How To Lead With Tough Love

Nextdoor cofounder Sarah Leary shares how her company grows and adapts by guiding people out of their comfort zone.

How To Lead With Tough Love
[Image: Flickr user Robert Couse-Baker]

As a rapidly growing private social network for 38,000 U.S. neighborhoods and counting, Nextdoor is designed to help people feel more connected and at home in their communities. But as a leader and entrepreneur, Nextdoor cofounder and VP of marketing Sarah Leary believes that the best things happen when people leave their comfort zone.

Sarah Leary

“You need to have people who are smart, and they’re motivated, but, probably above all else, they are people who learn and adapt based on the situation in front of them,” says Leary. “How do we bring people into a situation where there are going to be a lot of uncomfortable moments and the path forward is very unclear?”

This is particularly important for startups like Nextdoor, she says, because “You can’t just go hire someone who’s built a private social network for neighborhoods before. It doesn’t exist. Even some of the jobs that we have here really haven’t existed before. We’re constantly trying to find people who are going to bring that adaptability to bear and help us create these roles and create the playbook that will allow us to scale beyond what we’re doing today.”

There are three key places throughout someone’s experience at an organization where this comfort with the uncomfortable can be tested and supported, says Leary.

1. The Interview

“I’m probably known as a tough interview,” says Leary. “I try and be nice for most of the interview, and I’m not a jerk about it, but I try and push people. An interview can be a very awkward situation where you want to get all the answers raised, and you’re trying to read the other person, and a good interviewer knows how to go through that process. A lot of times, I will go through a process and at one point, I might say, ‘Huh, that’s interesting. I’m not sure I agree, help me understand that.’ I actually look to see even the body language with how they respond. Some people will literally recoil, they’ll be like, ‘Whoa.’ That’s okay. I get that. It’s an uncomfortable situation, but what I’m looking for is, how do they respond. Do they respond with, ‘Okay, let me tell you why I feel this way.’ I’m looking for someone who will respect the debate and respect that that debate is about the idea and certainly, no less personal, but what you’re looking for is people who can handle those situations, think on their feet, and adapt very quickly.”

For example, Leary might ask an interviewee for an example of what they think is a well-marketed product. “I’ll say, ‘What do you think they do well?,’ says Leary. “I’ll have them go through the whole thing, and they’re building it up, they’re telling all these great things. Then I’ll be like, ‘Great. Let’s say you’re the competitor. How do you respond and how do you adapt?’

“That immediately is like, ‘Whoa. You just changed the rules on me and now I have to take what I just said and I have to compete against it.’ That’s not me being disagreeable, that’s me forcing you to take a different position and really take on a different perspective and create a thought process on the fly because so much of what we’re doing requires there to be an ability to adapt to changing situations. The ideal scenario is someone who light ups like a Christmas tree and they’re like, ‘Oh, cool. I get to think about it from a different perspective.’ They actually are energized by the changing nature of the discussion and the ability to take on different hats and handle it.”


2. The Marketplace

“When someone shows up at Nextdoor, I can’t just hand them the playbook and say, ‘Here are the five things that you need to do every day,’ says Leary. “More often than not, I give them a set of problems and I tell them, ‘Here is the direction that we want to go in,’ whether that’s a particular goal, a date, or a metric. I say, ‘I want you to go figure it out.'”

But instead of having people sit down at a whiteboard or computer to figure it out, says Leary, “It’s much better to come up with a hypothesis and get outside the building and test it. Learn how people are reacting to things. Really get those primary insights from real users, or partners, or whomever it is you’re trying to work with. We have a whole philosophy at Nextdoor, whether it’s around products, engineering, marketing, community management, is to start with a very simple test in a controlled way and get it out there and learn as quickly as possible.”

Invariably, says Leary, there will be mistakes. But “if you can learn quickly from it, then you’ll get to the right answer relatively fast, and that answer is informed with real feedback from the market. That’s very inspiring to people because it gives them a process by which they can learn. A lot of this is just being able to create a process of learning, and innovating, and adapting, and to take risks without having to do it on the biggest stage. What I find is that if you can have one of those experiences early on in someone’s career, they feel empowered that they can learn and tackle almost anything.”

3. Weekly One-On-Ones

Leary’s proactive approach to giving direct feedback is something, she says, “that when people describe my personal style, they highlight this. I think it comes from the fact that this is how I want to be treated. I want people to be forthright with me and tell me if I’m doing something wrong. I want them to tell me if I have something in my teeth.”

Leary says that for her it’s all about creating a culture where honest feedback is valued and craved. “I think that it’s really helpful for people to feel as though they know where they stand. The worst thing that you can do to someone is not give them feedback, because it’s almost as if you’ve given up on them.” She has a standard format for one-on-ones that covers “the people on your team, the project that you’re working on, and you.”

“They always want to start with the people on the team and the projects where they need feedback, and then at the end, ‘How are you?’ They’re like, ‘I’m fine.’ I’m like, ‘We have five minutes, we’re going to sit here, how are you?’ I will literally leave the awkward silent moment because I think people sometimes feel a little embarrassed to be like, ‘I’m good. I’m happy. I’m sad. I’m motivated. I’m stressed,’ whatever it is. I want to know how people are feeling. I want to get a sense of the pulse of the team and just where people’s mindset is at any point in time. That’s about getting insight so we can adapt. It’s also about building trust.”


If people are having personal issues, for example, Leary says, “I think that it’s important that people feel comfortable to say, ‘Look, this is my reality right now. It’d be good if I could get a little leeway here ’cause I need to go straighten some things out.’ That’s authentic. Yes, I want to get feedback and, yes, I want to help people get better at what they’re doing, but I also want to build teams where people feel like they can bring their authentic self to work and that we accept that, embrace that, and use that diversity and that authenticity to our advantage to do amazing things.”


About the author

Evie Nagy is a former staff writer at, where she wrote features and news with a focus on culture and creativity. She was previously an editor at Billboard and Rolling Stone, and has written about music, business and culture for a variety of publications.