“The Customer Is Not Always Right”: Cindy Alvarez with Lean Customer Development (Video + Transcript)

Cindy Alvarez / Director, UX / Microsoft


Cindy Alvarez: I’m Cindy Alvarez, and right now I’m on a flight heading back from Johannesburg, so you get a pre-recorded talk from me. I’m going to talk today about why the customer is not always right. First of all, I want to start off by saying where did this thing even come from? Where did we start with the phrase, “The customer’s always right?” What does that mean? Why is that important to us?

It primarily comes down to the fact that we want our customers to come back and buy more things from us. We want them to like us, and that makes me realize that customers are not just external people who buy our products, they’re also people that we work with every day. There’s a lot of things you can do to make those relationships better, whether they’re talking to customers who are external to you, or the people who are next to you every day. Let’s dive right in.

First of all, let’s think about what’s our desired outcome. I think when we say things like this, we tend to think of things like units sold, or increasing usage, but fundamentally, we want to understand the underlying problems that customers have — whether that’s the one buying our product, or our coworkers because understanding is the only way we can hope to solve their problems.

We really, let’s be honest, want our customers to like us, we want our coworkers to like us, and we want to find the best possible solution for the problems that we’re facing.

That best possible solution isn’t always obvious. What do we do with that?

Most of us have been through the scenario where a customer came to us, they asked for something, we built it, we delivered it, and then it didn’t actually solve their problem. We’ve wasted time on something, and we have to support something that didn’t really meet their needs.

When people ask for solutions, they’re asking for their assumption of what the solution to their problem is. A lot of times, they haven’t really thought about the problem they’re really trying to solve, and honestly that’s not their job.

It’s our job as product people to think about how we’re going to come up with solutions.

For example, let’s say we had a customer who came to us and said, “I need to rent a car.” Now, on the face of it the best possible customer service would be to rush right out, and get that person into a car rental agency, and put them in a car as quickly as possible.

If we’re bound by things like SLA metrics and we have to respond to customers within a certain number of hours, or we have to respond to every single user voice, or every single email query, then we tend to game-ify ourselves into these non-optimal solutions.

Let’s think about why that person asked for a car. It could be that they’re about to go shopping, they don’t own a car, they’re going to buy a lot of groceries, and they don’t want to take them home on the bus. It could be that they’re having a vacation, and they want to drive along PCH and take in the scenery. It could be that they have a lot of relatives in town, and they won’t all fit into their tiny Prius.

For each of those scenarios, there are different solutions that may make more sense.

In one case, it may make more sense for someone to grab a Lyft, in some cases maybe you need to actually rent a van, and in some cases maybe you can borrow a car from a friend. If you’re actually out on a vacation and you want to take that drive along the coast, then sure, you do need to rent a car… but in that situation, you probably want to rent a fun to drive car. You don’t want to rent a beater or an SUV.

If we just rush someone straight to the car rental agency, we’d end up with that subpar solution.

As customer-oriented product people, we have to take a step back and ask “why?”

This is something that we also need to do internally, and I find this happens even less often internally because we assume that we understand the why’s.

As soon as we’re working in an office with someone, in a team with someone, we assume a shared context that doesn’t usually exist. There are people that I have literally sat across from for weeks on end, and yet we’ll still have underlying assumptions that are different from each other.

The “why” is always more interesting, it’s more useful, it’s more actionable, and it’s more trust building than the “what.”

That last one’s a little bit interesting because people think that asking “why?” sounds almost a little accusatory. If you have a small child, you know it can actually get pretty annoying when people keep asking why.

We need to add a little padding around it, but fundamentally when people ask why, what they’re actually saying is, “I want to know more about this. I am interested in you, I care about what you have to say.” As opposed to what, which has this whiff of, “how quickly can I get you out of my hair?” That’s not how we want to build these relationships.

Let’s think about it: someone comes to you, they have a request. It could be the customer who says, “I need to rent a car,” or, “You need to build this feature,” “You need to support this use case.” It could be your boss who has given you a task, “You need to do this thing. You need to manually sort through this data. You need to write this spec.”

The first question we really have is: “What’s the problem you’re trying to solve?” That can be pretty tricky to ask because if your boss says, “Do this,” and you ask, “Well, what’s the problem you’re trying to solve?” your boss might just say, you know, “Get on it. Let’s do it.”

Again, we need some padding, and so we want to say, “Okay, just to make sure I understand it seems like the outcome you’re looking for is X, is that correct?”

If your boss says, “Manually sort this data,” what they probably want is clean data. If someone says, “Get me a drill, “ they probably want quarter inch holes, but you need to validate that.

The best way to do it is give that, “Just to be sure I’m clear, this is the outcome you’re looking for, is that correct? Am I missing anything?”

This gives people the opportunity to step in and say, “Actually, this is the thing I needed,” or, “Actually, here’s some more information that I assumed that you knew, but you probably didn’t.” Or, “I’m sure I’ve told you this a billion times.”

Having been someone who’s managed teams, I have always had things that I’m pretty sure I said a billion times, and yet either I didn’t, or people didn’t hear me. It doesn’t really matter because the outcome was the same, and they weren’t privy to that information, and that meant they weren’t going to do as good a job as if they had the information they needed.

We want to ask why. Why do you need that done? What’s the outcome you’re hoping for?

A lot of us, when we’re interacting with customers, what we hear is basically a demand for features, and it’s hard to ask why because what they really want to get to is when. When are you going to build this thing?

It’s useful to take that step back. I like to announce it as such, and say, “You know what? Let’s talk about delivery deadlines sometime in the future, in a few minutes, right? But just a second. I want to be sure I understand something. It sounds like you’re asking for this feature. Just to be sure I understand, if we had already built it, what would it allow you to do? Essentially, how would it make your life better if you had this thing?”

The thing that I found surprising is that when you ask people some polite version of “how would it make your life better?” a lot of times you get a non-answer.

You’ll get an answer like, “Well, it would just be nice to have.”

We don’t have time for building things that are nice to have.

How would it make your life better? What would it allow you to do? When someone really needs something, they’ll have a story for you.

“Uh, you know, it would take me half the time to sort my data. Oh, I wouldn’t have to waste head count on this position. We could start coding tomorrow.” When people have a story, that’s something worth doing.

When a customer comes to you and you say, “What would it allow you to,” sometimes you get the non-answer of, “But your competitor has it.” That’s actually just pushing the can down the road a bit, and what you say to that is to say, “Okay, I understand. You’re right, our competitor does have that feature. I’m curious if you were using that feature with Google, Facebook, et cetera, what would it allow you to do?”

I can’t count the number of times I’ve had customers who say, “Well, it would just be nice to have.”

If the reason that you’re going to lose a feature sale is because of a checkbox feature that someone’s not even going to use if they go to your competitor, that’s not something we should be trying to win on.

You may lose a sale in the short-term, but you’re going to have someone who isn’t really having their needs met, and they’re ripe to be plucked back in a year or two.

We ask, “How would it make your life better?” Maybe we hear that it really wouldn’t, and then we proceed.

Sometimes you’ll hear a variation like, “It might be useful in the future,” and, again, kicking the can down the road a little bit, and you got to ask one more question which is, “Okay, I’m curious how do you see your organization changing in the future?”


“Well, you said it might be useful in the future. I’m curious how are things going to change such that this might be useful in the future?”

You want to be very polite and smiley, you’re very nice about this, but the point is if you don’t know how the future’s going to change, and I don’t mean the next five years because no one knows that. I mean the next six months.

If someone can’t give you an answer, then it’s not a real need.

It’s a wish, or maybe it’s leverage to try and get a deal. Or maybe it’s just someone who’s trying to look smart in a meeting, and I think we all know the people who are in meetings trying to look smart, being loud, man-splaining you, et cetera. “How will it make your life better? What do you anticipate changing in the future?”

The other thing is that when we jump in trying to understand problems, or provide solutions, a lot of times it’s useful to know what people are already doing, and how they feel about it. That sounds so incredibly simple as to be obvious and dumb, and yet I have been surprised by the number of times I’m in meetings where we really don’t know. Sometimes it’s, “Hey, could you take a step back? I’m just curious, could you walk me through what you’re doing today? I mean, I know high level, but I’d love to see the details.”

When someone walks through a process for something, you might see exactly where their pain point is. Maybe they asked for this feature that’s a widget, but you can see that actually they’re having a hard time with this other area, and the widget might be one solution, but as a product person you can see it’s actually a poor solution. Or it’s something that will be applicable to this customer and no others.

In a meeting, a lot of times, where there’s a debate between people who think that one side’s doing it right, and the other side’s doing it wrong, a lot of times that comes down to an assumption about what each side is actually trying to do.

“Could you walk me through what you’re trying to do,” is a good way to defuse that, and let people say, “Look, this is just what I want,” because that’s, at the end of the day, what we’re trying to do.

We’re trying to help people get what they want done.

If we do that, we will seem amazingly smart, and helpful, and kind, and everything else. It’s a really good hack.

“Could you walk me through what we’re doing today?”

This is also really great advice when you get put into a new role. Let’s say you got promoted to manager. Congratulations! You can’t just step in, of course, and say, “This is how we do things now.” You can try, but you’re going to get a mutiny.

If you join a new company, a new role, people have established practices. Some of them are good, some of them are bad, and if you don’t know the history of why people are doing one of them, you don’t have a lot of position to say, “Let’s do things differently.”

If you can go into a new organization, or a new customer, and say, “You know, walk me through what you’re doing today. Okay, that’s interesting. Okay, you know, how did that happen in the past? Do you have a sense for how that decision was made ? How’s that going? You know, if you could change anything about it what would it be?” This kind of conversational approach gets people to trust you, and it gets you a lot more insights than you would ordinarily have.

Now, I’ll note one thing here, is that taking that step back and asking supposedly “dumb” questions can be particularly tough if you’re a woman, and if you’re in a meeting where you think people are just a little too quick to think that you are asking dumb questions. This is where it’s useful to borrow a new person. This might genuinely be someone who’s new on your team, or you could literally just grab one of your coworkers and ask them to come into a meeting, this doesn’t work internally but it works well with customers, “Come into this meeting pretend to be the new guy, new gal.”

The new person has a lot more freedom to say, “Hey, I bet everyone in the room already knows this,” — hint: they don’t — “But could you walk me through what you’re doing today?”

You will get a ton of insight out of that, and the customer won’t actually mind getting to repeat history, and probably halfway through their diatribe they’ll be like, “You know what? We didn’t even tell you that our entire back end system changed in the last year, did we? (haha).” Yeah, that’s probably something that you should’ve known.

“What are you doing today? How is that going?”

Once they’ve finished talking about that, then you’re going to reiterate. This is active listening. This is the thing that makes you feel a little bit like a kindergarten teacher, but trust me, it works. I wouldn’t tell you this if it didn’t.

“It sounds like you need to do X, and Y, and Z. It sounds to me, like you’d be happier if magically these things were fixed. Is that accurate? Am I missing something?”

Give them that option to correct you, or to add things.

Now, there’s a magic thing that happens once you’ve reiterated back, which is that you have absorbed like 80% to 90% of people’s anger at this point, even if you don’t actually solve their problem. They’re amazingly happier that you took the time to understand it in the first place. There are studies to back this up. Stanford has been doing some research with doctors and malpractice, and they found with a control and experiment group, that surgeons who made a mistake, and apologized were much more likely to not have suits brought against them, or if there were, they settled for much less money. Essentially, if someone sewed a sponge in you by mistake… you really want to hear that person say sorry. If they don’t, you’re going to take them to court for all they’re worth, so we can do that.

That leads to my next point, which is — apologies are free.

Any woman who’s ever worked for me knows that I always tell them, don’t apologize. For your ideas, don’t apologize. Don’t say I’m sorry about this idea, or I’m sorry that I want to do something a new way.

But when it comes to a customer who is feeling wronged, who is feeling like, I’m already upset, go ahead and apologize because that de-fangs even the angriest customer.

If someone comes in and they’re furious, “I can’t believe that you’ve lost my data. I’m going to quit your account right now, this is ridiculous,” and you say, “I’m really sorry. We did that, we lost your data. That’s really awful, and I don’t want that to ever happen again. Let’s see what we can do about it.” Those are magic words.

It’s very hard for someone to hear something that is humble and accepting of responsibility, and keep yelling at you. They trail off, “Well, you better see what you can do.”

Give them out, apologies are free.

It doesn’t matter if it’s not your fault, if someone lost their data through something that was user error, it doesn’t matter. You’re not going to talk them into that. Telling people that’s the way the feature was designed has never made anyone happy ever, so apologize. You can do that.

Apologies are free. They’re also rare, especially good ones.

Follow-ups are also rare.

Even if you didn’t provide the answer someone wants, just the fact that you reach back out to a customer, or a coworker a couple weeks later to give them an update, “Hey, I looked into that solution. It turns out we’re not going to be able to address it. I’m really sorry, I just wanted to let you know,” people are amazingly happy about that because they never hear it.

The traditional vendor/buyer relationship is, “We’ll put it on the roadmap,” and then it’s on the roadmap, and it’s on the roadmap, and they never actually get the feature.

Internally, when people have suggestions, “Oh, we’ll consider it. Oh, put it in the suggestion box,” and there’s never any closure.

That’s the final thing I have to talk about: people like closure.

As humans, closure makes us feel satisfied. We like to know that something is going to happen even if it’s not the thing that we expect.

Customers and teammates don’t have to agree with your decisions, but they need to know why you made them. They don’t even need to understand why. It’s just that they need to know that you didn’t have malicious, or stupid reasons for making your choice.

“Based on these reasons, I am making the decision to do X.”

Someone may disagree, but they’ll grumble, “Well, I guess I understand why you’re doing it. I still don’t agree with you, though.”

That’s okay, customers in that scenario are going to be a lot happier.

In this case, someone’s come to us, they’ve demanded a feature, we basically talked them out of it, we’ve explained why, and yet they’re still not furious at the end. In fact, a lot of these customers end up being incredibly loyal because even though they’re not getting what they want, they know that you understand what they need. This works both internally and externally, and it’s been tremendously useful in my career.

The bar is really low for honest communication, and for digging in to find out what the underlying problem is.

We can do better, and it’s an amazing hack that most of the people around us don’t know about, so we should take advantage.

The customer is not always right, to be honest, no one is always right, but you can, and should control your own narrative. That means taking in what you’re hearing, and reflecting on it, and asking questions, and redirecting it to something that is more positive, and something that you can control.

I’m sorry am not able to take questions live, but I really do answer them.

I’m @cindyalvarez on Twitter or cindy@cindyalvarez.com. If you have questions, feel free to shoot them over to me. And that’s my last piece of advice: when people say it’s okay to ask questions, they mean it — take advantage. Enjoy the rest of your conference everyone!

“The Art of the Interview: How to Evaluate and Handle Candidates in Your Pipeline”: Aline Lerner with Interviewing.io (Video + Transcript)

Aline Lerner / CEO & Founder / interviewing.io
Gretchen DeKnikker / COO / Girl Geek X


Gretchen DeKnikker: Hey, everybody, welcome to our next session. Couple housekeeping notes. Make sure that you ask your Q&A at the bottom and then vote them up so that we know which ones to ask when we get to the Q&A section. The videos will be available online just after the sessions wrap up. Without further ado, I’m so excited. I’ve just met Aline and I’ve become a super fan in one phone call. It was a little crazy and so now, I stalk her.

Aline Lerner is the co-founder and CEO of Interviewing.io, which she’ll tell you a little bit about, but I think the product is pretty interesting especially for the audience here. She’s going to be talking about the art of the interview and really looking at it from the angle of not just you being the interviewer, but what are the other elements and what kind of feedback do you get? So, without further ado, welcome, Aline.

Aline Lerner: Hi, everybody. I’m also a huge fan of Gretchen’s and have been stalking her since I met her, so it’s definitely been mutual. Really excited to talk to all of you today about technical interviewing, probably through a lens that you haven’t seen before, because we have some cool data that normally you don’t get. Rather than talking about what makes someone a good interviewee, today I’m going to talk a little bit about what makes somebody a good interviewer.

I’m the CEO and co-founder of a company called Interviewing.io. We are a practice platform for technical interviewing, but we’re also a jobs platform, so if you do well in practice, you get to talk to top companies. The cool thing is everything is anonymous. We collected a ton of data and I’m going to share some of the things we’ve learned today. I’m just going to jump right in. All right. Great.

How it works — once you’re a user of our platform … this is a little bit of setup so you know where our data is coming from. Once you’re a user of our platform, you can see some time slots, grab one, and then, at go time you log in, and you get a mock interview with an engineer from a top company who is good at interviewing and good at giving feedback. After each interview, there is feedback, which you’ll see in a moment. Top performers actually get to interview with companies right on our site and those interviews are anonymous as well. After each interview, whether it’s real or whether it’s practice, there’s some metric feedback. This is the feedback form for interviewees. Hopefully, you can see some of those questions. We ask things like, how was the interviewee’s technical ability, communication ability, and problem-solving? Then, the interviewer will ask stuff like … we’ll ask the interviewer to rank the candidate on stuff like technical ability, problem-solving, and communication, and then, we’ll actually ask the candidate to rate their interviewer and this is what this talk is about.

Normally, as most of you know, an interview is one way. You don’t really get to rate your interviewer and if you do it’s a survey afterwards and it’s not right then. We ask everything from whether you want to work at this company and with this person to how excited you’d be. Then, we also ask how you think you did and that will come up at the end. Great.

We have a ton of data. We’ve done about 20,000 interviews on the platform and I’m just going to get down to brass tacks and show you feedback snippets. We try to distill a lot of signal from these and come up with a few broad categories for what the traits of good interviewers look like. This is going to be more data-driven and hopefully less about platitudes. I’m really excited to answer your questions at the end.

Before I get into the details, one thing, a lot of people think that if you work at a company with a top brand, it’s a really good crutch. If you work at a Google or a Facebook, you don’t have to be as good of an interviewer. That’s not strictly true from the data that we’ve seen. In fact, we saw no statistically significant relationship between brand strength and whether people wanted to work with employers on our site. Brand will get candidates in the door, but once they’re in the door, they’re essentially yours to lose, so keep that in mind.

The first kind of huge thing that we noticed among candidate feedback was that when you’re interviewing people, it’s important to be a human being. So, for each of these broad categories, I’m going to show you exactly what the candidates said. For instance:

  • “I like the interview format, particularly how it’s primarily a discussion about cool tech as well as an honest description of the company. The discussion section is valuable and may better gauge fit. It’s nice to have a company that places value on that.”
  • “Extremely kind and generous at explaining everything they do.”

When I’ve listened to some of these interviews, and I haven’t listened to all 20,000, but I’ve listened to a lot, the best interviewers are people who take the time to get to know the candidate even though interviews are anonymous. So, what are you working on? What do you want? Then, they’ll create a narrative where their company is the next logical step in that candidate’s journey. So, everything you’ve ever worked for is going to culminate in you working here.

Here’s the bad:

  • “A little bit of friendly banter, even if it’s just, ‘How are you doing?’ at the beginning of the interview would probably help the candidate relax.”
  • “I thought the interview was really impersonal. I could not get a good read on the goal or the mission of the company.”

Choosing the question. This is a very erudite topic of discussion, and I know everybody has opinions on what makes for a good interview question. We just have the data, so I’ll just tell you what the data said. So, here’s feedback from people that thought the question was good:

  • “This is my favorite question I’ve encountered on this site. It was one of the only ones that seemed like it had actual real-life applicability and was drawn from real or potentially real business challenges.”
  • “I like the question. It had a relatively simple algorithm problem and then built on top of that.”

One of the recurring themes here is that candidates are used to these generic algorithmic problems and what really gets them engaged is taking it to the next level and tying it into something that your company actually does. This is especially true if people may not have heard of what you do, or you are in a space that by default doesn’t get people excited. Anything you can do to get in the candidate’s head and ask them something interesting and then have it stick after the interview is over is going to be good. Then, candidates also feel like you put in effort.

One of the things that we’ve noticed is that whenever there’s this notion of value asymmetry in an interview, so the candidate is expected to put in work, but the interviewer is not putting in work, that’s not good. You want it to look like you’ve put in work yourself.

Here, let me show you some of the examples of bad questions:

  • “This is not a good interview question. A good interview question should have more than one solution with simplified constraints.”
  • “Question wasn’t straightforward and required a lot of thinking, understanding of setup.”

You don’t have a lot of time with a candidate. You want to make sure that the time that you do use is used on being able to build a connection with them and then actually seeing if they can think rather than jumping them through hoops.

“Is there any way to sharpen the image? Text is blurry.” We’ll send out these slides afterwards. Sorry about that, guys.

That’s really one of the most important things too is making sure that you are getting signal from these people in a way that’s not arbitrary. Setting up the problem to gauge whether somebody’s a thinker and a problem solver rather than catching them on arbitrary a-ha moments.

Writing a really good interview question is hard. It takes time, especially if you’re going to tie it something you do at work, it’s even harder.

One of the best tricks that I’ve seen for doing this is coming up with a shared Google Doc for your entire team or really any collaborative software. Doesn’t matter. Any time you do something at work that made you think, and it doesn’t have to be cool. The bar for whether it’s cool can be really low so you don’t have to worry about it, but any time you do something that you think was non-trivial, just throw a quick line in that doc.

Then, you can come back later and look at all the cool things your team has done and use that as a jumping off point to craft questions that are unique to you. Then, candidates will be like “You did put in the work,” and you do stick in their heads a little bit.

Asking the question itself — One of the best interviewers I ever met was a chief architect at a large software company. He used this expression that I really liked. He said that the purpose of an interview is — “can we be smart together?” That just really stuck with me, and I think that the way you ask the question can really determine whether you can be smart with somebody else or not.

Here are traits of good interviewers when it comes to asking a question:

  • “He never corrected me. Instead, asked questions and for me to elaborate on areas where I was incorrect. I very much appreciate this.”
  • “The questions seem very overwhelming at first, but the interviewer was good at breaking it down. I like the fact that you laid out the structure.”
  • “I’m impressed by how quickly he identified the typos in my hash computation.”

Engagement is, of course, important when you’re asking the questions so you actually have the opportunity to see what it’s like to collaborate with somebody.

Another really important part of this is, and you can see this in the feedback, is layering complexity. This idea of taking a question that can start off very simply at first and then building on it. Building on it in a number of different ways and you can set up benchmarks and say, “A candidate that’s good enough is going to get through the first three portions of the question. Somebody who’s really good is going to get through four and someone who’s exceptional is going to get through five. Then, somebody who gets past that is probably going to challenge the interviewer. The sooner you can turn something into a discussion between equals and an opportunity to collaborate and problem-solve together, rather than a one-way exercise where you’re trying to see if somebody’s stupid or not, which is the worst way to interview, the better it’s going to be.

Here are some examples of poor interview feedback:

  • “It was a little nerve-racking hearing you yawn while I was coding.”
  • “What I found more difficult about this interview was the lack of back and forth.”

Anything you can do to engage with candidates and build on a question is going to be the best and if you can couple that with the previous point, come up with questions that are original to your company and layer complexity in ways that other people couldn’t, then you’re going to be in a very good position.

What happens after the interview? This is one of my favorite takeaways from our data, and it’s completely counter-intuitive. As you recall, we ask people how they think they did on the interview as candidates and then we also ask interviewers how the candidate actually did. We actually graphed this. The x-axis here is the actual score on a scale of one to four for somebody’s technical ability and then the y-axis is their perceived score.

As you can see, there’s quite a bit of imposter syndrome. In fact, we found that imposter syndrome plagues a disproportionate number of our users. So, what is imposter syndrome? It means that you think you did poorly when you did well. Now, here is the crazy part. If a candidate did well and they think they did poorly and you don’t give them immediate actionable feedback and let’s say you let them sit on it for days, they’re going to get into this whole self-flagellation gauntlet.

They’re going to leave that interview and then they’re going to start thinking one of two things: either they’re going to think, “Man, that company didn’t interview me well. I’m good at what I do, and I don’t think that company knew how to get it out of me, so they suck.” Even worse, what’s going to happen is you’re going to think, “Oh, I’m a piece of shit. Now, they know I’m a piece of shit, and I totally didn’t want to work there anyway.”

What ends up happening is unless you tell people they did well, immediately after they did well, you end up losing a lot of good candidates because, by the time you get back to them, they’ve completely talked themselves out of working for you.

So, don’t let this happen. Don’t let them gaze into the abyss, and give people actionable feedback as soon as possible.

Actually, I saw one of the comments. I want to leave a few moments for questions, but one of the comments on the side was “imposter syndrome is a women’s curse.” We ran some data on our platform to see if imposter syndrome is more prevalent in women or whether it’s distributed across both genders. As it turns out, both men and women are equally plagued by imposter syndrome.

The other interesting thing that we learned, and we haven’t written about this yet but we will, is that the better you are at interviewing, the more prone to imposter syndrome you are, and the worse you are, there’s the opposite called the Dunning–Kruger effect where you think you did well when you, in fact, did poorly.

Thank you, guys. I’m really excited to answer some questions. My email and Twitter are also on the slide, and I’m happy to answer them offline as well. Sorry, I saw some of you said some slides were blurry. We’ll send them out afterwards, not sure why that happened.

Gretchen DeKnikker: Great. Thank you so much. We have a few questions here and you guys still have time to submit and vote some up. So, the first question is, what do you think of take-home projects instead of whiteboard style coding interviews for those who grew to dislike them?

Aline Lerner: Yeah. I wish I had it with me. I drew this picture a while ago called the value asymmetry graph and I mentioned it in the talk as well. Value symmetry is this notion that we have two sides, both of them are putting in equal amounts of work. I think that if you’re a company with a top brand, you can get people to slog through a lot more shit than if no one’s ever heard of you. When you’re deciding as a company whether you want to use take-home challenges, that has to be one of the things you consider is, how badly do people want to work for you? If you’re Google or Facebook, at least before you get into the interview, at which point the playing field doubles a little more, people are probably going to be much more motivated to work for you than some company that just started and has no funding. You can’t always look to those companies and say, “If they use a challenge, we can too.”

If you do use a challenge, just like with interview questions, the best ones tend to be ones where it’s thoughtful and where it’s representative of the actual work because then the candidate is getting some value out of it… doing this work is going to be like the stuff I’m going to do every day, so here’s a preview.

On Interviewing.io, what we’ve seen is the customers of ours that have people do coding challenges after their technical interviews — and if those challenges take longer than an hour, the best people tend to drop out because in this market, engineers are flooded with opportunity. If you make them do work, they’re probably not going to do it unless it’s really, really interesting work or some companies pay people. If you have something that’s going take five or six hours, consider giving them a consulting fee and see if that changes anything. But, you should probably just have a really good challenge that people want to do or not have a challenge at all. That’s different for data science and engineering also. Sometimes that makes more sense. For software, you probably don’t want to do it.

Gretchen DeKnikker: I have one I want to put in because we’ve heard this a few times. We’ve been recommending it and everyone’s like, “It’s in private beta. How do we get access?”

Aline Lerner: Yeah, we’re opening it up really, really soon. So, we have a really long waiting list and we’re so excited to get through it. For now, we’ve been favoring people that are still in the U.S. because it means that we can place them a little more easily. We don’t always look at it, but in tie situations, we’ll potentially look at someone’s years of experience because we have more job openings for senior folks than junior ones. Regardless, we are working on a way to open it up and I expect it will be opened up by next quarter. So, everyone that’s on the wait list, I’m really sorry and if you have job interviews coming up soon, send me an email and we’ll see what we can do.

Gretchen DeKnikker: Yeah. Awesome. Yeah. It’s a great problem to have though, right?

Aline Lerner: Well, we really want to move on from that and just open it up, but yes..

Gretchen DeKnikker: Next question is, I’m unfamiliar with it but very interested. How anonymous is anonymous, first names, voices? Does that anonymity help level the playing field for women and people of color?

Aline Lerner: Yep. When we say anonymous, we mean truly anonymous. Everybody gets a handle. So, my handle on the platform is nihilistic defenestration. If you ever run into … I think I’m the only one that has that. IF you run into that, it’s me. It’s why I quote Nietzsche and wear black, but, in some cases …

For practice interviews, you can hear people’s voices. From voice, you could potentially glean gender and we don’t mask accents. However, we did just two days ago, we just got a patent on real-time voice masking. In real-time, we can make women sound like men or men sound like women or make everyone sound androgynous. If a company wants to use that for their interviews, then they have to turn it on across the board. If you let candidates decide, then there’s this other bias notion, who turns it on and who doesn’t. This way it’s turned on for everyone and we leave that at our customer’s discretion.

We did try making everybody change genders in practice to see what effect that would have and we found that surprisingly, at least to me, it didn’t really change how people did. So, women didn’t do better when they sounded like men and men didn’t do better when they sounded like women. We did notice that women were doing a little worse across the entire platform and I was confused by that ’cause I don’t think women are worse at computers.

What ended up being the case was that women were disproportionately quitting the platform after one bad performance in practice. Once you corrected for people that were quitting after one bad performance, well, the gender-based disparity went away entirely. So, we’re actually rerunning that data now that we have a lot more interviews and we’ll report back. Back then, we had a lot fewer, so all of that … As if the case with science, or in our case, pseudo-science, the stuff can be overturned.

Gretchen DeKnikker: All right. I’m going to do one more. We have 1,000 questions. I think we could mostly stay on this topic all day. You do have a blog, right?

Aline Lerner: Yeah.

Gretchen DeKnikker: So, if you want more from Aline, check out the blog on Interviewing.io because she’s-

Aline Lerner: I’ll put it in the chat.

Gretchen DeKnikker: Perfect. Yeah. There’s a ton of information. So, I’m going to do one more. You touched on this a little bit, did any data, anecdotal or otherwise, bubble up around bias? For example, knowledge of algorithms, which can indicate recency of learning, younger candidates or those who got computer science degrees versus coming from alternative backgrounds?

Aline Lerner: Oh, God, yes. There’s so much bias. The most compelling bias or, I guess, the strongest signal of bias that we’ve seen has been against people with non-traditional educational and work backgrounds. If you didn’t go to a top school and you didn’t work at a top company, it’s going to be really, really hard for you to get in the door. What we’ve seen repeatedly, and this is the thing that blows my mind, is with some of the bigger customers that we have where they get a lot of inbound applications, people have applied, they’ve gotten rejected at the resume screen, so before anybody ever interviewed them, and then they came in … Then, they used our platform, practiced and got good enough to … or, in many cases, they were already good enough, but they got access to our employer portal, interviewed with those companies, and actually got hired.

Of course, once they unmasked after their interview, the recruiting team can see, “Oh, shit. This person is in our ETS but we rejected them six months ago before anyone talked to them. Oh, shit. There’s something wrong here.” In fact, 40% of the hires we’ve made in the last two years have been people that would have been [inaudible 00:21:03]. Companies admitted, they’re like, “Well, I never would have … What the Hell?” That’s why we insist interviews be anonymous, or they actually had been turned away by that employer.

Gretchen DeKnikker: All right. Well, I would love to stay doing this. Thank you so much for coming in and giving this talk. I think it was hugely valuable. Everybody, we’re going to take a short break. We will be back in 15 minutes, so go grab a snack and some coffee and we’ll see you at 1:20. Bye.

Aline Lerner: Bye, everybody. Thank you for having me.

Gretchen DeKnikker: Thank you.

“CTO’s Lessons Learned on the Journey from Software Developer to IPO”: Cathy Polinsky with Stitch Fix (Video + Transcript)

Cathy Polinsky / CTO / Stitch Fix
Angie Chang / CEO & Founder / Girl Geek X
Sukrutha Bhadouria / CTO & Co-Founder Girl Geek X
Gretchen DeKnikker / COO Girl Geek X


Angie Chang: Hi! Welcome to Girl Geek X Elevate, our first virtual event for the Girl Geek Dinner community. My name is Angie Chang, CEO and founder of Girl Geek X, and this is Sukrutha Bhadouria. We wanted to say “thank you” for joining us this Wednesday morning for our Girl Geek X Elevate. We have been hosting Girl Geek dinners here in the Bay Area for over 10 years — we’ve hosted over 170 dinners at 100 companies, over 100 companies — and we are excited to be able to expand and have world domination. When we thought about 10 years of Girl Geek Dinners, we wanted to rebrand and say…

is for the community, our community of 15,000 women. It is not just dinners — it’s events and podcasts and webinars and different formats that can help us reach more women globally. Our community of women has grown over the last 10 years, and we’ve heard lots of feedback from women that want to tune in to last night’s dinner by podcast, on their drive to work, or whether they want to tune in from where they are, which is not necessarily where we are in San Francisco. We’ve also taken this chance — and this opportunity to partner with mission-aligned companies, and today we’re grateful to have the support of fantastic mission-aligned sponsored like Mozilla, The U.S. Digital Service, PayPal, SalesForce, Intel AI, Clever, Quantcast, and interviewing.io.

Gretchen DeKnikker: Is that me now, Ms. Angie?

Angie Chang: Yes.

Gretchen DeKnikker: Okay, hi everybody. I’m Gretchen DeKnikker, COO here. To build on what Angie was saying about how we are looking to change things going forward, and expand. We’re very excited, that we’ve worked very, very hard to have our speakers from a wide range of backgrounds today. 70% are women of color, and 40% are black and Latina. And we had a very special focus on that. We wanted to make sure that we’re bringing underrepresented voices to the table. The whole thing was to create opportunity for women to gain visibility and recognition and to share with the community. I think at this particular time in history, it’s really important as we get a seat at the table as women that we pull up another chair and that we be very mindful of the limitations that are greater than just being a woman, and the challenges. So just being more supportive there.

We do want to have more voices at our table. We’d like to invite in ideas on bringing more women of color into the fold, your guys’s ideas on how do we partner and bring more male allies in. These are all things we’re gonna be focusing on now that we’re on the other side of this event. Part of wanting to do this particular event was, like Angie said, to reach more people. But also to … Another thing that we’ve heard is mid- to senior-level career women aren’t necessarily represented strongly at the events, which is understandable. People have other things to do in the evenings.

We wanted to create this opportunity because as you grow in your career, the theme today is growing from a manager to a leader. So what happens when you become a manager of managers. In every stage of your career, the job is different. We have some great sessions today to help everybody on that journey.

We’ve got one on self-awareness and ego with Minji Wong. We have one on the art of the interview, especially around the candidates interviewing you with Aline Lerner from interviewing.io. We’ll talk about delegation and empowerment and advocacy with Arquay coming up just after Cathy. And planning and goals and finding those metrics that matter. How do you lead by metrics when you’re not doing the work yourself, and you’re not in there every single day. And I think we’ll get into that a little bit at the engineering panel at the end of the day. So, Sukrutha.

Sukrutha Bhadouria: Yeah, hi. I’m actually so excited because I’m seeing people dial in from everywhere all over the world, how cool. I saw people dialed in from San Francisco, Florida, and I also saw someone comment on our shared earbuds. For me, why we’ve been wanting to do this, especially have technical women give talks, not just about leadership, but about … because there’s more important things to talk about. Then we have talks about security, team learning, and just keeping yourself up to date in terms of your technical skills.

Why is this important is because you and I got into women on stage talking about what it’s like to be in technology beyond just what it’s like to be a women in tech.

So we have speakers from Facebook, from LinkedIn, from Salesforce who are going to be providing their insights, their experiences. And hopefully you all have, not just lessons learned, but you also leave with inspiration today to keep at it, going forward with it. So with that, I’m super excited to introduce Cathy, whose our first speaker, so who’s going to be speaking next.

Cathy Polinsky: Good morning, everyone.

Sukrutha Bhadouria: So really quickly I wanted to introduce Cathy. Cathy is the CTO of Stitch Fix, which is awesome. Cathy and I first met when Cathy was working at Salesforce as an SVP. She’s going to talk about her journey. What I really definitely want to call out is right now she leads the engineering team at Stitch Fix, and supports the company’s efforts to deliver services that meet the clients’ needs. Cathy has been working in great companies like Yahoo!, and Amazon, and of course Salesforce where we met. So Cathy, go ahead. I’d love to hear what you have to say.

Cathy Polinsky: Fantastic, thanks. And thanks for this opportunity. I just really appreciate having an opportunity to network and talk with other women. I just got back from a board effect meeting two weeks ago where we were talking about needing more women representation on boards, and more women representation in the industry. As many of you all know, we’ve come really far, we’re seeing a lot more women in the industry. But as the numbers come back, they can be kind of depressing that even though the number of women in software, in technology organizations has grown, the percentages haven’t changed that dramatically over the last decade.

I hope we can work together to build a more inclusive community and support system. I wanted to share my story of how I got to be from a kid who grew up in Pittsburgh, work my way through to be a software developer, and now to a CTO at Stitch Fix.

It’s hard not to be able to see everyone here. I’m not sure how many of you know of Stitch Fix. I’m hoping that there’s a lot of clients out there, but I’m sure there’s many of you who have maybe heard of Stitch Fix, but don’t quite know what we do. So let me just start a little bit with that so you can get a sense of what I do on a day to day basis.

Stitch Fix is really disrupting how people can find clothes and items they love, and look and feel their best every single day. So as many of you probably have shifted your buying behaviors to online, I’m the same way. I hate going shopping. Before I even learned about Stitch Fix, almost all of my purchasing was done online. I never really go to the store, and yet when I’ve tried to buy clothes online, it’s a really broken experience. There’s so much that goes in your head when you walk into a store. What items you think that look good for you and match your style preferences. And there’s so many things that go in your head when you walk into a dressing room to figure out whether something looks good on you, your complexion, your body type. There’s a lot that goes into thinking about your wallet and your price preferences for whether you’ll take that item and spend that money to go to check out.

When you go online and try to buy something, you get a flat image, you may get a review, but you won’t really know if that person is like you, if they have the same style preferences that you may have, or the same body type. So Stitch Fix really disrupting that business. You fill out a detailed style profile. It’s kind of like a dating profile. Everything that goes in your mind for what you do when you’re walking into a store, and what things generally work for you, and what things don’t. And then you get paired up with a personal stylist who takes that information, paired with tons and tons of algorithms and data science with detailed recommendations that are tailored exactly for you to pick items that will work for you. You get a box delivered to your door, you don’t know what’s gonna show up in that box. You open it, try it on at home. Hopefully find things that you love. But easily return things back that you don’t. You only pay for what you keep.

This was just so disruptive when I really got behind the scenes to learn about this business model and what it was doing and how we’re impacting clients lives that I was really excited to join this group, and now I’m the CTO. My role expands across engineering, IT, product management, and security. So it’s a pretty expansive role, and every day I get to do something different, and I’m learning new things as well.

I just feel very fortunate to have this job and to work with such amazing women here at the company. But I wanted to talk to you about my path to get here. It hasn’t always been easy, but I’ve had a lot of support along the way. I wanted to talk to you about things that I’ve learned along that path, and support systems that I have really benefited from that we can also help others along the way, as well. So I mentioned I grew up in Pittsburgh, Pennsylvania. I was in elementary school in the early 80s, and no one had computers at home. Personal computers were just spinning up and the Apple 2s were starting to make an entrance into elementary schools. What’s amazing is that Apple really wanted to nurture that community. They were giving grants out to schools, and donating computers to elementary schools. I heard they even had a surplus of Apple 2s when they launched the Macintosh and say they were really thinking about how they could use that for good. And I was one of the beneficiaries of that. My school took advantage of those programs and created a computer lab, and my teachers loved it. Every week we had a computer lab time where we got to go to the lab and learn computer programming.

My first language was Logo, which was a little tiny triangle on a screen, kind of like the predated Scratch, and you can draw little pictures. You can draw boxes and houses and make simple commands. But it was a real programming language. You could do loops and you can do procedures. It really started that spark for me of what technology could be. I carried that forward for quite some time, even though, after elementary school there were no real programs for me. Our middle school and our high school really didn’t have many computer classes. In high school, I was told about a program at Carnegie Mellon, which was near where I lived in Pittsburgh for a summer program for computer science. And I applied and got accepted into the program, and it was amazing. The morning was taught by a computer science professor at CMU. It was about algorithms and data structures. And the afternoon was special projects where I go to see an arm and try to program an arm robot to make knots and do some object orient programming to make and solve mazes.

After that summer, I really thought that this was something I was interested in and I’d want to pursue. And I had a lot of encouragement in a way through the professor that I got to meet at CMU who talked to me about colleges and talked to me about studying computer science going forward. That spark that I had through both teachers and professors really carried me a long way to thinking about this field because frankly a lot of people of my generation, a lot of women in my generation are only here because of having that spark from someone else, generally a family member. There’s generally someone, a dad, an uncle, even a mom who was a scientist, or someone in that field, but I didn’t have that. But the teachers and the professors that I did engage with really were my spark to enter in the field.

Fast forward, I went to a small liberal arts school in Philadelphia, Swarthmore College and studied computer science. Had a lot of support there for programs around women in technology. And then when I graduated in ’99, it was the peak of the dot com boom, and off I went to Seattle to work at Amazon.com. It was quite an amazing ride, and just every month we were launching new stores. The growth was pretty crazy. The company growth was amazing as well.

It was not easy as I was one of the few women, certainly on my first team, I was the only woman. But I did find my little support group. I had friends that I got to meet, people who helped me through that way as I was trying to figure out a team that worked for me, and I’m forever grateful for that.

I was also there during the rocky bubble burst of the dot com industry, and I had thought that I had missed the interesting times at Amazon, and I wanted to leave and go see what it was like to work at an early stage start up. So I left Amazon, came down to the Bay Area, worked for a small start up, saw it go up and down, and realized it’s not fun to work on software that doesn’t get used. And I swung to much bigger companies since. I went to Oracle right after, which was probably a little bit of an overcompensation. But it was there that I really was starting to do team leading and thinking about being an engineering manager.

A piece of … I have a fun story about that, of I just happened to be meeting with an old friend, and was telling him that I was interested in being an engineering manager, and that I was thinking that I might transition to doing that within the next couple of quarters, it wasn’t gonna happen immediately, but I didn’t think anything of it. And then three weeks alter he calls me up and says, “Hey, there’s a position open for an engineering manager at Yahoo! that I think you’d be a great fit for, you should apply.”

And that just really surprised me. I never thought that another company would consider me for an engineering manager since I had never been an engineer manager. And it never would’ve happened if I hadn’t shared that story and spark with the friend of mine.

Advice that I give a lot of people is to be really free in sharing what your passions and interests are. You never know what opportunities are out there, and people will see you in a different light when you share those aspirations. So figure out things you want to try. Figure out things that you might want to do, and then tell people. It might be a different technology that you want to try, or a new project that hasn’t even been spun up for your company, but your manager or your colleagues may look at you in a different light when those opportunities come out and think of you as a perfect person for that fit.

Fast forward, I went to Yahoo!. It was the most trafficked site on the internet when I was there, ahead of Google. It was a pretty vibrant time when I first arrived. It kind of got rocky. I had my first baby there, and it was … I was working on a really tough project as we were revamping our ad network and really trying to figure out what was coming next for the business. I’d say one of my lowest points of my career happened there where I came back full force after maternity leave, I was excited to be back, I was excited to work on new projects. I even raised my hand to work on this brand new project that was revamping this architecture. Several months after that, I was realizing things just weren’t working. I was really unhappy. I was not feeling like I was being a good employee, not feeling like I was being a good mom. I’ve always felt like I was just chasing to get home in time to relieve the baby sitter, and my baby had stopped eating… I was breast feeding and pumping at work. Even though I had a good enough supply, she was gradually drinking less and less milk every single day. So I felt like this just isn’t working, I need to figure something else out because I don’t feel like I’m doing either job well, from being a great engineering leader, or a great mom. And so I quit — I went in, I went to my boss and I said I was gonna be quitting, and I made up some story about doing some other project.

To my surprise, they all tried to convince me not to leave.

So my boss really asked me a lot of questions. I hadn’t really felt like I was doing that good of a job, so it was really surprising to me at first that they would make all of these overtures to keep me to stay. Other peers and leaders also came to talk to me. And then finally the VP of the business came to talk to me. It was someone I hadn’t engaged with that often. He asked a lot of insightful questions, and I was really trying not to go into details or trying to make it into a way that they would convince me to stay. But he got to a point, and he said, “Cathy, I don’t feel like you’re asking for what you want, or what you need” and that really struck me.

And then he paused and he said, “I don’t know if I can give you what you want or you need, but you’re not even giving me the chance. So if you can think about what it would take to for you to be happy and successful, let us know and give us a chance to make that right.” And that was just such a powerful moment for me. And I was like, “Wow.”

It was the same advice someone had given me before about sharing things that I need and want for transitioning into being an engineering manager. But it was that same advice in a very different context for me when I was going through a difficult time in my job. So I really took a step back and said, “I’m trying to do too many things. I’m trying to be this amazing engineering leader and get the next promotion. I’m also trying to figure things out with my baby. I’m trying to travel to the different sites for these leaders. And I just need to figure out sequencing and not try to do too much at once.”

So I pared things back, I said I’m not gonna do these travel trips for the next 3 months. I also flew my mom out and she helped me with my baby while I looked for a new childcare provider. I got through those next three months, and I decided to stay. What happened after that is I got into this groove, things were doing much better for my baby, things were much easier for my job. I figured out how to do both of them a different way than I was doing it in the past. It really helped, potentially even saved me to stay in the industry at a time that was pretty difficult. It was really thanks to that VP Sandeep who had that conversation with me and made me look at things a different way.

Fast forward, I then went … Yahoo! had a lot of difficult times. I was looking for what’s next, and I had my eyes set on Salesforce. I came into Salesforce and I got to work on a lot of different really great initiatives, but I also got to see a different company that was really focused on giving back. It made me think about that time at Apple, how they influenced specific education and schools and students studying computers where Marc Benioff, the CEO over at Salesforce really wanted to think about how he could give back by not just being a company that makes a lot of money, but also is really successful in helping the community at large. So he created a 1–1–1 model, 1% of time, 1% of equity, 1% of the products were given to non-profits.

I think this is something we can all think about how we can use the power of the institutions that we work for to make a different in our broader community, helping to support other girls, helping women in technology, persons of color, helping with diversity and equality is something I feel like I been it for and I would like to roll forward to others.

I learned a lot working there, and I also feel like I had a lot of advantages working for a company who really cared about equality. So Marc had a program when I was there. He had a quarterly leadership meeting, it was called ECOM at the time. He would bring in his leaders and go business by business and go through the financials of the company. At one point he looked around the room and said, “Where are all the women?” And there may have been a chuckle or two. But after that he said, “No, we need to fix this. I want 30% of the room for all of my meetings to have women in them.”

It didn’t mean that the people who normally would’ve been invited didn’t get to come, it meant that another seat was pulled up to the table. I really liked what Gretchen was saying about just pulling up another chair is really what gives people different opportunities and advantages. I got that opportunity at Salesforce. I was invited to some meetings with really high level leaders at the company, and I got to listen in and engage and learn how the company was operating at that level, and that really helped prepare me for this role as a CTO. And I think that’s something that we can all think about is how can we pull up another seat to the table to give people an opportunity to see what’s going on in your meetings, to see what’s going on in your company, and to have broader access in this industry.

So fastfoward, I’m now at Stitch Fix. It is an amazing job, it’s great to be in this role. It’s something that I’ve always aspired to do and to be. But what I never aspired, and had hoped to work for as a company, that has such high gender diversity. Stitch Fix is 84% women, which is just amazing. Every day I walk into rooms that I’m completely surrounded by such amazing women. That’s something that was so difficult than any other company that I had ever worked. I had been used to being one of the only women in the room where I’ve gone and done the count and said, “Wow, what percentage of women are here today,” and I’ve stopped doing that. After being in a room with 60% women and 70% and 45% women, you don’t really need to do the count anymore. And what I found what’s amazing when you have that level of gender diversity is you really can be your authentic self. I remember early on in my career just wanting to fit in and be one of the guys. I wore T-shirts and jeans and wanted to kind of be appreciated for my technology, and not stand out as different than anyone else.

And now I get to wear dresses every day, I get to be myself, I don’t have to think about how I’m phrasing things or to couch my thought process or argument in a different way to fit in with the culture of the company. I feel like when you have a broader diversity group, everybody can just be themselves and focus on the business, focus on the clients, focus on how to make a difference. And that’s what’s exciting to me.

I love working at big scale companies, I love working at growing teams, growing technology, growing architecture, shipping software, and that’s what I get to do every day here. We’re in this amazing growth phase at Stitch Fix where we’re launching new business lines, where we’re growing our business. And it’s the technology that you see on the website, but it’s also everything that goes underneath it to power it from tools to run our warehouse to tools for our styling organization. Tools also for merchandise, of how we pick and buy and plan and allocate the right inventory for our business. I love wearing T-shirts and jeans sometimes too, and I love wearing dresses, and I love that I can choose. My aspiration going forth in this industry is that we can all be our authentic selves at work, that we can be recognized for what we do.

I hope that I’m seen as a great CTO, as a great technology leader, and not just a female CTO. And that my aspiration is that there are many more of you who rise to these levels as well, and that we can form a great community and support network. I think that that’s essentially my story that I wanted to share today. I think Sukrutha, we may have wanted to open things up for some questions? If anyone has any questions, and you want to type them in, feel free. Oh, there you are, hello.

Sukrutha Bhadouria: Hi, I was looking at everybody’s comments. A lot of people were talking about how they’re loving your story and the honesty with which you’re sharing it. I see a question asking about who your current inspiration is.

Cathy Polinsky: I have to say my biggest inspiration right now is my CEO Katrina Lake. Katrina was a young CEO founder who came up with this idea while she was in business school. She was fascinated by eCommerce disruptions and the sense that the apparel industry was one of the few industries that had not reached double digit online sales, even six or seven years ago. And the sense of the reason is because the model was broken and she had an idea for a different way and a different model. It has not been easy for her. As a young female CEO going to Sand Hill to raise money was not a cake walk. So she really focused on how she could get to profitability as fast as possible so she wasn’t dependent on that industry. And the thing about her is she is just such an authentic leader — she is so smart and savvy, but does not put on airs and is really someone that I’ve watched her, as she’s had her first baby, and navigated the world of pumping and nursing and things that I hid behind. I remember one of my stories of pumping while I’m eating, and having a one on one and someone saying, “What’s that noise in the background?” I’m like, “What noise? I don’t hear any noise,” and not really being that authentic about what was going on and what I needed, really just trying to hide what was going on. And that’s something I don’t think she even thought twice about hiding anything about. She’s not trying to be a role model as much as just authentically is navigating that aspect of being a mom and being an amazing CEO.

Sukrutha Bhadouria: That’s awesome. Someone also pointed out about the fact that there was a podcast where Katrina shared her story. But I do see a lot of questions speaking to your story about Marc Benioff noticing not enough gender diversity and then trying to make a difference. How does one who is not in that level of influence… How would somebody else who would get impacted by a change like that… How would they bring about the influence when they’re not in the seat of power? What advice would you have for people like that?

Cathy Polinsky: I think we could all try to help at whatever level that we’re in — really raising this as an issue to your boss, or thinking about ideas about how you could help, whether it’s the community, or a local university that’s near you. Maybe it’s letting people shadow you in your job and bringing a seat to the table. And then it’s also the opposite of asking — asking, “Can I come to this meeting?” I think that people … It may not always work out for you, but it will never work out if you don’t ask. So really being able to assert yourself and to see if another seat could be brought to that table.

Sukrutha Bhadouria: That’s awesome. And next question, and I am seeing a lot of people asking similar questions, so I’m just summarizing the next question. It seems like a lot of people want to know how do you identify when is the right time to jump at an opportunity, or navigate towards a specific opportunity to grow in your career?

Cathy Polinsky: I’d say the thing I’ve always done is try to look at what are the big opportunities out there that no one is going after, and being open to them. I was going to talk a little bit about managing up. The aspect that has worked for me both as a manager, but also as a strong number two to other of my leaders is to really open myself up to understanding what are the big challenges that my boss is having at any given time, and see how I can make a difference —

What are the big chargers, what are the big opportunities that we’re going after. What are the gaps that we see and how can I lean in to make myself available when there’s challenges. I feel like that’s always helped me, whether it’s a brand new initiative that got spun up, or someone’s leaving the company, someone’s moving to a new role and there’s a gap in the organization. Really saying, “Hey, how can I help? Is there something that I could be doing here? I’d love to take a shot at helping on these projects.”

The way that I’ve always been able to do that is to build a great team. I love to delegate and hire the best people that I can and load them up as much as possible in the same way. And that gives me the space and the capacity to take on more when I am in a growing opportunity that needs more help.

Sukrutha Bhadouria: One quick comment I do want to add is that people are asking for all of your questions to be posted in the ask a question list. So just in case you’ve been posting them in the chat but not in the ask a question list, if you put it there people can vote. Next is actually one of my favorite questions. There are nine and counting votes for people who want to hear more about the differences in responsibilities and duties of being a software developer, an individual contributor, versus a CTO. How did you transition between those roles, what is the main differentiator do you think? Or the biggest challenges.

Cathy Polinsky: Let’s just talk about software developer versus manager because it is this really interesting thing that the things that help you be most successful as an engineer are not necessarily the things that you need to do once you’re an engineering manager. And that’s something that we’re not sure … We talk about that a lot at my staff meeting of if that’s true for a lot of other fields. I get the impression that that dynamic is not always as clear as it is in software development. When you’re focusing a lot on how you’re working on coding and projects and building up your technology skills, those things are great and important to lean on so you understand the projects are going on track, but there’s a whole other aspect of how you’re managing people and projects and initiatives that you don’t necessarily always get to do as an individual contributor.

It was a very challenging and different experience for me, but one that I really loved. I feel like as a software developer, you get these CS highs — You solve some problem, you are excited about getting to a solution that works, and that you can push out and deploy, and that’s just exciting that you get to see that solution, you get to see people using it, and you get to see the difference that you’re making.

When you’re a manager, and you’re not actually writing the hands-on code and influencing through people, things take longer. You can’t always see the, “Hey, I’m trying to give people advice and coaching them in this way. Am I getting through to them? Is this working? Am I shifting the team to be better or not?” It’s not that you can see that on a day to day basis, but that your impact is much broader, and if you can stick through it and realize it’s not the same as that every day, every hour, continuous feedback loop that you find other ways to see your impact, and that you can be really proud of the people and lives that you can influence.

That’s what I really love about the job is that I can have a broader influence and every day is different, as I mentioned. I’m working on a lot of different types of projects, a lot of different types of focus. And I think that’s the thing that also changes as you take on more and more teams, as you go from being a manager to a manager of managers, or a CTO. I was saying as I was making that shift, things when you’re a software developer can go quite fast. You can have a great day, and then you can have a bad day. Depending on the big challenge or bug or issue that you’re dealing with, things are a little slower as an engineering manager. You see the challenges and you’re working towards fixing them, or you’re seeing things working really well, and they stay pretty well for quite some time.

But when you have a larger scope of influence with teams that suddenly don’t have much commonality between them, you can go from one meeting and think, “Wow, things are finally coming together for this group and I can see the light at the end of the tunnel and things are going great.” And then you go into a whole different meeting and you go, “Oh, now I have this other problem that I have been neglecting that I really need to help nurture.” It’s just a different pacing, and just being open to those shifts are really important — and to finding different people to get advice from because this job changed quite dramatically.

Sukrutha Bhadouria: Yeah, totally. I can’t totally relate because I’m going through that as well myself. Thank you so much Cathy, I wanted to thank you from the bottom of our heart to get started with what’s our first ever virtual conference. Your talk was so inspiring, we see it through the comments, and we feel it too. All of the questions that came in, thank you for asking those questions.

Cathy Polinsky: Thank you for organizing this and thank you for inviting me. It’s great to be here.

Sukrutha Bhadouria: Thank you. Over to Gretchen [for our next session] …

Cathy Polinsky is the CTO of Stitch Fix. Prior to Stitch Fix, she was SVP Engineering at Salesforce.