Product to Product: Pinterest’s Lulu Cheng on taking care of your product team’s well-being

Product to Product - Lulu Cheng

Welcome to the first episode of season two of Product to Product, a podcast for / by product people!

Listen to the episode below:

For our second season we’ve decided to shake things up. This season, each episode will focus on a specific theme: the human side of product.

We’ll be having candid convos with product people who will be sharing real-world, practical stories of navigating the human-related aspects of the product space. That means we’ll discuss topics like handling tricky relationships with non-technical team members, how to effectively think like a product manger, and how to disrupt human behaviour with human-centered AI design (just to name a few topics!).

For our first episode of the season we’re joined by Lulu Cheng, product manager on the Discovery team at Pinterest. When Lulu first joined Pinterest in 2015, her primary objective was to ship quickly and hit her KPIs. But as she got more comfortable in her role—and the product space—she realized she wasn’t really asking her team, “How are you doing?”

So she made it a personal priority to focus on her team’s “wellness.” Was her team motivated? How was team morale? How are they handling the stress that comes with the role? She realized healthy team members = better team performance = a better product.

So Lulu spoke to my colleague Eleni Deacon about concrete and proactive steps she takes to put her team’s well-being front and centre. Plus: what does this focus on team wellness ultimately mean for her team’s overall performance and product strategy.

The episode can be listened to above, and we’ve also included a transcript below. You can subscribe to Product to Product on iTunes (here) and Google Play (here), or get the latest episodes delivered to your inbox by subscribing here.

Eleni: Hey Lulu, thanks so much for doing this. I’m really excited to talk to you today.

Lulu: Hi, thanks so much for having me.

Eleni: Before we get started in the actual conversation, can you just tell me about yourself and your role at Pinterest, what do you do there?

Lulu: I am a product manager on our discovery team. I’ve been at Pinterest for a little over two years now. Before that, I was at Dropbox, I was on the product marketing team there, and was one of the first marketing folks to join their growth team, where I did a mix of the marketing and product work, and that’s kind of where I first got my initial taste of product work. Before that, I spent some time at Microsoft up in Seattle, and in what feels like a very previous life now, I started out as an investment banker in New York, when I graduated from college.

Eleni: So what do you do in your current role at Pinterest?

Lulu: On the discovery team, our charter is really to think about how we surface the best recommendations to Pinners. So that spans a number of different services in the app that includes home feed, search, a product called related pins, another product called visual search. So, it’s a pretty broad team, and then within that there’s a bunch of sub teams. So my focus is currently on the home feed product, and specifically working on a new type of recommendation that we’re hoping to ship to 100%.

Eleni: Can you tell me about your specific team. How big is the team you work on? Give me the lay of the land of your team itself.

Lulu: It’s fluctuated over time, because that’s something unique about working on a feature that’s brand new. But in general, the team that I work with is unique in terms of other teams at Pinterest. There are some teams at Pinterest that are completely backend focused, and thinking exclusively about the quality of the recommendations that we surface. Then, there are other teams that are predominately more finance-focused, and thinking about how the actual features and user interactions on the different platforms play out.

"When you build that trust & rapport over time, it makes it easier to navigate difficult times."

The team that I’m on, what I really like about it is that it spans both of those sides. So, I get a chance to work on the backend side, and thinking about how we leverage a lot of our existing data pipelines to power this new type of recommendation we weren’t necessarily able to do a year ago. Then, also, on the front end side, what is the best way to surface that new type of recommendation to users?

But the team has been as large as probably eight engineers, and between engineering design, we had eight folks, which arguably for a product that isn’t live yet is actually a bit too many cooks in the kitchen. So, yeah, we’ve slimmed down over time, and primarily focused on the backend, actually.

Eleni: Are you the only product manager on the team?

Lulu: I am. I am the main PM, yep.

Eleni: So, I know we’re going to be talking about wellness and prioritizing your team’s wellbeing during this conversation. I’m wondering, when you first started working on this project, what were your main objectives? What were your priorities right at the very beginning?

Lulu: Our priorities in the beginning were really to figure out if we had a prototype that had legs. So, essentially the way that this project kind of spun up is it came out of a design sprint where one of the designers on our team basically asked “What if we had this UI mechanism on home feed that was able to push content to users when they came to the app?” So that’s a pretty simple, straightforward idea—a lot of products have this. But, how do we make that work for Pinterest? What’s the content that will be most relevant and compelling to pinners?

So, we had this new UX paradigm, and we had a bunch of different options for different content that we could slot into it. We basically did a round of user research in the very beginning where we showed a bunch of different types of content to pinners to get their feedback on what they might find interesting. From there, we were able to basically pick one specific type of recommendation that performed particularly well in the qualitative research, and we also realized, we were pretty confident that we would be able to deliver on the expectation of the quality of content that pinners would expect—and that we would be able to reiterate on that going forward.

So, I think that was a big milestone, and then from there, our goal has consistently been to find a way to surface these recommendations to pinners in a way that, at the moment when they’re going to find it most valuable, and to basically minimize distraction. Or, we use this term at Pinterest called cannibalization, where any time you introduce a new feature into the product, your ideal goal is that you incrementally increase the amount of time that people spend on your app, or how engaged people are. But, inevitably, there does end up being some surface trade off. So, that’s also been something that we’ve been thinking about.

Eleni: When you first started, not even just in this role, but you can think back to earlier in your career, how did you prioritize the idea of wellbeing of your team and yourself?

Lulu: To be completely honest, that wasn’t something that I paid a lot of attention to when I first started out as a PM. My focus, when I first started, was really just trying to get a lot of, I guess in my mind, what I called the basics down. And also in transitioning from marketing to a pretty technical team at Pinterest, there was a lot of ramping up to do on just the technical backend side. So, I would say that it really hasn’t been until I started working on this more long-term feature, where it’s unfolding over a number of months, and it’s not completely certain whether or not it will even ship.

"That was when I realized how much the team picks up on each other’s emotional energy."

There’s been a lot of ups and downs, and it’s been through that process that I’ve realized how important it is to keep a pulse on team morale, and momentum. The investment that you put in over the long run, like taking five minutes at the beginning of your team meeting every week to do a quick icebreaker, on the surface might feel like a waste of time. Why are you doing that?

But, it’s one of those things where I’ve learned a bunch of really interesting anecdotes and just personal things about my teammates that I don’t think I would have had a chance to learn otherwise. When you’re able to build that trust and rapport over time, it makes it easier to navigate difficult times.

Eleni: Can you tell me about the moment, or maybe an event that precipitated your interest in making a wellness a priority? Was there a particular experience that led to you being like, “Oh, I think I actually need to pay attention to this and focus on it?”

Lulu: I think it was more of a gradual realization. But there are actually a couple of moments that stand out. One is actually not even when I was at work, I was just catching up with a friend, and the question came up: how’s work going? I noticed that that was the first time where instead of answering that question from the perspective of how quickly are we moving, or what do our experiment dashboard data metrics look like, my actual first thought was to think about how does the team feel? How do all the individual members of my team feel? Do I feel like they are happy and feeling motivated? Even though our last experiment wasn’t super promising, does there still feel like there’s energy and excitement about the problem that we’re solving? I remember that was a little ah-ha moment for me.

Then the second moment was after a team meeting, and someone like the product analyst on our team pinged me over Slack, afterwards. She was like, “Hey, are you feeling okay? I said, “Yeah, what prompted that question?” She said, “I don’t know. I felt like you were a bit quieter in our sync today.” That was when I realized how much the team picks up on each other’s emotional energy. And especially as the PM, when you’re in this position of leadership, and people are looking to you for direction, but also to set the overall tone of things.

Eleni: So once you realized that you wanted to prioritize having more personal connections and helping people feel good at work, where did you start? What were some of the first concrete steps you took?

Lulu: I think that one on one’s with key members of your team they can be pretty informal or formal depending on the person. Every person on your team is going to have different preferences for how they like to communicate what motivates them. Why are they waking up every day to come into work? What are their longer term career aspirations? Do you know what those are? So, I think getting to a point where you have a good sense of what that is for each person on your team, and also how they like to work together. As a PM, I think it’s really your job to pick up on that, and to adapt how you communicate and interact with that person accordingly.

So, yeah, if there’s an engineer on your team who is fond of walking outside, maybe that’s how you sync with them, or if there’s someone who really prefers just to do slack updates, that’s also great. I think that’s just getting up to speed on people’s individual preferences in terms of communication and what motivates them is important. Then zooming out, on a broader team level, there’s, I mentioned doing ice breakers during our team meeting. I think being super transparent and over communicating, so making sure that whatever decision is being discussed, you always choose the forum with the widest audience, like where it makes sense. I think that really helps to build just a sense of trust and inclusion.

Eleni: I’m curious about the one on one’s, how did you change your approach on one on ones? What were you doing before and what are you doing after, or now?

Lulu: I think when you read about some of this stuff online, the kind of ground rule is, oh, you should try to have a one on one with almost every engineer on your team, let’s say. I think that while that definitely makes sense for some teams, I’ve realized, as a PM, and we joke, but part of your jobs is, a lot of times, just having meetings. But, from an engineer’s perspective, meetings often aren’t their favorite thing. So, I think just checking in with them, and being like, “Hey, I was thinking that it could be helpful for us to have a regular sync and check in with them all on the cadence that you would prefer.” Then, also, if their preference is “If there’s every anything that you need to get a status update on, just ping me over slack. I would prefer to do it that way.” That’s also totally fine—I’ll just make that mental note.

Eleni: Do you use your one on ones mostly for status update type stuff, or is it more personal, what’s going on with you, how are you feeling? How do you balance that?

Lulu: I would say, it’s situational, or I kind of go in and the time is very flexible. So, we’ll go in and, depending on where we are with the feature, how I kind of sense they’re feeling that day, how much we have to talk about, those things always kind of shift. But, for example, I had a recent one on one with one of the engineers on my team, and she had actually just spent that morning with our head of engineering who was hosting some product folks from We Chat that morning.

"You want to enjoy other people’s company; not just be a robot from meeting to meeting."

I was really interested just to hear how that had gone, and I could tell that she was also excited to impart some of what she had learned. So, we spent the bulk of our one on one actually just talking about that, and it was more higher level product talk. That’s one recent example.

Eleni: What about the ice breakers? Tell me a little bit about that. What do you do? Is it like games? Just kidding.

Lulu: People joke that making ice breakers is like a skill, and it’s something that I should list on my Linkedin profile. But I take genuine pleasure in coming up with what I feel like are pretty unique questions, or questions that will elicit stories.

They’ve ranged. I try to keep them seasonal, so if it’s the holidays, or if it’s Valentine’s day, like often they’ll be themed. But some of my favorites have been asking people about their earliest childhood memory, their worst roommate stories. Also, I’m realizing, this sounds a lot like dating profile questions, but it’s all the same! It’s in that same spirit of just getting to know people better.

Eleni: Do you think, I feel like a feeling that I feel sometimes, and I know a lot of my colleagues feel, there’s just so many meetings, and meetings consume you. When you just want to get from one meeting to the next as quickly as you can, and there would potentially be resistance to the idea of spending five minutes talking about your childhood memories. What do you say to those people, and what is the value of making that investment in a meeting?

Lulu: I think about this like the rainy day savings analogy. It’s one of those things where often you don’t, or oftentimes when you see the most payoff from something like this is when things start getting a bit bumpier, or there are decisions that come up that are a bit more controversial, and people have strong opinions. I think that when you “pay into this piggy bank” of just good rapport and getting to know your teammates on a more personal level, then there’s that underlying foundation of trust that then helps you weather the times when there are strong differences of opinion. I think that that’s definitely one piece of it. Then the other piece of it is just you spend so much time at work. You want to enjoy other people’s company; not just be a robot from meeting to meeting.

Eleni: It almost sounds like the kind of thing where, like there could be a case made about how this is so off topic; it’s a waste of time. But then at the same time, it’s making the meeting more casual, and just not as work-related. I feel like it might make people more present. They get into the zone of the meting a little bit more because it starts with something that’s more personal and removes them from whatever they were doing two minutes before coming to that room.

Lulu: Yeah. I think that’s a great point, and I think there’s definitely a difference in just the energy when you sit down and you know the first few minutes are going to be just more casual and fun, and you expect to laugh. I generally almost always laugh during our icebreakers. I think that’s awesome.

Eleni: Have you started to see results from contributing to your emotional piggy bank at work? What are the results you’ve started to see?

Lulu: Recently we had a moment on the team where we were at this juncture where we had to make a decision, and there were a lot of strong opinions on two sides of the issue. It was an interesting learning experience for me, because I think this is where my leadership style or natural state is to be more consensus-driven when it comes to decisions. I think that this particular decision, it was one where there were strong opinions from a design perspective, but when we zoomed out, the actual impact to pinners, based on our experiment data, basically it was a coin toss. Either route that we went down, there wasn’t a huge difference in terms of our metrics.

"Something I believe is, the more informal and frequent the feedback, the better. "

So, there were strong opinions on both sides, and then later, when we were doing a post mortem of what had happened, there were also some tough conversations that we had to have a team around how do we work together? How do we make decisions more efficiently? Those were some of the harder conversations I’ve had at Pinterest. So I think that it would have been a lot harder to have those conversations without having established just that trust and that rapport going into it.

Eleni: This maybe is a segue from what you’re saying, but I know one of the topics that you’re really passionate about is feedback, giving it, getting it. What role do you think feedback plays in someone’s sense of wellness at work?

Lulu: I think this is changing, but I think a lot of times feedback is still relegated to twice a year performance review conversations. I think under that model, if things just build up over months and months, and then you have all of this emotion and expectation and anticipation going into this one conversation. Something I believe is, the more informal and frequent the feedback, the better. I would much rather get the feedback in that way when the stakes are much smaller, and the context from whatever you’re referring to is still fresh in people’s minds. It just makes for more productive feedback.

Eleni: How do you encourage your team members to give you feedback?

Lulu: The best way, I think, to do that is to keep asking for it, and to reiterate the fact that you are welcome and, you’re inviting their feedback. Yeah, you sincerely welcome their feedback, and I think also that it’s helpful if you can make that request specific, right? So if a coworker comes to you and is just like, “Hey Lulu, I’m really trying to get a promotion next cycle, and I’d love to get some feedback from you on how things have been going.” That’s a very broad request, and that kind of puts the burden on the other person to sit there and be like, hmm, okay, what’s worth flagging to this person.

Whereas, it’s a very different thing if you go to a coworker and you say, “Hey, I’m really trying to work on my public speaking and presentation skills. So during the next meeting that we have together, if I have to present something, can you just pay attention to how confident I seem, or my volume? Am I making enough eye contact?” Get specific and concrete, and that makes it so much easier for the person to give you that feedback. So I think honing in on identifying the areas that you’re trying to improve, and then identifying maybe people on your team or in the broader company at large that you feel like do a really good job at the thing that you’re trying to get better at and seeing if they’d be willing to give you some feedback.

Eleni: So, I know that you’ve been working on a product that’s been a long term project. I’m wondering how your emphasis on your team’s wellbeing has impacted your ability to actually ship. What impact has it had on the concrete product itself?

Lulu: This focus on wellness has helped the team be pretty generative when it comes to ideas to test. It’s also resulted in an environment where people are very comfortable speaking up and expressing their point of view. So I think we’re able to get a lot of diverse perspectives that come out of that kind of environment, and I think that’s helped the team, especially recently when we’ve been really trying a bunch of experiments in parallel. It’s helped us to come up with different approaches for solving something that we might not have considered before.

So, I think that’s been one concrete thing. I think another aspect of it is just as a PM, I’m thinking about it has been a long journey. I was looking at some of our experiment metrics, yesterday, actually, and there’s a variant that’s looking promising. So in terms of next steps, we can either continue iterating on that experience. There are definitely a bunch of variables and things that we can change that I think would make the metrics look even better. But at that point, you’re thinking about, “Okay, we are nine months in, and actually, probably the thing that will be best for motivation and for morale is to just get this variant shipped and iterate from there once we’re live to everyone.” So, that’s the call that you’re making, that’s very much influenced by how the team is feeling.

Eleni: How does your team manage stresses that might come from outside your team? I know for product people, they’re dealing with a lot of stakeholders, and that can often be one of the bigger pain point. How do you manage that on your team?

Lulu: It’s a tricky balance, for sure. So, there are three buckets of external stakeholders. So, there are teams whom we need to collaborate with to reach our goals. There are teams that want to partner with us to leverage what we’re building, to meet their goals. Then there’s leadership, and there’s the executive team, and the direction they’d like the team to point towards. So, I think each of those three groups requires their own approach.

For the most part, like with other teams that we collaborate with, I let the team basically run pretty autonomously there, and to reach out to the different engineers. Then, the second group of other potential teams in the company where I want to collaborate on something that’s mutually beneficial, those are always fun to think about. That for the most part, tends to be pretty self-driven from the team.

"This focus on wellness has helped the team be pretty generative when it comes to ideas to test."

Then, on the leadership side, that has been one area where I’ve spent more of my time. Until this thing has launched, it’s unproven. So I think you’re constantly having to justify why are we spending these resources on this thing? What will it unlock for us in the future? So that communication of what the team is doing, the vision, and then also just the transparency and the consistent communication and updates, I think, has been something where I’ve invested a lot of my time.

Eleni: How has focusing on your team’s motivation and morale impacted the way that you care for yourself?

Lulu: So, I think after that conversation that we talked about earlier, where the analyst on my team pinged me, and she asked “How are you doing?” I realized that whether I know it or not that my personal energy communicates a lot to the team. So I realized, okay, it’s important for me to come into work and to be energized, and well rested. That’s important. I think sometimes you forget just how much role your exterior presence can have on others. So, I think that’s been a good reminder that sometimes just taking a little break and stepping away, or making sure that you’re well rested is also important.

Eleni: If there was another team that wanted to make this their focus, make wellbeing their focus, what small actions do you think they could take on right now to get the ball rolling?

Lulu: Well, I think we’ve established that I love icebreakers, so I think that’s a pretty-

Eleni: That’s the first step, is break the ice.

Lulu: Yeah. Just let your curiosity guide you. What do you want to know more about your teammates? I think it starts from a genuine place of curiosity about the people on your team and who you work with, and just a genuine desire to get to know them better. Yeah, so I think that that’s the most important thing, and then I think what we talked about earlier in terms of really getting a good grasp on how everyone on your team likes to work, and what motivates them.

Especially when you’re joining a new team, it’s really important to, in those initial introductory meetings, to get to know that about everyone on your team, so you have that foundation going forward. Then, I think over time I would encourage other product managers to think about when someone asks you the question, like, how are things going? How’s the team doing? In addition to thinking about how quickly you guys are moving, what the metrics say, I would encourage you to think about the morale of your team and how that feels, and to factor that in into that answer.

Eleni: So Lulu, can I get you to tell us where we can find you online?

Lulu: Yes. I’m on Twitter @lulu_cheng, and I also have a newsletter that I send out, it’s a tiny letter. I think it’s just

Eleni: I have a confession to make. I’m on that. I signed up for it two years ago when I first started my job, and now I read about your life and it’s great.

Lulu: Oh, that makes me so happy! Yeah, I was just about to say it’s not actually really work focused, but I talk about a lot of the feedback, and personal growth stuff, I think that’s something that bleeds over into my work life. So if that’s your jam, I call that the truest me on the internet.

Eleni: Hm, I like that. Lulu, thank you so much for chatting with us, I really appreciate it.

Lulu: Thank you so much, Eleni, this was a lot of fun.

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Tarif Rahman

Tarif is the Digital Content Specialist at Roadmunk. He's got a penchant for storytelling, enjoys bringing creativity to the tech world, and has an aversion to Netflix (don't judge).