Hiring for Culture Fit and Hurting Hearts 💔

Who knew hiring as a small, bootstrapped team was so tough.

A few months ago, we began our search for a Customer Success Manager. It was an entry-level position. The short version is we wanted someone to take the heat out of the relatively low (but still distracting) volume of support tickets that come through to the team every day.

Although they would be the only ones solely responsible for support, it wouldn’t really be a managerial position—despite the title—any more than I would be considered a marketing manager.

With that in mind, we posted out a job ad and sent our feelers far and wide. I sent out a message in a couple of support communities, while Jake and Jarratt shared the listing in a couple of communities they’re involved in.

The response was unexpected. We copped a little criticism, and had the opportunity to learn from some occasionally vitriolic feedback from unsuccessful applicants.

Does the Culture Have to Fit? 🧤

As a team of three, it’s funny to think of HelpDocs as having a culture. But it does. In fact, it’s probably the most well-defined culture I’ve experienced in any company I’ve worked at.

I’d only been in the team for a couple months when we began hiring again, yet our culture formed fast and enough for it to be at the forefront of our minds.

We knew by then the next hire would have a distinct and crucial impact on the culture. It would evolve, crawling out of the comfortable primordial dynamic we’ve cultivated, to become something reminiscent, yet entirely new.

The current dynamic works. As I said, it’s comfortable. We’ve developed a huge amount of trust and transparency in a short space of time and can laugh and joke together.

Perhaps most importantly, we get along and work well together—well, remotely! We can have a little workplace banter on Slack without worrying about offending one another.

It’s a great situation for us but makes it very difficult for a future hire.

When I joined, it was easy. There wasn’t really a defined culture, only an idea of one. Jake and Jarratt were the only people on the HelpDocs team, so we all got to play a large part in helping define the culture. An exciting experience all round.

Any future hires will need to fit into our culture while also challenging it. After all, we don’t want to create an echo chamber.

A week or so after I returned from my honeymoon, and a few weeks into hiring, the founders had been struggling through hundreds of applications. They were trying to whittle down to people who they wanted to interview.

My role in hiring this time round was more limited. More a sounding board and second opinion than a hiring manager. But since openness is a key tenet of our culture, we all got on a call to discuss how things were going.

One of the weirdest things about working remotely is dealing with time differences. As the dynamic duo sat in front of their hotel in Auckland, the night fell in behind them. Conversely, I sat blinded by the sun blasting through my living room window in the UK as my lively cocker spaniel undertook a rare moment of calm and curled up next to me. But I digress.

After a few minutes dancing around the subject, we got into the state of play with hiring.

Some candidates came with great experience but an inflated idea of salary. Others without the experience or technical expertise. Still more that would be great for us in the future, just not in a team this small.

There was one candidate that the three of us really liked at this stage, but had an air of bravado that would usually make them incompatible with our humble, unassuming team.

“Maybe we should just hire someone who doesn’t fit”, Jake suggested. It wasn’t sarcasm per se, but a simple conversation catalyst. And it did its job. We discussed for a while, going back and forth on what we meant by culture fit, and how important it was to a hiring decision.

What became clear is how important it is to know how we wanted the team to evolve, and what we wanted to avoid. It’s like a climbing rose. Pruning at deliberate points encourages the plant to grow in different directions. 🥀

In such an early stage of the company, we knew we wanted to expand our culture by hiring someone that wasn’t us, but we had to be specific about what that was.

Unfortunately for the applicant, brash bravado wasn’t quite it.

Seeking Diversity 👀

We are completely transparent within the team. We share everything. The highs and the lows. The positive personal messages of encouragement from amazing people on Twitter who enjoy the blog; and the negative criticism in its various venomous forms.

If I’m honest, I expected some backlash while we were hiring. Diversity in tech is a touchy subject, and for argument's sake we are a 100% white, 33% cis-heterosexual male team. Jake and Jarratt have a little heritage Greek and Mexican respectively, but I don’t think that counts.

That’s where I thought the backlash would come, but it didn’t.

Our team's relative lack of diversity is something we are all acutely aware of. As a very inclusive group of people, it's something we sought to change that with our hiring.

As a result, it seems the majority of applicants gave us a pass on our current diversity, for the promise of the future. Perhaps it was our use of inclusive language, or how we encouraged under-represented groups to apply.

In the end, we got hundreds of applications. Most interestingly, upwards of 70% of the people who made it to interview were from under-represented groups.

One of the biggest benefits of hiring remotely is being able to tap into a global talent pool. It's such an unfair advantage it feels like we're cheating other companies. Talent is globally distributed, but opportunity is not.

Pushback from Damaged Pride 😤

One of the things we do well, I think, is reply to every candidate. While receiving a rejection never feels good as a candidate, it takes the sting out a little when someone's taken the time to actually hit send on an email.

Unfortunately some candidates disagreed.

While diversity never became an issue, we did get some backlash from unsuccessful applicants.

I guess it’s expected. Though, I’m not sure what a moment of self-gratifying frustration vented through the keyboard at a faceless hiring person really achieves—save for a lifetime on the hiring blacklist.

On our call Jake recounted some of the memorable responses to rejection emails with a pained look in his eyes.

I should point out none of us has much hiring experience from the hiring side. HelpDocs has only ever hired people the founders knew personally (or friends of friends) before, rather than having open applications. So this kind of backlash was way out of our ballpark.

For Jake and Jarratt I think the most confusing—and probably hurtful—response was being called out as homophobes by an unsuccessful applicant. For context, they're a married couple. 🤷🏻‍♂️

I think the applicant was searching for a hidden agenda behind the term “not a great culture fit”, and managed to unwittingly vindicate the decision not to proceed. Jumping to baseless conclusions and making wild accusations is definitely not part of the HelpDocs culture.

Our culture is always to offer a good experience, so naturally we try to take any kind of feedback on board. Even if it’s hard to hear.

You suck and it hurts my heart 💔

For me personally the most confusing and painful messages were from people who perhaps misunderstood the scope of the role, and bashed us for what they believed to be low salary expectations.

We were told the salary we’d proposed was a joke, that we were using “remote” as an excuse to pay less. One person even remarked that the job “hurt [their] heart”—even though they ended up submitting an application anyway. 🤷🏻‍♂️

This kind of response was a massive shock. It was 100% not what we were going for. While Jake did his best to try and shield Jarratt and I from it, it still had an impact. We all felt like we’d let people down. As I mentioned, we share everything. 😔

We’re not hiring managers, but I thought we had a pretty good grasp on it anyway. Were we really being so tone deaf with it all? Sure, it was only a couple of comments out of hundreds of applications, but even one person thinking of us in that way is disheartening.

Personally, I didn’t really know what to think. I was a little hurt by it to be honest. As a big remote work advocate, the most painful to me was the idea that we—HelpDocs—were using remote as an excuse to pay less for talent.

As a team, we saw it differently. We see remote as a way to make work-life balance achievable. Salary doesn’t come into it, at all. It doesn't matter if an employee is based in Bali or Silicon Valley, we feel the salary should be the same.

In the end, despite getting some great applications, we didn't end up hiring for the Customer Success Manager role. We had to turn away some brilliant people due to a lack of culture fit, or salary expectations we couldn't meet, and ultimately had to return to the drawing board.

Maybe one day we'll cross paths with the perfect hire. For now, we'll keep sharing support tickets between ourselves. 🙃