How to tell if someone is the right fit for your team

I’ve always wanted Doc Marten boots.

They’re rugged, they’re durable, and—I cannot stress this vehemently enough—supremely cool. Last week I woke up and decided it was now or never. At the shoe store that same morning, I was on a mission. I found the right aisle and the style I wanted—the perfect blend of cool and durable and (barely) affordable. Heart racing, I ran my finger down the shoe boxes to find that magic number I needed. My size: 8.5. I slid them on, and my heel locked into place with a satisfying thunk. I cinched up the laces, struck a casual hand-in-pocket pose, and gazed down at the little angled shoe mirror thingy.


…I hated them.

My feet fit, mathematically speaking, but they felt like the foot equivalent of having a poppy stuck in my teeth. They looked great as far as boots go: They were black, they were shiny, they were imbued with an objectively perfect tread-to-upper-to-lace ratio. And yet… I couldn’t deny the simple depressing truth in the stupidly small mirror for ants that lay at my feet. I looked like the disgruntled older brother of Ronald McDonald.

Sometimes everything can look great in theory but in the cold light of reality?

It just … doesn’t … quite … fit.

In this article, we’ll look at the elusive art of finding the right fit for your team. We’ll look at why it’s important, what makes it so complex, and lay out four key questions you can ask to narrow your odds of finding the perfect candidate.

Table of Contents

Why it’s great to choose wisely the first time

If you buy into the old adage that time is money, then hiring and training new hires has to be one of the greatest recurring monetary expenses of running any business. Before we dive into how to tell if someone is the right fit, let’s quantify what’s at stake. How much does recruitment really cost?

  • Of course, you have the basic costs—things like placing job ads, setting up equipment and software, and the like. These simple administrative costs typically run to about $5,000, according to recent benchmarking data published by the Society of Human Resources Management. Not great! But manageable.
  • Then you have all the selection process “soft costs,” like the time your interview panel needs to run interviews, deliberate, shortlist, and finally offer a position. Oh, and after that, there’s the induction process. That requires yet more company time and may also involve training and certification costs.
  • And floating above all of that like some great billowing cloud of entropy (eep!), you have opportunity costs. All that time you had to spend on finding someone? That was time you couldn’t spend on getting all the day-to-day stuff done.

Crunch those numbers, and you’re left with some big costs.

The ballpark figure depends a bit on your industry, but the general consensus across recent HR recruitment benchmarking is that the real cost of hiring tends to hover at around three times the salary for that position.

But let’s put our calculator back into the bottom desk drawer where it belongs and look now at what you can do to make sure all that outlay works in your favor.

Choosing the right candidate: How to narrow your odds.

So, let’s imagine you’ve shortlisted down to three or four potential clients. They all meet the job description specifications on paper, and they presented well in the interview. ”

Here’s the moment where we recommend you let intuition take over a little by asking four deceptively simple questions:

Are they here for the long haul?

First on your list of intangible ponderables is the question of time. How long are they likely to stay with you?

Now, of course, no one has a crystal ball. People move on for all kinds of reasons, a great many of them entirely unpredictable. But you can compare the breadth of their skill set against the limitations of the job description. You can cast your mind over their interview to think about what drives them—not just monetarily but emotionally … intellectually … heck, even instinctually.

If intuition is your copilot for this question, at least let empathy sit in the back seat to hand out snacks and manage podcasts. Or, to put that chunk of advice far more sensibly …

Put yourself in the applicant’s position.

Oh! And you know this already, but it’s worth throwing out a reminder that people want to feel special. They want to live out a heroic story where they level up, move from one challenge to another, and one day prevail.

Will this shiny new job give them that kind of experiential sandbox? At least for a reasonable length of time?

Is this someone worth investing in?

To be clear here, your calculator should remain imprisoned in that desk bottom drawer for the duration of this conversation. We’re not using the word “worth” here in the sense of ROI or how long it’d take for this person to become cost neutral; by this point in the process, you’ll likely have counted every bean there is to count already.

Nope. The challenge here is to think of “worth” in the bigger, swirling, weird, fully human sense of the word. A conversation about true worth can take you to some interestingly twisty-turny follow-up questions, like:

  • What perspectives can they bring?
  • How would they think differently?
  • How would their mind bounce off the minds of everyone else?
  • Do they bring diversity and difference to the table?

And, of course, Ruby being Ruby, we really want to hang a bright, golden lantern off this notion that worth and worthiness walk hand in hand. We can do much better as a team when each constituent member feels acknowledged, recognized, and respected.

You can read more about the grand project of being kind and excellent to one another here.

Predictable observation?



Who are they as a person?

Finally, it’s worth taking a bi(iiiiii)g step back and asking the broadest question of all: who are they as a person?

People are complex—even more so than boots.

The right candidate for your team may “fit” for a host of difficult-to-define reasons: They may possess a dazzling array of “soft” transferable skills. You may have intuited, for example, that they possess a deep and natural ability to empathize with people. Or you may have observed they’re imbued with an almost uncanny aptitude for active listening.

Emotional intelligence, interpersonal skills—in fact all that soft and squishy stuff—can make a profound difference to your team’s impact … especially if they’re customer-facing.

Let’s see that old Casio calculator quantify that!

The right fit

Here’s the difficult yet oddly delicious truth of it. Finding the right fit for your team isn’t readily reducible to a formula. It isn’t something you can brute force with a spreadsheet or hash out to the accompanying bleeps and bloops of a vintage calculator—even one of those fancy solar-powered ones.

Ultimately, your best bet is an intuition-led conversation about the person behind the resume.

And if they’re wearing a swanky pair of Doc Martens? Well, that’s just gravy.