The 5 Things you Learn from Working at a Creative Agency
The Mad Men days are long gone, but a stop here can still make a difference in your career
Welcome to the latest entry in The Workaround. You’re in good company with thousands of fellow entrepreneurs and innovators!
I’m Bob, your host. My mission here is to share personal, behind-the-scenes stories of the ups and downs of my career leading tech startups and corporate innovation.
I write to make you think, smile, and discover a shortcut to success or a trap to avoid.
Here we go…
Last weekend, I joined a group of friends for an annual trip. We’re all middle-aged guys who get together to hike, play music, drink beer and bourbon, and compare notes on family and work. We’ve been doing a version of this annual trip for nearly 15 years.
It all started when we worked together at a digital+creative agency, Bridge Worldwide. So, our conversations eventually led to stories of our trials and tribulations together. Over a six-year period, the business grew from 60 people to over 400—all in our office in downtown Cincinnati. Nearly 1,000 different people worked at Bridge at some point.
Bridge was a unique experience for all of us, and it holds a special place in my heart. It’s where I left my corporate role, had my first entrepreneurial experience, started my first services business, and first exited.
I had worked with many creative agencies in my brand marketing job before joining Bridge, but I was quite shocked when I first joined the company and learned how the sausage was made from the inside. I went from a relatively cushy position to one of leading a client service team that had experienced at least one employee resignation each week for 12 straight weeks.
As I came aboard and grabbed a shovel, I realized that only half of my “work brain” was still relevant—the part that knew business and marketing strategy. But I’d have to re-grow the other half from scratch and quickly learn how to lead people, service clients, and win new business in an alien agency environment.
The first few weeks were pretty damn tough…I remember driving home from the office, endlessly listening to Cold Play’s “The Scientist” and questioning my career decision…
Nobody said it was easy, no one ever said it would be this hard
Oh, take me back to the start
But each day got better. We added processes, trained our talent, and continually learned from our mistakes. Bridge grew from $10 million to +$40 million in those years, and after a bidding war, we were acquired by WPP. Almost 20 years after I started there, the business is still running at the same location, with some of the same employees and clients (now rebranded as Grey).
My weekend mini-reunion made me think about how much I learned during this time and how much I packed into the half-brain I regrew there. I think anyone in business would benefit greatly from a tour of duty at a creative shop. Here’s what you’d come away with:
1. Fake it Until You Make It
If you’ve only got time to read one of the lessons, this is it—a realization that nothing really has to exist until a client pays you to make it so. Here’s a quick story:
One day, we received a Request for Proposal (RFP) from a large financial services company. They were looking for an agency to redesign its entire consumer-facing web experience. This would represent over $1 million in revenue for us and potentially lead to a relationship with many millions more to come.
But RFPs like this usually go out to dozens of companies and come with long lists of capability requirements. Clients use the requirements to cut down these lists of candidates. I remember one of the things this company listed: Persona Design.
I had never heard of this concept before, and neither had anyone at the agency. So, I hopped on Google and printed off several articles about this somewhat new (at the time) approach to user experience work. I talked with some members of our team who worked in UX and wrote up a process in a few hours. Now, we could check the box that we offered Persona Design. After months of work, we won the pitch competition and started re-applying this shiny new process to current and new clients.
(Side note: After telling us we won the work, the client said she hadn’t secured the budget yet. We did about $100k of total work for them instead of the $ millions we expected. I guess even clients can fake it. “Nobody said it was easy…”)
Working at an agency teaches you to be fearless and break the rules that might restrict a traditional company. You learn that it takes time for a client’s thoughts or your ideas to turn into reality. Once the money comes in, there is always time to learn how to make what you faked—or hire an expert to do the work for you. This has been incredibly helpful in my startup work.
2. How to Work with Artists
Creatives are a unique species. While you took college classes in accounting and marketing, they had their designs and writing critiqued to the point of tears. The universal muses call them to channel something from nothing. And they can think outside of whatever box you draw them into.
The best of them are also a little bit crazy. Those who hear the calling are just wired differently. I could tell stories about dealing with some extremes of the creative agency world: physical fights, drugs in the office bathroom, and swingers’ parties after company offsites. But mostly, they are just really, really unique and interesting people.
For all their challenges, we business folk desperately need them for our companies to be successful. They take our boring packaging, product claims, and new and improved products and turn them into something that actually earns customers’ attention and precious dollars.
I led the Account Services team at our agency, among other roles. We mainly served as the bridge between our profit-minded clients and our creative-focused designers, copywriters, and creative directors. Everything between the two was a negotiation, and these plays were performed daily.
Through trial and error, we learned how to push back on clients and coax creatives to adapt. Over time and with mutual success, this dance takes on a performance of its own. Today, I highly value any work artists do—from the landscape architect working on our new lawn to the designer who tweaks our TikTok videos on our company’s influencer marketing campaigns.
If you can inspire creatives they will change the world.
3. Lots of SuperBowl Games
Most traditional jobs involve the same thing every day, forever. Our stream of workflows, quarterly deliverables, annual plans, and countless emails, Slacks, and Zooms can feel like a modern assembly line. Even at the end of the calendar year, we plan for what happens next summer.
There’s no start, no surge to a climax, and no end to the work.
But not so in the agency world. Rather, it’s a constant series of contests with winners, losers, celebrations, and suffering. We get to play in a Super Bowl nearly every day.
Each presentation to a client is a kind of contest. We choose a strategy to present, order our slides, and build up to the idea we’re desperately hoping they buy into. Then, we await the theatrical thumbs-up or down. Either way, we head to the bar afterward to relive the drama and reset for the next one.
Each new business pitch is a ticket to a competitive tournament. Twenty firms enter, but only one will take home the glory. RFP responses cut the field to 10. Capabilities presentations weed out the unworthy, and a Final Four are invited to fly out and pitch in the client’s fancy conference room. Games within games are played to position the contestants for a slide edge in this ultimate, creative bake-off. One is selected, and three get the bad news. And we all await the next RFP and a chance to play again.
(Side note: This is why I get less interested in college and pro sports the longer I’ve been in business…Why watch others play their sport when I wake up and get to play my sport—company building—each day? I know, I’m the odd one. Agency work might have made me so.)
It’s a show, a game, a story, and I think it’s closer to what the best human work should be. Business+Philosopher Naval has a great analogy: ”We should work more like lions.”
I always loved the “sprint hard, then rest” model of agency life, and I think a lot of our work would be more enjoyable and of higher quality if we got off the assembly line and sprinted more often.
4. The Art of Client Service
Agency work often feels like business on hard mode. There are countless competitors and no real competitive advantages. You’ve got to fight for each project, and your clients can fire you at any time, for any reason. Judging creative quality is extremely subjective, and measuring its sales impact is still very hard. And while everyone wants to push the innovation envelope—learning how to do new stuff comes with many mistakes and can kill profitability.
But challenge makes us better—especially when it comes to serving clients. And since we’re going to serve somebody in any work we do, working at an agency can accelerate these skills and your career.
If you’re a regular reader, some of the client success lessons I learned will be familiar from previous posts, including:
Show and tell how the work was done behind the scenes
Nail the little tests that clients will use to judge you
Be Productively Paranoid about risks to your business
Handle complaints by jumping all over them
My time in the agency world powered all of these lessons—and dozens more that I’ve got outlined for future posts!
5. So Many Businesses
A key to success in business and life is being exposed to many diverse people, places, and situations. The novelty expands our minds to what is possible and helps us choose directions that best suit our skills and interests.
Agencies deliver diversity by the truckload.
Over the course of a year, you might work on projects for dozens of different clients and industries. Each brings new challenges and unique creative solutions, keeping your mind alive, learning, and moving quickly.
And after dealing with so much novelty you begin to see the bigger picture. Businesses operate in industry silos, but you see that so many of the problems are the same across them. Often, a solution in one category can be applied to another, and you can bring clients work that they never would have thought of.
These insights and opportunities go far beyond external creative projects. Because you are embedded within your clients’ organizations to some extent, you begin to see different ways to work and unique cultures at play—all with the emotional detachment of not actually working there.
Look at your agency career this way and pay attention to your diverse client base's many external and internal dynamics. You can really start to “see the Matrix” of business in a much shorter period than you might with long client-side career stints.
Armed with this experience, you’ll be faster at making connections and know enough to be dangerous in many fields. This accelerated knowledge can help you quickly pick career destinations that fit your calling or develop startup ideas that address the problems these companies face.
Creative agencies aren’t necessarily the sexiest companies to join in today’s job market. The 30-second “big idea” is dying. Holding companies and their clients continually squeeze the art and excitement out of the work. The entire industry is holding its breath over the threat of AI.
But creativity will always be the key to connecting brands and their customers, and this skill isn’t taught in business school. As a company leader, you must discover and inspire creative talent that can power your products and services. The business models might change, but creative life will find a way.
How we might work together…
My team and I lead Hearty, a boutique recruiting service that helps tech-forward companies hire proven talent. Our senior team of operators sources and screens, saving you time and money. When you need help, let’s chat.
Need help with a software project? Perhaps a product MVP, a project that requires outside help, or a fractional CTO for key strategic decisions? Our team at Shipwright Studio has worked together to build multiple successful startups, and we love helping leaders turn their dreams into reality. We're the team our clients trust for software built to last.
Looking for Influencer Marketing and Content Creation? The team from our previous company is back by popular demand with A2 Influence. We’re ramping up now and would love to share more.
Feel free to schedule time together during my Open Hours for questions, feedback, networking, or any other topic!
BONUS: Cool Content of the Week
A little something I found meaningful. You might agree…
Newsletters are BS
Speaking of agencies, a few weeks ago, I spent time with Ben Greenberg, co-founder of the growing strategy, branding, and marketing agency BS, LLC. He was just about to pull the trigger on his company’s first client/partner newsletter.
I shared my perspective—which I hope is what comes through in this weekly Substack:
First, it’s all about adding value to the recipient. This keeps you in the inbox and away from the unsubscribe button. Business will come eventually if you focus on their needs first and last.
Second, write in your voice about what you love. This will power you through consistently writing—a task that is always important but not urgent. Make it feel fun rather than a chore. And your unique voice will bring the humanity we crave in a world of A.I.-like blah-blah.
I was incredibly pleased to receive Ben’s first email last week. (To be clear: I take zero credit! I think Ben finished it days before we spoke.) I’m sure you’ll agree it’s got the value and uniqueness that already sets it above 99.9% of the marketing spam content you’ll find in your inbox.