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Our Startup's Biggest Hiring Fails From $0-250K/Month

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I’m proud of the team we’ve built, but it hasn’t been easy. Here are the mistakes that hurt the most.

If you visit any business’ About Us page, you’ll almost always find a header that looks something like this:

“We [solve a particular problem] for [a particular customer].”

The constant, among all businesses, is the very first word: “We.”

As cliche as it sounds, the foundation of every successful business is its people, and without great people, it’s going to be very, very hard for you to succeed.

One of the most frequent pieces of advice I get from entrepreneurs who are working on their second or third success story is that after the earliest stages of growth, hiring should be a CEO’s number one focus. If they can’t do that well, then nothing else matters.

Even the best ideas collapse on the shoulders of people who can’t execute on them.

Finding, hiring and keeping amazing, talented, driven people has been something I’ve been trying to do since Groove’s early days, and after three years of it, I’ve had plenty of stumbles.

Some were minor and resulted in nothing more than a bit of wasted time. Others cost us dearly in productivity and oozed toxicity into our culture, taking months to recover from.

Today I’m sharing the most painful (and important) mistakes I’ve made when it comes to recruiting and hiring, in the hopes that I can prevent you from making them yourself.

1) Not Checking References Thoroughly Enough

Look, I know that references are an incomplete way to vet a candidate.

I know that candidates cherry-pick the people that are going to give them the most glowing reviews.

And I know that those who like a candidate are unlikely to say bad things about them.

Still, I think it’s important to call the people that the candidate provides as a first step.

But, as I’ve learned, it’s even more important to go beyond that. The startup world is a small one, and access to members of many of the teams in our community aren’t more than a few clicks away via email or LinkedIn. Reaching out to someone that you know via mutual connections—carefully, of course, and with respect to the fact that the candidate’s current teammates may not know that they’re interviewing—can save a lot of headache down the road.

Years ago, we had a hire who lasted all of two months. He was great in interviews and the references that he provided checked out, but he simply didn’t deliver when it came time to work. Months after we parted ways, I found myself at a meetup event with an acquaintance who had worked with the hire before. Without revealing too much, it quickly became clear that a quick phone call to him before I made an offer could’ve avoided the bad hire.

Ever since then, I’ve done my best (discreetly and respectfully) get third-party validation on potential new hires.

2) Wasting Too Much Time Chasing a Candidate

Hiring well takes a lot of effort and time, but it can take far too much time if you let it. And one of the ways to do that is to spend too much time chasing a candidate that’s unlikely to join.

Of course, this applies less to high-level executive hires; the pool of qualified candidates becomes more and more limited as the level of experience and expertise needed increases, so expect to spend a lot of time on these types of hires.

But for most positions, there are a lot of excellent candidates in the market.

And just as in sales, you’ll get better results chasing the ones that already want to work with you, versus those that don’t.

I learned that the hard way two years ago, when I happened across a developer that I thought would be a great addition to the team. One meeting led to three, and before I knew it I was throwing everything I could at him to convince him to join Groove.

Ultimately, he declined. But not before I had spent eight weeks upping my offer and, frustrated by the sunk time cost I had already lost, acting increasingly desperate.

Funny enough, we made another hire for the same role (that has worked out incredibly well) not two weeks later.

While it can be tempting to go after highly qualified candidates, these days I try my best to look at the big picture and be a lot more considerate of the cost of pursuing someone who doesn’t want to join us, which can hold us back from hiring other great candidates who do.

3) Hiring Too Fast

There’s an old cliche in the startup world: “hire fast, fire faster.”

The idea is that in a startup, you need to move fast and not dwell on decisions, so hire fast, and if it turns out to be a bad hire, cut ties right away.

After the last few years, I’m not sure I agree. At least not with the first part.

Perhaps I’ve just been burned by some of these other fails, and that’s made me more cautious. But every single time I’ve regretted making a hire, I had made that hire too fast and without enough consideration.

“Hire fast” might apply well to well-funded startups that have to quickly deploy millions of dollars and build a team to generate rapid growth, but for a bootstrapped business with a small team, every new hire changes the team in a way that everyone can feel. And I’ve found that it’s so, so important for me to be more careful and methodical (rather than reactive and rushed) in making offers.

On multiple occasions, this has helped me find even better candidates that came along while I was deliberating on a less-than-ideal (but available) hire.

4) Not Firing Fast Enough

I have, however, learned (painfully) that while hiring fast isn’t for me, not firing fast enough can be absolutely crippling.

On small teams, bad players can be toxic. Whether they’re simply not pulling their weight, or something far more insidious (like ego) is at play, a weak link degrades the whole chain.

A founder friend said something to me a few months ago that made it crystal clear why I had been slow to fire in the past: because it was a reflection on me.

The fault of a bad hire doesn’t lie with the hire. It lies with you for making that hire. You’re the one who pulled the trigger, and that’s why it’s hard to fire: you’re admitting to making a bad decision.

None of us like to be wrong, but one of the hardest lessons I’ve learned as a founder is that being wrong is a lot better than letting a bad situation get worse; I just hadn’t been applying that to firing.

It’s a tough conversation and a crappy feeling, but not cutting ties with an employee who doesn’t fit isn’t fair to your team, your customers or your business.

5) Not Knowing Our Core Values (And Putting Talent Over Fit)

One of the biggest priorities we’ve been focusing on this year is putting together Groove’s core values.

Real core values, not cliche motivational phrases. The things that drive us.

While these are a work in progress, the project has made something very clear: having a set of defined core values makes hiring MUCH easier.

No matter how talented a candidate is, if they don’t fit your core values, they won’t be a good fit.

I was especially excited about one hire some years ago that was at the top of their league in terms of talent. Everyone that I asked to talk with them came away impressed.

But a few weeks in, it became clear that this person wanted their hand held. They wanted to work on “high-level stuff” and complained—or got upset—about having to do anything that they considered beneath them.

Our core values are still being revised, but some form of “scrappiness” will absolutely, 100% be one of them. It’s core to the way we’ve built this company, and it’s core to the way we want to move forward.

If that candidate had been held up to the test of our core values, it would’ve been a much easier pass.

6) Flip-Flopping on Being Remote or Colocated

It’s only recently that we committed 100% to being a remote team for good.

It happened after one of our advisors, David Hauser, put me on the spot at our quarterly retreat.

You have to choose, you’re either remote or you’re not.

Before then, we had always been remote, but I had concerns about whether it was scaleable. About whether it was really the future of Groove.

And those concerns translated into constant flip-flopping, including a spell where I was only looking to hire new employees in the New England area.

This was a big fail on two fronts.

First, it hurt team morale, as employees wondered whether they’d eventually be asked to move.

And second, it hurt hiring, as I spent my time chasing candidates that were the best I could find in the area, but that wouldn’t have shined nearly as bright when compared to the best I could find if I had broadened my search.

I spent weeks chasing candidates that I felt like I was settling for, and it was a distraction that slowed us down for far too long.

Finally committing to remote has opened the world back up for us and made hiring fantastic talent without compromise much, much easier.

How to Apply This to Your Business

Hiring is hard. It’s absolutely critical to growth, but it’s very, very hard.

You’ll make mistakes. You probably already have. I know I’ve made many.

But every mistake is an opportunity to learn and do better next time. And I hope that by sharing my biggest mistakes, I can help you avoid them in your own business.

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About the Author

Alex Turnbull is the CEO & Founder of Groove (simple helpdesk software for small businesses) who loves to build startups and surf.

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