How to Grow Your Culture Career with Design Thinking

Emily Heist Moss
June 3, 2019

“I want to work in culture.” Vanessa Shaw hears this statement every day. She is the founder of Human Side of Tech, and is a learning designer and facilitator who has worked in the culture space for more than a decade. People she meets, especially those who work as office managers and administrators, always want to know how they can shift their careers to focus on building culture.

Designing culture can range from Human Resources and benefits, to event management, to community outreach, to employee engagement. For companies today, culture is either an asset or risk to achieve business success. Organizations are in need of culture-focused professionals who help contribute to building and facilitating an effective culture that helps employees and companies meet their goals.

One key skill Vanessa uses to think strategically about culture is Design Thinking. It is a pragmatic approach that can help you identify and solve a real problem, as well as develop your executive skills. Applying the Design Thinking process to a cultural issue at work can help you demonstrate the value you add to your organization on a small scale and potentially pave the way for a new role and greater influence.

Where to start in Design Thinking

The key to building your culture leadership, says Vanessa, is to get experience problem solving without biting off more than you can chew. Begin with something that affects you personally. “You’re an employee, right?” says Vanessa, “You have an experience. Are there things you love at work? Or things that aren’t working for you? Where can you innovate?”

Once you have brainstormed a few potential projects, Vanessa suggests considering an Impact/Difficulty chart to find a good starting point. Imagine a 2x2 grid, with Low Impact and High Impact on the left, and Low Effort to High Effort along the bottom. Put potential projects in their appropriate quadrants and then choose one from the low Impact/Low Effort quadrant. You’ve got to start somewhere!

For example, maybe the way your office celebrates work anniversaries has gotten stale. Literally, there’s always a cake, and it’s always stale, and no one has any fun. How could you reinvigorate this milestone in a fresh, exciting way that benefits your colleagues and your company? How could you use this small improvement to showcase your skills and find bigger ways to get involved?

What exactly is Design Thinking?

Before we get to stale cake and how to fix it, let’s delve into the Design Thinking process as it applies to life at work. There is no shortage of Design Thinking 101 pieces, and Vanessa has authored a few herself.

In short, Design Thinking helps us understand what currently is, then walks us through a series of structured exercises to get to what could be. Design thinking can be applied to a product, like a chair. How might we make this wooden chair that kids hate, better? More ergonomic? More suited for using laptops than pencils? Design thinking can also be applied to an experience, like walking through a museum. How might we make this experience more clear? More educational? More interactive?

With Design Thinking, you cultivate empathy for the customer (or employee) to understand the experience in its current state.

Next, you work to define the problem. It’s not enough to say “how might we redesign the employee anniversary celebration?” You need to understand your goals, but also ensure that you are leaving the question open enough to really understand the problem and find a solution. Instead, the question might be, “How might we recognize employee anniversaries so that they feel like an important member of the company?"

When getting started, seek to understand before setting out to solve. Then, define a problem statement with How Might We formula, before you start coming up with ideas for solutions.“This is the step people skip,” explains Vanessa. “They go right into an idea they have without defining the problem they’re solving.”

As a gut check, Vanessa suggests imagining your project as a bullet point on your CEO’s talk about company values. Can you imagine them saying “At our organization, one of our values is X, from the way we do business at the top, all the way down to how we celebrate workplace anniversaries.” Your solution should align with your company’s shared values.


How do you apply Design Thinking to your challenge?

“Design Thinking is all about convergence and divergence,” explains Vanessa. You start with convergence by honing in on a specific challenge (like celebrating workplace anniversaries). Then, you let your ideas diverge by brainstorming many possible solutions.

Use an idea-generating activity like whiteboarding, writing ideas on post-it notes, or doing a “popcorn” round of ideas with your group. Vanessa even suggests something as fun and colorful as making a Pinterest inspiration board. “Stay away from PowerPoint at this stage,” she emphasizes, “It’s about volume and variety of ideas, not perfection or layout or detail.”

“When you have a big pile of ideas in front of you, converge again by picking a few to test.” Prototyping is the next stage in the Design Thinking process. For those new to this kind of strategic process, Vanessa explains that “perfect is your enemy.” It’s like pancakes, she says, “The first pancake is terrible. That’s okay. Finish the prototype and test it. It’s important to see it through.”

When you have an idea that you think answers the “How might we” question, try it on! For the next few months, test your new anniversary-celebration plan, and gauge the results. Think like an anthropologist. Observe people’s responses, ask questions, document the results. 

How do you take it to the next step?

Although you’ll start with a small issue that you’ve personally noticed, eventually you’ll apply this same process to bigger problems with greater organizational impact. First, work on a project that you care about. Next, think about an issue that affects your whole team. Then, consider a challenge facing your manager. Finally, what are the concerns of your executive leadership team?

What do executives tend to worry about? Big picture issues like risk, profitability, turnover, productivity, brand reputation. At scale, these issues seem huge and tough to tackle, but if you bite off a piece you can work on and improve, you can contribute in a meaningful way. Over time, you’ll bite off bigger and bigger projects.

The goal of this exercise is start practicing executive level skills now, at your level, in a way that scales as your career progresses. Proving your ability to think critically and systematically on a small project gives you leverage to ask for more responsibility down the line. “Showing your manager how you can think, even if the details turn out to be wrong, showcases of your work and will get you recognition for leadership ability and growth.”

Vanessa says, “The bottom line is that instead of saying ‘I don't like this thing!’ about your work, you start thinking and acting like a strategic leader.”

Become the expert on your company

Vanessa frequently hears entry level employees griping that they aren’t in the meetings, or that they don’t have enough information to know how to contribute on a cultural level. Do research!

She says. There’s lots of information publicly available. “Consider yourself an explorer,” she advises. “Read up on your company in the news and set up google alerts to stay current, check your Glassdoor reviews, Google common issues facing your industry, read the earnings reports and employee engagement survey results.” There are clues if you go looking!

“Every workplace challenge is a design opportunity just waiting for a designer,” Vanessa concludes. “There are not enough people who look at workplace challenges that way. People are apathetic or complaining or too nervous to take action. Those that try will always have an advantage.”

Human Side of Tech Workshops, photography by Scott Roeder.

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