20 Ways to Become A Better Strategist

Doug Kleeman
Aug 22, 2017 · 12 min read
credits: Alex Gray

There are plenty of articles swirling around the web offering very practical processes, frameworks or new perspectives aimed at building the future of brand strategy and account planning.

This is not one of them.

See, planners love to talk process. Rarely do we discuss practice.

I’m talking about those small, simple, surprisingly enriching habits we can do to help us operate better as creative people. Routines we can return to and repeat, over time, in order to compound our creativity. Interests and skills that can prevent us from devolving into lifeless robots.

The reality is, we can ramble on about Porter’s 5 Forces till we’re blue in the face — it won’t necessarily make us more inspired, more creatively fulfilled or more imaginative in the way we approach the craft of brand planning.

So instead of penning another post with some elaborate consumer mindset matrix that you can copy-and-paste into your next strategy presentation, I figured I’d instead offer up 20 ways to help you become a better strategist. A mindset, rather than a skillset.

It may seem trivial. It may seem impractical. But even if there’s just one thing in here that you start using, I’ll consider it a roaring success. And of course, it’s not an exhaustive list, so I’m interested to know what works for you.


Archive your media consumption

Books, podcasts, news stories, documentaries, interesting YouTube clips. Diversify. Record all the media you consume, on paper. If you want, distill it into one sentence once you’re done, or write down the one thing you found most remarkable about it. It may sound obsessive. And it is. But if you subscribe to the idea that creativity is merely connecting the dots, you need to start by collecting more dots. Either you’ll quickly find holes in your media diet, or you’ll begin to see more patterns in the world around you. Win, win.

Write your own textbook

Before I landed my first job as a strategist, I had zero experience in the field. Zilch. But what I did have was a surplus of post-graduation angst, way too much time on my hands, and a handful of empty notebooks. So I read blogs, consumed industry articles and scribbled down a bunch of bad ideas that now make me laugh. I filled notebook after notebook with random quotes, stats, useful insights from studies on psychology or human behavior, diagrams of business frameworks, lists of branding principles, even slides from noteworthy Skillshares. It’s still a habit I hold today, and it’s probably been the most beneficial contributor to my own work. Become an obsessive archiver. Create your own course syllabus. Write your own textbook.

Go to a bar by yourself

Or coffee shop. Book store. Park. Doesn’t matter. Some place where people mingle. Free yourself from corporate captivity and head out into the wild. For some odd reason, it seems as though strategists and account planners today don’t get out into the real world very often (even stranger, we’ve begun to celebrate them whenever they do). Which is why the smallest, simplest thing I’d challenge you to do is to go interface with complete strangers somewhere. Observe the way people interact. Ask them questions. Listen. Don’t be a creep. It may feel awkward at first, but you’ll come away with something special. And the truth is that the more awkward, terrifying, or contrived this may feel to you, the more you probably need to actually go do it.


It’s as simple as this: if you work in a creative industry and don’t meditate, you’re leaving potential on the table. So start with this: 10 minutes a day for 10 days. It’s that easy. If you don’t notice any difference in your mental state, then feel free to discredit everything else I say from this point forward. I genuinely believe in it. And some of the smartest, most creative people I’ve worked with are believers, too. You know that uncomfortable, anxious feeling you experience when you have 30 open tabs on your browser? Same thing happens inside your noggin, day-in and day-out. You may not even realize it. But it clouds and corrodes your mental machinery. Use meditation as your mental disinfectant.

Set yourself back 40 years

“You have to understand the past to understand the present.” Those are the words of famed astrophysicist Carl Sagan, but it’s pertinent advice for marketing strategists, too. In an industry so obsessed with timeliness, it helps to recognize and appreciate timelessness. Because as much as we like to nerd out on Snapchat’s latest ad offering, or Mary Meeker’s mobile adoption charts, or some clever campaign execution that just sprouted up on every industry trade website, the reality is that you can learn a lot about the future by better understanding the past. By understanding the things that haven’t changed or will never change. By recognizing behaviors, attitudes or ideas that withstand the test of time. You can check out The Anatomy of Humbug or The Book of Gossage or 100 Ways to Create a Great Ad or A Master Class in Brand Planning or even check out John Griffith’s Out of the Box Thinking. Anything that provides a peek behind the curtain of Nowness.

Make writing a practice

A common first mistake is thinking you’re not a writer. That it’s a domain reserved solely for people with ‘creative’ in their title. Nonsense. If your job depends on articulating ideas, you need to write. Not to mention, you need to write with clarity, with simplicity and, at times, unfettered imagination. Fortunately, there are a lot of good books out there to help anyone, in any position, get a better handle on how to write. Annie Lamott’s Bird by Bird. Stephen King’s On Writing. Steven Pinker’s The Sense of Style. Kurt Vonnegut’s rules for writing. There’s a bunch. Bonus: George Saunder’s “What Writers Really Do When They Write.” Or just stop reading bad books from bad writers. Life’s too short for that.

Study shareholder reports

For better or for worse, Wall Street runs this world. And since shareholders determine so much of the business world today, both directly and indirectly, these publicly available artifacts are invaluable. They give you a better sense of how corporations actually create value in the world, how they communicate that value and how they intend to build on that growth moving forward. Learn the basics. Know what to look for in a balance sheet. Understand a company’s levers for growth. Look at the language they use. Better yet, invest a few hundred bucks in a company. Monitor its ebbs and flows for a few months. It’ll teach you more about business than any advertising award show case study.

Debunk your own opinions

Strategy requires decisiveness. Problem is, decisiveness sometimes breeds certitude, self-assurance, maybe even cockiness. Be suspicious of certainty, everywhere you see it. One of the great qualities that make strategists so valuable in the creative process is their innate sense of contrarianism. Their recognition of biases and blindspots. The ability to put thoughts through the scientific method. So to build up this elasticity of mind, I say, spend more time exploring contrasts. Refresh your critical thinking skills. Study the dichotomy of debate. Watch FoxNews and MSNBC in the same sitting (but stop before it makes you depressed about the world). Covet thy contrasts. Ultimately, it’s about listening more, not less, to the opinions of those you disagree with. Because having answers is great. But having perspective is, too.

Follow creative visionaries like you follow sports teams, Beyonce or Game of Thrones

I‘m always fascinated to hear how other creative people talk about their work. Creative people beyond the world of advertising or marketing. I’m especially partial to architects and industrial designers — the way they share inspiration, the way they describe their creative process, the words they use to articulate experiences, and the manner in which they frame the challenges they overcame. It’s inspiring to hear them talk, and it’s a kick-in-the-ass reminder that you don’t need a bunch of slides in a Keynote deck to sell an idea. Go find inspiration external of your industry. It’s everywhere. Simple stuff, like James Victore’s YouTube videos, Netflix’s Abstract series, or a podcast on the craft of songwriting. For God’s sake, let’s broaden our creative aperture beyond just marketing.

Go for a walk

The benefits of walking on creativity are really starting to stack up. Personally, I’ve been amazed at how quickly it can jumpstart thinking. My advice: make it a daily ritual. Even if it’s just 5 minutes or quick spin around the block. Take a colleague. Talk things through. Bond. It’s a useful way to really get to the heart of something. Not only can this more casual setting help bullshit-proof your talking points and weed-out all the wicked jargon, it may be one of the handiest ways to get outside of your own head a bit. As Søren Kierkegaard once said, “I walked myself into my best thoughts.” And suffice it to say that dude had some pretty profound thoughts.

Start an observation journal

In his book Choose Yourself, James Altucher recommends writing down 10 new ideas each day as a way to develop your “idea muscle.” The thought is, most of these ideas will probably suck, but it’s the regimen the matters most. Instead of ideas, you may find it beneficial to create a shortlist of observations or insights you have throughout the day. It can include seemingly minor realizations, like the way people act in elevators, or the way runners acknowledge each other on the streets or your own quirky theory around how people’s fashion choices correlate to their usage of certain slang. I don’t know. Get weird. Something might stick. And whenever the duty to “uncover an insight” for a project finally comes along, it won’t feel so daunting. And who knows, maybe it’ll all eventually culminate into something brilliant like this or this or this.

Get tactile

The screen is your enemy. At least at first. So before you even begin to design a presentation or outline a narrative or self-edit your thoughts, it helps to get out of your own head and put things down on paper. Not Powerpoint. Not Google Docs. Paper. Use sharpies, stickies, index cards. Pull out a blank page and free-write for five minutes. Draw your own version of an input canvas. Make lists, sketch diagrams, give yourself a nasty paper cut. It helps. A strategist’s own self-induced demand for irreducible simplicity often makes this type of playfulness seem verboten. But it gets the brain to fire in different ways. And there’s a bit of magic in making a mess. Plus, it often results in interesting creative stimulus that can help inspire others, or even make them feel a bit more like an active participant in your own process.

Master the interview

Say what you want about Howard Stern, but the man extracts answers out of people that no one else can. I’m amazed at how great interviewers can do this. They strip away people’s protective layers like old coats of asbestos-laden paint. TV legends like James Lipton, Barbara Walters, Larry King. But there’s also a new wave of noteworthy people today on YouTube and podcasts. People like Sam Jones, Brian Rose, Krista Tippett, just to name a few. Watch their body language. Listen to their line of questioning. Notice how they navigate the subtexts in between spoken sentences. The point is, we stand to gain a lot from speaking less and listening more. And being able to ask the right question, the right way, at the right moment, is some sort of alchemy.

Write poetry

Hold on, hear me out. This one’s more important than you think. Writing poetry trains you to choose your words wisely. Admittedly, it’s hard. Really hard. And it can be incredibly uncomfortable at first. But reduction is an art-form. And simplicity is key, right? You’ll quickly notice how many of the words we use on a day-to-day basis are (at best) entirely unnecessary and (at worst) downright confusing to those around us. Start writing. Obsess over details. Revise, refine, rework. With a little bit of patience and a commitment to practice, you may be astounded at how drastically it changes both the way you express yourself and how you communicate ideas. Plus, poetry almost serves as a sort of creative liposuction for buzzwords, cliches and other egregiously overused language.

Channel your inner comic

Comics are critical conduits of cultures and society. Sounds overstated, right? It’s not. The role of the comedian — among many — is to observe people’s behaviors, the words they use, their assumptions and habits and idiosyncrasies that all too often go unnoticed. For comics, truth is currency. Jokes make us laugh because they make us think. And that’s why stand-up comedy is incredibly relevant to any aspiring creative individual (aside from also being utterly enjoyable). Have a go at writing some of your own comedy bits. Revisit the beautiful world of satire writing. Sign-up for an improv comedy course. Not only will it get you to think, it will get you to think fast. It’ll teach you about universal truths. It’ll teach you about delivery. It’ll teach you how to rediscover your own sense of playfulness. And it’ll teach you the importance of not taking things so devastatingly seriously. We‘d all stand to benefit from taking things a bit less seriously.

Analyze the anatomy of stories

People who work in advertising are all storytellers in the same way that people who live in Los Angeles are all actors. Hogwash. Instead of trying to become the next Rumi, maybe start by simply unpacking the methods that other master storytellers use to hook you. Virtually any story — a news article, a TED talk, a documentary — can be dissected into distinct elements. What’s the main thesis? How do they support or prove this thesis? What’s the narrative arc? What are the chapters of their story? You can usually identify the sequences of stories with a little extra effort and attention (case in point, most business books have one core idea behind them — no matter how ‘big’ they claim their idea to be — even a cursory glance at the table of contents can give you a better sense as to how the author chooses to present their story, offer evidence, explain its implications and, ultimately, persuade you).

Maintain logs

Logs are just daily recordings. You can use them to monitor your personal finances, track fitness goals or tally up your basic to-do lists. Anything, really. But logs are important because they operationalize two things that all strategists continually need: perspective and progress. Logs remind us that making shit happen takes time. It also takes dedication, an eye for effectiveness and a step-by-step plan for actually getting there. Don’t overthink it. Start small. Ideally, something in your personal life you want to achieve or get better at. Set goals. Figure out the ways to best get it done. Make adjustments as you go. It’ll add rigor to your personal life. And it’ll bleed over into your work eventually.

Bourdain yourself

Yes, I just turned celebrity chef and television personality, Anthony Bourdain, into a verb. But it’s a helpful one. I’ve long admired the way Bourdain (and really any travel writer) looks beyond their own understandings of the world in order to gain a new perspective of the people around them. It’s a good way to live your life. Certainly more interesting. Truth is, I’ve never stepped foot inside of a mosque. I’ve never attended a polo match. I’ve never competed in an organized dance competition nor have I ever traveled to Southeast Asia. Yet each one of these experiences have their own unique subcultures, traditions, vernacular, symbols and social norms that make them remarkably distinct and special. It gives you a slightly better sense as to why people act the way they do. Why they believe what they believe. You get to see the underbelly of what matters to people. Keep notes. Take pictures. Absorb.

Teach others

Inside of you is a set of experiences, ideas and opinions unique to you. Cherish it. There are a ton of eager students, junior strategists or otherwise aspiring professionals who could gain a lot from learning from you. Pay it forward. Even if you have no altruistic bone in your body, consider this: teaching is hard, and chances are, it’ll actually make you better at what you do. Because one of two things will most likely happen. One, you’ll realize how much you still need to learn. Amazing, damn that ego. Two, you’ll quickly find that explaining basic concepts — like, say, how to write a creative brief or how to find insights or how to ask provocative questions—all help to solidify and simplify your own process and approach. It filters out superfluity. It refocuses you on the foundations. And, let’s not forget, it serves to help out others that could really benefit from face-time with a devilishly brilliant strategist like you.


There’s a great quote from, of all places, Winnie the Pooh: “Don’t underestimate the value of Doing Nothing, of just going along, listening to all the things you can’t hear, and not bothering.” It’s an important parting sentiment. Because sometimes it actually helps to stop being a strategist. To stop experiencing life through the lens of what can this teach me about brands or marketing or the current state of media? To stop defining yourself by your day job. To stop over-thinking, over-exerting, over-internalizing every passing idea that swims through your head during the course of the day. Close your laptop. Get out of the office. Spend time with people who don’t work in advertising and marketing. People who have never heard of Cannes Lions. People who don’t care which agencies you’ve worked at in the past. People who never utter words like “value proposition” or who sling around slang like “authentic brand connections” or who refer to their friends and families and other people they pass throughout the course of their day as “consumers”. Go have fun. Indulge. Enjoy something mindless. Take care of yourself. Temper the flames. Don’t be your job.

    Doug Kleeman

    Written by

    Strategy at Preacher

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