3 Lessons from 100+ Design Interviews

by Michael Anthony, Producer at Workday

“At Workday, design is about people. Connecting the people who build the software, the people who design it, and the people who use it.” — Tamara Hale

We start every interview with the same question: “Can you tell me what you had for breakfast?” This gives us time to adjust sound levels, change the framing, and dim the lights. Today, almost everyone responds with, “Just coffee.”

It’s the final day of Design Week, a 3-day conference for the Workday design community. And to be fair, last night was a late one. Visiting from a remote office in Victoria, BC to Workday headquarters in Pleasanton, California, my favorite part of the week was getting to know my new colleagues outside of work.

Understandably, everyone’s a little slower today. The lights we’ve set up in the hallway are too bright for this early in the morning. But we soon get to talking.

Best Laid Plans

All week, my team has been recording interviews with Workday Design during the breaks between presentations. The idea started simply enough. With over one hundred team members gathered together for the first time, we wanted to ask them a set of open-ended questions about design. Just a casual chat on camera. When would we get an opportunity like this again?

Over the next few months, I’d also fly to two more of our international offices, comb through weeks of footage, and eventually produce an interview mini-series exploring some of the biggest questions facing our designers: what design means to them, how to be successful, and what impact they want to have on the world.

I want to share three lessons I learned along the way about the importance of listening to your community. More than anything else, I want to encourage you to try this with your team at your company. I’m not saying film an interview miniseries. I’m not even saying write a blog post. But give your people an opportunity to speak their mind freely and you’ll be amazed at the things you’ll learn.

What is Design Week?

Let’s start from the beginning. What is Design Week? Design Week is an internal conference put on by and for members of Workday’s global design community. We brought together people who had worked together for years but only ever spoken through video conference calls. Now they were singing karaoke duets or playing cornhole together. “You’re much taller than I imagined!” I heard several people remark.

For speakers, it was an incredible opportunity to present your ideas to the entire design community — an incredibly enthusiastic and encouraging captive audience. Think of it like giving a great TED Talk at a really supportive family reunion. It made the interviews we recorded feel like home movies. We wanted to document the energy and excitement of the conference and still give the people who hadn’t presented an opportunity to share their ideas.

Six Questions and a Softball

The plan? Ask 100+ designers across Workday the hard questions.

We asked over 100 of our colleagues, from senior leadership to fresh interns, to answer the following questions in 1 word:

1. What does design mean to you?
2. What does design mean at Workday?
3. What is the culture of design?
4. What makes a designer successful?
5. What impact should design have on the world?
6. How was Design Week?

We wrote the questions as a way to get to know our colleagues — what makes them get out of bed in the morning and come to work? All told, we recorded over 50 hours of footage from people passionate about design, and broke each question down into its own video. Here’s what we learned from that process.

Lesson 1: Don’t Think Twice

Sometimes constraints promote creativity. Cynthia and Stella consider their one-word replies carefully.

One way we kick-started creativity was to pose an impossible constraint. Answer a broad question like “What is design?” with just one word. Of course, there was pushback. And cheating. But limiting people to one word helped in two ways.

First, it gave us short and sweet soundbites with which to organize and structure our videos. Later we could comb through the footage and place similar answers together. We color coded the responses until a human heat map appeared. Putting similar sets of soundbites together brought forward themes which we then linked together into a natural storyline.

Second, posing a one-word constraint forced our participants to focus. Trying to distill really big ideas into a single word sparked a lot of creativity in their answers. It led them to reflect deeply on what was truly important. We had five minutes with each person and six questions, so pairing things down to the essentials meant we could interview everyone who signed up. It also meant that each person thought hard about what the question meant to them. That dramatically improved the quality of answers we received.

Lesson 2: Let Go and Trust

“When you trust people, you get great things done.” — Beth Budwig

If you’re anything like me, the idea of asking difficult questions about people’s jobs fills you with anxiety. What if the answers aren’t usable?

Personally, I’ve seen too many corporate culture videos where the answers feel inauthentic and the participants feel coached. The fun feels staged. This was the last kind of video we wanted to make. Authenticity and spontaneity requires tremendous trust between interviewer and interviewee. At the time, I was also brand new to design. So how could I get people I was meeting for the first time to trust me and really speak their minds?

One of the first things the team did to promote trust was to let go of our expectations. We had no message in mind to convey through the video; we’d let the participants tell the story. No coaching, no staging. We left the answers open-ended, we let anyone sign up, and we listened, really hard, to what each and every person had to say.

We also made it our goal to interview everyone in the organization, regardless of tenure and title. Several participants, each new to the company or still working as interns, were surprised we wanted to hear their opinions just as much as the opinions of the more senior leadership. In many cases, those new employees gave the strongest answers. It surprised me how committed the whole team was to this idea of recording everyone. Even after Design Week was over, we flew to remote offices and recorded hours of footage with anyone we had originally missed.

So in short, we built trust by removing expectations, creating a safe space to share, and actively seeking input. In return, everyone we interviewed gave us honest, thoughtful answers. Of course, opening up the interview process like that carried risks — it meant giving up control over what was said. But one interviewee, Beth Budwig, said it best: when you trust people, you get great things done.

Lesson 3: Ask, Don’t Tell

“Design is a communication medium, it is a language that gives meaning to articulate ideas and concepts.” — Ben Taylor

Finally, the main lesson from this interview marathon was the importance of asking, not telling. In early brainstorm meetings, we came up with a lot of great ideas for what we might want to say in a Workday design video. But those ideas were nowhere near as interesting, honest, or insightful as the answers we received. Sometimes it’s worth asking a question, even when you think you know the answer.

There was also a lot of value for participants. We wanted to hear from everyone, and everyone had something they wanted to say. Even when we ran late into the evening and the rest of the teams had gone out to dinner, people stayed in the hallway, lining up for their opportunity to talk with us. They had thought long and hard about these questions and valued the chance to share their ideas with the rest of the company, and, as of today, the public.

Asking your colleagues, leaders, and peers about what they find important is a great way to get to know them. From my own experience I feel much more engaged when I feel heard and understood by my colleagues and my company. There’s a lot to be learned by talking to our people this way. We spend a great deal of effort recruiting top talent and surrounding ourselves with brilliant people, so we shouldn’t be surprised that they have inspiring answers. We just need to ask more.

Summary

“There’s a saying: a rising tide lifts all boats. That’s sort of what I feel like the design team community is here for.” — Angelina Di Francesco

So, if there’s one thing to takeaway from our experiment, it’s to try it yourself. If you haven’t already, ask yourself and your team: Why do they do what they do? What impact do you want to have? What is your culture really like? It doesn’t have to be a video series or a blog post, but start asking questions. And most importantly, start listening.

Watch the full video series here and let us know what you think!