How to build empathy with users you struggle to understand

The digital nomad who is designing an app for the atomic midwestern family. The non-gamer who is designing a videogame UI. The sighted person who is building a touch interface for the blind.

Empathy is foundational to product design. We talk about it constantly: cultivating it, mapping it, building with it. But what happens when empathy doesn’t come naturally? What do we do when we don’t relate to our users, when their behaviors feel foreign or even frustrating?

I ran into this problem recently while designing a fitness app. I was stuck until I remembered the first time I’d overcome it: writing dialogue for a cartoon snake, of all things.

The Snake in the Room

In 2012, I joined Nickelodeon’s new flagship show Sanjay and Craig as a storyboard director. It was a catch-all role: writing, storyboarding, shaping jokes and characters. The premise? A boy and his talking pet snake. The tone? Wild, absurd, full of bodily functions. If you watched kids’ TV back then, you might remember it.

As we started breaking episodes, I hit a wall. Craig Slithers, the talking snake, was one of the main characters and I couldn’t write him. I just didn’t understand who he was.

Craig was bold, brash, and loved the spotlight. I was second-guessing myself after a rough project before Nick, trying to quietly get back on my feet. He was all noise and confidence. I, though gregarious, was trying not to get noticed.

Still, I had to write for him. I needed to understand his mindset, his instincts, his voice.

I tried outlining his traits. Rereading scripts. Mapping his arc. None of it helped. He felt flat, fake.

Eventually, I gave myself one small challenge: find one thing I had in common with him.

A Moment of Product Design Clarity in a Writers’ Room

I landed on this line in a script: “Craig was cool. Or, really, he wasn’t, but he believed he was cool.”

That clicked.

Not because it was funny. Because I’d been there.

At different points in my life, I’ve pretended to be cooler, more confident, more capable than I really felt. That little overlap, just a sliver (or slither) of shared emotion, was enough to get me started. Suddenly, I could write Craig. Not because I “got” him completely, but because I understood one emotional truth. From that truth, I could build. I had my “in”.

This “in” was my opportunity to immerse myself in the user and their needs like how Julia Benini wrote in her article on IDEO. The process I’d stumbled into is exactly what product designers do every day: observation, questioning assumptions, finding emotional truth, just with real people instead of cartoon ones.

Finding Your “In”

In UX design, we sometimes treat empathy like a light switch. Either it’s there or it’s not. But real empathy comes in layers. You don’t need to fully understand someone’s life to connect with them, maybe you just need to connect with one emotional truth. An “in”.

That “in” usually comes from research: interviews, fieldwork, usability tests. But even with great data, it can be hard to relate. When users act in ways we don’t expect, we get frustrated. We think they’re confused, irrational, maybe just wrong.

But they’re not. They’re just not us.

Instead of asking, “Why are they doing that?” ask, “What truth might explain this?” I didn’t relate to Craig’s confidence. But I did relate to the desire behind it. That was the crack in the door I needed.

Staying Curious

When you don’t relate to a character or a user, it’s easy to reduce them to a stereotype. Early on, I thought Craig was just chaos. Loud, pushy, needy. But the more I asked questions (what’s he hiding? what’s he afraid of?), the more I started to see the human side underneath the gags. That shift changed how I wrote him. Suddenly he wasn’t just loud. He was trying to seem loud, to cover something up. That made him real.

Users can be the same. When someone skips onboarding or drops out halfway through a task, it’s tempting to write them off. But those behaviors often come from something relatable: fear, frustration, stress, distraction.

While designing a fitness app for finding nearby workouts (a freelance project that has yet to see the light of day), I hit my own empathy wall. As someone who prefers solo training and finds social fitness apps like Strava intrusive, I assumed our users would want a clean, private experience focused purely on location and workout type. I designed around that assumption by emphasizing map views and filtering options while intentionally avoiding any social features.

But user interviews told a completely different story. People didn’t just want to find nearby running trails or hiking spots, they wanted recommendations from people they trusted.

One user told me –

There was my in. Instead of seeing social features as noise, they saw them as the most reliable filter for quality recommendations from people they trusted.

That feedback forced me to view my product from a different angle. Instead of building another map-based discovery tool, we pivoted to focus on trusted recommendations from your network. The core insight wasn’t about finding workouts nearby, it was about finding workouts that people like you had actually enjoyed. We redesigned the entire experience around a “recommended by people you know” social feed that surfaced workouts based on your connections’ activities and ratings.

Good product design comes from staying curious. Instead of fixing users, we ask what matters to them at the moment. We don’t design for quirks. We design for people. And when you find your “in” to empathize with those people, then you can find the best solution.

The Emotion(al) Moment

In creative writing, “voice” isn’t just how a character talks. It’s how they see the world. That lens makes them feel real.

In product design, we tend to focus on goals and tasks. But great design also reflects how users feel in the very moment they engage with a product.

Did they miss their coffee? Are they exhausted from their newborn baby? What were they hoping for, and is the product delivering that?

Users don’t come to our products as blank slates. They bring their full emotional lives with them: stress, distraction, hope, exhaustion. When we find our “in” to that emotional reality, we can design for their actual headspace, not an idealized version of it.

Empathy should show up in every interaction, not just the text.

From Snake Scripts to Product Design Sprints

As I have previously mentioned, my past experience as a storyteller in animation has shaped some of my UX philosophy. Writing Craig taught me how to understand someone I didn’t instinctively relate to. It forced me to find connection through questions, observation, and emotion.

This process made the leap with me to product design and it’s what helped draw me into this new path. In animation, you’re constantly thinking about audience engagement: what makes them laugh, when they’ll lose interest, how to keep them watching. I realized that product design is essentially the same thing, but instead of just entertaining an audience and keeping their eyeballs on your product, you’re helping users accomplish real goals that matter to their daily lives and keeping them engaged. Both require understanding psychology and designing experiences that feel intuitive and satisfying, but product design offered something animation couldn’t: the opportunity to make people’s lives genuinely easier, not just more entertaining.

To accomplish this we don’t have to become our users. We just have to stay open. Curious. Patient. Willing to look past the surface. If we find that one emotional truth to relate to then we have our “In”.

Empathizing with a cartoon snake was originally published in UX Collective on Medium, where people are continuing the conversation by highlighting and responding to this story.