Women in Product Management Series: Sara Wood, VP Product at Gap Inc.

Women in Product Management Sara Wood

For a new series of interviews with women leading product management teams, I reached out to Sara Wood, currently VP of Product at Gap, Inc in San Francisco.

I was curious to learn what led her to Product Management, the missteps and lessons she learned along the way, and advice that she has for new Product Managers.

When I asked Sara how she got into Product management, she shared that she started using network technology in graduate school for her own research and continued using it to collect and analyze data as a policy analyst in DC. When browsers became more ubiquitous, she realized HTML was an easier way for her to display data alongside her use of gopher and listproc for data collection.

As her expertise evolved, it became a hirable skill because she was ahead of the curve on how the emerging technology worked.

“The creativity of it all is what attracted me to digital media,” says Sara. “There were so many things that could now be done through writing a few lines of code. The first CGI script I wrote sent a fax! I’m not sure my kids even know what a fax is. Over time as the industry matured and people became more specialized in certain areas, I believed I was better at the Product Management piece than engineering and hands-on design. I liked analyzing the data, managing teams, and getting the strategy in place. I liked that you didn’t know what was coming next, it was the Wild West. It was an exciting time!

“Data is a pretty important piece of the puzzle to earn credibility. As I mentor and grow teams, I’ve had young Product Managers say, ‘I just don’t want to look stupid in front of my peers. I don’t feel comfortable pitching to the CEO.’ And when you unpack that, it typically boils down to the fact that data is hard for a lot of people. It’s only one piece of the job, and if you have any sort of hesitation that you didn’t understand it, or the visualization that you chose wasn’t the right one for that data type, there is a lot of fear in losing that hard-earned credibility.”

Product Managers have to be comfortable with data to tell their story (for tips on using data to be more effective check out Three Ways to Immediately be a Better Product Manager).

“Thing is, data isn’t the end all-be all either,” Sara continued. “It’s okay if there is a different interpretation. There is a bit of gut feel to Product Management that people need to be comfortable with as well. Evidence-based decision making is key, but if knowing what the data is telling you was always that simple, then every one of us would have built Facebook or Uber! It’s not so simple. There is a gut feel, a willingness to take a risk, and to stick your neck out when nobody else is really there with you. So there is a bit of both. That’s a hard thing to tease out. You have to be able to sell people on your idea. Assume that they might not be there yet. And that’s okay. Can data help you with that? And how do you add your gut feel and your passion alongside the data in order to advocate for your product.”

The Role of a Product Manager is that you’re not a king, you’re a shepherd. You need to help lead people to outcomes.

“The role of Product Manager is that you’re not a king, you’re a shepherd. You need to help lead people towards outcomes – and there are often many different correct paths. You can’t just say, ‘I’m the product manager and I’m in charge of the backlog.’ How you do that is to guide by truly knowing your stuff; know your data, have empathy for the user and a sense of the outcome you are driving and why, and be able to put those together in a way that is compelling. You have to do it in a way that makes people with another point of view feel heard. In my experience, if a stakeholder feels heard and listened to, even if the idea is not going to be put at the top of the backlog, typically they are okay with it because they have been listened to. In some cases, those stakeholders will become your biggest advocates for what you’re doing, and how you are doing it. There’s something in that combination for a product manager to understand, that investing in relationships across the company is critical. The analytical skills are easier for a product manager to demonstrate, but soft skills help them know how and when to apply that knowledge.

“When I have had to transition people out of my team,” Sara continued, “90% of the time is due to people skills. It’s hard to teach empathy and humility. I sometimes think people get into Product Management because they think, ‘the Product Manager is the CEO of the product,’ but it doesn’t mean you are the dictator.”

To up your game take the People Skills for Product Managers and Product Marketers training course.

When I asked about missteps along her career, Sara mentioned: burnout and not reading the signals.

“There were nights that I slept at the office,” Sara shared. “Not just one. I can’t count the number. You work until you literally fall asleep on the keyboard and get up the next morning and do it again. For a time, you feel really good. Like you’re the backbone of the company. Then over time you feel resentment setting in, and that leads to toxicity. You have to make space for clearing your head. Having those down cycles is where creativity really happens.”

Creativity strikes on the ski slopes with your kids or in the grocery store on a Saturday afternoon.

Creativity doesn’t happen when people are chained to a desk. Especially not when people or a company culture values the sheer number of hours spent in the office above all else. That’s a major misstep that Sara made and sees people still making it.

“In the startup world, there is still a strange expectation where the CEO expects everyone to work until 11:00 o’clock six or seven nights a week. Why do people want that? People are not going to be high performers if that is how they are expected to work. That was a mistake I made in my early career and I see people still making it today. It doesn’t actually lead to better results. And for me personally, it led to feeling undervalued.”

Another misstep that Sara made in her career was not paying attention to non-standard signals she was getting from the business or the market.

She is a believer that if you are a Product Manager and you spend too much time in analysis paralysis, it’s hard to focus on what makes your company or product differentiated in the market.

“Keep an eye on what is special about your company,” Sara recommends, “whether it be the culture, the community, the brand, or the product itself. The product is a piece of it, but all of the other cylinders have to be firing too. If you’re spending all of your time looking over your shoulder at the competitor who has a certain feature, and then you think you have to have that feature too (as opposed to crafting something that’s unique and special that actually transforms the experience of your customers) that’s a misstep for the business.

“Often in the tradeoff thinking that Product Managers do, they say the competitors have X and we need X. For all we know, the competitor is about to sunset feature X because it doesn’t work, and we don’t know that because here we are working 6 days a week until 11:00 o’clock at night to get feature X built. It’s a race to the bottom. That’s what leads to commoditization.

“I look at Slack. I’m close to Slack because there are so many great folks there from the Salon and Flickr teams (and was a huge fan of Glitch from the early beta). I look at what they’re doing and at first when they pivoted into workplace communications from a video game. I thought it was crazy, and now it’s however many bazillions in valuation. They got all of the pieces right. They didn’t care what features Microsoft’s Skype had. They said: this is the problem we see. And we’re going to add some really sharp brand marketing. And we’re going to have an approach to community that is different. And we’re going to invest in the platform as a product. And, oh, by the way we’re going to do all of these other things that are in our DNA that might not work – maybe won’t work – but this is what we think we should do. And they did it and look where they are. That’s the kind of focus and holistic approach that is hard to pull off for most startups.”

Another misstep for startups Sara mentioned seeing over and over is top-down decisions being handed to the team to execute, no questions asked — an approach she finds demoralizing for people at all stages of their career.

“There is a way to get to that same outcome,” she suggests, “and have employees feel they were brought along the journey. Kindness is free, treating people with respect should be rule #1. The result is better quality output and happier employees who are all in it together to make it work. That is not to say that there won’t be some top-down mandates, that should be expected and Product Managers need to understand that, lest they feel constantly insulted. But it shouldn’t be 100% of the time. That’s a big red flag for me when executives can’t listen.

“Even as a manager of larger teams,” Sara adds, “I try to keep myself in check. I typically ask: I am not your primary stakeholder, I’m not on the core team, but as the steward of the Product, I am A stakeholder. So treat me like one. Let me feel heard. If I have an opinion, it’s just my opinion. Don’t weight it higher than anyone else’s in the room. However, there may be a time, and it’s going to be rare, where I will say, ‘I know this isn’t the way you were going, but there are other reasons we have to go a different direction.’ I’ve only done that maybe five times in my whole career. I don’t pull the boss card very often. I consciously don’t do that because it erodes trust with the people I need to trust me the most. Instead I put in place clear guardrails, let people know the quality I expect, and through tight feedback loops, can hopefully keep things moving in the right direction.”

Some key advice from Sara is for women in Product Management to know everything that is happening within the product organization.

Know the key metrics, which initiatives are either in the pipeline or will be soon, and which people are involved in which investments. Whether it’s taking a product to market or an engineer who quit and left a gap. Know as much as you can about what is going on. Being in product in general is being at the hub. You have to develop a sixth sense of all the dynamics at play.

“I work with my staff on this. I’m one of their stakeholders. I don’t want to be surprised when I walk in to speak with execs and they know something about my team’s work that I didn’t know. I’m tough on that one. I can’t have their back, and support and advocate for their work, if I don’t know what’s happening. When you get to a pretty large scale, it’s hard to keep your finger on the pulse. That’s an important one. It’s a credibility issue.”

When Sara walks into a room with her peers, she doesn’t hesitate to speak.

“I’m a relatively confident person,” she explains. “I take a lot of time educating myself and talking to people. I often feel like I have an opinion. I talk a lot – too much. One of my own goals is to not talk so much, but at the same time, like many women in product management I know, I’ve also read the science that says a woman can speak a small percentage of the time and will be considered to have dominated the conversation. So I know those two things are working against me.

“You need to know the data and understand the dynamics at play when you go into a meeting with peers around a certain project or a strategy in general. With senior executives, that is critical. You need to be taken serious. As new execs come in, I believe I have to reestablish my credibility and show that I actually know what I’m talking about. I don’t feel anyone walks in the door prequalified. Respect is earned.”

Fear is a bad advisor.

On Sara’s wrist is a bracelet she ordered from Etsy (also former Salon and Flickr folks) that reads: “Fear is a bad advisor.” It is an expression she learned in Poland a number of years ago. When people feel inner resistance or are rooted in fear that they’re going to look stupid, fail, be out of a job in two months, whatever, that isn’t the best way to make the good decisions.

“When fear has held me back,” confesses Sara, “those are the times I regret the most. I try to remind myself that at the end of the day it’s going to be okay. The times I have felt most alive are when I have been willing to take a risk because I have felt strong and proud. That makes me a better mom, a better teammate, a better human. For example, being willing to speak up when I have an unpopular opinion about something and feel it might go off the rails. If I don’t say anything, and it does go off the rails, I think why didn’t I speak up? This is as important in my personal life as well. It’s hard to achieve all of the time, but that is my own personal goal.”

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