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A Starter Guide to a Career as a Strategist

Justin Watkins

October 2018

What advice would you give college students pursuing a career in marketing?

Learn to code instead? Invest in your 401k early?!

The local Ad Club asked if I’d do just this. Specifically on how to get started as a Strategist. The following are the slides/sketches I offered up to the future talent in our industry.

The path I took

I started as a maker and a generalist. Early on, UX/UI design and animation was my jam. I could code well-enough, but it didn’t charge my batteries. So instead of pursuing the quick money as a coder, I kept expanding my interests which lead to branding, then video, then search, then social. All along, I considered writing ability as the most important skill that did not come naturally for me. It took work. But I’ve stuck with it. Writing is thinking out loud. It demonstrates an organized mind.

Early in my career I recognized my naivety. I had no idea “why” I was doing the work. I only knew “how” to do the work. My goal was to be as good as anyone on the “how” and study my mentors that knew “why.” My hard skill sets kept me employed and in the conversation.

A few things taught me the “why”:

1) Smart people – surround yourself with the brightest minds who know far more than you

2) Reading habit – it can’t be overstated, people who read about their craft go further in their craft

3) Get close to the problem – walk in the shoes of your clients and their customers

Now, WTH is Strategy?

Let’s make sure we’re talking about the same thing. “Strategy” is one of the least understood terms in our industry. It’s easier to add the word “strategy” to a job function or deliverable than it is to truly deliver strategic thinking.

The simplest way for me to say it is – strategy is gathering raw facts, organizing them well and creating a direction that can be understood, adopted and achieved.

Those last 3 points are often overlooked. I’ve witnessed many brilliant minds fail to explain their insights in ways that the next person in line could run with. All too often it’s a presentation with lots of numbers and frameworks that are impressive but not applicable.

A good strategists is a seeker and wrangler of facts. Some qualitative. Some quantitative. Who can organize it into a single path forward. A window of opportunity for the whole team to look through and say “I see where you’re coming from and see how we can get to there.”

In short, it’s choosing what not to do.

Yes, we have all these options, but this is the best way forward.

To do that, it takes diversity of thought. It requires many input sources and types of thinking. It’s a balance of science and intuition to eliminate blind spots.

Strategists can be confused as the “smart ones.” I don’t see it that way. If given the choice between the lone genius toiling away in their office or the P.O.V. collector roaming the office for different opinions, I’d take the collector. They’re crowdsourcing inputs from diverse viewpoints then filtering it through their expert lens. Much better.

TO DEMONSTRATE

I asked a few strategic thinkers at Native to share their pro-tips as well:

Greg says:
Once you realize that everyone else around you is winging it (to an extent), you’ll realize that “faking it” requires more rigor, insight and courage than you might have thought. Strategists must be comfortable feeling uncomfortable. So get dirty, go deep, experiment, fail (fast), iterate, rinse, and repeat.

Allie says:
Soak up knowledge like a sponge, but there’s no need to use big words or overcomplicate projects to prove yourself. The role of strategy is always to simplify.

Matt says:
Strategy is curiosity, research, and analysis. We can teach nearly everything but curiosity. You have to be interested in solving unique problems and care about their outcomes. A curious researcher leads to high-quality analysis. Detailed analysis informs future business decisions. So ask lots of questions now. Learn what drives a company’s business objectives. Measure everything. Find what marketing activities influence those consumer actions.

Olivia says:
Stay flexible. It’s a balance of serendipity and intentionality. Be willing to tackle unexpected challenges as they come along, but stay focused on your big-picture goals.

Stay curious. Putting forth a little extra effort to learn something new will put you miles ahead. Also, don’t take yourself too seriously.


WHERE TO START

Here are three paths I’d say you can take to get started:

1) Go deep – start as a specialist in either analytics, social, search, media or writing. Once you’re operating at a professional level and have a new interest, switch it up. Those hard skills will pay off later on. To do this, consider a larger agency with many disciplines.

2) Go broad – start as a generalist by wearing multiple hats, typically at a small shop, where you can achieve a professional level of two or three things. Just make sure the small shop has true expertise.

3) Go for it – jump right into an entry-level strategy role. These are harder to find. Sometimes it has the word “strategist” in the title, but is mostly tactical. If you do land a true strategy job early you’ll likely master the soft skills ahead of the hard skills. Make sure you find a way to develop the hard skills, too. They’re always useful.


I took Door #2. But you do you. Whatever you decide, follow these tips:

1) Surround yourself with the smartest strategists and mentors you can find.

2) Don’t stop reading. If you need some recommendations, here’s my list.

3) Experiment with a side project. Write the brief. Do the research. Communicate your idea.

4) Enjoy it. Advertising is supposed to be fun.