November 22, 2013

Advancing the discipline of Creative Strategy: Jennifer Maples, Creator of Strategy TNT

Photograph by Sarah Deragon of Portraits To The People.

I discovered Jennifer Maples via a tweet that I noticed about a meet-up called Strategy TNT. Jennifer is a Creative Strategist. Here, she talks about this emerging role, the monthly speaker series she founded to focus on topics related to creative strategy, and more.

On being a creative strategist

How did you arrive at what you do as a creative strategist?
Was there an initial encounter of “strategy” that played a role in your path toward becoming a creative strategist?


I was educated in visual anthropology and studio art, and worked in my college art gallery. I thought I wanted to be a curator, but after a short term in the real-world art scene, I realized I wanted to create experiences for people beyond white walls. So, I started talking to people I admired. First to young alumni from my school, and then to creative professionals who were producing the kind of work I found most interesting.

Strategy and human-centered design came up pretty quickly, but creative strategy—and the path to get there—wasn’t so clear.

Collaborating on the finishing touches on a project.
Photograph courtesy of Adaptive Path

What were essential activities/steps you took to start and establish yourself as a creative strategist? And why were these activities/steps important?

Building my community and owning my worth. When starting something new, it’s easy to fall into self-doubts and a case of imposter syndrome. Finding people to say yes and encourage you is step number one. Rena Tom of Makeshift Society was the first person to say “Yes” to me when I pitched my first major project Strategy TNT, a speaking series I created on all things strategy. Makeshift Society and Strategy TNT were integral in building my community and confidence that I had unique, valuable perspective to offer the creative strategy space. From the first night, Strategy TNT has consistently sold out, and soon people I admired started reaching out to me to collaborate.

Once I had built my confidence, I started defining myself in the community by my choices of projects. People care about your point of view, but you’re also made up of the projects in your portfolio.

Presenting a concept for an app to promote public safety 
at Adaptive Path’s GovJamPhotograph courtesy of Adaptive Path

Creating a prototype to demonstrate the app experience. 
Photograph courtesy of Adaptive Path

Getting semantic here: You call yourself a creative strategist? What is this job title’s comparison to design strategist, innovation strategist, or just plain strategist?

I have thought a lot about these semantics, and truth be told, depending on the client, I’ll change my title again on the portfolio I present.

My profile doesn’t quite fit into the traditional molds, so “creative” strategist captures what I do most readily. My offering is somewhere between human research and experience designer. By observing people and researching context, I help organizations understand people and design delightful experience. Those other names sometimes create confusion about my background. “Design strategists” typically have a more specialized visual or product design background, “strategists” usually have a financial background or MBA, and “brand strategists” often went through an advertising accreditation program. My profile doesn’t meet those criteria, so I had to come up with another fitting title. Creative strategist seemed appropriate—and it has helped clients understand my atypical background more quickly.

“Innovation strategist” feels more comfortable than those other monikers, but it isn’t always accurate. Innovation seems to imply that my work yields something new and shiny. But, some of the best work has been simplifying products or repositioning a challenge. For instance, when doing user research for’s HCD Connect platform, I suggested that we cut products functionalities that were confusing the user experience. Is that innovating? I’m not sure it really is. But it is a user-facing strategy.

My offering »

To me, the word and concept of strategy is intimidating, because it’s loaded and, at the same time, mysterious. What is strategy?

That’s hilarious—because talk to most people outside of the design bubble and “design” or “creativity” hold this same sense of mystery and intimidation. To me, strategy is problem-solving effectively. Someone doesn’t hire me to maintain the status quo; they hire me to solve a problem, often in creative, inventive ways.

The best designers are strategists at heart—their visual or experiential problem-solvers. With the release of David and Tom Kelley’s book Creative Confidence, there’s increasing excitement about people embracing their creativity. But what about designers embracing their role as strategists? As the people who imagine and create people-centered outcomes? I wish more designers aspired to run the boardroom.

What is strategy’s purpose or obligation
in our society, the world?

Well, in my world, strategy is at its best when it’s human-centered. So with that lens, strategy has an obligation to the people it serves. I think that the most interesting trend right now in strategy is the movement for resilient systems.

Who are your strategy-related influences?

I could talk about my admiration for J.Crew’s Jenna Lyons and Micky Drexler for far too long. Their reinvention of that brand’s perception and financial make-up has been brilliant. I think that Airbnb’s Brian Chesky and Joe Gebbia have demonstrated that designers can (and should) lead businesses. And if I could be anyone for a day, it would probably be Debbie Millman. I’m really inspired by the diversity and intelligence of her work.

Presenting our prototype for feedback. 
Photograph courtesy of Adaptive Path

How important is it for you to follow your instincts?

Pretty important, but I think the greater issue for me is feeling confident voicing those instincts. Instincts are often emotional, visceral and aren’t rooted in discernible facts. Following your instincts won’t fly in many traditional workplaces. I think that’s why I work best in design or human-centered environments. Emotions and intuition are more highly valued in those communities. There seems to be an agreement that experience—regardless of logic—is the reality.

I appreciate your work experiences in design and research. I took classes at the Institute of Design, Illinois Institute of Technology, and co-wrote the Wikipedia entry about Design Methods. So I’m aware of the human/user-centered attitude and approach. What does “human/user-centered” thinking and doing, particularly the toolkit of design methods, mean to you? Do you prefer human or user-centered in terms of language? Please elaborate.

I noticed that—I admire IIT and the work I’ve seen from their alumni. There’s such great human-centered thinking coming out of there. For anyone interested in digging deeper into these topics, be sure to check the IIT Institute of Design out!

As for Design Methods, I’ve found myself more concerned with the values of the practice than the specific methodologies themselves. It seems like, at least in the Bay Area, everyone knows how to position themselves as a design thinker and to describe themselves as “empathetic.”

To me, being human-centered means valuing what it means to be human—emotions, idiosyncratic behavior—on the same plane (or sometimes greater than) logic. That’s where you can often locate the difference between a human-centered practitioner and people playing the part. Our current mainstream society primarily values logical, quantitative thinking and sees human behavior as secondary, or even as something we need to “logic our way out of” at times. I don’t believe that. I think when you design for people, logic stops mattering so much. Logic is a system we created for understanding information and can be manipulated. Being human is unshakeable. That said, we need more quantitatively competent human-centered designers since we often need to communicate ideas to colleagues in logical, data-based formats.

I prefer “human-centered” because the term is more universal. In the day to day though, I’m guilty of using “human-centered” and “user-centered” interchangeably. Again, I’m more interested in the values of the people who are using those words.

Napkin sketch concepting for a collaboration with Form & Future.
Photograph by Laura Helen Winn

Introducing Emily Eisenhart’s talk on activating idol spaces.
Photograph by Bryon Roche

Strategy TNT’s crowd gets settled in Makeshift Society’s clubhouse.
Photograph by Bryon Roche

You invented a monthly meet-up called Strategy TNT about all-topics related to strategy. I must applaud you for this, and delighted to know that you were inspired by CreativeMornings. I’m a CreativeMornings enthusiast, attending and writing about the gatherings in Chicago. How do you make this happen? Is it exclusively you? If you have a team, how do you persuade them to get involved? How do you envision this event moving forward?

I’m a big fan of CreativeMornings, and the international community the series has spawned. Though, CreativeMornings’ audience is primarily centered in the design community, which can feel insular to me at times. I wanted to create a space with a lot of the same values as CreativeMornings, but that casts a wider net for cross-industry conversation. As I mentioned earlier, “strategy” tends to be a more approachable word for people outside traditional creative industries, so, I purposefully positioned the series under the strategy umbrella.

The idea had been marinating in my brain for a while, but things really took shape when I pitched Strategy TNT to Rena Tom of Makeshift Society and she said, “Yes.” We put a date on the calendar for just a month after I pitched. There’s nothing like a deadline to make you figure things out quickly.

My aim is for the audience to represent as many different fields as we can get. I’m interested in Strategy TNT illuminating those moments when empathy enlightens strategic direction. I want talks to focus on the “aha!” moment when a designer/writer/educator/doctor/social worker figures out what resonates with their audience and uses that knowledge to inform a change in strategic direction. My hope is that we can shift attendees approach to strategic and creative problem solving.

Basically, it’s been me, with the generous support of Makeshift Society, and friends along the way, particularly Payal Patel who is supporting Strategy TNT’s growth of community and content. In terms of keeping folks motivated, compelling content and exposure to stellar professionals does the trick. I’m lucky to be in a place where people are approaching me about getting involved—and that said, if you’re reading this and want to be involved, please get in touch! Email me.

My vision is to solidify Strategy TNT’s platform and purpose, and then grow the model to more cities. Creative strategy is a newer and ever-evolving field, so there’s still some room to define it. My hope is that Strategy TNT’s community can contribute to that conversation.

Strategy TNT’s presentations are followed by intimate conversations 
between audience and presenters. Photograph by Bryon Roche

Caitlin Freeman of Modern Art Desserts signs books for attendees 
after her Strategy TNT presentation. Photograph by Bryon Roche

You are currently working independently. What are the advantages of this kind of work lifestyle? And what are some must-don’ts to be an independent worker?

The level of flexibility as an independent is a tremendous advantage. Though, managing that flexibility is a learned skill that I’m still in the process of learning. America’s system doesn’t offer a safety net for an independent lifestyle, so make sure you have a your own safety net—like regular clients and savings—before you take the leap to independence.

I also appreciate your broad skill set. Have you experienced push-back, even indifference, on your professional broadness, for example, people not feeling what your “strengths” are? What are ways to constructively argue with this perception?

Yeah, I sure have. My work spans design, brand, communication, customer experience and probably a few more broad buckets, so defining my expertise can be tricky. At a traditional design agency, I don’t have enough product or visual work in my portfolio. At a big ad agency, I’m too design-centered and don’t have enough big brand campaigns under my belt. So, I’ve shifted my focus to:
  1. Startups that need generalists who can offer multiple skill sets
  2. Bigger companies that have research and development departments and understand the value of cross-disciplinary people
It’s hard for people to understand my design-speak definitions, so I often lean on more familiar language—like “market research”—and concrete examples to help people understand my work. Once they understand what I do, I can explain how my philosophical approach differs from traditional “market research.” With the emergence of cross-disciplinary, generalist degree programs—California College of the Art’s Design MBA program for example—the now superfluous use of design thinking, I’m optimistic we’ll be seeing more organizations valuing generalists in the near future.

How do you get the word out about what you do?

Strategy TNT has provided a great platform to share my work and an excuse to introduce myself to some amazing professionals in the Bay Area. Creating a presence online and going to in person professional events has grown my network tremendously.

How do you attract work and clients?

Leaning on my network. And saying yes to stretch projects—they grow your offering. Most importantly, have a strong, authentic online presence.

“Stretch projects” are those projects that are outside of my comfort zone, or something that I’ve never been hired to do before. As a consultant, you sometimes find yourself in the position of having to convince someone of your capacity to “stretch” to do something—that can be scary, but that’s when you learn new things.

What is your definition of growth, as it relates to business?

The ability to stay curious. I mostly think about growing my ability to take risks, try new things and bounce back.

How would describe your business’ work culture?
And why is it important?

Flexible, but with high standards. When working with clients, I need to understand what’s important—and what’s not—quickly and target my energy accordingly. It also helps to have a sense of humor.

On creativity, design, working

Design writer Alissa Walker wrote an article called “Women in Industrial Design: Where My Ladies At?” Where are the Ladies in Design/Development/Strategy at?

You know they are around. And they’re networked. In the community and thought leadership space I see lots of women leading the conversation—Debbie Millman, Tina Roth Eisenberg, and my friend, Rena Tom, to name a few. More women tend to come out to Strategy TNT—though, I will say men in the audience speak up more often. My concern is not so much that we’re a talented 10th (which seems to be the case by the numbers in Alissa’s industry), but that the way women in design and strategy organize can be seen seen as feminine community-making, like a some-sort of quilting bee (says, this girl who sews, crafts and quilts).

Female community is important, and so is being taken seriously as professionals. Given the reality of the current landscape, I think there’s extraordinary power in mixed gender leadership teams. I’m leading content for Hike Conference, which is co-led by a male-female leadership team Jason Schwartz of Bright Bright Great/The Secret Handshake and Laura Helen Winn of Smart Design/Form & Future. Before this project, Laura and I have hosted professional events in San Francisco, often with female speakers and a primarily female audience. It’s awesome to connect rock-star women, but it can also be insular. I’m excited to see how Hike goes from a gender perspective. With a mixed-gender team in the lead, I have a feeling it’s just going be awesome professionals being awesome, regardless of gender.

How do you handle disagreements while you’re working?

Know who has the power in decision-making and be smart about your battles. If I have an inherently different opinion than the decision maker, chances are I’m not going to change their mind, so it’s best if I constructively adapt my work. On the other hand, if I know I have the ear of the decision maker, I’ll voice my dissenting opinion directly.

When I interview clients, gauging their value structure, particularly of the decision makers, is part of my checklist before signing. If we’re on the same page about values and objectives, it’s smooth sailing.

What part of your work is particularly trying,
and how do you deal with it?

Being patient and enjoying the process. I’ve quickly learned you never “arrive” so if I think my process is “a grind” I’m bound to burn out soon.

Every time I enter my home, I’m greeted by my favorite linoleum print 
I created in college. Photograph by Jennifer Maples

What is your workspace like? How does it contribute
to doing the quality of work you want to do?


I tend to cover my home-office desk with paper, but when I can see the bottom of it, it’s an antique wood desk I picked up at the Alameda Flea market. I live in a studio apartment in San Francisco, so my main room functions as a live-work space. The room is filled with old objects, many from my family—model wood birds I carved with my grandfather, a Diego Rivera lithograph print inherited from my great grandmother, needle point artwork from my grandmother, family photographs dating from 1960’s back to the early 1900s—and found objects I’ve picked up over the years. While I do most of my work on the computer, I also have watercolors and HB pencils closeby. I guess some people might call it a creative workspace, but I think I’ve assembled it more to feel like it has a sense of history. I’m not as interested in creating new things as much as I am in interested in contributing to the history of people—particularly to the history started by the people I admire.

I’m also a member of Makeshift Society and will work out of their clubhouse several times a month. I love the clubhouse because it’s the only coworking space I’ve found that brings a similar energy of history and home.

I often spend afternoon working in a comfy chair beneath a Diego Rivera lithograph called Sueño inherited from my great grandmother, an antique map of the “East Indies” from my grandfather and an old window pane I picked up at a salvage yard. Photograph by Jennifer Maples

What tools do you use and recommend to work on ideas
and make them grow, to collaborate and get things done?

Social media has been a better tool to collaborate and meet like-minds than I ever would have liked to admit. I actually wrote a Medium post about it.

Meeting online is a starting point, but meeting in person is where the collaboration really begins.

Watercolor patterns and sketches produced while in the California Sierras. Photograph by Jennifer Maples

How do you stay creative? What are some of your sources
of motivation/inspiration?

Oh, I’m afraid that I have the usual answers here: reading; drawing; writing; cooking; painting; tinkering; pursuing my passion projects.

One thing I’ve been told is a bit different is the way I think about creative inspiration, which is in line with the creative confidence movement that’s gaining momentum. I was trained as someone who critically digests creative information, and am constantly growing my confidence to be a creative practitioner. This often surprises most people. I don’t consider myself naturally imbued with creativity, but rather, I feel that I have to practice at it constantly.

The two skills that I focus on honing are my storytelling and visual design skills. I often ask myself how much I’ve been “digesting” creative information and how often I’ve been “exercising” my creative skills. As a storyteller, I’ll “digest” information by listening to podcasts, read short stories (especially Alice Munro), and long-form journalism, like The New Yorker. Then, I’ll balance that by composing hand-written letters and drafting expository writing on design trends. Similarly, I’ll collect pieces of visual inspiration, and then encourage myself to do my own sketches. I’ve recently tried to combine these two creative activities by watercoloring hand-written post cards.

It also helps to create a safe space around exercising creativity. I like to think of it more like creative play. Creating got a lot easier when I found an encouraging creative community, and I always feel better when I get outside—not because I’m romantically “inspired” by nature, so much as I feel safe trying something new in isolation. No one’s around to judge.

What is your definition of bad design?

Bad design doesn’t serve people or a purpose. By design, it is not understandable or doesn’t resonate with the viewer on the right note. I have a lot of aesthetic opinions, but I’m willing to lenient on visual design if something is supremely functional.

If you were asked, “Jennifer, I know you do strategy work, and I want to do what you do, how do I start?” What’s your response?

If you’re intrigued by strategy, you’re someone who likes to solve problems. And you’re probably already doing it wherever you’re at. So what problems do you want to solve next? Read up on that field and start talking about what you’re already doing in that industry’s language. Meet as many people in the field as you can. Creative strategy is an undefined, emerging industry, so you have to make opportunities to make it.

Any other aspects of your work that would be interesting to creative practitioners and aspiring product/business makers?

I’m leading up the content development for a new conference in San Francisco this April called Hike, that I mentioned earlier. Hike is a one-day conference for graduating design students and new designers of all stripes. Our goal is to guide attendees in finding the design career that’s right for them. We’re inviting speakers who are passionate about sharing advice through talks, and teaching beginners through workshops. If you’re a rookie creative or someone who’s looking to move careers, you’ll want to attend or at least follow along.

I’m also in the process of developing a workshop on creative confidence with my friend Peter Rubin that I’m pretty excited about. That workshop will be focused on helping creative and non-creative folk alike find their path.

Neither of those projects have homes on the Internet quite yet, so for now, following me on Twitter—@stratejen—is the best place to find out upcoming details.

How does the city of San Francisco contribute to your work? And what makes it special for startups/business/creativity-at-large?

I’m sure San Francisco contributes much more to my work than I imagine. I often think to myself, “How lucky am I to live right here, right now?“ Sometimes when I’m walking around the old alleyways of my Hayes Valley neighborhood, with cranes constructing new dot-com funded high-rises just a few blocks away, I have to pinch myself.

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All images courtesy of Jennifer Maples.

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Typeface of quotations is Akzidenz Grotesk
designed by Günter Gerhard Lange.

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