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Art of Leading

Glenn Kelman

“Diversity Is a Top Five Priority For Me, and It Can’t Be A Flavor of the Week.”​

January 7, 2020

Spend time with Glenn Kelman, the CEO of Redfin, and you’ll be instantly struck by his refreshing candor and thoughtfulness about the challenges of effective leadership. I first interviewed Glenn seven years for my Corner Office series in The New York Times, and was eager to reconnect with him for my “Art of Leading” series for LinkedIn. He shared smart insights about building a culture of inclusion.

Q. Your leadership team seems a rarity in business – there are more women than men on it.

A. True. I still think we have a ways to go on that. But when our Chief Technology Officer, Bridget Frey, first started at Redfin, there were no women in the Seattle engineering office, which was the main office. Having Bridget onboard changed everything. We suddenly became much more effective at recruiting women, and having a more diverse team helped us build a better product.

The people who buy houses are women, and most of the real estate agents who help them buy houses are women. We had shipped key pieces of software that didn’t have the features that our real estate agents needed, that our customers wanted, and I don’t think it occurred to us to ask what was missing. Having a more diverse team really solved that cultural challenge.

Q. Was there an inflection point when you decided to be more intentional about this?

A. I went to Berkeley. I’ve always believed in the importance of a diverse society, but I ran a business that wasn’t. I’d never squared my ideals with the reality of a world that I could influence. Then I was confronted with my employees saying to me, what are we going to do about the fact that I’m still one of the only women here, or I’m still one of the only black people here?

You realize this happened on your watch, and you want to be proud of the company, you want to be proud of your legacy, and I wasn’t. You also have to have a conversation with your board as diversity becomes more of a priority because nobody wants a CEO who’s got a political ideology or a social ideology. It has to be a business ideology — we’re going to recruit better talent to build a more sustainable company, because we’re going to have a better connection with our customer if we’re diverse.

“Nobody wants a CEO who’s got a political ideology or a social ideology. It has to be a business ideology.”

I don’t want to suggest this is finished work. There are so many people at Redfin who are proud of what we’ve done, and there are so many people who think we need to do much more. There isn’t a person of color in our most senior management team, and I wonder how it feels to be a person of color at Redfin and not have that role model.

One change that really surprised me was when I brought on Selina Tobaccowala, who was the first woman on our board in many years. I didn’t think anyone in the company would notice or care because board meetings happen once a quarter in this closed-off room in a corner of the company and then board members head to the airport.

But immediately the women at the company felt very differently about it and told me so. They thought that if they had an issue with an executive or with me, it wouldn’t be a lost cause to bring that to the board because there would be someone who would understand how they felt.

Q. What other frameworks have you developed for thinking about diversity and inclusion?

A. I think most people see diversity and inclusion as a recruiting issue — to find the talent and then persuade those people to join the company. But I would start with inclusion, retention and development because if you have one black person in your company, every other black person who interviews at your company is going to ask him or her, “Well, how is it here?”

And that person needs to have an amazing experience despite the loneliness of it. So you just have to try harder. The first woman who walked into that all-male engineering group probably didn’t love the demographics of it, but we worked really hard to try to get her because you’ve got to start somewhere.

Q. I do sense that there’s a gap between the walk and the talk in many companies. People are saying they value diversity and inclusion, but often it’s not reflected at the management-team level.

A. Change is hard. One thing I’ve been clear about with advocates for diversity at Redfin – and I count myself as one of them – is that diversity is not my number one priority. Diversity is a top five priority for me, and it can’t be the flavor of the week where, when I’m talking to a group of women or some people of color or some diversity advocates, it’s suddenly really important until I walk out of that room and don’t care about it.

It has to be something that you can sustain where it is one of your top priorities at all times, but it’s not your only priority. The company has to serve customers well and make great products and generate profits.

What I’ve struggled with is just how many hires are made based on social networks — how much currency there is within the office of one person knowing another person to be able to talk about what’s really going on. Why is my work not getting the approval or recognition that it should? What am I missing?

I have found that if someone’s 20 years younger than me or if they’re black or a woman, that’s just one degree more difficult for them to have a real conversation with me, whether it’s to ask for help or to ask why I may seem so hard to please or whatever it is. And those conversations go a long way. It’s like if you’ve ever butted your head against a wall with a boss, where you just couldn’t break through, and then finally you went on a walk or you had a beer and you see eye-to-eye and everything got easier.

Q. A big part of creating a culture of inclusion is making sure everyone you hire believes it’s important. How has your approach to hiring changed over time?

A. We put together a lot of teams where there’s someone from the retail business and someone from the technology team working together. Some of our engineers used to feel it was almost burdensome, but now when we recruit engineers, we look for people with a blue-collar work ethic who don’t have a sense of entitlement. When we find people with a sense of humility and service, we’ve done much better. You can hire a rock star who is good at writing algorithms and machine learning and everything else, yet they may not connect with the person they’re actually trying to help. They’ll just make the wrong product over and over again. That’s why one of our mantras is “everyone sweeps the floors.”

“I do feel that some job interviews are like a Lemony Snicket story.”

Someone once told me that the fundamental question he always wants to ask in an interview is whether you consider yourself lucky. He doesn’t ask that question anymore because there are some religions that don’t believe in luck. But I do feel that some job interviews are like a Lemony Snicket story — a series of unfortunate events where the person goes from job to job and the company stinks, the boss stinks, the colleagues stink.

Part of good fortune is you make your own luck and part of it is that you never feel entitled to it. You never feel that it was just because of what you did. You have that realization that we’re lucky. I believe that Silicon Valley is going through a moment of hubris or entitlement — this belief that we deserve to be on the front page of a magazine and have an incredible IPO and make billions of dollars. But that just isn’t going to work.

Q. How have you evolved as a leader since we last spoke seven years ago?

A. Once you’ve been in the chair for a few years, there’s an enormous amount of cocooning that happens with the CEO. You build a really tight team of like-minded people, and you also build a culture that is really just some kind of group narrative that may not admit a lot of new ideas.

That may allow you to move very quickly in a very constrained way, but every once in a while, evolution has these mutations that are grotesque and bizarre but ultimately very powerful. And they’re so painful but you have to sort of create room for them, and I worry that I don’t.

I think there’s a benefit to almost any kind of change, and once you recognize that, you just have to be that change yourself or you have to leave. And I love my job too much to leave, so I’m trying to just be a different CEO every few years. 

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