233: Analogies are OP

233: Analogies are OP

How to rapidly build rapport and communicate complex ideas


One of the biggest secret weapons in my coaching arsenal is analogies.

We all use analogies and metaphors without thinking about it. Even the first sentence of this article compares analogies to a secret weapon - something hidden and powerful. Here's how you can leverage their impact in your role as a founder, outlier, and high performer.

In my coaching practice, analogies are especially good at helping clients feel truly understood.

When someone tells me they're struggling with their business and feeling lost, I might say, "It sounds like you're wandering through a dark forest, not sure if you're going in circles." If I nail it, they light up with recognition: "Yes, exactly!" They know I've tapped into their emotional state without just parroting their words.

This opens up new ways to explore what's going on. I might suggest a way forward, or they'll often build on the analogy themselves: "Lately I've been lying down in the forest waiting for dawn, but the sun never comes up." By running with the metaphor, they're actively engaging their problem in a new way.

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That's the second superpower of analogies: creative problem solving.

Analogies stick in your brain because they're visual and memorable.When you see how one situation maps to another, you can unlock new strategies or get clarity by comparing your situation to something more concrete.

When you're dealing with abstract stuff like product problems or marketing challenges—especially in tech—things can feel pretty fuzzy. But when I say something like "you've set up shop at the busiest intersection in town," founders immediately get why it's tough to grab attention for their product in a crowded market.

Analogies turn the complex into the familiar. When a product owner needs to explain a new feature to their team or a potential client, an analogy can make it click instantly. Think about how everyone remembers "mitochondria are the powerhouse of the cell" - we all know what a powerhouse does: it powers things up.

Some of history's biggest ideas spread because of great analogies. Einstein made relativity digestible by comparing space-time to a rubber sheet warped by heavy objects. This helped people visualize how a gravity well works - the deeper you fall into it, the harder it pulls.

Charles Darwin made natural selection make sense by connecting it to something people already knew about: artificial breeding. Just like farmers shape their animals' traits through selective breeding, nature does the same thing over millions of years, creating all the wild diversity we see in living things.

In computing, we lean heavily on office metaphors to define functionality. We put digital stuff in "files" and "folders," and use icons like magnifying glasses for search and paper planes for sending messages. These metaphors bridge the gap between the physical world we know and the digital world we're figuring out.

Here's how to use analogies effectively in your own communication. First, make sure you really get the concept you want to explain. If you don't, start there.

Then, think about what's familiar to your audience—everyday stuff like relationships, shopping, or sports. Beyond general concepts, you can create stronger connections by picking topics your audience really cares about.

For instance, with my tech founder clients, I often talk about social dynamics using coding analogies (pair programming, staging environment, etc). If you know your audience is into certain hobbies, shows, or interests that you also understand well, use those as your jumping-off point. The personal connection makes the analogy hit home.

Focus on the key parallels between your analogy and your concept. No analogy is perfect, but aim to nail two or three clear connections. Then, let your audience explore the analogy themselves. Watch how they respond - you might need to try a few before one really clicks.

Analogies work because they tap into a learning principle called scaffolding. People learn new stuff more easily when they can build on what they already know. Think of an analogy as a bridge from familiar territory to new understanding. It creates a framework that helps others really get your point or feel understood in their situation.

Learning to deploy analogies is a skill that takes practice to learn. But like using downtalk, sitting up straight, and making eye contact with the webcam, you can make it a habit over time and become a more effective communicator.


Jason Shen

The Outlier Coach—helping founders build conviction in what's next · 3x venture-backed startup founder (acq by FB) · Author of 'The Path to Pivot' & 'Weirdly Brilliant' · ADHD · Former NCAA gymnast