Forgot your AirPods? Don’t worry, you can still enjoy one of our favorite episodes of the Product Love Podcast. Check out the full transcript of our fun chat with Cindy Alvarez of Microsoft below. 

Eric Boduch: Awesome. So, welcome lovers of product. Today I’m here with Cindy Alvarez. Cindy, why don’t you kick this off by giving us a little overview of your background?

Cindy Alvarez: Sure. So I am currently a product manager. I think I’ve held every UX and product-related title there is: researcher, interaction designer, design lead, and now product manager. I started out with a psychology degree and an intention to be a college professor and went horribly awry. And then I had a plan to be in startups for a career, and the last startup I worked for got acquired by Microsoft, so the best-laid plans keep going awry but they keep working out well somehow.

Eric Boduch: So talk to me a little about the background in psychology, has that helped you as a product manager?

Cindy Alvarez: Yeah, I mean, it’s not that I’m referring back to case studies, but so much that we do is based around how humans interact, and how we respond to information and fears, and wanting to look good in front of our peers, and wanting to feel accomplished. All of that feeds into how we pick products and build products. There’s so much where we go in with an opinion or idea and it’s just like, “Wait, let’s dial that back, we know what’s really behind it.”

Eric Boduch: Yeah, I imagine that would be a huge help. I remember I had Nir Eyal on the podcast and we were talking about Hooked, and the background of consumer behavior and how that affects products.

Cindy Alvarez: Not just consumers either. I feel like there’s a lot of, “Oh well, consumers do this.” Enterprises do all the same wacky stuff, they just, there’s a veneer of formality around it, but it’s still, humans are weird and irrational.

Eric Boduch: Well I mean enterprises are just made up of lots of consumers, right? They have the same habits.

Cindy Alvarez: Yep, exactly.

Eric Boduch: I mean, it’s interesting too to think about that. I at least, I’m a little older, so I grew up in an age where enterprise software was old and clunky and had horrible user interfaces. Now consumers have the iPhone and products like that, and now so you have that push into the enterprise where people are expecting interfaces that were like they were getting at home, so it really kind of shows that those consumers really were just little pieces of an enterprise. It was inevitable that that happened.

Cindy Alvarez: Yeah, absolutely, and I think, it used to be that when there was only one tool for something, or it was very difficult, we accepted this sense of you’re gonna have to, for example, people used to put in all earnestness in their resumes that they knew Microsoft Word. Because when there was only essentially one-word processing program that was a difficult thing, you had to master it, you would take classes, you would read the manual. And now there’s no tolerance for reading the manual. If you can’t jump in and figure out how to use it, it’s not actually very useful. And so there used to be these sort of giant swaths of enterprise software, somewhere in there is the feature, enroll in three days of training to find it, and there’s just very little tolerance for that.

Eric Boduch: Yeah, now it should be there, you should understand it inherently, but if you don’t, you just google it, right?

Cindy Alvarez: Yep, yeah.

Eric Boduch: So talk to me a little bit about a product problem you’re really excited about right now.

Cindy Alvarez: Well I think it’s just that, we as consumers, whether we’re on our own or in an enterprise, are so used to having these very precision apps that will do exactly what we want, or precision solutions. If I want something I can go on Amazon and search and exactly that thing will appear. So we’re much more discerning about what we need, and we’re much less willing to take “expert testimonials.” So you see a slickly packaged marketing video, and there’s this greater and greater skepticism towards it. It’s like if your product was really good, wouldn’t you just show me what it does? And I think that poses this interesting challenge because in the past, if you had a big enterprise product, you could kind of stuff a whole lot of things in there, and odds were that you get at least some of it right. And so people would buy the giant package because somewhere in the box of goodies is the two or three features I need.

Cindy Alvarez: Now, you can’t do that, people don’t want the box of goodies, like I don’t want to rummage through this thing, I want exactly the thing that works. And it means as product people, we need to know exactly what this thing is that people need and build that because there’s very little tolerance for “here’s a box of stuff and somewhere in there is what you need.” It’s like I want to see out front on the label, I want to start touching it and poking it right away. And if I don’t see that, I’m gonna google it and someone else will have that for me. So it’s just, there’s very little room for error.

Eric Boduch: Yeah, I mean the whole buying cycle of software has changed with the cloud too because of that. You now have to keep giving value to a customer, because those contracts, even if they are, even if they’re longer than a month, even if they’re a year, even two years, they end. So this concept that I grew up within the software space of shelfware is really kind of vanishing, so if there is shelfware, it’s only there until you realize you have a contract you forgot to cancel kind of thing.

Cindy Alvarez: Absolutely. And I think because there are more alternatives, that contract doesn’t actually mean that people are still using and getting value from your product, and I think a lot of the old school companies had this realization that “Oh, we go back, when we send the field sales back out to renew that contract, our customers stopped using it six months ago. They switched and we didn’t even know.” And that was kind of this big wake up call across the industry, and now you’re seeing a lot of investment’s been put into measuring usage and being more in touch with customers, but that decision point, it does not make it and forget it, it’s continually being reevaluated.

Eric Boduch: Yeah, I mean that’s one of the reasons the company I work at, outside of doing this fun podcast, that company exists, right? Just to help people understand, is your software being used? How is it being adopted? How can you improve engagement?

Cindy Alvarez: Yeah.

Eric Boduch: All of those things that become now critical because of the way software is bought and consumed today. So let’s go to your background a little bit. You talked about startups, and now you’re at Microsoft. Talk to me about that transition and why you made it, I guess why you made it is obvious, Yammer got acquired by Microsoft, but talk to me about how that transition has been, and you’ve been at Microsoft now for a while.

Cindy Alvarez: I have, I’ve stayed.

Eric Boduch: So you’re liking it.

Cindy Alvarez: Yeah.

Eric Boduch: So tell me about all that.

Cindy Alvarez: I used to joke that I worked at Microsoft through no fault of my own, and then I deliberately switched, so I was working on purpose, and I sent out an email to people after I made that transition, I moved from Yammer, the acquired company, to actually the Visual Studio Org, and the email subject line was “I’m not dead yet.” And essentially, it was something that I had to explain, like, “Why are you working for Microsoft?” Because most of the people that I’d worked with in my earlier career, that was kind of a baffling choice for them. Because from the outside, it’s changing, but Microsoft still has a lot of the same perception from the outside as it did in the 90s, kind of the evil empire, this massive bureaucracy.

Cindy Alvarez: We’ve all seen the comic with the organizations with the guns all pointing at each other, and there’s some truth to that, but it’s actually changed pretty rapidly, and I usually tell people that Microsoft is not one big company, it’s more like 100 loosely federated little countries and depending on what country you’re in, you might have a very different experience, and I’ve been kind of touring the countries that are the closest to being in the startup world. And I think there’s … a lot of people rightfully mock the notion of, “Oh, it’s a startup within an enterprise” because you can’t really emulate the start-up existential struggle, but there’s a different one which is almost harder, which is when you’re a startup you have to succeed, you have to put out something that gives people value or else you’re not going to raise your next round of funding.

Cindy Alvarez: Within an enterprise, you’ve got to put out something that people believe in enough to abandon their old habits and their jadedness and their learned helplessness, or they’re just, “I’m used to this,  and now I’m gonna go do this new thing.” And you basically have one chance to bring people along, or else you’re not going to raise that next round of buy-in, and I think it’s actually a little bit harder because if you’re trying to raise money and one VC turns you down, there’s a whole lot more to go to. If you burn down an organization within a company, you can’t go back in six months and say, “We’ve pivoted, we have something slightly different.” They’re like, “Yeah, I remember you, we didn’t trust you last time and we still don’t.”

Cindy Alvarez: So it’s a different existential crisis and it’s kind of a much more human one where you’re convincing people, and you have no formal authority, I’m not Satya, I cannot make anyone within Microsoft do anything, I have to convince them that it’s a good idea, that it’s better than the thing they might have been doing for the last decade. So it’s incredibly challenging and really fun.

Eric Boduch: Yeah. It’s a new set of challenges, right?

Cindy Alvarez: Yeah. And people have been remarkably receptive, I think that’s the other thing. And that has changed dramatically, from the time when Yammer was acquired, just about six years ago, there was a very strong sense of, “Look, acquired startup, we’ve been doing this for 30 years, we know what we’re doing, don’t tell us anything.” And post-Satya, and post- the world changing, it’s a very different internal story now, it’s saying, “Look, we were really good at one way of doing things, that still works for part of the company, and for another part, we need to learn all these new skills, and we’re open to it.” So that’s really cool to me. I go up to Redmond and there are people saying, “How do we learn to do more of this?”

Eric Boduch: Yeah, I’ve always had a soft spot in my heart for Microsoft, even when people were putting them down during some of the Ballmer era, but I feel like Microsoft has become cool again, it’s like the cool place to be.

Cindy Alvarez: The cool place. You know I feel like in today’s political and social climate, we’re the good guys, and there are not that many good guys. I’m not saying we do everything perfectly, but there are a lot of things I see coming out that I’m like, “I’m proud of that.” It sounds cheesy but I am proud to be associated with this company.

Eric Boduch: So now, something else you’re associated with, you wrote a book, Lean Customer Development, and really, lean customer development is a variant of customer development, that concept that, at least the lean part of, that you created, right?

Cindy Alvarez: I can’t take credit for that, actually that’s O’Reilly’s Lean series, so I think everything, the title just needed to have “lean” in it. But if you read the original, Steve Blank’s Four Steps to the Epiphany (a fantastic book that needed an editor), there’s a second version which is better.

Eric Boduch: It was a little tough.

Cindy Alvarez: Yeah, but his customer development flow chart, it was a whole lot of boxes, like a PowerPoint slide’s worth of boxes, and it’s not inaccurate for defining a new market, it’s also completely overwhelming to most people. So it’s like, “Let’s take and slim that down, let’s take and make this look like a process that people have faith that they can do.” And that was really kind of the exciting part of writing that book was saying, “I know we can do this, I know this was possible.” It’s not a skill that a lot of folks have, whether you’re start-up or enterprise, that sense of “I’m not going to reality distortion field you,” like in a startup, and “I’m not going to paternalistically tell you this is what you want,” as enterprises did for a long time. It’s this directed sense of “What are you trying to do?” Not “tell me what you want” because that doesn’t work, but, “What are you trying to do? Well, tell me more about that.” And you’re sort of fumbling around in the dark and somehow you get to the end and you’ve discovered, “Oh, now I understand what this person’s trying to do, and based on the insights I have as a product person, I think I know what I could build for them.

Eric Boduch: So let’s get back to that customer wants and needs in a second, I don’t want to lose that thread. But what inspired you to write it as a book, and I guess now I just learned something today, you didn’t pick the title lean, if it wasn’t lean, what would you have picked? It would have been blank customer development.

Cindy Alvarez: You know honestly I don’t know if I would have used the phrase customer development, because a lot of people have no idea what that means. I was kind of aiming for customer insights, which is really kind of what it is. So how did I get to write it? I was in a startup at the time, and I was talking about this, I was talking about talking to your customers, and uncovering needs, and I kept going to other startups and giving it as a talk and going to meetups and giving a talk, and I was getting a little tired of giving the same talk, and I was like, “Maybe I should write a book.” And so I did.

Eric Boduch: Awesome. ‘Cause that’s the way to do it. And you can just be like “read my book for …”

Cindy Alvarez: Yeah I’m like “In chapter two …” I actually don’t remember what’s in it, that’s the weird thing, is now it’s like four years later, and I still talk about many of the things in the book, and also other things I’ve branched into, and someone will ask me, “Is that in the book?” And I’m like, “I don’t … maybe? I’m not sure.”

Eric Boduch: It’s amazing how that changes, or how your perception of what was there adapts and evolves. I just look at some of the things I’ve written in the past or spoke on, and I’m like, “I think I talked about that, but I’m not sure.”

Cindy Alvarez: Right, and everything is just what you know, that’s the classic curse of knowledge, the biases. We have a hard time understanding other people don’t see what we see.

Eric Boduch: Yeah.

Cindy Alvarez: In my mind, they’re all the things that I talk about all the time. And I can’t believe that you don’t know where I’ve talked about them, which is ridiculous.

Eric Boduch: It is. But I completely understand that. So let’s get back to the wants and needs. How do you differentiate wants and needs? How do you tell project managers to think about that?

Cindy Alvarez: Sure. So there are plenty of competing quotes about customers don’t know what they want, et cetera, and as humans, we’re terrible at predicting the future, and this isn’t an, “I’m smarter, the customer doesn’t know.” This is a fundamentally human thing. We think that we want things that we don’t necessarily want. And so, people who have kids, this is very obvious, your kid is like, “I don’t want that shirt.” And it’s not that they didn’t care about that shirt, it’s that they needed a nap, or they shouldn’t have had that second cupcake, but they’re not intellectualizing that, and you from that position of remove can see, “I know what is upset with you.”

Cindy Alvarez: So we think we want things, and we’re not very good at it. So we ask for something based on our sense of what we’re going to want in the future, which is flawed and also based on our sense of what is possible, because I think because we don’t like to look stupid, we don’t want to ask for something that sounds crazy. So if someone says, “What do you want with this product?” we say, “Well, what is there today, I want to make that 5 to 10% better” and this isn’t conscious, this is just what our brains are doing, they’re like, “Eh, you could ask for this much more.”

Cindy Alvarez: But the consumer is not the industry expert, they are not a product bench, they have no idea what’s possible most of the time. So they ask for these constrained solutions, and if we just build those, they’re not actually going to be happy. What they need is something different, what they need is, you need to get from point A to point B, you need to sell your house, you need to get your kids ready for school, you need to renovate. Whatever the need is, you’re gonna have to do it, it’s not your job to know how to solve it, its the PM’s job.

Eric Boduch: Yeah I think that’s important and it triggered a thought, something I haven’t thought about before, but I believe it’s a falsely attributed quote, Ford said, “Oh, if I had asked people what they wanted, they would tell me faster horses.” And maybe the reason they said that was because they didn’t want to say something crazy, like you said. There could have been people who said, “I want a vehicle that’s all mechanical and never breaks down that I don’t have to feed, and is gonna get me there faster.”

Cindy Alvarez: It’s ridiculous.

Eric Boduch: But it sounds kind of ridiculous, so of course the customer is gonna be like, “Yeah, I want faster horses,” right.

Cindy Alvarez: But if you’d ask, I like to turn that around too, and say okay, if you asked the customer what they wanted, they probably would have said faster horses. If you’d said, “Look, what’s terrible about riding your horse to get from one place to another?” Then you might have gotten some actual needs there. It’s like, “Oh, well when I get from one place to another, I’m all sweaty, there’s mud splattered all over me, it hurts to ride a horse for too long.” There are problems that an automobile clearly solved, but if you just say, “What do you want?” you’re going to get a bad answer. If you ask, generally, “What’s wrong with your situation today, how could it get better?” You get something that’s very different.

Eric Boduch: Yeah, absolutely. It’s funny, you had in one of your blog posts I believe a pirate, and I think of “ARR” I think of annual recurring revenue, and there’s a lot of “ARR’s”, evidently pirates did very well in the software world, but in particular, part of your “ARR’s” the AR in there is activation retention, and that’s something you’ve talked about and written about, so talk to me about what advice you give project managers regarding activation and retention.

Cindy Alvarez: So, you know, I like to put things back into human terms. Activation is I have faith that this is gonna do what I need. So to get people to activate, you need to give them that faith. If you wanted someone to go into a building, and you’ve got a door, and you can’t see through it, its an opaque door, you want people to come in. Are they gonna come in? Like, I don’t know, they hesitate, it doesn’t look that friendly. Whereas if you have a nice clean, open door, with a window, maybe it’s even propped open with a sign that says come on in. That gives me faith that I ought to do that.

Cindy Alvarez: So, activation is, how can you make it clear to someone that this will probably do what you want and retention is it doing what I wanted it to do? It’s very simple, it sounds kind of foolishly simple, but it’s the question we keep asking. And I think it’s very easy for humans to mistake effort for impact, I worked really hard on something, so it must be good. And that’s not true, it’s maybe not fair, and it’s frustrating, but you can work incredibly hard on a project and have it not actually make someone’s life better, so that’s always the criteria we need to look for, how do we make someone’s life better? When you are making someone’s life better, you will retain them. Its very simple. Unless someone else can make their life better in a dramatically better way, but not even a little bit, 10% doesn’t make people change products, 20% doesn’t. The theory is something has to be nine times better to get people to switch.

Cindy Alvarez: So you really just need to hook that initial, “What did you want to do, okay we’re more or less doing that for you.” But a lot of times, its just step outside of yourself, “What does someone want to do, is it doing that thing?” We can write tons of specs, or we can write long, glorious-sounding blog posts, but it all kind of comes down to that “so what” question.

Eric Boduch: Yeah. I think it’s interesting. I’m not a big believer in the nine times better, but I do believe it can’t be incremental.

Cindy Alvarez: Yeah.

Eric Boduch: It has to be multiple, whether it’s twice as good or close to twice as good. If I do something that’s painful and it takes me two hours every day, you can cut it to an hour, that’s awesome.

Cindy Alvarez: Yep.

Eric Boduch: If you’re saying, “I’m going to save you five minutes,” I’m like, “And I have to learn a new system and do a new thing.” And I was like, “Ah.” And then I don’t know if I believe you.

Cindy Alvarez: Right, right.

Eric Boduch: That it’s going to really save the five minutes.

Cindy Alvarez: ‘Cause it’s the faith, right? Like, “Are you really going to save me five minutes?” It’s like when you see those signs outside stores. It’s like, “Liquidation. Everything up to 70% off.”

Eric Boduch: Yeah, absolutely.

Cindy Alvarez: And you’re going, “There’s one thing in this store that’s 70% off and everything else is 10% off. And I don’t believe you.”

Eric Boduch: Yeah. That reminds me of a story. I remember I loved this old e-commerce retailer, one of the early ones. And they used to have like two or three sales a year, and you knew you were going to get great deals. Because I’m one of those guys who are like, “I like nice clothes, but I never, ever want to pay full price for them ever. I just can’t do it.”

Eric Boduch: So it’s like those sales would come around, and I’ll be like, “Check it out. I’ll buy some stuff.” Every single time, I bought something. And then they got to the point, I think after they went public, there was a sale every week, then every two weeks. And so I got to the point where I was like, “I just don’t believe you that it’s a good deal.” So now instead of shopping with them twice or three times a year, I didn’t shop with them at all.

Cindy Alvarez: Yeah.

Eric Boduch: Because I just don’t know if it’s true.

Cindy Alvarez: Yeah. We save up that level of belief. Amazon should never have more than one Prime Day.

Eric Boduch: Yeah, absolutely. Completely agree. Maybe you can get a Prime Day and a Black Friday.

Cindy Alvarez: Yeah, yeah. You have to make it pretty ’cause it’s Christmas.

Eric Boduch: If you start coming up with new holidays that come up every month …

Cindy Alvarez: No. Then you won’t trust it.

Eric Boduch: Then yeah, exactly. We’re going to be like, “Ah. There’s no impetus to do something.”

Cindy Alvarez: Yeah.

Eric Boduch: Because you’re like, “There’s going to be another one next month and it’s not going to be any better.” And then it just feels like every day. It brings us to this topic of bias pretty nicely. So talk to me about cognitive biases and other biases that product managers often find themselves having.

Cindy Alvarez: Yeah. And cognitive bias is a really interesting topic, and I found that one of the things I like to bring up is it’s oftentimes the entry point for folks who might be skeptical about the squishy human stuff. Cognitive bias is a really good way to explain that because there are so many great examples that apply to all of us.

Cindy Alvarez: And so our brains are set up to pattern-match and to fit in with our society and to make snap judgments, and that’s great if you’re running from wooly mammoths or you’re trying to get shelter with your tribe or you’re not eating the poison berries. And that’s why we’re all alive, ’cause our ancestors did this. But they’re terrible at nuance.

Cindy Alvarez: And so there’s a lot of ways where our brain tries to protect us from feeling uncomfortable. So this notion of cognitive dissonance, it’s like when you have two ideas in your head that are conflicting. It’s really uncomfortable and we tend to look for a third way out. And the classic example is if you ever redesigned a website or launched a product and you’re really proud of it, you think it’s really great and customers are complaining, and inevitably someone will say, “Maybe these are the wrong customers” or “Maybe the customers aren’t that smart,” because that’s a third way out. Because otherwise, you’re saying, “I’m a good product person. I designed this product, but people don’t like it. So how can I be a good product person if customers don’t like it?” And our brains don’t want to even go there, so we’re like, “Maybe the customer’s dumb.” Ah, we feel better. Except that’s not accurate.

Cindy Alvarez: And so with that one, in particular, I always tell people there’s something very powerful in saying, “Let’s just assume this thing is true. Now, let’s just assume that the product is flawed in some way. What would we do?” And setting it up as a hypothetical allows you to kind of relax and say, “Well, if the product is really having problems, I guess we’d watch people and see what they were trying to do.” And then you do that and then you realize that perhaps the new product, the new website redesign looks fantastic but you inadvertently hid something that everyone was coming to do. So you can bring those things together.

Cindy Alvarez: And there are many that are along those lines, like trying to prevent us from an uncomfortable feeling. We tend to justify purchases that we’ve made ’cause we already made them, it’s too late. And so we tell ourselves it was a good idea. We rationalize the decisions we’ve made in the past. We think that we knew it all along. The number of people who said that they predicted the 2016 election outcomes, none of them did but they all are like, “Well, if you read that thing I said, surely I was hinting it.” No, you weren’t. But that’s what we do, and it makes us feel better.

Eric Boduch: Yeah. It’s that social desirability vibe there, right?

Cindy Alvarez: Social desirability is huge. We want to seem like good people. And so there are so many things that we ask. All of our natural instincts of questions to ask customers are leading questions, they’re yes/no questions. We say things like, “Wouldn’t you like it if …” And when you ask me something that starts with it, I’m probably going to say yes without really thinking.

Eric Boduch: It’s a lot easier to say yes.

Cindy Alvarez: It’s a lot easier. And look at you. You seem like a nice person, you seem very enthusiastic, your body language, you’re leaning forward and you’re like, “Wouldn’t you like this?” I’m like, “Yeah.” And I’m not thinking at that moment of trade-offs. You haven’t actually asked me for a commitment. It’s really easy for me to say yes. But the truth is it might not make any sense.

Cindy Alvarez: And I do an exercise sometimes where I say, “Turn to your neighbor and see if they want this pen that you just invented that never runs out of ink.” And people will turn and they obediently say, “Would you like this pen? How would you like to have a pen that never runs out of ink?” And the question that very few people think about is, “How often do you write with a pen?” And if the answer is … if it’s me, not very often. I do most things on laptops. Or you can say, “When’s the last time you bought a pen?” And again for me, I subsist on free conference pens and stolen hotel room pens. I literally cannot remember the last time I bought a pen. If you have made a pen as a product, I am not your customer. And yet if you ask … if you hold it out to me and ask, “Don’t you want it?,” I’ll say yes.

Eric Boduch: I can’t remember the last time I had a pen run out of ink.

Cindy Alvarez: Yeah. I can ’cause they’re free conference pens.

Eric Boduch: They run fast.

Cindy Alvarez: I have an infinite supply of them. If a pen runs out of ink, I literally throw it in the trash and grab the next one out of a box. It’s like … it’s continuous to me.

Eric Boduch: I guess I lose those free conference pens faster than they run out of ink.

Cindy Alvarez: Yeah, yeah. That can also be the case. So the way we ask the question, we so often ask the wrong question. And the thing is that no one corrects us. Very rarely does the customer say, “You know what? That’s not what you should be asking me,” because we don’t … for one thing, it seems kind of presumptuous and for another our brains just kind of go with the flow. We’re like, “Yeah, sure. I’d like that.”

Eric Boduch: But that’s a problem for product managers.

Cindy Alvarez: Absolutely, because we ask the question that is kind of hinting at the answer we want to hear. And so when we ask a question that’s biased, we get an answer that’s inaccurate and then we set up a whole business model, a whole product, around the assumption that we are meeting customer needs, and we’re not.

Eric Boduch: Oh, I see that too in retention all the time because a lot of … you want to talk to the happy customers because those are easier conversations.

Cindy Alvarez: Of course.

Eric Boduch: Or at least you think they’re going to be. And so you end up talking to happy customers all the time and that becomes like survivorship bias, correct?

Cindy Alvarez: Exactly. Exactly. And your happy customers and the people who are willing to talk to you are also outliers because talking to vendors is sometimes fun but the people who answer emails first tend to be the people who are extreme users. And so you listen to them and you’re like, “Oh, we need to add this filter, we need to add this option.” And pretty soon you have a product that’s full of toggles that this subset of customers loves and most people are like, “This is really complicated. I have a washing machine that’s got like 16 buttons on it for all these variations. I use two of them. I use cold water wash and sanitary. I don’t know what the other ones are there for.” Probably someone said, “Would you like a button that does this?” And if you asked me that, I would’ve said, “Sure.” And now every single time I do laundry, I’m hovering with my finger over the buttons like, “Uh, that one.” It slows me down every single time.

Eric Boduch: It does the same for me too.

Cindy Alvarez: Yeah. It’s ridiculous.

Eric Boduch: So other biases that PMs should avoid.

Cindy Alvarez: Oh, we love our ideas so much. We love solutions. We really want to solve things ’cause that’s who we are as people. We want to build things. And so as soon as there’s a problem, we leap from problem to solution so quickly. “Maybe we can do this.” It’s like, “Wait, wait, wait. Let’s back up. Let’s make sure we understand the problem.” And that feels like, “Ugh, that’s not fun. That’s not the fun part. I’m not designing. I’m not mocking up. I’m not spec’ing out. I’m trying to understand what this person’s trying to do.”

Cindy Alvarez: And so there are so many times when we see a problem and we just jump to, “Maybe we should do this.” And then there’s a debate internally about is that the right solution, and meanwhile, we’ve never actually said, “So what’s terrible about riding on a horse?”

Eric Boduch: Yeah. And I think we can expound upon that a little bit. Getting to the real answers, what advice do you give PMs on how to approach that? 

Cindy Alvarez: Yeah. Because if you ask people directly, they tend to not tell you. And there’s a variety of reasons, in part because in the first question I don’t really trust you yet, right? You might seem like a nice vendor. We’ve talked for like 30 seconds. I don’t know how much I can reveal. I don’t know how much you’re interested.

Cindy Alvarez: And one of the things I say in the book is, when you ask a question of a customer, you need to be silent for an uncomfortably long time. Because the impact that happens when you say, “Tell me about how you do this” and they give you a three-word answer and then you say, “Great,” you just signaled to them, “That’s all I needed to know.” It’s like when you run into a friend on the street and they ask you how you are and you say, “I’m fine” and they say, “All right. It was good to see you.” That’s saying, “I don’t want to hear that your cat died or you got a promotion. We did the formalities and that’s it.”

Cindy Alvarez: And so we need to go beyond that. So we ask a question and then we ask it again, and then we ask a roundabout question. And we’re really kind of listening for the point where someone brings emotion into the conversation ’cause that’s really how they prioritize. So you ask someone about their commute and they say, “Oh yeah. My commute’s terrible.” There’s not a lot of emotion there. That’s a little bit of social desirability bias actually coming into play ’cause we’re all supposed to complain about our commute, right?

Eric Boduch: Absolutely.

Cindy Alvarez: Yeah. It’s like that’s what people do. It actually feels terrible not to. My first kid slept through the night almost immediately and people would ask, “Are you tired?,” and I’d say, “Oh yeah. I’m exhausted,” ’cause it seemed like a terrible thing to do to be like, “No, she sleeps. I get so much sleep now.” Kid two caught me up by the way, so my karma did balance out. But yeah, I told all these people I was exhausted when I was not because that’s what social desirability bias does.

Cindy Alvarez: But on the other hand, you might get someone who says the inverse. “Tell me about your commute,” and they’re like, “Ah, it’s fine.” Those are … If you read that as a transcript, you would get it wrong. But you’re like, “Oh, tell me more about that” and they’re like, “Well, I mean, I guess I can’t really avoid it. There’s traffic everywhere.” This is a problem. We want to dig into it.

Cindy Alvarez: And so the things at face value we often can’t take. And there’s a difference between if your commute is 45 minutes but you’re driving along, you’re driving on 280, you’re on this beautiful highway and there are trees and fog and you’re like, “This is nice,” or you’re in stop-and-go traffic. Those are very different. So we want to listen for those points where people bring emotion in and say, “Well, tell me more about that.” And it can actually feel a little bit rude, right, because they seem upset and we’re just poking at them like, “Tell me more about your pain.” But that’s actually how we get to a real answer.

Cindy Alvarez: And so a lot of times people are doing something that they say is okay but it’s not, or they say it’s terrible but their face is not … they’re still smiling, their shoulders are relaxed, they’re leaning back in their chair. It’s not terrible. Something is terrible. We need to fix the things that are terrible.

Eric Boduch: So let’s dig a little into product managers and their careers. What should product managers do for their careers? Or maybe phrase it another way. What are product managers not doing that they should be doing for their careers?

Cindy Alvarez: So product management is such an interesting thing because most products that most of us work on are not famous. Most of us are not working on Facebook or LinkedIn or an iPhone. And so when you are working on one of those products, there’s this sort of presumption of competence, of greatness, like, “Oh you worked on the iPhone? I love my iPhone.”

Cindy Alvarez: For the 98% of us who don’t work on one of those kinds of products, it’s hard for people outside your company to know how good you are. And if you’re a designer, you have a portfolio. If you’re a product manager, how do you actually prove to the world that you’re good and you’re smart? And I think the mistake, and I made this early in my career and I see other people make, is not always maintaining a portfolio of people outside your company who know that you’re smart and that you’re good, that you have these particular skills. And it’s basically actively managing your career.

Cindy Alvarez: You might be happy where you are today. Hopefully, you are for an ongoing amount of time. But it’s always good to have that sense of, “If my company’s shut down tomorrow, who are five people who would vouch that I’m a good hire?” And if you don’t have those, you should go out and get them. And it doesn’t mean you have to go moonlight, you have to go consult, but volunteer, give a talk somewhere, write a blog post. It’s always important to have that sense of people who will vouch for you.

Cindy Alvarez: And I find it’s also … forcing in that way makes you get outside the building and pick up new ideas and learn new things, meet new people, which just helps you be a better PM.

Eric Boduch: Yeah, absolutely. I think getting outside the building is important for lots of reasons.

Cindy Alvarez: Yeah.

Eric Boduch: You can develop some of those people that would vouch for you just by talking to customers.

Cindy Alvarez: Yeah. There are customers that I had back in the KISSmetrics days that I still keep in touch with, and that was eight years ago I think. But we had good conversations about the product they were using then and they’re still people that I can point to and that will sometimes ask me for advice and vice versa.

Eric Boduch: So diversity inclusion, something that you’ve talked about, I wanted to ask you if you could recommend an action for companies or people to take to create more inclusive workspaces. What would you want them to do?

Cindy Alvarez: Yeah. So diversity inclusion is such a tough thing for people to tackle and there are definitely … there have been a flurry of articles about diversity fatigue and people just get tired of hearing about it, which we haven’t made even progress for people to get tired of hearing about it yet.

Eric Boduch: Agreed.

Cindy Alvarez: But the thing that helps underrepresented folks a lot is actually something that’s good for your company and good for everyone else, which is to be very concrete about what you want out of an employee, both from the hiring stage and the promotion stage. And the crisper you are, the more likely you are to recognize people from diverse background’s talent.

Cindy Alvarez: So what happens traditionally when we get into interviews is we like people who remind us of us, and sometimes that’s because they went to the same school or they like the same restaurant. But a lot of time it’s someone who is like us in terms of gender and ethnic background. We just feel comfortable around them. We think, “Yeah, I’m going to hire them. They seem great.” And then we get into someone who is not like us and we don’t have that immediate sense of affinity, and we tend to retroactively say, “Well, I don’t know if he was as strong on this. Well, I’m not sure if he’s done this particular task before,” and we extend the benefit of the doubt to people who are more like us.

Cindy Alvarez: So the more we can have a crisp set of, “The most important thing for this role is this. This is the evidence that would convince us that someone was a great designer or good at convincing others or worked well with engineers.” Same thing for promotions. If you have kind of that bullet point list of, “This is what a senior engineer looks like,” then it’s so much easier to compare against someone and say bullet point for bullet point, “Yeah, actually she’s doing great.”

Cindy Alvarez: And even as a woman advocating for women, I’ve had the experience of looking at someone and saying, “Oh, is she ready for a promotion? Oh, I’m not sure” and then looking at the bullet point list and going, “Well, actually, yeah, yeah, yeah.” And having that written down was the thing that nudged me out of my sense of complacency of thinking, “Well, this person, she doesn’t do things the way I would do it.” She doesn’t have to. She’s achieving results. So objective criteria.

Eric Boduch: I like it. I think that’s a great way to approach interviews, conversations, raises, opportunities for promotions. I think that’s solid.

Cindy Alvarez: Yeah. There’s a lot of research actually showing that the more objective your criteria are, the more likely they are to benefit everyone, but especially women and people of color. And you look at government agencies, the military, that’s where you tend to see a lot of traditionally underrepresented backgrounds rising to positions of power, because there is that boilerplate list.

Eric Boduch: That’s interesting. So let’s talk about the future of product management. What trends do you see coming up?

Cindy Alvarez: I think we’re going to continue to see this … the micro-product, the thing that does exactly what you need. We’re seeing increasing decentralized decision making is how I put it within the enterprise. So even in my startup background, I’ve always been in enterprise software. And that used to look very much like single decision-maker, there’s time set aside for evaluating a product, and there’s kind of a top-down rollout. And so your sale cycles were slow, but you had to convince only one person.

Cindy Alvarez: That, for a variety of reasons, is kind of going away, and it started with bring your own device. Companies realized, “Hey, we don’t have to pay for your cell phone bill if we let you bring your own cell phone.” And it’s spread to the realization of, “Wait a second. If we roll out one tool to everyone and that tool is kind of crappy, everyone’s having a terrible experience. But if we let one team try out a new tool and they have a terrible experience, we’ve isolated that damage and we can just tell everyone else not to use it.” And on the contrary, if one team is using a tool and they’re having a great time, well then we should try to help spread it around the company.

Cindy Alvarez: So we’re seeing decisions get pushed down to the team level, to the individual level. And when you do that, you’ve basically got people who don’t have time set aside for that criteria. They’re just thinking about, “What do I need to do for my job? Does it do this? Yes or no?” So they’re not looking at feature checkboxes, they’re not looking at marketing videos. So again, we have to be very precise about what people want. But it’s also very gratifying because we have much closer contact with that user. We’re not selling to a buyer who may or may not really understand how something’s going to be used.

Eric Boduch: It also makes those interactions with their users really important, right? Because if that first initial entry point to that team doesn’t go well, it’s going to be very hard to get in the enterprise.

Cindy Alvarez: Yeah. So if you can’t win someone over, we internally joke about these, the lunchtime software developer is someone who’s trying out a tool during lunch, and if they can’t start building with it over lunch, they’re not going to adopt it. They’re just going to push it to the side. It might actually do exactly what they need, but if it takes two hours to figure that out, that’s probably an hour and a half too long at least.

Eric Boduch: Yeah. That’s a really good point. Things need to be as intuitive as possible. They need to help users get time to value, get their jobs done. Very important in an environment like that.

Cindy Alvarez: They may not necessarily have to be simple or they may not necessarily be able to be simple, but that entry point needs to be. In the UX field, this has been known for a while, this is a concept of progressive disclosure it’s called, which basically means only show the user a little bit of information at a time so you don’t overwhelm them. That’s where we got signup wizard essentially. But that’s what the whole product has to be like. It’s not just once you sign up, it’s what is the first task someone needs to do, let’s let them do that, and then we’re going to layer in complexity because the reality is that not every interaction is going to be that clean. There are going to be edge cases. But I don’t need to know about them on day one or even day 10.

Eric Boduch: It’s interesting too because that progressive disclosure fits the feedback too. Like we ask people for an NPS, it’s really simple, zero to 10. You give us a score. Now, the smart product managers look for those sixes or those fives and are like, well, reach out to them and like, what can we do to move you to an eight or maybe even a nine. Now it’s like they’re already invested a little bit to give you feedback so they’re likely to give you more and have that longer conversation where if we had asked them upfront can I have a 15-minute call to talk about how you’re using our product and how it can be better, a lot of them would say yes. But because they get in, they kind of get committed with that five or six.

Cindy Alvarez: Absolutely. Once we’ve given you some time, we’re going to give you more. And it goes back to that post-purchase rationalization. If I’ve given you five minutes of my time and you asked for more, if I say no, that’s basically admitting that the five minutes was a waste and I don’t really want to do that. So at the subconscious level, unless it was a really terrible interaction, I’m going to keep giving you more time because I want to justify the time I’ve already given you.

Eric Boduch: Absolutely. Awesome. We’ve talked about a lot today. What are your top takeaways listeners should take? There’s a lot of takes there.

Cindy Alvarez: I think it’s just really crisp on what do users need to do, are we doing it? And it’s just, I find it so useful to just stop and ask that question. No matter what it takes. Sometimes it takes kind of an unnatural posturing. I find that when a new person joins the team, that’s a really natural way to ask it because of course, they have to ask what do users want to do and are we doing it?

Cindy Alvarez: Sometimes you need to kind of fake it and bring people in from another team. Borrow a coworker, borrow a friend who works at a different company and get them to come ask that question because explaining it to a newbie is a really good way to make everyone stop and wait a second, if that’s what customers need to do and I’m looking at our priorities for next quarter, those don’t really line up. It’s so easy to drift. So just go back to those principles over and over. So what, is it doing what I need? Do I have faith that it’s going to do what I need? Is it doing what I need? And just repeat that every week.

Eric Boduch: Awesome. One of my favorite things that you wrote, and I’d be amiss if I didn’t bring it up, is what features your customers ask for is never as interesting as why they want them. That’s like one of the favorite things I’ve heard you say. Gets you to think about that, right?

Cindy Alvarez: So now when people ask for features, my recommendation, I say, if you already had that, how would it make your life better? And you’ll see this interesting division between people who have an answer and people who kind of stop and like, well, that means they don’t really need it. If somebody doesn’t know they don’t really need it.

Eric Boduch: And even if they can’t answer that, and a lot of cases we look at it and say, like, I had a conversation with Ryan Singer about calendaring in Basecamp, and the question came down to, what are you using it for, why do you want it? Because often what they’re asking for and what they think they need is a feature isn’t the best way to solve their problem.

Cindy Alvarez: Absolutely.

Eric Boduch: Well, I have a couple of questions. I’d love to turn this to you a little bit and see what we can get out of you here. Do you have a favorite product, whether it’s software otherwise, and why it would be your favorite?

Cindy Alvarez: This is a question that I have been forbidding people to ask in interviews because I feel like I’ve never answered this well.

Cindy Alvarez:  So, what’s my favorite product? We could define it by like what do I use all the time? Is Facebook my favorite product? No. I mean I use it all the time but I don’t have a particular fondness for it. They have achieved a utility which is there a lot of people that that is the easiest way to contact.

Cindy Alvarez: Think about something that’s really useful. I use a to-do list app called Due D-U- And the thing that I like about it is actually also its most annoying feature which is you set a reminder and at the due date it will push notify you every minute until you either do it or you reschedule it. That is incredibly annoying and it also means that it’s really handy for making sure you do the thing. Is it my favorite product? No, but it’s very effective.

Eric Boduch: I could see it being very effective. I could see if it escalated to my wife too, especially if it’s something she wanted, that would really get me to do that because she would just harass me too, wanting to see the app that I could reschedule.

Cindy Alvarez: The precision of it means that I put in ridiculous things like don’t forget your jacket. You’re like, I know I’m going to leave in about 20 minutes, I’ll put don’t forget your jacket and it’ll ping me at like 19 minutes and then 20 and the 21 and then I don’t. Yeah.

Eric Boduch: It’s interesting you mention, it’s never a question you’ve asked at an interview. I have never either. Like when I’ve interviewed product managers, I’ve never asked that question.

Cindy Alvarez: People I used to interview with would always ask it and I was always infuriated because I felt like this is not telling me anything about.

Eric Boduch: No, no. I like asking like, if you had this product, if you owned this product, what would you do differently?

Cindy Alvarez: What would you take away?

Eric Boduch: Take away is a great one. Or how would you take it to market is a good one. I like hearing those kinds of stories. If in that organization product owned some of the go-to-market for that offering. Similarly, on the marketing side, it’s fun to say what you saw as a good product launch and why did you think it was good and then what would you do a little bit differently.

Eric Boduch: This question I do ask when I interview people, which is three words to describe yourself because I think it’s interesting to hear what words they pick. And then I always usually will dig into one of them and be like, why do you pick that word? What drove you to that?

Cindy Alvarez: So yeah, let’s see. I’ll cheat a little bit, I have a phrase refreshingly blunt because I am. I am also a complainer and highly optimistic.

Eric Boduch: That’s an interesting combination of those last two.

Cindy Alvarez: I fundamentally believe that things will get better, we can do the impossible. It’s highly motivating to me to complain about things until I actually fix them. I think that’s a, it’s a psychology that I find I often have to explain to new people because like I complain a lot. I do it because I have faith that we can be better.

Eric Boduch: Yeah. It’s like the Du app for you too, right? It motivates you to make those changes. I get that.

Cindy Alvarez: The things that are comfortable, like comfort does not really motivate anyone to do anything differently. It just makes you keep on doing. So like, you know, introducing those sharp edges or those little pricks, those are the things I’d be like, oh, I just have to do something about this. And that’s where all the, that’s where all the good things come from. The good products, the good process changes. From someone saying, this is too easy. We need to make it a little harder and then we discover something. 

Eric Boduch: Well, thank you. This is great.

Cindy Alvarez: Thank you.

Listen to the full episode here.