Technical Empathy

Despite Arsenal not winning enough trophies (😭), I’ve always taken solace that at least the Gunners have a heritage of liquid footy; technical brilliance is woven into Arsenal’s DNA.

The Gunners’ flowing style has always been spearheaded by playmaker maestros—Cesc Fàbregas, Santi Cazorla, Mesut Özil and now Martin Ødegaard - and at the core of their brilliance is what what legendary Arsenal manager Arsène Wenger calls “technical empathy.”

“In training sessions we emphasized technical abilities above all. Passing the ball is communicating with another person, it’s being in the service of another person. It’s crucial. For the pass to be a good one, the player has to put himself in the position of the person who’s going to receive it. It’s an act of intelligence and generosity, what I call technical empathy.” — Arsène Wenger

In other words, these players instantly process everything—the positioning, the preferences, the pressure—and deliver passes that anticipate exactly what their teammates need to successfully execute the next action, before they even receive the ball.

Contrast that to the “hospital ball” - the pass that gets your teammate clobbered.

The Iceberg

Every expert is carrying around a massive iceberg of knowledge. The tip—visible above the water—represents what others can see, while the vast majority remains hidden beneath the surface. Writer Steven Johnson describes the challenge as “condensing the iceberg”—deciding which small portion of our knowledge to share at any given moment.

I recently read Pachinko, a novel covering generations of a Korean family, spanning from Japanese occupation in the early 20th century to the 1980s. Beyond the gripping story, I learned a ton about the history of Korea and Japan, making me think “Holy shit, how much research did they have to do, just to write this book?!”

Like imagine the research iceberg beneath Pachinko—the countless books, interviews, and historical documents the author must have digested before distilling it all into a cohesive narrative. Here’s a good example of Pulitzer winning, biographer Robert Caro’s process.

dependency
Rebecca Skloot conducting research for "The Immortal Life of Henrietta Lacks"; originally found in Condensing the Iceberg

This is exactly what Arsenal’s maestros do on the pitch. They take in the entire game state—an iceberg of tactical information—and condense it into the perfect weighted pass. They don’t overwhelm their teammates with every possible option; they deliver precisely what’s needed at the moment.

And this applies beyond soccer and novels. It’s fundamental to effective knowledge work.

Technical Empathy at Work

Amazon’s writing culture is essentially a formalized mechanism for technical empathy. When you craft a one-pager, six-pager, or PRFAQ, you’re forced to condense your iceberg. The writing process becomes a disciplined exercise in distillation: What does my audience need to know? What can I leave out? What’s the clearest way to express complex ideas?

The result respects the reader’s time and attention while providing them exactly what they need to understand the issue and make decisions. It’s the corporate equivalent of Ødegaard’s perfect through ball—anticipating needs and setting others up for success.

But technical empathy extends beyond formal documents. As an AI scientist building proofs-of-concept with large language models, I navigate complex workflows that chain together multiple AWS services and LLM outputs. When collaborating with engineers, I have a choice: I can dump my entire mental model on them (a hospital ball causing cognitive overload), I can withhold crucial details (another type of hospital ball), or I can practice technical empathy.

The latter means creating artifacts that translate my mental model into something engineers can build from. What context do they need? What implementation details matter? What can I abstract away? I’m looking for that sweet spot of information sharing.

Meetings provide another clear example. Meetings are inherently low-bandwidth information channels—thirty minutes with ten people means 300 minutes of collective time. Technical empathy here means:

  • Inviting only essential participants
  • Setting tight, focused agendas
  • Staying within allocated time frames
  • Ensuring everyone gets exactly what they need

The hospital ball equivalent? Dragging in unnecessary people, running over time, or hosting a meeting that could have been an email. How many times have you sat through a meeting where only 10% of the content was relevant to you? That’s the knowledge work equivalent of a pass that leaves you exposed to a vicious two-footer.

What makes the best players and the best collaborators isn’t just raw skill—it’s the ability to make others better by anticipating their needs. Whether on the pitch or in knowledge work, technical empathy is about condensing your iceberg to deliver exactly what others need, when they need it, in a form they can use effectively.

The next time you prepare a document, plan a meeting, or collaborate across teams, ask yourself: Am I delivering a perfect through ball or a hospital pass? Your teammates’ success depends on your answer.