. And I hope that you have some really great questions for me. Otherwise, I’m just going to keep talking about how much I love Girl Geek. So I hope you have questions. Aw, thanks. I’m reading the chat. Everyone is so kind. Thank you. I’ll sit here. I’ll smile.

Arquay Harris: Thank you. Oh, that’s so nice. I don’t know, I should be reading these out loud. It’s very sweet. So I’ll do a little self motivation here and I got a couple questions in chat. And Angie definitely correct me if I’m wrong, if I’m supposed to wait for the moderator, please, someone hop on, but otherwise I’m just going to go through these.

Arquay Harris: The first one is what would you say were the two most difficult things you encountered as you climbed to your current position? Ooh, that’s an interesting thing, right? Because first, I want to just dig into the climbed to your current position thing, because I used to talk a lot about self-advocacy and about how to advocate for yourself and how to advocate for others. And I always talked about thinking about your highest aspiration.

Arquay Harris: And I would say that when I was a little baby developer, I don’t know that my highest aspiration was to be a VP of Engineering. Actually, I would say that it was not because VPs manage directors who manage managers who manage ICs. And the thing that I really loved about management was kind of that one to one connection. Right? And so given that, I think that, that maybe possibly is inherently what I would say was the most difficult thing, which is, I think when I give the talk about self-advocacy, I talk about thinking about your highest aspiration and making sure that you reevaluate it.

Arquay Harris: Because for me, one of the reasons why I never really aspired to be a VP of engineering is because the prototype in my mind is like Andy Grove, right? He’s in khaki pants and he’s wearing a blue shirt and he’s an older white gentleman. And it’s just not something that I really saw for myself.

Arquay Harris: And so I think part of that is just challenging that mindset and thinking like, “You know what? This can be whatever I want it to be. I can define what this looks like.” And I mean, yeah, there’s just the normal things, like big issue of low expectation being a woman, being the only or being the first, those things are also very hard.

Arquay Harris: And so the thing that does give me hope is that I really do feel like things are changing. I hope that answers your question. It kind of got existential, but I think that’s basically just said a thank you so much for asking.

Arquay Harris: The next question is… Oh, okay. This is kind of similar. Thank you so much for sharing such a practical way to handle decision-making. What has been your biggest hurdle to overcome in this area? Oh yeah. I mean, I would definitely say two things.

Arquay Harris: The first is making sure that you have information at the right granularity level, right? Amazon has this concept of kind of like one way doors, which is… And I employed this a little bit with my team a one way door is a thing that effectively you can’t walk back and a two-way door is a decision that you can make, but it’s pretty easy to roll it back.

Arquay Harris: An example of a one way door would be like, may I use $3 million to build a new job queue or something like that, right? Like something where there’s some sort of big implication either financially or internet or time wise or something like that. And so I think it can be hard to know what those one way doors are because sometimes a thing that seems insignificant and small could actually have a years long implication on your team and on the company.

Arquay Harris: And so kind of really getting enough information at the right granularity level that you can make those kinds of decisions. And I think that’s probably just like a pretty hard hurdle to overcome. And then also just the not knowing if you’re making the right decision too, because you never really know until you have the benefit of hindsight and then you can look back and it was either… It’s that context thing, it was either right or wrong. Yeah.

Arquay Harris: So next question. You said decisions are made in isolation. How do you keep yourself accountable and also protect your mental health? I think I’m going to tease apart and I think I know of what you mean by that. Did I say something around how they’re intrinsic, like how they’re… I’m not sure, but I would just answer it and say the way that you can protect your mental health is this whole being easy on yourself.

Arquay Harris: I think a lot of times, particularly when people get to really senior positions, they put this pressure on themselves, like, “Everyone is counting on me and if I make a mistake what’s going to happen?” And I think as a woman and as a black woman especially, there’s this very famous XKCD comic that I quote a lot where the first page is someone is teaching a guy math and it’s like, “Oh, Bob, doesn’t get math.” And then the next page he’s teaching a woman and it’s like, “Women don’t understand math,” right?

Arquay Harris: There is just like every single thing that you do has this added pressure because you are representing an entire race or an entire gender or an entire culture or whatever it is. And so I think that the way to kind of protect yourself is to just acknowledge that you’re not going to get this perfect every single time and that’s okay. That’s part of learning and growing. And I wish that I could say that is the thing that I always knew. Definitely not. It is the thing that I developed over time and the longer that I do it, I think the easier that it gets.

Arquay Harris: Ooh, this is a good one. What is the most difficult decision you ever made? Coming in hot, I love that. That one I would say any time that you’ve had to terminate someone or put someone on a performance plan or something like that, those are always the hardest decisions because you know that that decision that you’re making, just the ripple effects, you’re affecting again that person’s family, their potentially their ability to support their family. You could even be potentially affecting that person’s ability to get another job, right? Based on their performance at this role.

Arquay Harris: And so early in my career, this was a thing that I had to sort of develop some kind of framework around. And whenever I’ve had to do that, I asked myself these three questions. And then this is my kind of way finding, the first question that I asked myself is, am I being transparent? Meaning if I have to let someone go or performance manage them, will it come as a surprise?

Arquay Harris: Will they just be like, “Oh, I never saw this coming.” No, hopefully that is not the case because I’m communicating with them. The second thing is, am I supporting this person? [inaudible] and then I always say is if you need help, I will extend a hand, but I’m not going to carry you, right? Now, and what that means is I will support you. I will give you feedback. I will try to make it so that you can get better and improve. And then all those things considered. If it doesn’t work out the last and most important question that I ask myself…Those things considered if it doesn’t work out.

Arquay Harris: The last and most important question that I ask myself is that I act with integrity meaning was I secretly whispering behind this person’s back? Did I put them on a pit, but really I just want to fire them? And so, having this North Star really helps me with difficult decisions. And I have developed these frameworks about decisions like that that I have to make in my life. But as a leader, that would never get easier no matter how long, for me anyway, how long you’ve been doing it.

Arquay Harris: Do you have advice for other female leaders of tech teams? I mean, sure. Yeah, I think I would say develop a support system because I don’t really feel that I have that coming up because it was so isolating because I was generally either the only woman … I mean, there’s many teams that I worked on where out of dozens and dozens of people, I was the only woman. And certainly, I’ve worked on teams where out of dozens or maybe 100 people, I was the only black person and it is very hard.

Arquay Harris: And so, when you don’t have that community, you can start to second guess yourself and make decisions … decisions become hard. And I’ll give one anecdote that I’ve shared a few times which is I once had a conversation with a white male, [inaudible 00:36:36] white male. And I asked him, I said, “Imagine if every single day you had to go to work and every single person that you worked with was a woman. And now imagine every single one of those women was black.” And that is the reality for so many of us in tech where we are just so marginalized.

Arquay Harris: And one of two things would happen. You would either try to assimilate as much as you can, you would try to get yourself a head wrap or maybe you’d get some braids or something while you were trying to fit in as best you can or you would completely second guess yourself and not have any semblance of self. You wouldn’t get their references. You would have no idea who Issa or Molly were. You would just be confused all the time.

Arquay Harris: And so, for other female leaders, that is quite the reality particularly at the senior levels. I mean, we can cite many, many companies where the only person in their executive leadership or the only person on their board or whatever is just one woman.

Arquay Harris:This isn’t what you asked but this is one of the reasons why I joined Webflow, why it was so attractive to me as a company is that my partner who’s the VP of Product, JZ, who is the best person ever. Still I’ve really tried, I cannot think in recent memory of another company where the VP of Prod and the VP of … Oh, my time? Well, it was a great anecdote but JZ is amazing. That was the TLDR. But I think that was my last question. It’s been great. So, thank you so much.

Angie Chang: Thank you, Arquay. I really love your engagement with the audience. Sorry to leave you hanging, I was typing away. I was like, “Oh no, I have to find her window,” so sorry. Thank you so much for taking all the questions. I love your quote and your talk and thank you so much. Everyone, this is going to be on YouTube later. So, if you missed it today, since I know we’re all busy people, this will be on YouTube. Don’t worry about it. You’re registered. You’ll get it in your email. So, thank you, Arquay so much…

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