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I’ve made my fair share of hiring mistakes over the years. In past jobs I’ve hired (and eventually had to fire) incompetents, slackers, and one seething gentleman whose eye twitched whenever he got angry.

I’ve gotten better at hiring though, especially since I joined Tailwind. Of all of the places I’ve worked, Tailwind has the strongest hiring ethos, and the best results to show for it. This year our talented team worked together to more than double our members, hitting 100,000 back in October. That’s amazing growth for a revenue funded startup! We’re not only good at finding world-class talent, we’re good at identifying cultural fit too. That shows in the number of long-term employees we have.

Finding technical talent is a huge pain point for many companies. In this post you’ll learn the levers that we use to hire as effectively as possible.

A Fairytale Recruitment Story

Over the past five months we’ve been searching for a content marketer to join our team. We just landed an incredible hire in Peg Fitzpatrick, co-author of The Art of Social Media, and a finalist for this year’s Social Media Examiner Top Social Media Blog.

She’s going to be our Director of Content Strategy and Social Media and her mission will be to turn the Tailwind Blog and social media accounts into indispensable sources of Pinterest and Instagram marketing information. Something she’s already done on her personal blog, as well as professionally for Canva in the design space. She’s been a longtime advocate of Tailwind. She’s been telling us that she loves our tool for years and now she gets to tell the world!

The Competing Pressures of Urgency and Fit

It took me five months to find Peg though (or more accurately, for her to apply), and five months is a long time to be actively trying to fill any position. There’s always a tradeoff between how urgently you need to fill a position, versus the potential cost of hiring the wrong candidate.

You find a good, but not perfect candidate. Do you stick with them, or do you pass and hope the next one will be even better? Tough call. The clock is ticking.

Some recruitment professionals encourage CEOs to impose a 45 day cap on hiring timelines, with open positions being shelved for 6 months if the hiring manager can’t find anyone in time. While move fast and break things is the usual startup mentality, when it comes to hiring team members, taking time to make the right culture fit is key. Rather than forcing a compromise that could hurt us in the long-run, we try to take a more balanced view and ask the really productive question…

What Levers Can We Pull to Make Recruitment More Effective?

The ideal situation is that we find and hire an excellent candidate quickly. There are two levers we can pull to make this outcome more likely:

1) Increase the amount of talent we have in our pool (the number of candidates under consideration).

2) Increase our ability to identify the talent from our pool and the speed at which we recruit them.

There’s a third lever that looks more like an axe with a big red handle. It’s called compromise. We can always start swinging the compromise axe and…

3) Increase our willingness to hire candidates who aren’t an adequate fit

At Tailwind we’re getting better at number 1 (growing our talent pool), we’re incredibly good at number 2 (identifying fit), and very, very, critically bad at number 3 (compromise). That’s why it takes us so long to hire.

But it’s deliberate, and the results are glorious. Glorious!

I’ve honestly never worked with such talented and committed people. I finally understand why everybody makes such a fuss about teamwork: in an company with A+ talent and zero politics, teamwork really does make the dream work.

In an company with A+ talent and zero politics, teamwork really does make the dream work.

Levers to Grow Your Talent Pool

There’s a reason why companies have recruitment specialists and pay headhunters obscene amounts of money. There’s a lot more to recruiting than just posting a job to Indeed. The more effort you put in, the more that you stock your talent pool, the less likely it is that you’ll have to compromise on any not-so-great candidates.

a. Retention

If you’re going to focus somewhere, start with a happy, healthy culture that people want to be a part of. Build a company with a clear mission that employees can get behind, reward performance fairly, encourage an ownership mentality and eradicate politics.

Tailwind’s mission is to make world class marketing available to everyone. With marketing growing in complexity every day and a lot of businesses struggling to keep up, that’s a mission I can get behind.

The last thing you want to happen is to lose one of your existing team members while you’re off hunting for new talent to grow your team.

So be deliberate about creating a culture people want to be a part of.

And ask your team (your homegrown heroes) to share your open positions with their network.

The stronger your culture the easier it becomes to leverage your existing team to get the word out about positions. After just 8 months here I’ll tell anyone who will listen about how great working here is, but I’m a marketer, that’s how I think.

In my experience people in other departments often need a gentle nudge to share open positions, not because they don’t want to recommend their employer, but because it just doesn’t occur to them.

b. Allow remote work

By requiring potential hires to live in the same town as your company, or be willing to move, you’re reducing the size of your available talent pool exponentially. By 1000x, even if your office is in New York. I have failed in the past at managing a remote employee, so I know how hard it is. Both sides have to make an incredible effort to communicate, both in terms of volume and quality of communication, but at Tailwind I’ve seen that it’s totally possible.

Our new marketing hire, Peg, is remote. She’s worked remotely for years and so far (with the help of Slack and Google Hangouts) things couldn’t be going much better if she sat right next to me.

Some teams are fully distributed and don’t have an office at all. Personally I think it helps to have an anchor in one or more cities (Tailwind have offices in New York City and Oklahoma City) so that you can recruit deeply from the communities you’re embedded in, while being able to access the broadest possible field of remote applicants.

One way that we take advantage of having local offices is by attending events and meeting potential future hires out in the community.

And by sponsoring or hosting events. We’ve hosted startup pitch days, social media influencer parties, code academies, and more learning meetups than you can shake a stick at!

c. Start your search earlier

We started looking for a Content Marketing Manager about two months before we actually needed the position filled. That decision effectively doubled the amount of time we could spend looking. We’d found a couple of strong candidates after just one month. One was out of our price range. The other seemed willing to try content marketing, but we felt like it might have been a compromise for them. We passed and it took another two months before we saw other strong candidates come through, and one of them was Peg.

If we hadn’t started early, we wouldn’t have been able to make the difficult call to pass on a fairly strong candidate after just a month of looking.

d. Craft a job description worthy of your ideal candidate

At Tailwind we really pour our heart and soul into our job descriptions. Stuffy job descriptions are for stuffy jobs and we don’t have any of those. Here’s the job description for the Content Marketing position Peg just filled. It might be the best thing I’ve ever written.

That’s important, because it’s the nectar, the bait. If you want world-class talent to apply for your position you’ll need to show them what an incredible opportunity this is for them. That you’re the kind of company that cares about the little things. That you’re the calibre of hiring manager they can get excited about working with.

This line in our job description was so attractive to Peg that she brought it up in her interview. Twice!

“Our ideal candidate will be an authentic, positive and energetic team-player without the burden of a pesky oversized ego.”

When you’ve written from the heart, and what you’ve written has resonated, the stars have aligned. It’s like that “me too!” moment in a romantic comedy.

Of course by injecting your culture into your job descriptions you will also turn off candidates who would likely be a poor cultural fit. That’s a good thing as it will save you the trouble of interviewing them.

e. Be flexible on salary and title

Jobs and people aren’t one size fits all. If a fantastic candidate applies at your company but they’re too qualified, or not qualified enough, think hard before turning them away. Taking a risk could pay off.

When I was the Director of Inbound Marketing at BigWing Interactive, a digital marketing services agency in Oklahoma City, I managed to recruit former Lead SEO at Moz, Ruth Burr Reedy. She was a real stretch for our budget, but she ultimately landed the company on the Moz list of Recommended SEO companies. That one endorsement drove about half of our online leads. A+ players have a way of paying for themselves.

A+ players have a way of paying for themselves.

f. Be willing to train the right temperament

You can stretch your salary offer to secure exceptionally experienced talent, but you can also stretch your willingness to train people with the right interests and disposition, if needed.

For the product team at Tailwind one important question that gets asked during recruitment is, “What are your passion projects?”. Developers rarely come through the door knowing everything they’ll ever need to know, but if they work on their craft in their own time, they’ll learn twice as fast.

Alex Topiler, our Head of Product, said, “Our product team’s recruitment strategy centers around finding people who love what they do, have an unquenchable thirst for learning, and a willingness to go outside of their comfort zone. Couple that with a fit with our cultural values, and we can be pretty confident they’ll do well here.

“For people to be successful, they need to be challenged.. and one way to ensure you’re challenged is to be constantly learning”

When scaling a marketing agency I would often put out two descriptions for the same job. One for a person with experience doing the job, the other for a “trainee”. About three quarters of the time we’d end up hiring someone from the much broader “trainee” pile because the raw material was richer.

At Tailwind we don’t post two job descriptions, but we often end up hiring someone who aspires to the job over someone who is already doing it elsewhere, because we’ve seen greater potential in the more inexperienced applicant.

g. Encourage your team to be flexible and grow

By allowing people to make an impact in the best way that they can, even if it means going outside the typical role of their job description, you can encourage them to grow. Allow them to follow their passions even if that means they end up doing more, or something different from what they were originally hired to do. The key is allowing people to pursue what they love, and not box them into a predefined set of tasks that they might find themselves no longer a fit for.

Packaged into this idea is proactively hiring for adaptability. Which is exactly what you don’t want if you plan to put someone in a box in a silo, but could give you just the flexibility you need when building out your dream team. At Tailwind, our teams are small and agile, and we’re all jazzed about personal growth. It makes finding a role for talented people easier when your team can adapt and remold itself around a newcomer’s skill set.

Of course as teams grow they generally want to start hiring specialists who are the best at what they do, because at that point its less about filling gaps and more about leveling up the team’s strengths. This especially makes sense when specialists can help to train and empower others and make them stronger.

h. Maintain a “Must Hire” list

If you’re committed to working with the best you should be proactive about meeting them. When someone’s work catches your eye, reach out to them and say hi. There are dozens (at least) of reasons why this is a good idea. One is recruitment. I want to work with the most talented and interesting people possible. That’s why I maintain a list of people I want to work with. When I have an open position, the first thing I do is write down all of the people who I know who could rock it, and I reach out to them.

Our co-founder, Alex, has an even smarter approach, “Rather than asking someone if they’re interested in your position, ask if they know anyone who might be interested in the position. It’s less direct, but most people typically think of themselves first when asked that question, and you usually hear back, ‘Actually, I might be interested in this… tell me more!’.

“If you don’t, you’ve already asked them to help you recruit and hopefully increased your reach via their network. Serendipity happens more often than we think… except it’s not really serendipity… it’s a concerted effort to increase our chances and create our own luck.”

i. Build a brand

As obvious as this seems, I’ve seen it play out. When your brand gains traction and people start to care about it, the quantity and quality of your applicants can double over night. Nothing unusual about that. A strong brand helps recruit team members as well as customers.

Peg didn’t apply to Tailwind out of the blue. She already loves and trusts the brand. She sees sees working for Tailwind as a worthwhile contribution.

j. Learn how to hire

For a lot of hiring managers more candidates means more of a headache. It’s all time you have to take away from ‘real work’. That’s absolutely the wrong mindset. Hiring is the single most important thing you do as a manager. When done right, it’s the single most effective way for you to multiply your personal impact.

A big advantage to increasing your pool of candidates is the rate at which you can learn about what you’re looking for. The more candidates you see as a company, the better you can evaluate new ones coming in. If you just see one candidate and deem them to be good enough, you’re not actually comparing them relative to someone else. That is a very flawed evaluation.

Levers to Pick the Real Talent in Your Pool

So now that you have a fully-stocked pool of talent, how do you make the most of it? How do you find the best of the bunch? Again, Tailwind impresses me on this front. Here are some of the things I’ve observed here.

a. Move fast

There are lots of little tips to make hiring less time-intensive. The more quickly you can say no to people who aren’t going to be a fit, the more time you can spend with those who potentially might be.

Ask for salary requirements up front so you can at least make sure you’re in the same ball park.

Quickly phone screen only those who have potential, but be ruthless.

Select just a few who have a shot at the position to go through your actual interview process.

b. Know what’s essential

If you’ve crafted a really thoughtful job description you’ll have been forced to sit down, slow down, and think about exactly what it is that you need this person to do for you. You’ll know what’s essential and what isn’t. Screen your candidates accordingly.

Have your interview process mapped out in advance. Know what you’re testing for at each stage, and how you’re going to get to the truth. At Tailwind we have an 8 step interview process. A multi-pronged approach involving all the different departments, projects, presentations, skills deep dives, the works.

It’s a lot, I know.

Typically when we tell hiring managers at other companies everything we require our candidates to go through they’re amazed. One remarked to our CEO the other day, “And they actually do it?”

They do. The good ones don’t even blink.

If you think about it, who wouldn’t want to work for a company that is (and can afford to be) that selective?

Added bonus: by the time they join, they’ve already met most of the team and are ready to dive right in.

c. Ask the essential questions without actually asking them

If you can’t make it through our interview process without expressing your frustration you’re not Tailwind material. It happens. If we’d asked those people outright, “Are you hard working and determined?” doubtless they would have told us that they were.

It’s crucial to test your applicants and not just take them at their word, since people are notoriously unreliable at representing themselves, and sometimes even at understanding themselves.

Our CEO and co-founder Danny Maloney likes to start interviews with this question, “Tell me what you know about us – and what you don’t yet know but want to.”

He said of the question, “It may seem simple, but starting in this way dramatically changes the course of the interview. Instead of me defining where we go over the next X minutes together, I ask the candidate to point me to where they need to go. People who will thrive at Tailwind know how to set an agenda, how to speak their mind, how to ask great questions (including the hard ones). They probably entered the room hoping for this opportunity- and preparing a long list of good questions. A strong response to this question will instantly expand the time I budget for the interview. A poor response likely means I’ll cut things short- and soon.”

If you know what it takes to make it in your organization (and you need to), you can design your interview process like an obstacle course that will let your talent shine while tripping up anybody who doesn’t have what it takes. You want to get so much deeper than what they know, to discover how they think, who they are, and crucially, who they have the potential to become.

d. Hone in on your concerns

If you’re really listening, even the strongest candidate will give you some red flags.

At Tailwind we take extensive, exhaustive, notes as we interview. Then we share them in Slack for everybody who is involved in that person’s interview process to read before they interview them. A candidate may feel like they’re being interviewed by a new person in one of the later rounds, but in reality their fresh interviewer has read every pertinent thing that has been said so far in the process. They know exactly what remains unanswered, exactly where to probe deeper.

e. Get to the truth

Here Tailwind’s focus on really listening to our members to inform our product roadmap bleeds into how we interview. Holding what we’re really trying to discover in our minds, then not asking it directly, but indirectly, and repeatedly, until we’re satisfied that we’ve gotten as close to the truth as possible.

If I was trying to discover how hard working a candidate is I might ask them what they’ve done that they’re most proud of. How big their ambitions are. How has their determination been tested in the past?

I love this moment from our notes on Peg’s interview. Emily, the Head of our Customer Success Team, shares how she played dumb while interviewing Peg.

“I countered with a “bad idea” to see how she would handle me, the idea, and how to move forward- which resulted in an explanation of how to take my idea and turn it into a positive, ‘Well that’s a good idea, but it might be better if it we do it this way since it would be more efficient for users’. Which could show that she is willing to listen and won’t put others down for bad ideas, willing to give it a go and guide towards the better way forward.”

Our CEO responded on Slack with this message.

And our co-founder and Head of Product, Alex Topiler, gave it the thumbs up. Which shows you how crafty they both are.

My favorite quote about writing, and perhaps about life, was scribbled in the notes of the unfinished manuscript of F.Scott Fitzgerald’s The Last Tycoon.

Action is character

Anytime you can put someone in a situation where you can observe what they actually do, rather than listen to them tell you what they would do, you’ll be much more likely to get at the truth.

That’s why a substantial project is a part of our hiring process. It allows us to observe a candidate in action, rather than just listen to them tell us how capable they are.

The Third Lever – Compromise

Sometimes, despite your best efforts, you’ll run out of time and you’ll have to pick from the candidates you currently have in your funnel. In that circumstance you may have to compromise a little. Commit to working to bring the best out of them. It’s not the end of the world.

But NEVER compromise on cultural fit

We’d rather have a B player than an A player who is a bad cultural fit. If you haven’t invested in articulating your organization’s culture, you need to, even if it’s just to make sure that you don’t inadvertently hire someone who is a bad cultural fit.

All of my recruitment horror stories from past jobs have come down to one thing – hiring bad cultural fits. This can happen because you don’t understand your culture well enough, you don’t understand the candidate well enough, or because you do understand your culture, but you compromised on cultural fit because you thought something else (urgency, scarcity, experience) was more important. It’s not.

At Tailwind, during one culture self-discovery exercise (it felt more like a voyage), we asked the team “What one thing should Tailwind never do?”

Here are some of the team’s answers:

Get stuffy

Compromise the value individuality brings

Dishonor anybody’s contribution

Be indifferent

Be isolated

Be hierarchical

Think we’re better / be proud

Lie, cheat or steal from anyone.

Have ego

Be defensive

Use negativity as a shortcut

Blame people

Be hollow or shallow in our relationships

Value time spent working over work completed

If you hire a bad cultural fit they will be uncomfortable and then unhappy in your organization, they’ll struggle to produce and struggle to bond. It won’t end well. The very worst situation you can get yourself into is hiring a manager who is a bad cultural fit. They’ll be culturally tone-deaf and hire more bad cultural duds, creating a silo, a subculture, and perhaps fundamentally undermining the culture.

As long as you aren’t compromising on cultural fit you can always pull the “compromise” lever (or perhaps best think of it as an axe) when you run out of time. But hopefully you won’t have to. You’ll have a well-stocked talent pool and be more than capable of pulling the best talent from it.

Welcome to the team Peg. You’re the catch of the day!

If you’re interested in joining the #tailwindfamily you can see our current open positions on our About Us page.