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Growing a Product Management team presents a unique challenge. Since the role of Product Manager can differ from company to company (or even between multiple product teams at larger organizations), it’s pivotal that you know how to hire the right person with the appropriate expertise who can help lead your team to success.

For insights on best practices for hiring product managers, we spoke to Ellen Chisa, VP of Product at rapidly-growing startup Lola Travel.


Ellen Chisa of Lola TravelUserVoice: What’s your experience hiring for PM roles?

Chisa: When I decided I was leaving Kickstarter, we were looking to replace me and I did a bunch of the interviews for that. By the way, they’re hiring for that role again and it’s a super cool job. Somebody should definitely go do it.


What should you look for when hiring a product manager?

The biggest thing for me is people who are curious and really want to learn more. To some extent product managers do like a lot of stepping up and filling the gaps in the organization, and it’s nice to have someone who is looking for those, and then figures out how to teach themselves how to do that.

That was one of the fun things here at Lola, because I was the first person at the beginning. I did everything. I made a financial model, and we now have a really talented VP of finance, and hers is much more detailed and much more interesting, but I was willing to try that out at the beginning. So I definitely look for people who are going to step it up, and when the engineer goes on vacation, and there’s a bug, they try to figure out what’s going on and diagnose it. Or when the designer is gone, they open up that mockup if they have to. And most of the time, that’s very much a small company thing, you don’t want somebody doing it all the time, and you don’t want PM stepping on other people’s toes, but you want them, when it needs to happen, to be willing to try to get it done.

How important it is that the person you’re interviewing has been in a product management role before?

It depends on what you’re doing, right? If you want someone to join the team, and be good from day one, and not need that much help in ramping up and onboarding, it can really help if they’ve been a product manager before and they know exactly what they’re doing. [But] people don’t always have had the title when they’ve done it, especially at early stage startups.

You’ll see people who are this person who filled in wherever necessary, and a lot of the time that ends up being product work, and that can work really well. Or you’ll get someone who’s at a company that doesn’t have a product function but they were in marketing, and they were the marketing person who interacted with all the engineers. So you’ll definitely find people who did product, but didn’t have the title, and those people are kind of to my mind the same as hiring people that have the title, because they have that same skillset.

Other than that, I think adjacent roles can transfer pretty well, but it all depends what state your team is at, and how well you’d ramp them up. So for instance, I think right now, for me, it would be much easier for me to hire someone who’s been a UX designer who wanted to move into a product role, because they’d be easy on our team where we have those things together to let them make the flow slide over. I think you could do a little bit of this, lots of this, and then you’re going to take this project a little bit further to do the product part.

On that note, how much depth of knowledge should people have in disciplines like design, engineering, and business?

I don’t think they need it in all of those areas, I think for me it’s more, there is a very specific skill set that goes into it. I don’t mean technical in terms of how much CS you need to know, I mean technical in terms of there are things you do to be a good product manager. And I think often times people are like oh, you can just step in and figure it out, and that’s really not the case. You have to know how to do qualitative interviews, you need to know how to do quantitative analysis of the metrics, you need to know how to make a decision when you don’t have all the information and be able to cope with ambiguity.

“You need to know how to make a decision when you don’t have all the information and be able to cope with ambiguity.”

I think sometimes people are like, oh it’s just like this fuzzy role and you have to be good with people and then you’re in charge, and that’s not what it is at all. But in terms of the disciplines, I think it can be really helpful to be good at one of them. I think most product managers either came from some sort of marketing business role, and they have a lot of sense of the landscape of the market and what they want to do, or they come from a design background and just like making the user flows, or they like making the mockups. Or they come from a technical background and they really understand the limitations of what they’re trying to build.

But I think a lot of the time it goes back and forth, it can be your strength, but it can also be your weakness, because if you know how hard it is to build something [that can be limiting]….I was on a panel last night with a woman who mentioned this, it’s easier to say, oh I’m going to cripple my product vision, because I know that’s hard. Or if you care a lot on the design side, it’s easier to get in conflicts with designers. If you want to be the one designing it, even though possibly they’re better at design than you are, that’s why there’s a full time production designer and you’re the PM.

You have the advantage of being able to step in, but you have to also be willing to step back.

How do you look for that in a candidate? What kinds of questions do you ask to find a candidate who has broad enough expertise that they’re confident enough to step in where they need to, but who is also capable of knowing how to delegate and who should own what?

I definitely try to focus on asking questions where I want people to tell me what they’ve been doing before. I think it can be really problematic to ask hypothetical questions, like, “What would you do if your team was in a bad situation?” or “What would you do if you and a designer disagreed?”

I’d much rather hear someone tell a story. If I say, “Okay, what was the last time you really disagreed with a designer on your team and how did you resolve that?” And when I hear that I don’t want to hear someone say, “Oh, I just won because I’m the PM” or “I just let them decide because they’re the designer.” I want to hear more logic behind it, so how much conviction did they have going into that disagreement, how did they look at qualitative things, how did they look at quantitative things? I really want them to walk me through how they resolved that conflict.

What jumps out at you as far as problem solving? When do you say, “Oh that was a good solution”?

I think the best solutions are ones where people actually did end up agreeing, or people ended up disagreeing in a productive way. Hopefully you can make a convincing enough argument, or you can admit that you’re wrong. So one way would be like, “Okay, I decided that we should look at this metric and this metric said we should make the direction the designer said, and I realized that I had to support the bias.” The recognition of why that person had the wrong gut intuitions, the maturity to actually look at the metric, and the maturity to say, okay I looked at this metric and it was wrong, and the other person was correct and I want to go for it.

“The best solutions were ones where people actually did end up agreeing, or disagreed in a productive way.”

I think it can be hard, I would prefer a situation in which someone decided to do what the designer wanted instead, because I think there is a grace in being able to say, “I made this mistake as a product leader, and here’s how and I have this awareness, and I’m going to try not to make that kind of mistake again.”

Are there ever red flags when people are giving these kinds of responses where you think, I’m not so sure about that answer?

That’s definitely much more if someone’s like, “Oh we just did this way because of X” or “Oh, we just took a tie breaker” or “We flipped a coin,” because that doesn’t feel very thoughtful. It feels like it wasn’t that important to begin with, and why did they bother disagreeing if they were willing to flip a coin to resolve it? Or things where they were like, “Oh, I didn’t really feel like it was my purpose” because as a product manager, you should be willing to step up and help that thing happen, and if the answer is, we disagreed, and then we just never agreed and we just had this compromise, that’s not the sort of person I want doing product management.

Hard to imagine someone answering with something like that in an interview.

You’ll hear some really baffling things in interviews, I get a lot of people who, want to be in charge, or they’ve been a management consultant and they’re like, “Oh well, I wanted startup hours, but I didn’t want to do something technical or have to learn that so I want to be a PM.”

Do you think that the fact that the role does lie between technical and nontechnical spaces sometimes attracts people who are not a good fit? Who think that they can come into it blindly and hack their way through it?

Yes, I think a lot of people just don’t know what the role is, and they’ll go to a job site, and I think people don’t make it very clear what they need a lot of times in product manager roles.

How do you make sure that when you’re hiring product managers that you’re attracting the people with the skillset you need so you’re not wasting your time?

I think the first thing is to be honest about it, and what resources you have available. A lot times people want to claim that they’re open to having someone junior in and then training them. But when you think about, since people don’t study product management in school, how much work goes into training a junior product manager and how few product managers you usually have on a team, it can be actually somewhat easier to add another junior engineer, depending on the strength of your engineering organization. Because if you have three senior engineers who are all available at least part of the time, that’s enough. You don’t get teams very often that have three senior product managers who are hanging out ready to help, unless you’re at a pretty large company.

How does this work in action at Lola? I know you’re not hiring PMs currently, but if you were, what is it you’d be looking for in a PM there?

[At Lola], we try to make it very clear that we need someone who does have that design experience, either has been a designer, or cares very much about design, or gives good feedback on design. It’s not so much that they have to have a designer title, but they have to see design as being part of their area of competence.

Sounds like you need to be very specific about which discipline is most important at a given time in your company’s evolution.

Another [area of importance] is size of company. We’re really in a place right now, we’re so early on where we have a lot of white space, someone who has been hanging out in a very optimization-focused role wouldn’t necessarily be the right person right now, because we don’t have that much stuff to optimize yet.

It’s very different when you’re at Facebook and you have a billion people using the newsfeed, you can do a lot of optimization and that matters a lot, but when you’re a brand new company, you only have so many users, and honestly making a five percent difference doesn’t matter, making a ten X difference does matter, and the different skill sets as well.

A lot is made of “culture fit” as well. How important is culture fit to you? And how do you screen for something like that?

Yeah, I like to frame it more as culture add. There’s this great essay that one of the engineers, he was at Etsy (I think he might have moved to Slack recently) but he calls it mapping the potato. You’re really trying to figure out all the things that someone’s bringing to the team, not just like, do they match these things that you already have.

One of the things that I really like about our team now that I look for, is do people really bring their whole selves to work? One of our travel consultants likes to bake cake, and she has done graduation cakes for her kids and all sorts of stuff, and so one of our parties, she made this really elaborate cake and brought it in for the team. That was really neat, ‘cause that’s something she just personally likes and then does it.

Our CTO runs really seriously, and we started a little running club at work where we go running along the harbor together sometimes at like four thirty, five o’clock in the afternoon. So I look for things like that, where people would be willing to come in and kind of tell everyone else here about what they do and what’s cool, and get involved.

But it doesn’t necessarily mean they have to stay late, it’s not like I expect them to want to hang out with everyone all the time. It’s totally fine to be introverted, it’s totally fine to have your own life and have things going on; we have a lot of parents here. But it’s more about when people are here, I want them to feel like they can actively participate and get to know their coworkers.


Ellen Chisa is the VP of Product at Lola, a membership service that plans, books, & manages your travel. Previously, she was a Product Manager at Kickstarter and Program Manager at Microsoft. She’s on leave from the MBA Program at Harvard Business School, and received a B.S. in Electrical & Computer Engineering from the Franklin W. Olin College of Engineering. In her free time, she likes to write and travel.

Sara Aboulafia

About Sara Aboulafia

Sara Aboulafia is a Content Marketing Specialist at UserVoice with a background in freelance writing, content marketing, and journalism. Outside of work, Sara writes and performs music, binge-watches comedy, and spends an unhealthy amount of time futzing with technology before happily retreating to the woods.