From Awkward to Awesome: The Secret Sauce of Memorable Interviews with Design Leaders

I’ve discovered that the magic of discovering guests and giving them a platform isn't found in perfect research or meticulously crafted questions. Rather, it lives in those authentic human exchanges where vulnerability meets curiosity. The most memorable conversations emerge not when I’m perfectly executing an interview strategy, but when I’m truly present, listening deeply, and allowing the unexpected to unfold naturally between two people.

Beyond the Resume: Finding the Right Voices

When scouting potential guests, I look beyond impressive titles and portfolios. My process involves:

1. Identifying Authentic Thought Leaders

I seek directors and designers who aren’t just accomplished but have developed a unique perspective. Their LinkedIn profiles might showcase impressive work, but I’m looking for evidence they’ve reflected deeply on their practice and industry. When preparing for our Adobe Creative Connections session with Mattel’s Senior Industrial Designer Adam Miller, I discovered his fascinating work with the Hot Wheels Advanced Play Team, revealing someone who could speak authentically about both the creative and technical aspects of designing products that delight children (and let’s face it, plenty of adults who still make “vroom vroom” noises when no one’s watching).

2. Assessing Communication Style

Before inviting someone to a show, I look for previous speaking engagements, articles, or social media presence that demonstrates their ability to articulate ideas clearly. This isn’t about polished perfection—sometimes the most insightful guests are those who speak candidly rather than in rehearsed soundbites. Someone who can make complex design principles understandable without putting you to sleep is worth their weight in Pantone swatches.

3. Seeking Diverse Experiences

The most compelling conversations often come from guests with unconventional paths. When preparing for our “The Creative Recipe for Buzzworthy Marketing” Creative Connections session with Sprinkles CMO Michelle Wong, I was intrigued by her unique journey from agency account management roles to becoming a Chief Marketing Officer. Her education at Le Cordon Bleu and agency experience applying creative strategies across different food brands—from cupcakes to health-focused restaurants—offered the audience valuable insights about adapting marketing approaches while maintaining authentic brand storytelling across diverse consumer experiences. Plus, anyone who can make me hungry while talking about branding with color deserves a platform.

Laying Groundwork: The Invisible Foundation

The research phase is critical but should remain largely invisible to your audience—like the number of hours I spend stalking potential guests online (in a professional way, I promise):

1. Do your homework, then forget it

After a quick meet and greet with my guest to understand what projects they’d like to focus on, I study them—their work history, published articles, previous interviews, and social media presence. For the Creative Connections show with Brian Ossip from Whole Foods Market, I analyzed their social content strategy across platforms before our “Delicious Ideas for Eye-Catching Social Content” event. This preparation allowed me to ask informed questions while remaining flexible enough to follow unexpected conversational threads. And yes, I did spend an embarrassing amount of time scrolling through their bakery posts (and their Berry Chantilly cake) at midnight. For research purposes only, of course.

But instead of showing off my research, when I asked Brian about his favorite projects during the livestream, it led to his hilarious story about carving pizza boxes for their Halloween content. That authentic moment revealed more about creative problem-solving than any prepared question could have.

2. Find the Human Story

Look beyond professional accomplishments to find the personal narrative. When preparing for my podcast conversation with Los Angeles-based community-builder Paul Mendoza, I discovered his passion for community building stretched back to his early days at UCLA while working as a TV script coordinator. This allowed me to frame questions around his journey rather than just his achievements. The best interviews happen when you can make someone forget they’re being interviewed and instead feel like they’re just having coffee (or something stronger—this is design, after all) with a friend who’s weirdly well-informed about their career trajectory.

3. Preparing Without Over-Scripting

I follow question frameworks rather than rigid scripts. For each interview, I identify 3-5 core areas to explore, but remain open to abandoning them if more interesting directions emerge. This balance of preparation and spontaneity creates authentic moments that resonate with audiences. It’s like having a GPS but being willing to take that intriguing detour when you spot a well-designed stationery shop.

During the Conversation: Creating Safe Spaces for Authenticity

The actual interview is where preparation meets presence:

1. Start With Connection, Not Performance

I begin conversations by establishing rapport rather than diving straight into “important” questions. When interviewing Designer Amanda Hovest about her AIGA leadership journey for our podcast, I didn’t just ask about her professional accomplishments—we reminisced about meeting for the first time at the airport before getting on a plane to Denver. Those human stories reveal more about leadership style than any formal question could.

I focus on creating a comfortable space where guests can share their genuine experiences rather than delivering rehearsed answers. Plus, nothing breaks the ice like shared memories of design conference after-parties that may or may not have involved human pyramids.

2. Practice Active Listening

This seems obvious, but it’s surprisingly hard. I’ve learned to embrace silence and give guests space to think. Some of the most profound insights come after that awkward pause when most hosts would jump in.

During our “Ultimate Generative AI Prompt Guide” session, I noticed our demo artist Zach Perkins, hesitated when asked about ethical considerations. Instead of filling the silence, I waited—and then he shared a thoughtful perspective on responsible AI use that became one of the most valuable takeaways for our audience.

The most valuable skill isn’t asking questions but truly listening to responses. This means:

• Maintaining genuine curiosity about the guest’s perspective

• Following up on unexpected insights rather than rigidly sticking to prepared questions

• Embracing silence to give guests space for reflection

• Using non-verbal cues to show engagement (especially important in video interviews, where my “fascinated nodding” game is now Olympic-level)

3. Find the Balance Between Structure and Flow

While I have a mental roadmap for each conversation, I’m willing to take detours when they promise interesting destinations. In our Cheers & Tiers episode with Christine Sheller, we planned to discuss her AIGA Philadelphia leadership journey, but when her French bulldog’s snoring interrupted the interview, it sparked an unexpected tangent about community building across chapters. These unplanned moments often reveal the most authentic insights about how design communities shape our careers and lives

4. Discover the Story Behind the Story

In our “Igniting Emotional Sparks with Inspiring Stories” Adobe Creative Connections session, we explored how Pinterest’s creative team developed fantastical worlds for their campaign. Rather than focusing solely on the final product, I asked Xanthe Wells, Global VP of Creative at Pinterest, about the challenges her team faced with “limitless creative possibilities.” This revealed the messy middle of their process—the part most creatives are hungry to hear about.

Similarly, when interviewing Josh Silverman for our Cheers & Tiers podcast, I pushed past the polished AIGA success stories to uncover how he navigated disagreements about chapter direction in Rhode Island. Rather than just celebrating membership growth, I asked how he faced resistance beyond Boston to other regional cities—with some board members concerned about “stealing” members from neighboring chapters. This creative friction ultimately led to a more expansive vision that helped launch five additional AIGA chapters across New England. By highlighting this specific tension and its resolution, it illuminated a common challenge many design leaders face: the fear that expanding access might dilute their influence or resources.

5. The Technical Stuff Matters (But Not As Much As You Think)

Yes, good lighting helps. Clear audio is essential. But I’ve conducted interviews with guests while in their hotel rooms, in noisy school lobbies, and one time in their home loft when they interrupted the interview to run downstairs, in real time, to get a laptop charger.

The audience forgives technical hiccups if the conversation is genuine. They won’t forgive a boring, inauthentic exchange happening in a perfect studio.

Beyond the Interview: Building Community Through Conversation

The most successful interviews extend beyond the scheduled time slot.

1. Create Continuity Between Conversations

I often reference insights from previous guests, creating a dialogue that spans multiple interviews. When speaking to Brenda Mills about the 2025 Creative Trends, she remarked about the fantasy concepts that Pinterest was doing. My team quickly pulled up Pinterest spots to illustrate the point, as I had just interviewed Pinterest’s Global VP of Creative, Xanthe Wells, the week prior. This approach builds a sense of ongoing community conversation rather than isolated Q&A sessions. It’s like hosting a dinner party where everyone gets to meet everyone else, just spread out over months instead of appetizers.

2. Facilitate Connections Beyond the Interview

Some of my proudest moments come when guests form a connection with each other or with audience members after our conversations. After our “Plug into Innovative Consumer Tech with 3D Design” event, several participants formed an ongoing collaboration group that continues to share resources and opportunities. I like to think of myself as a design community matchmaker—without the awkward first dates.

3. Follow Up Meaningfully

I maintain relationships with guests beyond the interview, sharing how their insights have impacted the community and sometimes inviting them to participate in future conversations from a different angle. Michelle Wong from Sprinkles and I are LinkedIn besties, and I support her shared successes. After all, the design world is surprisingly small, and today’s interview guest might be tomorrow’s collaborator (or the person who remembers you fondly when you’re seeking freelance work at a cupcake bakery).

Practical Takeaways for Your Design Interviews

Whether you’re interviewing for a podcast, conducting user research, or speaking with potential team members, these principles can elevate your conversations:

1. Research deeply but hold it lightly. Do your homework, but don’t let it prevent you from being present and responsive. Nobody wants to feel like they’re talking to a human Wikipedia page.

2. Focus on creating safety before seeking insights. People share their most valuable thoughts when they feel comfortable and respected. Coffee helps. Snacks help more.

3. Ask questions that invite stories, not just information. “Tell me about a time when...” often yields richer responses than “What do you think about...” Plus, everyone secretly wants to be the hero of their own design adventure story.

4. Listen for the unexpected. The most valuable insights often come from tangents and asides rather than direct answers to your questions. Sometimes the best content happens when someone says, “Oh, that reminds me of this one time...”

5. Balance structure with spontaneity. Have a framework but be willing to abandon it when more interesting paths emerge. Think of your question list as a suggestion, not a contract.

6. Remember that technical perfection matters less than authentic connection. Your audience will forgive technical hiccups if the conversation feels genuine and valuable. They’ll never forgive a boring interview, no matter how perfect the lighting.

7. Create continuity beyond the interview. The most impactful conversations continue to resonate and create connections long after the recording stops. Like that one AIGA Leadership Retreat in Omaha that people are still talking about years later.

The true art of interviewing design leaders isn’t about extracting information—it’s about creating spaces where authentic insights can emerge naturally through human connection. When done well, these conversations don’t just inform; they inspire, build community, and advance our collective understanding of design’s potential to shape our world. And occasionally, they result in memorable stories about French bulldogs snoring during recordings that make everyone laugh.

What's your approach to having meaningful conversations in your design practice? Share in the comments below, or better yet, let’s continue this conversation in person at an upcoming AIGA event!