I'm a Classically Trained Pianist. Becoming an SE Felt Exactly Like Learning Jazz.
October 15, 2025
I grew up playing classical piano.
Bach, Mozart, Chopin — I could sight-read almost anything. I understood music theory deeply. I practiced with discipline. For years, I believed that musical skill was musical skill. That fluency in one area would carry over to any other.
Then I tried to learn jazz. And I completely fell apart.
Jazz is a different language.
The chords are more complex — 9ths, 11ths, 13ths stacked on top of each other in ways classical music rarely goes. The rhythm is fluid, not fixed. And the most important skill — the one that makes jazz jazz — is improvisation.
You can’t improvise from sheet music. You have to listen to the room, to the other musicians, to what just happened two bars ago, and respond in real time. There’s a framework underneath it all, a set of standard progressions and scales, but what you do with that framework in the moment is entirely up to you.
My classical training gave me foundations. It did not give me jazz.
I spent months humbled by this. A skilled musician, unable to play freely.
A few years later, I became a Solutions Engineer at HashiCorp — and had the exact same experience.
I understood the products. I had done the certifications, read the documentation, practiced the demos. I knew Terraform and Vault technically. By most measures, I was prepared.
But the first time I was in a live discovery call with a customer who went completely off-script — who had a problem I hadn’t anticipated, a technical environment I hadn’t seen, and a business context that changed every assumption I had made — I froze.
My classical training, the structured preparation, the rehearsed demo flow — none of it applied.
What the customer needed was jazz.
The parallel became impossible to ignore.
In jazz, you use a set of foundational elements — scales, chord progressions, standard forms — as a launchpad for improvisation. You don’t abandon structure. You internalize it so deeply that you can move freely within it.
In SE work, the same principle holds. The product knowledge, the methodology, the discovery framework — those are your scales. The real skill is what you do in the moment when the customer goes somewhere unexpected. When the technical question becomes a business question. When the demo needs to pivot. When silence in the room means something and you have to decide what to do with it.
That’s not something you can prepare for slide by slide. It has to be practiced, developed over time, through reps.
What changed for me in both cases was the same thing: I stopped trying to control the performance and started trying to listen.
In jazz, the best improvisers are the best listeners. They’re not playing what they planned — they’re responding to what’s happening.
In SE work, the best discovery conversations happen the same way. Not when you steer the customer toward your prepared narrative, but when you actually hear what they’re telling you and respond to it honestly.
I’m still not a great jazz pianist. I’m working on it.
But I think about jazz every time I’m in a customer conversation — especially the ones that go somewhere I didn’t expect.
Those are the best ones.
Have you found an unexpected parallel between something you did before tech and the work you do now? I’d love to hear it.