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Shepherd Your Product

with Sara Wood of Farfetch
Jan 22, 2019
Back to Podcasts
Shepherd Your Product | 100 PM
Shepherd Your Product | 100 PM

Sara: My name is Sara Wood and I lead product management at Farfetch.

Suzanne: Now, to say that you lead product management is a bit of a humble statement 'cause I think your title is something way more impressive like Global VP of Product, is that accurate?

Sara: Yes. It is. I report directly to the CEO, José Neves. I started about a year ago. The product development organization there is comprised of product managers, analytics, design, research, et cetera. We partner very closely with the engineering org and that's infrastructure, engineers, data scientists, et cetera.

Suzanne: Now, you have a long career and a long career in leadership, which I'm going to want to crack into. Is this role the most senior big responsibility role that you've ever had or is it really just context changing but responsibility staying consistent?

Sara: Yeah. Yeah, it's interesting. I've not had any two roles be the same. I've had bigger titles, smaller titles, larger companies, smaller companies, but what I do typically is the same. I help develop product strategy, I partner with the executives to understand how to bring that to life and take it to market and then I manage people in order to execute against that vision. I've worked in everything from very small seed stage companies, one of which went TechCrunch Disrupt, all the way through to Fortune 500 companies where I did exactly the same role that I'm doing now.

Suzanne: Right. How did you find your way into product to begin with? I know you'll have to time travel a little perhaps to answer that.

Sara: Yeah, I started this a long time ago. What attracted me to the industry is really the creativity. I moved to San Francisco in the first dot com boom and the challenges there were less about revenue models and community and things that we talk a lot about today and more about what does this forum do for us as a creative community? What can we do in terms of our writing, our arts, distributing information and knowledge around the world? I got into it before, though. I got into it just after grad school when I was doing research in Washington, DC as a policy analyst. I used a lot of the precursors to HTML to research things like patents, drug prices around the world, things like intellectual property law and from there I parlayed that into a career in the industry.

Suzanne: Was it product management then or ... 'cause there's this debate about product management is new, or it's really not new, but everyone's suddenly talking about it and everyone's suddenly wanting to be in product. What was the landscape and the definition of that role back then?

Sara: Yeah, it's a great question and I always talk about what I do. What I do is the same, frankly, from 25 years ago when I started, however the title product management did not exist for the first half of my career. Really, what a product manager is ... and it depends on the size of the company and the tech that you're going after, and the community, and the users et cetera what your job is. No two companies are the same. When I started, I was definitely not calling myself a product manager but I was doing things like defining releases and writing content. In some cases I was writing CGI scripts and pearl code to get things out the door. At the time, it was really considered a jack of all trades role. But it wasn't called product management. In fact, I don't even know what I called myself. I was in web development more than anything and really, again, inspired by the creativity of the new format.

Suzanne: Did you study coding or computer science formally or you were just like, "This is the thing we're doing, here's how you do it, go."

Sara: Yeah, I didn't. My undergrad degree is in English literature and my masters degree is in business. When I left business school, I moved to DC as I mentioned and there were a lot of really interesting technologies emerging. The internet was HTML 1.0 at the time. I used a lot of Gopher but what I was most attracted to was GIS which Google Maps effectively made obsolete but ... at least for the laymen like myself. Really just learned on the job and trying to figure out how to put together snippets of code in order to either collect data, to communicate with people on the other side of the world, or to put information out in the world through my research.

Suzanne: Wow.

Sara: Yeah.

Suzanne: Do you recall what was the first product leadership role that you had?

Sara: Yeah, it was at a company called Salon magazine, and it was actually the first company I was with that went IPO. We did a Dutch auction style IPO and it was really new and interesting at the time. What was exciting about Salon was it was a really creative place to work. It was disrupting the newspaper industry. A lot of ex-newspaper, like San Francisco Examiner and San Francisco Chronicle staff came aboard to help run this company. It was there that we all did a bit of everything. My role was effectively running product. I ran product design. We didn't really have all of the disciplines that we have today again, as the industry has evolved. More and more niche skills are specific disciplines that you want at the table as opposed to someone like myself just doing a bit of everything. At the time, it was product and design and engineering, the three, and you hear people call that the trifecta of product development. In today's world, that has evolved into analytics, user research, data science, infrastructure's often at the table, architect's a separate discipline that comes along with engineering so it's a much more full house of people. But, Salon was the first place that I got into product leadership.

Suzanne: At Farfetch ... what is Farfetch by the way, for the folks listening in? It's based in London but I think it's a global brand. Tell us about it.

Sara: Yeah. Sure. It's actually a Portuguese company and we are the first Portuguese company to go public on the New York Stock Exchange.

Suzanne: Oh wow.

Sara: That's exciting.

Suzanne: Did you ring the bell?

Sara: I did. Yes.

Suzanne: Cool.

Sara: My boss, José, he is a from a small Portuguese town and he started coding at an early age but he came from a family of shoemakers. When he was starting his career, he saw a real opportunity in the space of luxury fashion where there was no platform for the global industry. There's a real opportunity there, it's a $300 billion dollar industry, it's slated to be $450 to $500 billion soon. What he did was effectively plan a huge vision. It wasn't just that we're eCommerce. We don't just sell clothing. What we do is we've created a platform that is a marketplace. We are the global marketplace platform for luxury. What that means is, we don't own the clothing that gets sold through it's were connecting buyers and sellers through our platform. In that way, we're able to extend it into new places. For example, we have a whole offering called Black and White where people can come in like Proenza Schouler, one of the brands that uses our services, and they can build on top of our platform and run their own digital offerings as well.

We don't have this idea that it's all within our system. The whole point is that it's an open system and that any brands and boutiques can come and sell their inventory through us. Suzanne: You have quite a bit of experience in fashion, you were with Gap before. By design, is that just a passion of yours or just you get one role and then suddenly you're pivoting from place to place but keeping that constant?

Sara: Yeah, it's a good question. I did a lot of soul searching before I went to Gap. I had been in a lot of different types of companies before but I had never been in a company that made physical products and that was intriguing to me. When I was a small start up called Layer and we went TechCrunch Disrupt but it was a really hard job, it's going back a bit and very hands on and those kinds of companies, when you're the product leader, you're doing everything from writing stories to installing the sound system in the office to ordering the catering and it was really an exciting time to be a part of a tiny startup but then I wanted to go back to leading teams.

When I joined Gap, it was to lead a pretty large team of product managers and also global. What it got me was a step into retail and I wasn't so motivated specifically by retail though it's become a real interest of mine. I was motivated to learn a new industry that uses technology in new and creative ways. For me, at my heart and watching the industry grow over the last 20 some odd years, every company is a technology company today. If they don't believe that they are, then they're not going to be in business very long is my opinion. Gap is one of those and when I joined, it was with that idea of changing hearts and minds of people who work at Gap to say we're actually a technology company that happens to sell jeans and t-shirts, how do we do it better? How do we optimize what we do? How do we innovate what we do? How do we thrive in this new world?

I was very much attracted to that concept of a vertically integrated retailer for those reasons. Understanding how you look at cotton growing in the field to the warehouses that you use to the factories that you use, the logistics involved of shipping things from one place to another, all the way through to the customer experience whether that be online through a mobile app or website or in store, how are you served in store? That's where I started in retail was really to learn the ins and out of a new industry using my technology experience as the foundation.

I went to Farfetch because ... the thing about Farfetch is it really is a technology company at its heart. It's a platform company which is very interesting to me and the companies that I've worked in like Flickr or Wikia that really took that platform first approach, really motivated me, the part of me that is the true technologist it's very interesting to think about platform as an enabler for the business. Farfetch was really putting that front and center into what we do. In fact, when we filed for IPO, it was around the data platform. That was my part on the roadshow for Farfetch was to talk about that data enabled platform.

The other thing that Farfetch is doing that attracted me was it's taking a no channel approach and that again, is new in retail as well. From my years at Gap, some of the challenges that I saw, things like shoppers don't just shops in stores or just shop online, they shop everywhere. We're all human and as the mood strikes us, we do different things and it might be shopping or it might be chatting with a friend, but how do you actually get in front of customers where they want to be? Farfetch was doing a lot of thinking around that as well and breaking down the channel barrier which is interesting in retail.

Suzanne: It's fascinating to me that you were on the leadership trajectory and then you voluntarily sidestepped to go back to a more tactical small role and then as you described you went back. What I'm mindful of potentially folks listening in our audience, there's this tremendous pressure to do it a certain way.

Sara: Yeah.

Suzanne: Ladder up, ladder up, ladder up if that's the thing. Would you recommend that to somebody listening in who might be in a similar place where they've taken some leadership roles but they see a really cool, more grassroots opportunity but they're scared because is that a regression? Will they be able to come back if they don't like it?

Sara: Yeah. It's a really great question actually and one each and every time I think about where I want to take my career, it's one everyone faces, I think is what's the right role? I've been lucky in my career. I did grow at a certain clip to the point where I've launched some really killer products, things that millions of people around the world use that, and this is something I'll talk about today on stage, is that feeling of building something where the people using it don't know I exist. It's really humbling and really motivating.

I've gotten to do a lot of really neat stuff in my career in that way and for me, I'm attracted to a technical challenge. What makes a company at any size interesting or compelling to me personally? The advice I would give is is there a thread that you can see between one job to the next? Is there a story to tell? Does it resonate with you as a human? Because it is a large part of your identity, is what you do and where you spend most of your time. You want to be inspired by what you think about most of the time. If you're spending time on a small startup and you want to have that experience of getting hands on again, I definitely recommend it. It's very hard though. Then you go too far into management, you're very much removed from the day to day building stuff.

For me, that's been a really hard thing to go back and forth between because in my heart I'm a builder. I came up grassroots style. My dad's a farmer. I never studied computer science. I ended up in this career through just love of networked computing. I like that feeling of being able to get hands on. For me, if you look at my resume, I go back and forth between the two but they definitely have different challenges. You just really need to think who are you and are you motivated by going back and learning some of the new methodologies?

The other thing that I will say is that I believe for my own self, it's allowed me to develop my own sense of how to do this job. What is product management in general? How to manage and lead people in the workplace. How to promote and mentor them in their careers. I think a large part of that comes from the fact that I have tried out all of these different things and I haven't been afraid to go back and get my hands dirty. I think it helps keep me more modern in my thinking as opposed to rigid in the fact that, "Oh this is the way it worked last time, it must work the same way again." Because I don't believe there is any one right way to do product management because no two places do it the same.

Suzanne: Yeah. No, I mean what you spoke about just there is at the heart of what this podcast has always been about, is maybe if we talk to enough product people, we start to see where there are potentially some universal truths but then there are just all of these different edge cases or as I like to say, the official product management answer is, "It depends."

Sara: Yeah.

Suzanne: I'm curious whether you would consider yourself to be a technical product manager?

Sara: Yes and no. I was certainly more technical earlier in my career. The thing that I do try to stay on top of, and I would give this advice to a product manager of any level or stage in their career, is definitely get to know your architects. Get to know ... be able to white board the system's architecture. Be able to at least understand it, know what databases you use. Know what most people code in. I think that's really important for credibility. Nobody expects product managers to be technical. Some are, some make the jump from being an engineer into product management, but the more that you can understand their daily life and how frustrating it might be to be interrupted by a product manager who doesn't understand transaction costs of interrupting them, things like that. I think the better.

I consider myself technical but not so much as I used to be I guess is the answer to that but I definitely think it's worth the time and effort to at least immerse yourself, especially if you're new to the job. If you're not new to the job, don't be afraid to ask but ask your architect for lunch and have them sketch out a diagram and talk you through some of the challenges that they have. Ask an engineer out to lunch and do the same. Really make the rounds and do that in a one on one or informal way and I think that you'll pick up a lot of the technology and the things that are challenging the team in a way that you aren't expected to necessarily understand. The different code or the APIs or the SDKs that people are working with daily.

Suzanne: Beautiful. I'm sensitive to just being in this space with you, you have a lovely energy and it's very calming and I don't know if that's specific to just the activity that's going on here today but I'm curious how you would describe your leadership style?

Sara: It's funny, I've been told that I have a calm energy but the funny part is that I ... how I describe myself is different. I say that I vibrate at a very high frequency and I'm always worried that people pick that up because I think it's stressful to be around somebody who vibrates really high so thank you for that.

My style is definitely informal. That works to some degree. It, I'm sure, offends many people. I often joke. I wonder how many times HR's been called in on some stupid joke that I've made but I believe at the end of the day, we're all humans and we have a different role to play. If there's anything that I can do to help make a workplace community, and I do call it a community because we all need to live and work and breathe and eat together so, what can I do to make that a better place to be with my leadership style? Then, how you mentor people along the way. I think for me, I'm definitely more on the empathy side. I often joke when people move on to new jobs. I'm never upset or offended, I always think, "Oh my god, that's amazing," if it's something they're really excited about because at the end of the day, maybe I'll work for them someday, you just never know where life takes you. I think remembering that is really important. It's a really silly thing to say but I work in fashion, I always think of Project Runway with Heidi Klum, that one day you're in and the next day you're out.

It's true. It's just remember that. Nobody is in the same role forever hopefully. You just never know what these people that you crossed paths with, either for a short time or a long time, are going to do in their future or if you're going to cross paths with them again. I just think investing in that relationship is probably the first, most important thing you can do in an office environment and that's both as a manager but as a colleague as well. Just remember that you're out there doing your best. So, that's the start of my leadership style.

I'm also very hands off, I'm a little bit ... ADHD. My son is ADHD so I feel like I can self-diagnose reasonably well because we've spent enough time with doctors on it. But, I do see a lot of that in myself. Where I'm not good is with people that require a lot of micromanaging or handholding. I do expect a lot of people so I'm very empathetic and human on one side but I do expect people to bring their best and if they're not, I'm happy to work with them very closely to get them there but that's not a place that I want to spend all of my time is with one individual trying to get them either committed or involved. It's a hard run. Humans are complicated creatures. Just remembering at the end of the day that we all are human and we all have our own baggage that we might bring into the work one week but the next week we'll be back on our A game. That's roughly my style, I don't know if that's specific enough.

Suzanne: No, I think it's pretty evocative. You're here at Leading the Product, you're speaking, you have not yet done your talk …

Sara: I have not.

Suzanne: ... as of this moment. By the time this episode airs you will have done it. What is the talk called?

Sara: Where we landed is Navigating the Ever Changing Landscape of Product Management and the subtitle is Before and After IPO. It was a late change to the talk because I couldn't talk about it before. You go into a quiet period leading up to IPO. We're just coming out of that now, so we IPOed about a month ago. That allows me to talk more openly about it, with some degree of restraint. That's my titles, I'm going to be talking about what it means to be a product leader in an IPO situation.

Suzanne: Great. You've done that a couple times in your career.

Sara: Twice now, yeah. The first very early and I did not get to ring the bell the first time and this time I did get to be, I was on stage with the execs in New York, my kids were on the trading floor, it was a really incredible moment in my career. It was much more emotional than I thought. It was just a moment in time, but it felt like a celebration. It was really exciting.

Suzanne: Can you share with our listeners, especially those who won't have the benefit of being here and hearing your talk, maybe what are two or three of the key takeaways or wisdom moments from this life of pre-IPO post-IPO?

Sara: Yeah. Well, it's interesting because product managers can relate to this. It's frankly no different in many ways than shipping a new feature, right? Or working hard on a new product or a new release and having it go live and then being committed to taking care and growing and evolving that thing that you've just spent months building. The IPO is like that, it's a moment in time, but now that we've done it, it's the next chapter of our story. A lot of people talk about acquisition or IPO as an exit and that's frankly not true. It's not an exit, it's a renewed commitment to the product that you're working on and to the customers that you serve so that's the gist of it is that the role of product is critical from the start.

How we think about and describe the company is critical on the roadshow and driving understanding of what we do to analysts and bankers et cetera. Then, post-IPO our job is to continually drive value back into the company, through either incremental investments or through wholly new innovations that are risky, just as we did before. The job itself doesn't change, it's just a new chapter and with that new chapter comes new characters like shareholders, we didn't have them before, you know, public shareholders. We have quarterly earnings calls. Things like that, things that you really need to understand that you're not hidden away from peoples' judgment anymore. You're more in the open sunlight at this point. The job is the same.

Suzanne: Yeah. There's the expression, "What got you here won’t get you there," and I think the parallel of this in product leadership is that the product that you're managing at senior leadership levels are the people and the processes as well, how do you feel you've had to personally evolve in terms of your skillsets or where you over-index and where you under-index …

Sara: Yeah.

Suzanne: ... to succeed and thrive as a leader versus succeeding and thriving as a tactical in the trenches type of individual?

Sara: Well, for product, I think there's a bit of personal answer to that as well as just a general for this discipline. Product managers in my opinion, their number one required skill is relationship building. It's a soft skill. It's that ability to make people feel heard, truly heard, and to really adapt the way you're thinking about things to what customers are telling you or colleagues are telling you. That being said, there are times in my career where I've thought I had the answer or wanted to build it a certain way. As you move into exec, that relationship piece is still there but it's amplified.

My job is both to advocate strongly and fiercely for the discipline of product and the activity of building software. There's a lot of people that they work really long hours and it's really hard and if there's nobody advocating for them at the top, at the senior levels, it's not a nice feeling, right? They end up being treated like project managers who are just tossed a set of requirements and told to go build them and without that ability to own their own destiny. What I bring moving into that and this is again, post-IPO is the same, is someone who advocates for people on the ground and I feel like I do that fairly well because I've been that person on the ground through the years and I understand that challenge.

At the same time, though, my job is definitely to look after the best interests of the company. The P&L is something that I look at obsessively, look at the data, look at how we're driving incremental dollars from where, how does this strategy get pulled together and getting that alignment and buy in with the other execs and then my boss the CEO as well. So, effectively I'm sandwiched in the middle of protecting, I guess, or advocating for a large group of people that are at the heart of what we do as a technology company but also making sure that people are excited and bought into the vision that we've put forward as well. That relationship piece is critical to that, it's gaining trust, it's getting visibility in the right places, it's the ability to push back and have that be okay. That creates a tighter relationship once you get that credibility going and people see that your heart's in it for the right reasons.

For my own self, I'm pretty feisty and I guess type A might be applied to my personality type and then over the years I've definitely had times where I pushed for something or articulated something in maybe a too direct way or something that felt really emotional to me at the time, kept me up at night, I think everybody's probably had that experience in the workplace. I've toned that down considerably and it feels a better place to be and I would recommend others to do the same. There's a little bit, and this sounds terrible, but there is a little bit of just ... it's not about care, but I'm going to say it that way, caring just a little bit less because what that means is it gives more space to invest in the relationship and the trust and the credibility that you need to have to do your job.

If you stop being so tightly attached to the outcome that you're driving, you open up space to build trust and credibility and maybe you don't get your way that time, but next time you might have a better chance to being heard and advocating for something different. Failure is okay in that regard, and I think that's another thing too that takes some time to learn is ... the faster you fail, the quicker you learn and the less time you spend on something that isn't going to ultimately work and therefore you saved the company money. Also, getting into that mindset as well, you don't have to have every decision go your way, insofar as you've all agreed that failure's okay as long as you do it fast. That's allowed me to take my ego out of a lot of the conversations, let other people drive sometimes, whether that be bottoms up or tops down and be okay with that. Again, my job is still to advocate for the discipline of product in Farfetch and make sure that it's not entirely tops down. But it can't be entirely bottoms up either. What does that balance look like?

Suzanne: Yeah. You said yourself you've had the great fortune to work on so many incredible products through the years and you've done a lot. I'm curious, what's on the Sarah Wood personal roadmap in terms of that thing that you haven't yet touched or done and it's maybe just sitting out in the near term of something you want to push yourself toward personally and professionally?

Sara: Yeah, I'm not sure. I've been so deep into this career for so long and I've been very fortunate to build the career that I have. I've been careful with each step. I'm pretty happy with where I am. I love my job, I love the people that I work with, I haven't really thought that far ahead. Where I have thought is I'm ... on a more personal note, I'm a single mother, have been a single mother for about 10 years. My kids are now preteens so I'm actually thinking what does post having kids in my house look like and what does that do for my career? I think that opens up a different set of opportunity that I don't know what they are yet, but I'm starting to think about what that might look like, whether that be just more time dedicated into the job that I have now, or maybe more side projects. I used to do a fair amount of side projects earlier in my career where I would do coding myself or build a mobile app, that kind of stuff, just to stay fresh. Yeah, I'm thinking about on a personal level, what does my time and commitment look like once my kids are in college, I guess. What does that do--

Suzanne: Maybe if they're listening and they're like, "Mom, I'm 14, you don't have to shoo me out the door just yet."

Sara: They know, they're funny, they think that they basically think they could live alone anyways as it is. It's an interesting thing, it's the first time I've ever stopped to take a breath like, "What do I want?" As opposed to feeling like I'm trying to bring my all to the workplace, trying to bring my all to home, to my children. That balance is hard to strike because at any point you feel like one is suffering and you're walking the tightrope of I'm a terrible mother or I'm a terrible employee, how do you become great at both? Anyway, it's just a different mindset I'm in now, and it's only occurred in the last couple of months, frankly. Suddenly, they just seem independent, so I'm like, "Oh, there's more that I can do in my career in the near future," but I don't know what that is yet.

Suzanne: Yeah, well and what came up for me just hearing you reflect on that and it's also a big part of this show in particular is shining a light on all of these incredible people who are rarely talked about when we talk about successes. There's plenty of shows that talk to CEOs and founders as though just that one guy in the Valley had that idea and then magically it was this multi billion dollar business. Product managers, part of our identity, I mean, we have so many complications around identity because of context switching, but a big part of our identity is actually being comfortably in the background a little bit.

Sara: Yeah. Which I love.

Suzanne: Yeah. Cool. We do a segment on the show called Get the Job, Learn the Job, Love the Job. I'd love to just hit you with these questions real quick if you're down for it.

Sara: Okay.

Suzanne: I'm a senior product person, I've been in my career three years, five years, I've been showing up and doing the thing and I see there's an opportunity to get my VP title, right, or my director title. How do I get there?

Sara: Well, I guess, again, we talked about this earlier, is everybody's on a different career trajectory and I think it's important to first think if you really want to get there. Your life does change and a director or above position you're doing less hands on and more people management. There are ways now and especially as companies diversify and grow, to be an individual contributor and still get to those senior levels of the organization and be seen as a innovative thought leader without having to have those same titles.

For me, I think the advice that I would give is, it's hard to say. I think we all have imposter syndrome to some degree regardless of what you've done in your past or what type of personality you are, but I think the best way to get that job is just true confidence. It's confidence with humility without really exposing too much of your imposter syndrome that again, remember everyone has. I think what attracts employers to leaders and wanting to bring those leaders into their organization is they want someone to take a little bit of that mental weight that they have in running a company.

It's stressful over the long run if you look at these founders, again, like my boss today, José. He's been doing this now 10 years and he has a wildly successful company and he just needs to know that pockets of his organization are run and that he doesn't have to spend the time on it that he used to. The more that leaders can bring in the next crop of leaders to take weight off of them the better and I think that's typically what people start to look for if they're looking at a director or a VP.

They want somebody to come in with a point of view, not necessarily to change everything, not to come in with this is my way or the highway, but somebody to come in who is eager to learn the business, eager to learn the people, eager to be a good personal fit. I don't love when people use cultural fit for a reason to hire or not hire someone, I think that's a bit of a cop out to be honest, but I think there is something to that feeling of can I work with this person in the trenches when it gets hard?

Bring that level of how do you have hard conversations? How do you feel confident? How do you give the person on the other side of the table that you're interviewing with that confidence that you will take a load off of them effectively? That you'll get stuff done without having to necessarily be told every step of the way. If that requires you to fudge it a little bit and to pretend, maybe stretch into a place that you haven't before, that's okay, everyone does that at some point in their career.

I think that is how you get the next up, is you bring that confidence to the table and you really convey that you are the person for the job and that you are going to take a weight off of the person or the team that's currently battling the fires.

Suzanne: Yeah, I love that answer and I have a frame for this. I wrote an article about what I called pillar people and being a founder myself and being acutely aware of all of the different domains that you're juggling in your mind. If you think about it like a room, there's all of these structural beams. As a founder you're holding all of those and if someone comes along and says, "I'm going to be the one in this corner and I'm going to hold up this side of the roof. I can't take care of all of the others, you're still going to have to parse that out or keep doing it." When we have a pillar person, we can really let it go when we hire someone who purports to be a pillar person or who we think is going to help but really is only standing halfway up and they can't quite reach the ceiling then we still have to give energy to it. Be a pillar person.

Sara: Yeah. That's a great way to put it actually.

Suzanne: Cool.

Sara: That's exactly how it feels and recently I brought in a woman into my team and last year's been hard, Farfetch has been ... I've only been there a year but we work hard. We're excited to work on what we're working on and I brought in a pillar person recently. I'm going to steal that phrase, actually. Yeah, that's great.

Suzanne: Awesome. What about hard lessons learned on the job? Do you remember just a hard failure moment as a leader in particular? Or just that you see show up for people where it's like, "This is where it's real, this is where the practice is always more challenging than the concept?"

Sara: Yeah, I think in every job and probably multiple times a year per job I have those moments. They range from not trusting my gut earlier, everybody has a gut feel and the work of a product manager is a lot about trusting that gut but then looking at the data and figuring out if your gut was true. There have been times where I didn't trust it early enough or I let something go too long. That could either be in the product development phase so times where that feeling of sunk cost that we stuck into continuing to sink costs into something that probably should not have been started in the first place. Not having made that decision, it was a hard decision that I knew people would be upset about earlier and the longer it went, the most upset they would be later.

That's something I think every product manager needs to get comfortable with is that you're not always the good guy. You're not always going to be liked. You have to make a hard call sometimes and it's how you make that call and how you bring people into that decision that's important. You're never going to make everybody happy at once. I've definitely made that mistake of continuing on a path for a piece of code that should not have been. Similarly with people on my team not following my instinct earlier about strengths and weaknesses and helping that person. Maybe giving up on them too early without myself putting in the time to help them through. Those are things that I failed at or regret in my career.

Yeah, I think it all boils down to trusting your gut in all facets of who you bring to the job, whether that again be the decision making piece or the leading people into our ship piece. Another area similar and again, it's down to trusting your gut, is that confidence to speak up when you want to say something that you think is obvious, is not obvious to everyone. If you think it's silly or you don't want to be embarrassed, that can be a mistake too. There's no harm in speaking up. We all live in our own minds and we feel like we're under a microscope but at the end of the day, at a meeting, making hard decisions with colleagues or your time, you're just one voice of many. It's important to speak up because again, what's obvious to you isn't obvious to everyone else. Yeah, so some of the ... I could go into some specific details but mostly it's around sinking too much money into areas that in my gut I knew were the wrong place or not correcting team dynamics early enough and not speaking up or trusting my gut in meetings where important decisions were being made.

Suzanne: Great.

Sara: Yeah.

Suzanne: You've been sprinkling this throughout the conversation but what do you love about product management?

Sara: Yeah, for me, this sounds really weird, when I was younger and starting out, again, what attracted me was the creativity of the format. That's still true. But for me the creativity, I really geek out on data. Just on technology in general, I just find it really fascinating. Over the years I've lost my own personal creativity, if that makes sense, meaning in the earlier stages of my career I wrote a lot more, I did design work, I did a lot of different things. Product management is a way for me to keep my hand in the game of that creative mindset without having to be as creative myself. I get to work with engineers and if I think about the role of product, I have two creative disciplines as a partner. That's the designers, obviously, product designers and the engineers. I think that's something that's often overlooked is engineering in my mind is a really creative role, it's as creative as design work. If you put those two in combination, really interesting things can happen if you think of them both as your left and right hand at the creativity spectrum. For me, getting to partner with folks in the design field and engineering, to create working code, it's really exciting and it's something that I can't do anymore, so for me that's a way to stay very creative without myself being the designer or an engineer anymore.

Suzanne: Beautiful. Are there any impactful books, blogs, podcasts or other resources? We have a growing list at They don't have to be product specific, but just ones that really impacted you on your journey.

Sara: Yeah, that's a good question. I read differently now than I used to, it feels like I just read articles on Medium these days, but there's a few good ones on there. Hacker Noon, obviously is a great one. The guys at Intercom, the guy named Des Traynor there, he writes a really amazing product blog for their company website but it's really about general product management and methodology. It ranges from everything from how to think about customer service through to research through to planning a roadmap, that kind of thing. That's a really good blog that I do try to keep on top of.

There's lots of books out there, I just actually recommended one in the coffee line, it's an old one but a woman here was just telling me that she was working in a field where she was the first product manager brought into her company, but it's been around for a while and the engineers were making all of the product decisions before she joins and she was explaining some of the challenges that she had and Legacy code and interaction design. There's an old book, actually, that I recommended to her just now called The Inmates Are Running the Asylum.

Suzanne: Yeah.

Sara: It's a good one, it persists today. It's just a really interesting one, I've recommended that to a few people. I also love the book, it's from the '70s and I give it to people and it sounds like a joke and it is a joke and I give it as a joke but there's some interesting learnings there. It's called How to Lie with Statistics.

I love that because in this world now with big data and analysts and analytics teams and data science teams, we can tell a story about anything and we can actually find data to support our story. I just love when I start to hear in the workplace, somebody be like, "Oh yeah, but 4% of XYZ,” whatever it is they're trying to make their case, and I just love to pull out that book, How to Lie with Statistics because people need to stay intellectually honest when they're using data. I think that's something and a piece of advice I'd give for all product managers at any level. Know your data, it's your biggest tool. But it can also really come back to bite you if you don't use it properly, meaning you could say the basics like don't put your time series into a pie chart, that's obvious but it's also really just understanding the different metrics because when you're talking to execs they're looking at a different set of metrics, especially if they're a marketer or CFO, than you might be looking at with your engineers.

Just really understanding in that space of your company, what are the vanity metrics in terms of the high level versus what are the ones that actually make you tick and make decision making more clear? Anyway, that book is a fun one. It's still on Amazon I think and the used books resale section.

Suzanne: These are all a great reference. The joke that comes to my mind is that 84% of statistics are made up.

Sara: Yeah, exactly. Yeah.

Suzanne: Final question for you Sara. Is there a personal or professional mantra that you use to guide you through this wild landscape called life and executive life perhaps?

Sara: Yeah. I've come with a lot of opinions on random things and this one's maybe slightly controversial but I have a reason for saying it. A lot of the talk around product management is that we're the CEO of our product and I understand why that is said. What I'd like to point out is I don't personally say that, I say that we're the shepherd of our product. The reason I say that is because not even the CEO is in charge of their company, if you think about it. They have investors, the board, the execs, the people that work there, the customers who use their product. At the end of the day, if we are CEOs of our product, what we really are are shepherds. We're shepherding thoughts and ideas and people and really trying to invest in the relationships, as I mentioned before, and do care taking within a company and building that trust and empathy, not only within the company but then also for the people that use your products. Our job really is to shepherd the flock towards something better, towards greener fields, towards better decisions. For me, that's something that I keep in my heart just in general is that my job is really a shepherd, more than anything.

Suzanne: Beautiful. Sara Wood, thank you so much for being a part of our show and sharing some of your wisdom with us and good luck on your talk.

Sara: Thank you so much.

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