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As Greenhouse’s CTO, Mike Boufford built an engineering team that grew from one to 60 in its first five years — with zero regrettable attrition.

When he first shared this statistic with other engineering leaders, they were blown away. “Three years in, I started going around town saying, ‘I’ve had zero regrettable turnover,’” says Boufford. (In fact, it was at a First Round CTO salon where we first heard about this remarkable retention.) “As I realized that it was uncommon, it started to feel like a badge of honor,” he says.

But as the years ticked by and the team remained intact, a feeling of unease started to set in. “Around the four- and five-year marks, it started to feel different, like I was jinxing myself.” says Boufford. “When I saw that our recruiting team had modeled zero attrition for engineering during headcount planning, I had a pit in my stomach.”

It was a conversation with Greenhouse’s CEO that prompted Boufford to inspect this feeling more carefully. “He challenged me to examine why I was laser-focused on maintaining a 100% retention rate. And I was taken aback,” says Boufford. “Prior to that conversation, I’d never entertained the idea that there could be anything wrong with how I’d been thinking about retention. I had viewed it as an unmitigated good.”

Now, a few years later, and with a team that’s since crossed the 100-person mark, Boufford has seen a handful of engineers leave to take on new challenges, bringing an end to the engineering leader’s version of pitching a perfect game.

In this exclusive interview, Boufford reveals why he’s no longer hung up on attrition numbers. In sharing his take on what the industry’s conversation on regrettable attrition gets wrong, he makes the case for why we should all be talking about healthy and unhealthy turnover — instead of aiming for zero.

First, Boufford takes us back to the beginning by sharing how Greenhouse crafted a culture that made engineers want to stay, detailing the recruiting tactics and retention strategies that counteracted common impulses for leaving. Then, he flips the script by sharing why he opened a dialogue with his team about moving on, unveiling the leadership tools he used to jump start the conversation. Let’s dive in.

FROM 1 TO 60: EARLY-STAGE RECRUITING TIPS FOR BUILDING A TEAM NO ONE WANTS TO LEAVE

To better understand how he pulled off the feat of zero regrettable attrition, Boufford takes us back in time, recalling how he built Greenhouse’s engineering team from the ground up. “If I had to put my finger on why people stayed, I think it’s because from our very first hire, we spent so much time thinking through how the culture was going to be established,” he says.

That intentional approach to team building had an unexpected source of inspiration: contemporary philosopher John Rawls. “When I took on the opportunity to build Greenhouse’s engineering team, I took the responsibility of creating a new community really seriously. I started thinking back to a college course that I had taken where I learned about Rawls’ ‘original position,’” says Boufford.

For those who haven’t cracked open a philosophy tome recently, Rawls’ thought exercise works like this: You imagine a blank-slate society and are asked to develop a system of rules, values, and norms behind a “veil of ignorance” that shields you from any foreknowledge as to what advantages or disadvantages you might inherit. Because you could find yourself in any position in society, the exercise forces you to think about creating fair rules from an impartial perspective.

“In starting a new team, I had the chance to create a new ‘society,’ and I wanted to be really intentional about building the team that I’d want to be a part of. I thought about all of the things that had made me frustrated enough to move on from prior roles, and tried to build my team in such a way that those same feelings wouldn’t be conjured up in the engineers who joined Greenhouse,” says Boufford.

From the original position, you’re incentivized to do good and be just. When you create a new team or company, it’s a chance to design the group you always wished to be a part of.

Rev up recruiting — and plant the seeds of retention

With that philosopher's mindset lighting his way forward, Boufford set to work to assemble his team and gear up for hypergrowth. “Between the summer of 2014 and the summer of 2015, we closed our Series A, B and C, all in the span of about 14 months — which was insane,” he says. “We were growing incredibly quickly and we needed to win the talent war. We ultimately did — I hired 30 engineers in 2015 alone — but it wasn’t easy.”

During that period, Boufford took on much of the recruiting load for his team. “Early in the year, I handled cold outreach to hundreds of engineers, so I had to get creative with my hiring tactics. Just about every day, I had breakfast, lunch, dinner and drinks with engineers. I asked for referrals, then I asked my referrals for referrals. I started an engineering meetup in New York and got on the public speaking circuit,” he says.

“But at seed and Series A, the reality is that recruiting can be unbelievably hard,” he says. “You can meet with engineering candidates for every meal, every single day, but it’s still going to be tough to sell them on working for a company that they've never heard of. The hard truth was we had no brand equity and many of the candidates I wanted to hire had a ton of other options.”

Boufford turned his attention toward carving out a differentiated recruiting message — and drew inspiration from another function. “When I read SPIN Selling, everything clicked into place. It’s a sales book, but I found so much overlap with recruiting engineers. It unpacks solution selling as a principle,” he says. “Solution selling is about discovering pain points and demonstrating how your solution — or in this case, job — scratches their specific itch. You shouldn’t waste time talking about the perks if what they really care about is professional growth or programming in Go.”

A common mistake early-stage startups make is trying to hire every engineer that passes the technical bar. Instead, work to figure out whether your vision matches what the candidate is looking for. Misalignment between what you’re selling and what they think they’re buying inevitably leads to turnover down the road.

To suss out that motivation, Boufford relied on these two questions:

These questions unlocked emotional stories. “Most people have dealt with deeply frustrating moments at work — I certainly have. One year, while at another company, I had worked hard to achieve a lot of important goals, but during our annual performance conversation, my manager seemed to have no idea what I’d accomplished,” says Boufford. “It left me feeling that my work wasn’t valued, and I found myself frustrated enough to start a job search two months later. It was such an impactful moment — that conversation was about fifteen minutes out of my manager's life, but it changed the course of my career.

After hearing hundreds of stories similar to these in his conversations with candidates, Boufford noticed a few emerging themes. When engineers were dissatisfied at other companies, they often:

The final nail in the coffin for many, Boufford found, was a feeling of powerlessness to make their pain point go away — that’s when people head for the exits. Armed with these insights, he set out to solve for these challenges, hoping to find their antidotes and use them as cornerstones to anchor Greenhouse’s cultural foundation.

“By unpacking why people left other companies, I thought I could reverse-engineer reasons Greenhouse would be a place they would stay. In the early days, if I could lay out a vision of how we’d be different on those very targeted, specific fronts — and in the later years that vision rang true — then we could actually do less recruiting over time, because people would stick around,” he says.

People view candidate conversations as a recruiting tool. And while each is an opportunity to add someone to your team, it’s also a chance to figure out how to nail retention. Uncover what other companies are getting wrong — and make sure you don’t repeat those mistakes.

DIVING DEEPER INTO THE TACTICAL RETENTION STRATEGIES THAT NETTED ZERO ATTRITION

Determined to avoid these missteps, Boufford laid the groundwork for Greenhouse’s culture from the start. Here’s a closer look at the tactics that helped him attract top talent and drive down turnover:

1. Establish a culture of fairness and transparency:

To address common complaints around a lack of fairness, Boufford set out to intentionally build transparency. “People don’t trust that managers or companies are going to treat them fairly by default, so you have to prove it — and too many leaders forget that,” he says.

Here, he gets granular on how fairness can be woven into every part of the hiring, compensation, and performance review process, sharing examples of how Greenhouse pulled it off:

When you’re hiring engineers, make sure they know what they’re getting themselves into, and then work overtime to ensure you meet those expectations. That’s the recipe for getting people to stick around.

2. Solve for stalled professional growth:

In Boufford’s own experience and in hearing from hundreds of engineering candidates, growth was a lightning rod, an area where complaints — and turnover — spiked. “When I was developing as an engineer, I desperately wanted my managers to take my growth seriously. I’m a big believer in continuous improvement, and I wanted my manager to be a partner, mentor and advocate who would help me to get better, every day. I had high expectations. So, when I had a chance to build a management culture, I made growth a top priority,” he says.

In rapidly scaling startups, personal growth is often put on the back-burner in favor of moving fast and shipping. But even during crunch time, you have to carve out space for your engineers to learn something new — otherwise they’ll look to scratch that itch elsewhere.

Here are the tactics Boufford used to keep growth front and center at Greenhouse:

Mike Boufford, CTO of Greenhouse

3. Create a culture of respect:

Startup cultures typically emerge organically. “When people walk into a new community, they observe the social norms and, for the most part, act accordingly,” says Boufford. “If there's a healthy, respectful environment, most new employees will pick up on that and automatically adapt. That’s why it’s so important that the dominant tone be one that’s rooted in respect.”

Here are two tactics he used to intentionally shape the tone of Greenhouse’s culture as they scaled:

SWAP REGRETTABLE FOR A HEALTHY ALTERNATIVE

With a cultural foundation that addressed common causes of turnover, Boufford’s recruiting message resonated — the team continued growing and the engineers kept sticking around. But as he previewed earlier, while that zero regrettable attrition metric had become a badge of honor, it eventually morphed into a source of anxiety. After pouring so much energy into designing an environment with built-in defenses against common causes of attrition, Boufford was now grappling with whether he had been approaching retention with an incomplete perspective.

“As a manager, when someone on your team leaves, it can feel awfully personal, as though it’s a reflection on you, like you failed in some way,” he says. “But our job is to think about the needs of the people on our team. And sometimes what they need is support in taking the next step on their path. I’d go so far as to say that serving the true interests of the people on your team is always serving the best interests of the company as well. If people leave to do other things, and the story of their time at Greenhouse is one of fairness, respect, growth, and empowerment, then they will recruit the next generation of engineers for us by simply recounting their experience.”

Boufford decided to retrain his focus. “I realized I’d been too concerned with the number of people who may leave when what really mattered was why they want to leave,” he says. “When we talk about ‘regrettable attrition,’ we really mean ‘regrettable-to-the-company attrition’ – we’re putting the focus on the manager’s feelings about an employee leaving, versus the employee’s motivations for walking out the door. Maybe that person was treated poorly by the team and you’ve got a real cultural problem that needs to be addressed. Or maybe she got an incredible opportunity that perfectly aligned with her career path and she’s now going to be an ambassador for how far someone can go after working at your company,” he says. “There are healthy and unhealthy reasons for turnover — that’s where our focus should be, not simply on deciding whether or not the company mourns their departure.

Aiming for zero regrettable attrition is problematic, because it obfuscates the reasons that people leave — and the reasons they stay. Optimize for healthy behavior, not retention at any cost.

This new framing crystallized the path forward. “The right approach is to focus on doing what’s in the long-term best interests of the people on our teams. We realized that we needed to do more to normalize and spur conversation around healthy next steps. As counterintuitive as it seemed and after all the work we had put into making people want to stay, we had to open up the conversation about their whole career — not just the part of the story being written today,” says Boufford.

Nudging engineers out of the nest: tactics for encouraging healthy turnover

To kick off that conversation, Boufford started giving what he called the “gold watch talk.” Harkening back to the days when retiring employees were traditionally given a timepiece as a parting gift, Boufford gave variations of these talking points at All Hands:

“Given our lack of turnover, I wanted to create a feeling of safety for those who might be thinking about other opportunities. I wanted to remove the fear as much as possible. My main goal was just to communicate that I didn't expect that everyone would stay at Greenhouse forever, and we didn’t have to pretend otherwise or tiptoe around it,” he says.

On the heels of these talks, here are the additional tactics Boufford leaned on to continue the conversation around healthy turnover.

A framework for diagnosing cause of turnover

After adopting these tactics, Boufford noticed a marked change on his team. “We went from ignoring the elephant in the room to having career conversations in a much more open way,” he says. “Since then, a few folks have left, almost uniformly for healthy and exciting reasons.”

Now that he’s reframed his perspective on attrition — and has a few departure data points to lean on — Boufford has a more fine-tuned understanding of how he’d like to assess turnover.

The conversation I have with a person that is thinking about leaving mirrors the conversation that I had when I was first trying to recruit them: I want to know what they want to be different from the experience they’re having today," he says. “I want to see whether I have something I can offer to fulfill their needs, and if not, I want to get to clarity around how I can help them land in the best place possible.”

When someone is considering moving on, it’s either due to excitement about a new possibility or it’s a symptom of stress. If it’s the latter, I want to better understand the underlying forces driving them away. If it’s the former, I want to do all that I can to support them in their growth.

Here, he shares a few healthy and unhealthy causes of turnover, peppering in real-life examples from his experience at Greenhouse in the hopes that other leaders can use these examples to start thinking about turnover through this lens:

Healthy: “If every departure fell in this bucket, I’d be pumped,” Boufford says.

Unhealthy: In contrast, here are a few causes of turnover that would leave Boufford feeling that Greenhouse needs to do better.

“As we continue to refine this framework, I can see it becoming a key part of how we report on attrition at our next stage of growth,” says Boufford. “Regrettable attrition metrics may not be going anywhere for now, they’re still a helpful lens that helps us to understand what’s happening with people inside an organization. But, I’d argue that ‘healthy’ vs. ‘unhealthy’ attrition offers a sharper snapshot of what’s really going on in a team — and I hope it’s the direction we all start to move in as we rethink our approach to retention.”

As a leader, I want to make sure my departing employees are running toward something, not away from a problem here.

LEAD LIKE YOUR COMPANY IS A SPRINGBOARD, NOT A GILDED CAGE

While it might be natural to fear that having more open conversations about what comes next will unleash an exodus of talent, Boufford has found that it doesn’t necessarily open up the floodgates. “One of the engineers on my team confided in me that his goal is to be ‘employee number two’ at a startup. Well I definitely don't have that to offer — we’re a 300-person company now. But I told him, ‘I'm going to go find that for you. Send me your resume and I'll mine my network to make sure that you get that experience,’” says Boufford. “But as soon as I offered that up he said, ‘You know what, I actually want to give it another few months.’ He opted to pump the brakes. I think knowing that option is available, and being able to talk about it sincerely and openly, made a world of difference.”

Boufford’s own perspective on leadership has changed dramatically as well. “I want this to be a place where people can contribute, learn and, if and when it makes sense for them, leave to go do other great things in the world,” he says. “My goal has shifted from holding onto people for as long as possible, to creating the next generation of leaders that's going to fan out and make New York an even better tech scene. If this place is a great springboard for talent, we’ll never have a shortage of people who want to come work here.”

Photography by Michael George.

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