From Writer to Maker

Ashley: Hi, I'm Ashley, I am a product lead for commerce products at Venmo.

Suzanne: One of the things we talk a lot about here at 100 PM is the path into product management, because the theme that emerges time and time again is most of us didn't study product in school, a lot of the classes that are available now were not available, and everyone's got kind of a unique story, some more so than others, some are a little bit more predictable, I did an MBA, I got a computer science degree, you didn't do any of those things?

Ashley: Did not.

Suzanne: You were a journalist.

Ashley: I was.

Suzanne: Why don't you tell us how a journalist ends up leading commerce products for Venmo in Chicago.

Ashley: Yeah, my path into product management was a little different, or not typical, I would say, but started as a journalist doing very news-heavy, and really, when I started to think about getting into product, and it's not even really thinking about getting into product, but thinking about getting into technology I was working at ABC news in New York reporting on science and tech, I kind of a interesting time or in my mind, an interesting time.

My first tech story was about the very first iPhone, and there were a lot of things going on at the time, Twitter was just starting to get traction, and I was talking to all these people, interviewing all these people who were doing all these really interesting and amazing things and I started ... Sort of planted the seed in my mind of, "I'm writing about these people, this is great, wouldn't it be great to go from writer to maker?"

Suzanne: Did you ask to be put in the science and technology stream of journalism? Like how did you even-

Ashley: No.

Suzanne: No?

Ashley: No.

Suzanne: It just came around one day and they said, "Oh, by the way, Ashley, you're gonna be writing about technology from now on."

Ashley: Really there was an opening there, I was actually an associate producer on Good Morning America, which is really funny, but was looking for another path for myself. And sort of exploring what was there on the, really, this was at ABCNews.com what was available there, and this opened up to me and I said, "Sure, I'll try it." I mean I think the way that I describe the similarities between the journalist role and the product management role is that, in journalism, you get to ask as many questions as you want, and basically, pick a topic and just learn as much as possible about it.

Very similar, I think, our skillset, at least, to some parts of product management where you're just asking questions, asking tons and tons of questions, and it's not just that you have permission to do so, you're pushed to do so, and so when that science and technology role came along, I just thought, "Hey, I'll try this, see how it goes, don't know a ton about tech, let's learn about it."

Suzanne: Were you interested in it, initially, or was there kind of a sense, because I mean, not to date you, but we're going back to the original iPhone year, it wasn't the same landscape, is I guess what I mean. People weren't thinking about product and we weren't so deeply, deeply immersed in digital experiences, online experiences, so I'm just curious about how a young person like yourself says, "Well, let's see what technology is about."

It's not celebrating, it's like, now people on GQ startup founders are on GQ.

Ashley: Yes.

Suzanne: Like that.

Ashley: There wasn't the sex appeal then that there is today, but certainly, everyone that I ... It was a little bit of an unknown, but everyone that I talked to was just really passionate about what they were doing, and really, really smart. And I think that, in and of itself, is part of what got me inspired to kind of extend my horizons a little bit about what I could do with my career.

Suzanne: So what was your first product management role?

Ashley: My first product management role was at Nickelodeon, I worked on NickJr.com and also on a, it's gone now, but a social network for parents, at the time.

Suzanne: Okay.

Ashley: Yeah, I worked at Nickelodeon, and it was pretty interesting, I sort of found out about the job randomly, friend of a friend contacted me about it, didn't really have any idea what that role meant. And at the time, they even called it a senior producer role. So went in, talked to bunch of people, liked everyone I talked to, and thought, "Hmm, let's see, we'll try this out for a year, we'll try this out for some time, see if I like it." And I have not looked back.

Suzanne: I've had a number of people come into my class as product managers, and saying, you know, I always start by asking, "Why are you here? What is it that are your goals and objectives for ..." And they'll say, "I was recently promoted to product manager." I said, "Great." "I don't know what that is." So was there a defining moment for you in this first role at Nickelodeon where you finally understood what the job was?

Ashley: That's a good question, I don't know if it was a defining moment versus just a series of moments over and over and over again. I mean I think the thing, for me at least, what I found is that, you can learn what the job is, so you can have a list of tasks of, this is a thing, particularly at entry level, these are the things I'm supposed to do. But you don't really feel it or know it, it comes from continuing to do the task over and over and over again, and then you finally get it. And it sort of comes together, I think one thing I was talking to someone about was about product vision.

I think some people, obviously you need to have a product vision about where you're going, and sort of a larger view, but I think for some people there is a sort of solace in the doing, and you can be doing, doing, doing, doing and then all of a sudden in the doing, you're like, "Oh, this is where we're supposed to be going." There's something about being - I’m totally getting off topic here...

Suzanne: Or you're exactly on topic.

Ashley: There's something about being immersed in the details, and really immersed in the details, and I think sort of, that informs that larger view. And I found that to be true, at least in the larger view of my career and doing that role at Nickelodeon.

Suzanne: So, did you have developers that you were working with when you were there?

Ashley: Yeah, so-

Suzanne: And you had never built digital products before, I mean you were a journalist.

Ashley: I was a journalist and I had, you know, I was working at ABC News, I was working on ABCNews.com, so I was familiar in that a sense. But I didn't know what an API was, things like that, so I had engineers that I was working with, and also designers, and just a really, I think ... People can come in not knowing what they're doing into a team who's pretty experienced and that sense of great culture and is very accepting and willing to take on the overhead of that noviceness, you know, or cluelessness, maybe, is the word.

And I think I just learned on the job and had them, they really taught me and taught me how to do this. And you would think almost more than my managers at that point, it was really about those people I was working with on a day-to-day.

Suzanne: Well one of the things that comes up in conversations that I have a lot, especially with people who're looking to get into product management is really getting a sense of, "What is this environment that I'm going into?" Because what you describe sounds, frankly, like it was highly beneficial for you, you happened to be met with folks who were seasoned and who could carry the weight, as you describe. But that's not always the case.

A lot of the times people come into the role hoping for that, or they think, "Well surely somebody knows, because I didn't lie, I said I don't have experience, just a lot of will." And then they kind of throw you in, and the expectation is that you're just supposed to know what to do, and so that you would intuit it, or something.

Ashley: Yeah, and I think that's an organizational mistake that happens a lot. So I don't know if this is happening more frequently, but it seems to me that I've been doing this for a while now, and it seems to me that, particularly over the last couple of years that product has become, in some companies, at least, the sexy, cool job, the job that's making all the decisions, I think there's this wild romanticism about product that always makes me giggle a little bit, because I often think about it as there's some really rough parts of the job that I don't think is circulated very well, but...

Suzanne: But just to speak to that, I think Steve Jones played a big hand in giving us a viewpoint of ... Everyone thinks that, that is what you're gonna be doing as a product manager, but I think as you were starting to speak to, there's a lot of not so glamorous aspects to it.

Ashley: There's a lot of non, sort of, glamorous parts to it. To go back to the original question, so there's this image, this Steve Jobs-ian image of what product is or what could be. And people from different parts of the org want to come into it, or people really want to get into it, which is great. I think, then, though, the organization has to be ready. As a novice, I would not know, or I would not encourage people to go into a startup, for example, and have never, let's say, as a head of product, for example.

But you need to have an organization, it's nice to have an organization that is able to guide you so that ... And that the organization is willing to give that to you, because that can be a lot, even if you think about mentorship programs for engineering, being able...or apprenticeship programs, being able to take that on, not every size of organization can do that, and I think you need to ... or I think it's important, certainly beneficial to have an organization that acknowledges that, that is not expecting, if you never done this before, is not expecting you to just magically know.

Suzanne: Now, Nickelodeon's a big company, right?

Ashley: Yes.

Suzanne: How many people were working there, approximately, when you were there.

Ashley: I mean, I have no idea.

Suzanne: In the thousands?

Ashley: Sure.

Suzanne: Easily in the thousands?

Ashley: Easily.

Suzanne: Have you ever worked in the startup environment?

Ashley: Yes, a few times, and then sort of what I would call a quasi startup, which is Groupon. So after Nickelodeon, I came to Chicago and went to a startup that was about 50 people, and it was a very informative experience in the sense that I came on during sort of a hiring brash. They hired a bunch of people, and then nine months later, they let go of a bunch of people, so I was both in the hiring rash and then sort of the firing part. So what was interesting about going from Nickelodeon to that startup was, at Nickelodeon, there were a lot of functions that were kind of outsourced for you, so there was a data team, and there was a marketing team, and there were all of these different teams who did a bunch of things for you that you wouldn't have had to do or necessarily had to think about, or I didn't think about, because as a newbie, I wasn't sure if I was supposed to be thinking, didn't know what I was supposed to be thinking about.

Then I went from there to a startup where every resource is so precious, every amount of time is so precious, every person's time is incredibly valuable, so you have to know exactly what you're doing and know that whatever you're doing is going to have an impact, and that was, and being responsible for that and being held accountable for that. That was pretty amazing experience. It’s also a pretty amazing experience to understand the importance of making quick decisions in terms of what happens if the money is running out? Or what happens if the business isn't going the right direction? I think for a big company to make that kind of decision takes a very long time, it's not just gonna happen tomorrow.

Suzanne: Yeah I mean, certainly we talked about the sex appeal of products and startup, startup, startup, it's like, it's good that you share that story, because that's really actually the predominant story. The predominant story is, we got a bunch of money, and then we spent it all, and we couldn't get to product market fit, or we grew too quickly and we didn't know how to continue to create value for our customers or what worked in one sort of niche segment didn't translate to another segment as we hoped and if you're gonna play in the startup game, especially at the employee level in product, you have to be warned, prepared for, the possibility of that and hyper connected to, "What can I be doing from day one to potentially stave off the inevitable, or to steer this in a different direction."

Ashley: Yeah, because what you do absolutely matters. Where I think, definitely, at a bigger company, you can hide the shadows, not that you would want to, but that there can be projects that don't have, at least don't have as visible of an impact on the business ... The value for business. And that is very immediately apparent when you're a startup.

Suzanne: Yeah and I think it's just more fodder for examining what are the stakes that I like, am I risk averse, or not risk averse, and if you're risk averse, startups aren't for you.

Ashley: Correct.

Suzanne: The other thing that you bring up that I think is worth shining the light on, is process. So one of the things that I talk about with product management, it's nothing if it's not just a series of frameworks for how to think about scenarios. So here's a framework for how to think about prioritizing stuff. Here's a framework for how to deliver software more efficiently. And when you come into a startup environment, it's just an empty field, and so part of what you need to do is start to standup those frameworks and those processes, and to go back to your experience at Nickelodeon, I think this is another point where people who make those transitions like you did really kind of catch themselves not knowing what they didn't know. Because in one environment, you knew things that were already figured out for you, but then when they get removed, you're like, "Something feels different, but I can't put my finger on it, exactly." And you're like, "Oh, yeah, where is data? Who's looking after that?"

Ashley: It's good though, it forces you to develop skillsets that you might not get at a bigger place, and it's ... And it keeps you really focused, too.

Suzanne: So you left a startup, or did you go to another one, I mean, was that hiring and firing enough to scare you off for good?

Ashley: Not quite.

Suzanne: No? Went back for more?

Ashley: I left the startup and went to, what I would call, the quasi startup in 2011 to Groupon, which pretty much anyone you talk to in Chicago at this point has done some time in Groupon.

Suzanne: So it's like a cult here.

Ashley: Yes. Yes. Yes. Amazing, amazing place, really amazing experience. At the time, the product team was pretty small, I don't think they had yet opened a Palo Alto office. And every ... I remember this very distinctly, every Friday, I think there were five or six other PMs who would just all meet and have pizza and kind of talk about what's going on-

Suzanne: Wait, so this is pre-IPO Groupon?

Ashley: This is pre-IPO Groupon.

Suzanne: How many people are we talking? Because there are, what, 15,000 people now? Something like that.

Ashley: Wow, really? That's amazing.

Suzanne: Was it like 100 people?

Ashley: It was bigger than that, I'm trying to remember how big the engineering group was at that time, we have very, very large sales force, so we still had a pretty large sales force, so going in, it's pretty funny because they were hiring so many people at that time. So you would go into ... They had these orientations at a church around the corner, go in and just be filled with people, they had them every week.

Suzanne: Wow.

Ashley: Yeah.

Suzanne: So when you say it's a quasi startup, why do you define it that way?

Ashley: Because at that time, we still had regular contact with the CEO, with the leadership team, you were very in touch with what was going on, even though you would be at a smaller company.

Suzanne: Okay.

Ashley: Yeah.

Suzanne: So for you, that definition has to do with the connections to the leadership, you know, having seven leaders of management-

Ashley: Yeah, the connections to the leadership, the communication style, and I think just the feel of the place, not that startups have a certain feel, but everyone was really hungry, everyone was really focused, everyone was there to do their best work everyday, sometimes night. But you know, everyone was really devoted, and it was a lot of smart people and really amazing.

Suzanne: How did you end up at Venmo?

Ashley: Another winding story.

Suzanne: You've been winding that product path all the way.

Ashley: I know. So I was at Groupon for about three and a half years, and Chicago's really small, I fell into an opportunity, I don't want to say fell into, I had went to a startup, a mobile commerce startup as head of product. That was a huge deal for me to be able to basically run the show when it came to product. I was ready, I was very excited, it was very crazy. So we had, it was a 19 person startup, I was head of product, but also product manager, like product team of one, as you would imagine.

And it felt a lot like bringing some order to the chaos, even though the chaos part was also fun as well, so that's really where I ... And obviously I had all these tools, you have a toolkit for how you run projects, or how you roll out features, or how you do development, or how you ... you know, you want to run things. And that was really where I felt like all of those years of getting all those inputs from Nickelodeon and from the other startup and from my time at Groupon really came together where I developed a way that I want to work and try to further iterate on that with our team.

So now, it's been pretty interesting because from there, I brought that here, we got acquired by PayPal.

Suzanne: Oh, congratulations.

Ashley: Thank you, that was pretty great, so we got acquired by PayPal, brought a lot of that thinking here, it's been really cool to see how it's changed over time, too, so you sort of quickly, it's not even quickly, you know, but as the team has changed, how we want to do things has changed, the way we worked has changed, we like to try things out, if it doesn't work, we can rejigger and change directions with it, and I think that's been really interesting, and something that I'm really interested to hear from other people just how do things change, how do group dynamics change as the organization grows, as the product grows, and how does that affect the product owner process.

Suzanne: Just for clarity, so PayPal owns Venmo, which is where you are now, PayPal owns Braintree, of course we all know PayPal, and you all are co-mingling in the same sort of headquarters, how big is the Venmo team specifically?

Ashley: So the Venmo product and engineering team, I believe is about 60 people. We also, in Chicago, have a huge customer support team as well. So it's still pretty small, so less than 300 people total.

Suzanne: Right, 'cause I think where I was wanting to ask, or to take you was how do you go from being ... So you're in this startup, you finally have your head of product role, you get to put in all of the frameworks that you like the best, and then you get acquired, which is a big win, but then you're sort of back to, now you have to start to play by some processes that may have already been established, if not by Venmo, then certainly by the parent company.

Although it's still fairly small, so I guess you have a little bit of room to innovate and be creative inside that.

Ashley: Yeah, I'd like to think that we took the best of all of those things. So there are, I mean, really coming from a startup to PayPal, I very distinctly remember when I found out that PayPal had this state of the art user research lab. So what? We can use that? There are people who, professionals, who will do this for us? And basically, it's for free? It's just a thing that we get? And how valuable was that? That's so amazing. So there are a lot of, in terms of, I think my initial reaction when we got acquired was, there're so many perks here, so many tools that you would never have access to as a startup, which is so, so, so valuable.

Now, two years down the road, or almost two years down the road, which is crazy, the other benefit that we've gotten is, as we ... PayPal has a lot of experience doing some of the things that are very, very new for Venmo. So some of the spaces we're trying to play in, or that specifically my team is trying to play in, we can get some of what PayPal has already learned as inputs.

They're very different products, they're very different audiences, very different users, certainly, but that's enormously helpful.

Suzanne: Did they have a product manager war story, fireside chats where they're like, "Come in and I'll tell you about the time when PayPal, the year was this."

Ashley: Not so officially, not so officially, but you can definitely get that if you need that.

Suzanne: I mean, again, all of these things that you're speaking about and what you're talking about with Nickelodeon, these are the little things that add up to, "What is the product management experience that I want or don't want?" And you're right, speaking only from my own experiences and having always been on the entrepreneurial side and really deeply rooted in that startup world, it's like, I do find myself daydreaming, especially here in Chicago when I meet all these huge companies, lots of huge companies here. What would that be like if there was somebody that I could just say, "How do I do this?" But ...

Ashley: It's, I mean, the ... It's not all rosy, for sure, for sure, but at a startup, you can do whatever you want whenever you want to do it. You can't do that here. For good reason, but that was certainly ... I would say that was a ... quite an adjustment for the team when we got acquired. "We can't do whatever we want?"

Suzanne: "We can't say this to a journalist? We have to get it vetted by 19 different lawyers?"

Ashley: Yes.

Suzanne: What is your role, exactly, here?

Ashley: So I work with a team of junior product managers, we specifically, we're called the commerce team, specifically we are looking at trying to figure out how to bring Venmo as a payment method. Basically, how can users or shoppers start to use Venmo outside of the sort of P2P context that people are used to using, and Venmo is extremely popular, it is P2P payments platform, so people paying their friends for whatever, sometimes for rent, paying them back for going out to brunch, sometimes just being funny and paying them a dollar, a penny, and writing them a funny note, but we're really trying to expand ... We're looking at how we can expand beyond that, I build on that success and then expand beyond that for users to pay whomever, pay merchants, go shopping with Venmo.

Suzanne: Feel free to tell me if this is kind of in the lawyer danger zone of questions, but I guess what it raises in my mind is, where do the products start to delineate themselves? So you have, for example, Braintree, this is a payments company, of course we understand the history of PayPal, so they're all kind of different, and then playing in the same spaces, and then, do you have to, maybe the real question I want to ask is, to what extent does the Venmo team need to negotiate with the PayPal team, for example, to say, "Well, we're gonna take this as far as this line, and we promise not to try to tread over it.” Or, is it just like, "Go for it!"?

Ashley: It's more like, "Go for it!" I mean, I think it's really that these, all three products and PayPal has a bunch of products underneath it, are really for very specific audiences, and I think that's where we're differentiated, we are ... Our user base really skews younger, everyone uses the dreaded term "millennials" I'm doing air quotes right now because it just feels like, I don't like it. But-

Suzanne: What would you use instead of millennials?

Ashley: Young adults? I don't know, I don't know why I don't like that term, it just feels a little bit, it's shorthand and feels a little bit lazy, I think it's overused, it's like every New York Times style section story is a story about millennials moving to someplace that's not Brooklyn, I don't know, it just drives me a little nuts. But we have a very different user base, we certainly skew younger, our users are interested in overcoming that awkwardness of paying someone back, really. So that's where we are, I view the work that our team is working on is really where we're trying to go, and we're trying to push the boundaries of, it's almost like a mind shift. So you're used to using Venmo to pay your friend or to be silly. But how do we, then, allow people to use Venmo outside of that context, if they want to?

Suzanne: Where would you say Venmo is in the product life cycle? Is it still very high growth? Are you moving into maturity? What does it feel like?

Ashley: It's still very high growth. I think that we ... it still feels startup-y to me, but I also think that we're moving into a time where we are so high growth that we need to make sure that we're able to serve the needs of our customers, I'm really walking around this one.

Suzanne: Fair enough. So here's where I'm kind of going on this.

Ashley: We need to think about scale at this point. That's where the point, it feels to me that we're at a tipping point of where we need to be thinking about scale. Where we've been building, building, building, building, and it's completely paid off as we have seen amazing user growth, but I think what happens to all startups that grow up a little bit, we need to be making sure that we're scaling appropriately, which is a super boring answer, I think, but ...

Suzanne: No, that's okay, why I'm interested and why I think, maybe, our listeners could be interested is, you talked earlier about having product vision, right? And I think the difference between being in the tactical role or being kind of strategic, and this doesn't have to be specific to Venmo, but what I’m really feeling into is how do we, as product managers, know when we need to be thinking differently about where we're going, especially if we are beyond the point ... Like if you're in a very small organization, and you're lucky, maybe you have a really visionary CEO who already knows it's onto the next thing, it's onto the next thing, here's where we've got to be, here's what's trending.

As the company gets larger or as you take on more ownership and leadership. That falls more and more to a senior product person like yourself, a product lead. And then you have to be thinking about, "Well we're doing great!" And that's the thing, it's like, "Well we're doing great! Why change?" In life, it's like, "Why would I change? Everything is working?" But you change to make sure that you don't wake up one day and realize you should've changed two months ago, six years ago, whatever the case. Do you have any advice for folks to how to stay strategic, or be appropriately looking into the future?

Ashley: I think you always need to be looking at the future if you are beyond that, I would say, if you're beyond that day, if you're if at all beyond that day-to-day role, totally, but at the same time, when I was at Modest, I was the strategic person and execution person, everything. So I think my advice is that, you just always got to be thinking about it. It's very easy, or I don't know how some people are, but I enjoy execution, I enjoy the execution quite a bit. I like working with engineers, I like solving that problem, I like kind of driving it, I'm actually someone that I manage right now is on maternity leave, and so I'm also playing dual roles right now.

And we have a product that's about to launch, and it's super exciting, and I was sort of dreading going back to doing that very tactical, but man, I love it. I love it. But, I think part of why I love it too is that, that love for it, I do think can become a crutch, because it's easier to have a to-do list, to know what you need to do, or sort of have this set of problems, and just like, "Yeah, I can squash them. It's very satisfying."

Suzanne: Yeah.

Ashley: It's very satisfying for me at least. And you always need people who are going to execute, obviously you need to find the right people who execute, who are good at it. But I also think if you don't have that broader vision in mind, and this is also what we talked a little bit about earlier is sometimes I might not have the proper vision in mind, and I do think that being really in touch with the details, and executing, executing, executing, day after day, can then ... This has certainly happened to me where you're in the thick of it and you're doing it, but then all of the sudden, you realize, "Oh, this is the vision. This ..." it gives you insight, it gives you a little window of insight whenever it's sort of all clicks.

And having that level of detail and that level of understanding of what's going on with your team and really at a story by story level can really inform the whole thing for you, I know it's certainly worked that way for me, worked that way at Modest. I say constantly, keep both in mind. But I think it's good, so I think for the product person who's really just thinking that, I think it's a mistake, you know, that I think it happens all the time.

To think about product management about just, "I'm gonna think of great ideas and I'm just gonna be ... It's gonna be this visionary role, this Steve Job-sian model." Because I think it's very hard to have that vision without being really inter meshed with the details. Or having some sort of context to details.

Suzanne: Yeah. Well and I'll build on that by saying most of us are not wired for being strategic right off the bat. Execution oriented things are sort of taught to us even through school, it's like, "Do your homework. Read these exact pages. Write this exact report." And so, I think for me, there's an experience when I went to university and I had always excelled in high school, and candidly as a procrastinator, I was fortunate enough that I could sort of really not do anything until the last minute and pull it off without trying too hard.

If I wanted to try, I could do really well, the shift for me going into university was sort of like I was talking about earlier, suddenly, nobody told you exactly what you're supposed to be doing, it's like they removed that kind of framework. So strategy's a bit that way, it's like, you have to bring the framework, you have to bring the vision. The other side of it, I like to tell people just to take some of the mystique out of it.

Being a strategist is just being a good guesser, there's a creative component, especially if you embrace, kind of validated learning is one of your methodologies and experimental mindset, then strategy is just saying, "I think this is a good idea, now let's find ways to execute on that, preferably, incrementally over time to prove it, or quickly disprove it and move it on." So we equally have to encourage that muscle in ourselves, because if we're always in the to-do lists, then we're not growing as PMs, and we're not learning how to be creative and bolder and experimental in our thinking.

But the danger that you speak of, of getting stuck too much in one way or the other comes up a lot, where definitely, I've seen people ... The thermostat is set for execution, and they would just want to, "Can I just do it myself? Let me just stay here in JIRA just a little bit longer." And leaders, the flip side of this, getting kind of comfortable in the cushiness of not having to be in the details, and then someone goes away and suddenly it's like, "How do we do this again? What's our process?"

Ashley: Yes, yes, yes.

Suzanne: "How are you writing your user stories?"

Ashley: Yes, yeah.

Suzanne: Very good. We do a segment on our show called, Get the Job, Learn the Job, Love the Job. And I wanted to maybe frame the first question about getting the job through the lens of some of the experiences that are particular to you, so a lot of your experience was learning on the job, which I think is very exciting and one of the best ways that any of us can learn. So if I, or one of our listeners, is somebody who just got promoted to product manager that has no idea what it is, just came over, got recruited from journalism or any number of seemingly disconnected background, what would you say tome to encourage me to become the best PM I could be?

Ashley: Talk to your customers.

Suzanne: Okay.

Ashley: I mean, I think that's the number one thing, and I actually feel like, even as PMs, sometimes, we can lose touch with that. I think people can come up with a really cool idea, or they get very focused on the solution or the feature, whatever it is that they're delivering, and along the way, I've seen this happen so many times, it's happened to me. And along the way lose touch with the customer and the problem they're trying to solve. And I think if you can, number one thing if you're coming over, hopefully if you're coming from somewhere in your company, you already have a great understanding of your customer, and that's why you're coming over.

And that's why you've been tapped to move into this role, but I think that's the number one thing, I think number two, befriend and be lovely to your engineers, because really, really, a product manager is only as good as your engineers, and I think about this all the time, I cannot, I can't do my job unless my engineers are amazing, and not just amazing, not just, "Oh, they're good engineers. They're smart, or whatever."

But really engaged in, also having that customer focus and they engaged in solving problems for the customer. You don't want engineers who're just gonna do whatever you ask them to do, that's not what you want, you want partners who're gonna push back on what you're saying, gonna ask questions, and who're gonna be as interested as you are. I think in terms of learning the job, because then everything else you kind of learn, this is something that happened to me multiple times at Groupon where I was hiring for my team, and had a ton of people come in, and they looked so good on paper. They sort of had the perfect resume, and I didn't like anybody, and I just know, I just-

Suzanne: Doesn't that make you a common denominator? What's wrong with all these people?

Ashley: I know. But what ended up happening, and then again, just thinking, "Is this my bias to do this?" But just finding people from other parts of the business who have subject matter expertise, I can teach you how to do this job, I can give you tools, I can teach you the task that you're supposed to do, I need people who are so engaged and care and are driven and ready to do this. This is ... Product management is a really tough job. So I do think sometimes people don't quite know what they're in for, what they're getting into, and I certainly did not.

Suzanne: They’ve been listening, they've been following 100 PM all this time, and then they get to this interview and they're like, "Wait a minute, maybe this isn't for me, Ashley said it was hard." No, she loves it, that's why we're here talking about ... I'm putting you on the spot a little bit, but you made the point, buckle up and talk to customers, and you spoke at the outside of the interview of how your journalism background in a lot of ways readied you for much of what the skillset of product management requires, which is a curiosity.

I teach a lot about interview techniques. Is there one nugget that you can offer our listeners from having been journalist of how to ask the right kinds of questions, just a little?

Ashley: I think have a list of the kinds of things that you want to know or the questions, you know the answer to this.

Suzanne: I want your answers to this.

Ashley: Have a list of the kinds of things you want to cover, but don't just check down that list. You're responding to what people are saying, the people you're talking to are humans, they're not some sort of archetype cut out of central casting, they're real people. And really being tuned into that. I think the other interviewing technique that I've had that has worked really well, and it especially worked well in journalism is to just shut up.

Ask a question, people say they don't want to answer it, don't say anything else, and then eventually they answer it.

Suzanne: You're actually the second person that I've spoken to very recently who gave the exact ... I like the way that you framed it, it was another one of our guests, Wade, and he said exactly that, talk really slow, and people will instinctively want to jump in and throw out information. "Oh, go ahead."

Ashley: People don't like silence.

Suzanne: A colleague of mine used to say, "People leak data all the time, you just have to, as you describe, be prepared to, and willing to listen."

What about hard lessons learned. Surely all that time of figuring it out as you go, you found yourself in a situation where you thought, "Well that wasn't the best." Or if you could go back and do it differently knowing what you knew now, any advice you can offer for possible pitfalls in this hard job of product management?

Ashley: This again, goes back to kind of team dynamics and process, I think really not being afraid to ... If something is not working, this is true for everything, and if somethings aren't working, don't be afraid to throw it out immediately. Whether that's how you're working, whether that's part of the product and you can immediately tell, or you just kind of feel like, "This is not right, you need to trust your instincts here." Or just I'm really specifically thinking about process.

I think when we got acquired our team kind of tried to keep working in the way that we'd been working, but we were just a different team, we were getting ... People were coming onto our team from our Braintree and PayPal, and we just kind of kept grinding it out, we really needed to adjust, and when we did, it was amazing. But it took us a while to get there, and I think it's human to kind of cling to the things that are familiar.

But try as much as you can to let that go. You'll find out a lot faster whether or not you're working on - this is both true of of product, and just the process itself - whether what you're working on is gonna be successful, and that's really what you want to know.

Suzanne: I think to build on what you're talking about, you hear people say a lot, the number one reasons folks fail in product is falling in love with their own solution, and to even expand that idea, the minute we formalize something, be it a process or whatever, the minute we're like, "But I did that, why would I have to do it over?" I would say product management is a lot more like laundry than you think, it's never really done, so the less attached you can be to the completion, the perception of completing, the easier it is.

One of my favorite anecdotes about throw it out if it's not working comes from Leo Tolstoy, and I don't know if you know the story, but legend has it, he wrote 60 pages of the book before he realized what the story was. And tossed the 60 pages and started again. You're a writer, you know that's a tremendous amount of work to be 60 pages. It would hurt, but I see this a lot, that's the kind of ruthlessness that you have to have to your point. So I think that's excellent advice.

Why do you love this so much?

Ashley: I love being able to come into work and solve problems every day. I love the people that I work with. I mean the team is absolutely incredible. I think when you have ... It's pretty, not to get cheesy, it's pretty amazing what you can do when you have people who are singularly focused. Hitting the goal, or moving the needle in some way, or solving a particular problem what can happen. And I really think magic can come out of that. And I'm not ... I can't code, I can't design, I have hilarious memories at Nickelodeon doing my very first wireframe was terrible. But-

Suzanne: Did you sketch them or did you use the software?

Ashley: Sketching, I was trying the software, this was 10 years ago, it was really, it was rough going back then. But it's, for me, it's really the team, and then at the end, seeing what we've done, seeing what we've built, I think it's just so cool. It's really, really cool.

Suzanne: And remembering to celebrate those victories along the way, too, then.

Ashley: I think that can happen a lot. We actually ... This is something when the team, before we got acquired, try to do a lot of. Just remembering that you're moving, moving, moving, you're moving so fast. And it's just like constantly going to just stop for a moment and say, "Hell yes, we did this." It's pretty awesome.

Suzanne: Yeah, I agree with you completely. What about recommended resources, where would you direct somebody to get some sideline education, whether product management or beyond?

Ashley: Yeah, so this is a book I'm reading, right, I've not finished it yet, but so far, it's incredible, and it's funny because everyone on my team has been talking about it, and I had co-worker who said to me, "I keep trying to make my way through this book, but I read a few pages, and then after two pages, I have to think about how I'm interacting with people and how I'm working with people and it really makes you think." It's Camille Fournier's book.

Suzanne: Okay.

Ashley: It is called, and I have to look this up.

Suzanne: Alright, I'll put it in the show notes, Camille Fournier, what's the ...

Ashley: It's really meant to be ... She sort of frames it as a book for ... She was the CEO of Rent the Runway, she pitches it, or sorry, frames it as a book for engineering managers, but I think it's a really just great book to read about working with people. And team dynamics, and being a manager. Being a manager, and being in a managerial role and like in the technical world. It's pretty ... My husband laughs at me, because before I started reading it, "I am so excited to read this book." And he's like, "You are such a weirdo, no one's ever said that about a management book, ever!" And it's totally lived up to what I wanted it to, it's great.

Suzanne: It's a wild page-turner? You're up until two in the morning just squeezing-

Ashley: Not so much, but it's great, I'm just a little bit in it, I'm already feeling ... It cuts deep.

Suzanne: Well, and we have to be learning all the time, right? We talked earlier about the fear of being disrupted, or getting too comfortable in a product that's succeeding, and I think that can be equally true for us as individuals. As product managers or in any profession. If you stop paying attention to what the rest of the world is doing, and you stop checking in on which new ideas have entered the consciousness of the collective, then you could quickly become irrelevant, so reading and following up is a great way to do it, and I always advise, temper that with reality, I say sometimes, if I read Fast Company too much, I think, "Well what's the point of even living another day? I don’t know anything about anything." Because there's this perception that the whole world is very different than the one that we're in, and then you come back to your office and you're like, "Oh, yeah, no one's really caught up to that, the media's up in front."

Ashley: Yeah, I mean it's pretty funny how even if you just think about how development has changed at Nickelodeon, when people were just starting to talk about Agile, just trying to try Agile, and it wasn't Agile at all, looking back, that wasn't anything. But it's, yeah, it's pretty amazing to always compare what the ideal is and what is actually happening, and then taking everything and kind of making it work for whatever you got.

Suzanne: Yeah, yeah, wherever you are, you're there. Do you have a professional or personal life philosophy, side of the mug quote that tells us a little bit about how you like to operate in the world? Either at work or at home, or both?

Ashley: I always like to be learning and always like to be having fun. I do not ... I don't want to be doing this, so the minute this job or this industry becomes un-fun to me, or something about this becomes un-fun, I'm out. And I think I'll sort of find somewhere else just to spend my energy or passions, but you know, this job and this industry has just been, or this role, I shouldn't say that, but this particular job, they've all been great. Just have been really being able to, for me, being able to weave in that desire to learn. And having fun while I'm doing it. I really like to laugh at work. I really get to work with great fun people. And it really has to be ... We have to be working on things where I can just laugh a lot, even just getting acquired, we were coming ... I never worked on payments before. I didn't know anything about payments, I knew about how people shop online, so coming here and just, this is really opened a whole 'nother world to me.

Suzanne: We'll all follow you online so that if there's ever a future point where you proclaim whether it's via Twitter or whatever the next platform is, “I’m out. Product management is over because it stopped being fun and Ashley Phillips was onto it and onto the next thing.

Ashley: Well my husband and I have a plan B that we talk about all the time, which is to launch an ice cream shop.

Suzanne: Thank you so much for being part of our show, really appreciate your insights.

Ashley: Yeah, thank you so much.