Breaking In: Behind the Scenes of an Agency Hiring Process

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Written by Jaime Laufer,
• 15 min read

“How do I stand out? What are you looking for in a candidate? What will get me hired?”

As the Director of People Operations at Digital Surgeons, I’m asked these questions every day. Finding out how to get a job at an advertising agency has been a never-ending topic of conversation throughout my career, but every agency is unique. That’s why I’ve captured a recent hiring story from two points of view:

James Dowd, the Creative Director, who was “sort of” looking for the next great writer on his team, and Jimmy Burt, the eager young applicant, dreaming and hoping of landing his first copywriting job.

Enjoy a back-and-forth conversation that offers a behind-the-scenes look at some of the trials and tribulations that go into making someone part of the team here at Digital Surgeons.

Note: not everyone is as malicious as James through the hiring process. 

Jaime Laufer

Jimmy Burt and James Dowd

James Dowd:
This position had been open for over two years, and I was fine not filling it. The new writer needed to be perfect. No one had been.

So, when I got Jimmy’s portfolio, I said no. It wasn’t perfect. I was impressed that he worked so hard to develop a spec portfolio, but nearly every applicant had done so. A good portfolio is now like a college education. If you applied, I already assume you have one, and I’m not that interested in talking about it. I want to see more.

It wasn’t until he found multiple ways of getting personal messages to me that I said yes. Messages were passed through family, neighbors, colleagues, and even someone associated with the construction of our new building. He was relentless.

But, in my opinion, anyone that eager is worth talking to.

You can’t teach passion.

Jimmy Burt:
I was nervous.

It was my first interview at Digital Surgeons, and I didn’t know what to expect.

To settle my nerves a little, I made sure to get there early. So by the time the administrative assistant led me into the Red Conference Room, the butterflies in my stomach had pretty much all but disappeared.

And then she handed it to me: a daunting three-page, 20-question writing test.

The butterflies came raging back. And this time, with a vengeance.

“Oh, boy,” I said out loud to myself with a little laugh. “Is this a joke?”

Looking through the questions, I quickly realized this was not a joke, and I was immediately brought back to not-so-distant — and not-so-fond — memories of sitting in college classrooms, aimlessly going through entire exams, hoping to find that one question I knew the answer to.

For the next ten minutes, I anxiously battled my way through as many questions as I could.

I think I answered one of them.

Finally, by the grace of God, the door opened, and in came the People Operations Director, Jaime Laufer, a Creative Strategist named Michael Zimm, and the Creative Director, James Dowd: the man behind this devilish test that was guaranteed to haunt me.

They settled into their chairs, and before I knew it we were talking about everything from our favorite movies to our childhoods and past work experiences. I was enjoying my time with them, but in the back of my mind I couldn’t stop thinking about this test. I had to bring it up.

I started asking James specific questions about it, but each of them was met with a vague answer. “That’s up to you to figure out,” he would respond, or, “The answer is whatever you want it to be.” As much as responses like that bothered me, I was relieved when James told me I could finish the test on my own time and get it back to them within a few days.

A few days, I thought, now that’s more like it.

The remaining half hour involved good conversation, a bunch of laughing, and my horrible performance of an even worse stand-up comedy routine, which maybe — big maybe — we’ll talk about another time. At the end of the interview, I shook their hands, said my thank you’s, and nonchalantly slipped the writing test in a manilla folder, happy to know I didn’t have to deal with it for the rest of the day.

I give this test to all writing applicants, whether it’s for an internship or a senior role. But, it’s not actually to test their writing skills. It’s more to test how they think, and how they react to challenges. It’s designed to mess with them a little. No one passes, and to be honest, it’s fun to watch them squirm.

Beyond the test, I’m notoriously cruel to interviewees in that I’m inquisitive but completely stoic. Again, I want to see how they react. I’ve been told it’s clear I’m not interested in an applicant when I appear fully engaged and interested in them as a person, but I don’t think that’s really true.

It sounds horrible, but I do feel like I need to defend this castle. I don’t want to have a great, fun, lively conversation with them — we’ll do that later. For now, I need to quickly uncover who someone is, what they are capable of, and how they will handle tough situations. When they break on Day 0, they’re going to break on Day 1, and every day after — especially in a demanding environment like this, where smart, passionate people move very quickly and constantly challenge one another to think — to actually think!

I’ve never experienced a team, or company, like this, so being great and resilient are a must. If they have the will to succeed, we’ll teach them everything they actually need to know. As we say over here, it’s will over skill.

In terms of Jimmy, he did exactly what I look for. He did his research, he formed an opinion, he asked questions, he engaged personally, he filled the room with energy, and he never — not once — backed down from a challenge.

He laughed to himself a lot, most likely asking himself, “Is this guy for real?”

At one point, I asked him what he wrote that week (Note for future applicants: if you’re a writer who hasn’t read or written anything this week, you’re not yet a writer). He said he had been working on stand-up comedy, so I asked him to stand up and perform it. He did not hesitate for a second.

Being open to standing in front of a room and sharing your writing is part of the job. At all levels, writers must first put a piece of themselves into the work and then hang it all out there for people to observe and critique. It’s potentially the worst part of the job, but it’s also thrilling and crucial to selling our ideas, internally and externally.

As for Jimmy, it was the worst comedy I’ve ever heard. But, I respected the hell out of him for doing it with what looked like confidence, and a smile on his face.

I was feeling confident, and there wasn’t much between me and some downtime at home except for a short car ride.

And, a 500-foot walk down the hallway to the parking lot.

The kind of walk that’s just barely long enough to get you seriously thinking about things.

I started replaying the past year in my mind, looking back on my efforts to break into the advertising and marketing industry, thinking about all the time my mentors put into helping me out, the time I spent reading about and practicing copywriting, the emails to creative directors that went unanswered, the scores of applications that got lost in the mix, and the constant feeling of doubt — which was growing with each passing day — that I would never land a job in marketing or advertising.

At some point in this moment of reflection, I got to the door, and with my hand ready to push it open, I stopped.

I realized something: everybody like me had a portfolio, everyone had a connection at some digital marketing agency, and almost anyone could get a couple recommendation letters that made them look like a superstar.

None of it seemed to be working for me.

I had to do something to stand out from the crowd, to separate myself from everyone else, to finally land a job I so desperately wanted.

I had to finish that test.

No matter how long it took, I was going to sit down on a bench — in that hallway — and finish this ridiculous thing on the spot

So for the next two hours, I did just that, grinding through those 20 questions like only a good fourth liner knows how to do.

And although it was one of the more difficult tests I’ve ever taken, it was also a lot of fun. It was creatively challenging and downright bizarre. Questions ranged from the obscure, “Write a haiku about tacos.” to the deep, like “Describe your life in 3 words,” and my personal favorite, “How would you explain spaghetti to an alien?”

It became fairly obvious once I hit the taco-haiku question that this test wasn’t really designed to measure any level of knowledge. Creativity, sure, but it was simply too foolish and too strange to continue beating myself up about whether I was getting the answers right or wrong.

But I knew it was meant to be finished, and I knew that a question left blank showed a willingness to give up, or maybe just as bad, a failure to go and find the answer elsewhere.

As the wise writer Jason Rose once said, “If you don’t know the answer to something, ask someone who does. Or, make it up.”

I kind of don’t want to give this away, because no one realizes this while taking the test, but I WANT them to Google things they don’t know or understand. I’m always happy to answer questions, but when you’re doing a job, someone will not always be there to explain things, so sometimes, folks need to roll up their sleeves and figure things out. That’s a requirement of any professional anywhere.

Don’t know what a Harvard comma is? Google it. Learn.

Don’t know what a retronym is? Google it. Learn.

All the world’s information is out there, just a Google search away, and yet a majority of applicants leave answers blank. But, leaving things blank is giving up, hoping someone else will do it for you. It’s a sign of how they will perform as part of a team. Do they lean in, dig deeper, think further? Or, do they shrug their shoulders and look for an easier option?

So yeah, I was Googling the hell out of about 50% of the test. But the only thing that mattered was that I finished it. And after I did, I walked back down the hallway, popped my head into the Digital Surgeons office, and handed it to Jaime.

The look on her face told me I’d accomplished exactly what I set out to do.

By simply sticking around for just a couple of extra hours, I cemented myself in her mind, and I went from having a good interview to having a good chance at getting the job, or at least a call back.

And it was all because I noticed an opportunity in front of me, and then I seized it.

I pounced at the chance to separate myself from the pack, which was something I’d read about over and over again as the reason why this creative and that creative got their first jobs. But up until that moment, I repeatedly came up short in my attempts to do the same.

I suppose it’s just like writing a good headline: quality comes from quantity. At some point, I was bound to break through.

But it was less about repetition as it was about luck. If that writing test didn’t exist, then who knows? I could still be without a job. But at the same time, it was less about luck as it was about determination. If I wasn’t hellbent on getting that job, the thought of sitting down and finishing that test wouldn’t have crossed my mind in the first place.

It wasn’t luck. There was no way it was luck.

I’ve become accustomed to saying that no one passes this test. But, Jimmy made me rethink that. I think he might have passed. It’s just no one had ever done well enough to determine what success was. His test is now the benchmark, but don’t tell him I said that.

So that was phase one. Interview number two was with other people he’d be working with. He earned that follow-up, and everyone loved him, so that was another step toward him being hired.

Every organization — and certainly every agency — says they are focused on their people. But, in my experience, it is simply not true. Best available candidate, good portfolio, most affordable, right time at the right place, friends of a friend, was great in that single interview — this is how people normally get hired. The result is politics, back-stabbing, in-fighting, laziness, and complacency. I’m proud to say that while we can be tough in interviews, we actually find the people who work well together, and who can do great things together, because together, great people will lead to great results. A new employee is an investment, and if an agency doesn’t take the time to vet their investment and its potential impact, how can any client trust that agency and its team to support their business? Answer: they damn well can’t.

So, Jimmy’s next step was a critical point. It’s where I have broken other people, where they let their guard down.

It’s where I get them out of the conference room, and out of the office altogether.

At this interview, we go to a bar, a coffee shop, or just a walk, and we get to know each other. I actually engage like a human, and we talk like friends. This is where people reveal themselves. I’ve actually heard racism, sexism, and stories of devil worship in these meetings.

I knew I had Jimmy here. He seemed too good. I was going to break him. He would be revealed.

I asked him casual, fun questions, and totally direct, random ones, like, “What was the name of the lady at the front desk on the day of your first interview?”

He remembered her first and last name.

He not only had an answer for everything, we had fun.

I couldn’t break him.

Where a typical applicant’s facade would crumble, Jimmy continued being the person he promised to be: excited, hungry, passionate, intelligent, curious…what else can I ask for?

So, we decided he was the one — the person who would finally fill a role that was open for over two years with hundreds of applicants. But first, I was going to mess with him one last time.

I told him to call me on a certain day, at a certain time, and when he did, I didn’t pick up. I wanted to see what he would do.

The phone rang, I ignored it. He called back, I ignored it (I know, I can be obnoxious). Then, I got an email from him. He said he would try again later, and that I was probably busy. That was good, but he sold me with the last line of his email:

“I won’t let you down.”

We hired him that day, and he hasn’t let us down yet.

So, if you’re like I was, and you’re struggling to land a job at an advertising or marketing agency, don’t give up. If you’re working hard enough at it, you’ll get what you’re looking for sooner rather than later.

Keep sending out those emails and applications. Keep networking. Keep asking questions. Keep Googling things you don’t know.

If this is something you actually want to do, go make opportunities for yourself.

And most importantly, keep a close eye out for that opportunity to make yourself stand out from the competition.

And then do something about it.


Looking to break into the advertising industry? Hopefully you won’t have to deal with James, lol.

Seriously though, take note of the passionate effort displayed by Jimmy. Like James said, passion can’t be taught, but skills can. So, a great portfolio alone isn’t enough. Show your grit, your unique energy, and your will to take on any challenges with enthusiasm. All any digital marketing agency or company really wants are hard-working, dedicated people who will display thought, energy, and effort. That’s the secret to landing a job — any job!

If you have any questions about landing an agency position, tweet any of us here at Digital Surgeons!

Jaime Laufer

James Dowd

Jimmy Burt