Generative Research and Design Leadership with Josh Klenert | Episode #86

Josh Klenert has watched digital design mature from editorial products and early mobile apps to enterprise software and crypto experiences. His work included launching iHeartRadio when smartphone interaction patterns were still unfamiliar, overseeing design at the Huffington Post, building consumer and design-system experiences at JPMorgan Chase, and leading design at Bakkt. Across those settings, one principle remained consistent: teams need to understand the circumstances around a user's behavior before deciding what to build.

In this conversation with Dwayne Samuels, Klenert explains why usability testing is only one part of research, how qualitative insight complements analytics, and why communication becomes a core design skill as practitioners move into leadership.

What you'll learn

• Why generative research should happen before teams narrow their attention to usability

• How user context can expose product constraints that analytics alone will not explain

• Why regulations and accessibility requirements require interpretation, not mechanical compliance

• How listening, reflection, and deliberate communication help design leaders reduce silos

Start with generative research

Klenert distinguishes learning about people's lives from testing whether they can operate an interface. Usability research can reveal friction in a proposed experience, but it may arrive too late if the team has already made the wrong assumptions about the problem. He recommends making time early for generative research that explores what people want to accomplish, how they think about the subject, and where the product fits into a broader journey.

The early iHeartRadio work illustrates the value of context. The team spent time with listeners at home, at work, and during commutes. That research revealed connectivity problems when subway riders went underground, which led the product team to consider additional buffering. The solution also had to account for different business rules around streaming and terrestrial radio. The useful insight was not simply that playback failed. It connected the failure to a location, a routine, a technical condition, and a commercial constraint.

At Bakkt, the team studied people who were curious about crypto rather than designing only for people already comfortable with it. Conversations in participants' living rooms and kitchens helped the team understand how newcomers thought about digital currency and what they wanted to do beyond buying and holding it. For product teams, the practical lesson is to recruit for the audience whose understanding the experience must support, not only the easiest experts to reach.

Interpret data instead of surrendering to it

Klenert values quantitative evidence, including surveys at the end of a flow, but warns that a business can ask questions shaped mainly by what it already knows how to fix. A rating can indicate whether a flow worked, yet it cannot fully explain the needs, prior experiences, or expectations that produced the response. Teams can also select questions that steer results toward a preferred answer.

His recommended balance is to use analytics as input while preserving human interpretation. Generative conversations broaden the field of inquiry; usability tests evaluate a specific experience; quantitative measures show patterns at scale. None replaces the others. A team deciding what to investigate can first ask what the numbers show, then identify what remains unexplained, and finally speak with users whose situations represent those gaps.

This approach also protects teams from designing around executive anecdotes. Klenert describes the risk of decisions driven by highly paid personal opinions, where one leader's family experience becomes an informal requirement. Real customer stories give teams a stronger basis for challenging that pressure and can support more substantial product changes than narrowly framed analytics.

Lead through constraints and communication

Regulated products make interpretation especially important. Klenert recalls debating what it meant for required information to be one click away on a tablet, where people tap, swipe, and scroll instead of clicking. Designers need to understand the protective intent behind a rule, then translate it into a modern interaction without treating compliance and usability as separate concerns.

He applies the same standard to accessibility. Motion, haptics, and visual treatments may make an experience appealing for some people while excluding users with low vision, movement sensitivities, or difficulty perceiving color contrast. Product and development cycles create real constraints, but Klenert asks teams to judge design quality by who can actually use the result. Accessibility requirements can help keep inclusion present when schedules make it tempting to postpone.

For leaders, the final constraint is often their own communication. Klenert began as a heads-down creative practitioner and had to learn to listen, explain decisions, and communicate with executives, peers, and teams. He recommends pausing to consider how a message will work in email, Slack, or a presentation, then improving through repeated reflection and feedback. The goal is not more communication for its own sake. Clearer exchanges reduce silos and help teams work from shared understanding.

Listen to Episode #86