What No One Told Me About Hiring and Retention


In the 13+ years I’ve been running Location Labs, I’ve learned a lot about myself, human nature, and what it takes to get diverse people working happily toward a common goal.

Want to know what it takes? Pay attention, because I’m about to give away the ending: it takes more than you’ve got. At least, more than you’ve got today.

I can’t imagine more satisfying work than steering the course of the complex machine that is an organization. And there’s no way I could have envisioned, back in the glorified Boston dorm that was our first “office” (when I was probably a little too cocky and self-absorbed, as most of us are when we’re younger), that one day I’d actually have the personal and professional qualities you need to keep yourself and your company not just going, but thriving.

Today, our retention rate is 97%. It hasn’t happened by accident, and getting here wasn’t always pretty. I’ve made mistakes, and I still have a lot to learn. But being CEO has given me the opportunity to grow more adept than I thought I could be at honest self-reflection, genuine and lasting interpersonal connections, and inspiring leadership. Even if you don’t have what it takes today, you can develop the skills necessary to attract and keep motivated, loyal, satisfied employees. And maybe even become a more satisfied person, yourself.

Ultimately, the good news — or bad, depending on how you look at it — is that the secret to hiring and retention at a startup is … you.

Make it personal

You can have only one kind of relationship with people: a personal one. Use any other lens, and everyone you meet becomes just a metric.

This doesn’t mean you need to have 100 best friends. It does mean you need to notice crucial details, like names. I hear a lot of people nervously laugh off their “inability” to remember names. You cannot do this. Ever. You must put in the work to sharpen your memory and not only learn people’s names but learn enough about them that they’re not just a face in the crowd.

I’ve developed my own “Memory Olympics,” based on mnemonics and repetition. I didn’t make these exercises up, but I do take time to practice them. I’m a visual learner, so when I meet someone, I attach their name to something visually meaningful. Maybe their coat pattern reminds me of a favorite painting. Then whenever I see them, that associated image helps me remember their name.

You can have only one kind of relationship with people: a personal one. Use any other lens, and everyone you meet becomes just a metric.

Eventually, of course, you just know a person’s name because you know them. But the getting-to-know-you process will feel a lot better if you don’t forget their name 9 times along the way. Addressing someone by name is the most basic demonstration of respect — and being remembered is one of the best feelings in the world.

I also make it a point to interview every candidate, for every position. Why would you want to work at a startup before meeting the person leading it? To be fair, this gets more challenging as we grow, but it’s still a priority.

When I interview, I ask people why they’ve chosen their paths and what they’ve had to overcome. Because though the term gets tossed around a lot in Silicon Valley, we truly are a meritocracy. You don’t already have to have achieved professional excellence to be the right fit — you just have to demonstrate that you’ll take anything on, own your mistakes, and rally your team to move forward. We love underdogs.

I want to be myself, but I want to do it in ways that don’t prevent someone else from doing the same. Because my way isn’t necessarily the best way.

I also regularly examine my own habits and qualities and ask people I trust for honest feedback. I’m an emotional, demonstrative person. I’m enthusiastic, and I like to show it. I’ve learned, though, that this can come across as intimidating or too intense. I’m also a questioner, I grab things that interest me and drive to the origin, I challenge people. But what I consider the Socratic method can feel like aggression, can shut down dialogue or introduce fear of failure. I’m working on this. I want to be myself, but I want to do it in ways that don’t prevent someone else from doing the same. Because my way isn’t necessarily the best way.

Getting back to my temperament — “make it personal” also means knowing what you’re capable of, and what you’re not, no matter how much you evolve. For instance, I’m well aware that I wear my heart not just on my sleeve, but all over my face, in every gesture, all my body language. I’ve been told more than once, even by complete strangers, that I’d make a terrible poker player. And it’s true. I’ll own that. And while I’m glad I’ve learned to temper that when it means giving someone else room, I also know that my emotionality is directly related to why I hold sacred the relationships I have with the people I see every day. These people are why I come through the door. Building and nurturing our connections is what keeps me going.

I think to truly excel as CEO of a growing company, to make it rock-solid, these connections must be your ultimate motivation. It’s not for everyone, and that’s okay. Know your personality, know your needs, and know what the job demands. If the day ever came when I lost the ability to really prioritize people, or if for some reason I stopped looking forward to seeing my colleagues every day, I’d hang it up. Or if I were asked to lead 50 global offices, where getting to know my 50 direct reports, let alone their teams, would be nearly impossible, I’d show myself the door. And it’d break my heart. I’d miss every member of this team. A part of me would be gone. And not only because of the great work we’ve done together. Because of who they are and what they mean to me. That will always come first.

Hire on trajectory

Part of the fun of starting a company in a quickly changing industry is not knowing where you’ll wind up. The last decade has brought discovery and dead ends. Being the one who steers requires that I repeatedly re-evaluate our vision and seek counsel about how to let it evolve while still making smart decisions. Because without a guiding idea, employees have no direction, which can demotivate even the strongest people. At the same time, the strongest people also want to be part of deciding which way to go and welcome some level of ambiguity.

We don’t hire people to execute a bunch of tasks we’ve already thought up. We want them to help decide what those tasks should be. We hire initiative.

So when we interview, we don’t just talk about what needs to be done today, we discuss where we’re going. We’re honest about how a lot’s up in the air, partly because we don’t control the market, partly because every new hire could be part of determining our course. We don’t hire people to execute a bunch of tasks we’ve already thought up. We want them to help decide what those tasks should be. We hire initiative.

These are the same people who, if they’re unhappy at work, don’t let it fester and then silently leave. They do the work of examining themselves, challenge what needs challenging at the company, and work toward resolution. They won’t give up without a fight, and they won’t assume the fault lies entirely with others. And to keep people with this kind of integrity, we have to provide ample opportunity for them to be open. They have to trust and feel heard.

Hiring on trajectory also means finding people who are in it for the work, not the perks. They want to help the company grow, not just reap the benefits. In the early days, we actually prided ourselves on our bare-bones culture. We grew slowly, like an oak tree putting down taproots. And our soil was made of values like simplicity, frugality, and grit.

I’ve found that the best employees don’t ask if the grass is greener, ready to jump ship for the next new, sexy thing. They cultivate where they are.

We worked Monday through Friday, and then more on Saturdays. In a single, small room. With no air conditioning. In Berkeley. During the hottest days of summer. We got used to drinking cooked-on-the-burner-all-day sludge from a Mr. Coffee. We were the right company for people who liked making first-of-its-kind software from scratch, in 4 20-hour days. And who, like those first few of us, reveled in pinching pennies and powering through.

Today we have lots of perks. But the people who sign on and stay are more excited about the growth process than comforts and treats. If success brings espresso machines and free massages, they’re all for it. But those aren’t what get them up in the morning. They’re about the journey. I’ve found that the best employees don’t ask if the grass is greener, ready to jump ship for the next new, sexy thing. They cultivate where they are.

Be steadfast

I see a lot written about how to get employees to develop company loyalty, but not much about being loyal to them. To build a winning company, you must recognize what binds you, celebrate what’s different, and then protect each other, no matter what.

Being steadfast … means embracing, not just tolerating, different people, who are talented in different ways, with different ways of showing it. … That means meeting people where they are. Every employee doesn’t have to be like us to be one of us.

We’ve always been a magnet for misfits, and I wouldn’t have it any other way. I’m one, too. It makes for a fun workplace, but not one that everyone “gets.” For instance, one of our senior engineers was on deadline a lot in the early days, as we cranked to build working products for pitches (we preferred showing up with the real thing, not just a PowerPoint plan). He’d grind out code all night and stop for catnaps between 2 and 4 in the morning on the lobby couch outside our office. Even when things weren’t crazy, he was a night owl. It was just his process, and he kicked ass. Building management came by one day to tell me the night security guard had complained, that we’d need to tell our guy to cut it out. I smiled, said, “The next time the guard sees him napping, the only thing he should do is cover him with a blanket,” and thanked him for his visit. Bottom line: the engineer wasn’t interfering with anyone’s work at 3 AM, and it was a silly request. My priority was ensuring he had what he needed (and definitely not to mess with his mojo), not placating the building manager. What were they going to do? Cancel our lease?

Being steadfast is serious, too. It means embracing, not just tolerating, different people, who are talented in different ways, with different ways of showing it. As long as they come through that door, ready to kick ass, we have their back. That means meeting people where they are. Every employee doesn’t have to be like us to be one of us. We don’t want people to cut their hair or grow a ponytail or go to Burning Man or hate Burning Man or be less goofy or be more outgoing or anything that’s not true. Of course everyone can grow and evolve, and we hope to be a place for that to happen. But growth only comes when people feel you’ll stand up for who they are at the core, the parts of them that you shouldn’t want to change. We love quirks. We invest in them. It’s paid off, in more ways than one.

And on the most vital level, be loyal as your employees go through life changes. Births, deaths, illnesses, moves, divorces, marriages … sometimes the only solid thing someone has is their work. Be that for them. Make necessary allowances. Take the long view. It’s right, and not just for business.

Don’t let institutionalization erode culture

Culture’s easy when you’re small. Once you grow to a 50–75-person company, big shifts happen. Having close, personal relationships with everyone — beyond knowing their name and a few vital facts — is literally impossible.

This is the beginning of institutionalization. Though it’s a big, boring word, this inflection point doesn’t have to mean the end of what made you great. Keeping the good people who’ve gotten you this far and continuing to make the right hires is crucial, and possible, as long as you set the right tone: adaptability.

If you cling too tightly to cultural specifics, you’ll lose the real goal: preserving the spirit of the culture, its core values. So maybe your offices will get a little fancier, and maybe having happy hour with the entire company every Friday (now that there are more than 10 of you) isn’t realistic, but with the loss of those particular rituals comes room for new ones, created by the growing team.

If you cling too tightly to cultural specifics, you’ll lose the real goal: preserving the spirit of the culture, its core values.

You’ll also have to guide your team through uncomfortable changes that, even if they’re for long-term good, could alienate people. For example, performance evaluation and promotion are somewhat obvious when you’re intimately familiar with everyone’s work. The larger you get, the more processes and people you need to manage, mentor, and measure others. Handled clumsily, these can feel impersonal, off-putting. But while you won’t be 1 degree removed from every employee any longer, everyone should hear from you what will change and why, specifically. Hold town hall meetings. Offer regular open office hours. Most important, listen and follow through, so that new procedures can evolve according to employees’ needs, not just management’s.

Know when to take the backseat

Make opportunities for employees to share what they’re excited about in their lives, then get the hell out of the way. Someone’s into playing guitar and wants to organize a lunch-hour jam session? Offer the nice conference room and budget for some new chairs. Someone else is into knitting and yarn bombing (apparently this is really a thing)? Encourage them to use company email lists to gauge interest, then cover lunch for their weekly craft sessions.

If you want employees to thrive — and stay — they need to do more than talk about their passions with colleagues. They need to experience them together.

The best cultures are built on true friendship, and true friendship comes down to shared interests. If you want employees to thrive — and stay — they need to do more than talk about their passions with colleagues. They need to experience them together. So far Location Labs employees have introduced Jiu Jitsu, juggling, whiskey tasting, margarita making, rock climbing, Ultimate Frisbee, yoga, Dungeons & Dragons, sewing, typography, drawing, ping pong, white water rafting, and about a hundred other fun, invigorating, inspiring activities and pursuits. I wish I had time to do them all, really. I’m just glad to be surrounded all day, every day, by such enthusiastic, generous people. And I make sure to tell them so. Individually, and by name. As often as I can.

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