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How Flexibility is Used and Abused

How Flexibility is Used and Abused

Flexibility can be great—but it's no excuse for skipping the planning and structure of what you're creating. Here's how I learned to employ generative flexibility rather than extractive flexibility.

Welcome to the 7th Edition of This is Not Advice.

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man in green dress shirt playing trumpet
Photo by Jon Tyson on Unsplash

Today's topic is the way "flexibility" is used and abused.

When is being flexible a feature? And when is it a bug? When does flexibility make an experience better for customers or team members? And when does flexibility lead to chaos?

I'll get to my thoughts on those questions in just a bit.

But first, jazz.

I used to play the trombone. I was pretty good—although not nearly as good as I hoped I was. Anyhow, like a lot of high school and college trombone players, I played in the concert band and symphony orchestra, as well as every jazz ensemble I had access to.

I loved playing in jazz ensembles—for both musical and social reasons. But there was one part of jazz ensemble that I was utterly terrible at:


When you think of a jazz solo, you’re imagining someone improvising, whether you realize it or not. It may seem spontaneous and unplanned—even a bit wild. And sure, improvisation can be those things. But improvisation is actually a skill that’s carefully honed over years, really over a whole career.

Learning to improvise is learning scales. And variations on scales. Scales, and scales, and scales. You have to learn scales because they help you construct a melody on the fly. Without the base knowledge of scales and how they line up with the chords the rhythm section is laying down, the notes you play are jibberish.

So while an improvised solo is, in fact, improvised, it’s also the product of years of practice and study.

There is a structure that makes it work. And you’re welcome to deviate from that structure—but to make that work, you have to know what you’re deviating from.

I never committed to learning what I needed to learn in order to improvise. The time and effort required far outweighed my level of interest in the form. By the time I realized that I already knew I wasn’t planning a career as a trombone player. I never really had in the first place.

While jazz improvisation was never my jam, I do enjoy improvising in other areas—like teaching and speaking. And I’m good at it.

I can be quick on my feet. I can make things up as I go.

For example, I don’t rehearse the workshops I teach. Instead, I’ve learned certain structural techniques that allow me to move from topic to topic pretty smoothly. I have patterns that I use over and over again—even as the material changes, the patterns stay the same.

I prepare and then improvise. Prepare and improvise.

I know that putting in the work on those patterns and structural techniques—as well as being fully fluent in the material itself—means I can trust my instincts in the moment. I'm less likely to be flustered or caught off guard than if I were working off of a meticulously rehearsed script. My finely-tuned structure creates space for flexibility.

Oddly enough, recognizing that this is what I do is a relatively recent realization.

And because I didn't know planning and structure were what made me a good improviser in front of an audience, I could miscalculate.

I'd rely too heavily on my ability to make things up as I go and under-develop the structure I needed to improvise over. Or my confidence in my performance caused me to under-bake the administrative and logistical elements of a project.

That sucked for me, of course. Being caught flat-footed isn't fun. But it was in those moments when I realized that I'd skimped on the structure or logistics that I also realized I was making things unnecessarily difficult for the people I was working with. My reliance on "flexibility" actually made them question their own ability.

Being "flexible" is treated as an objectively positive value.

I don't think that's wrong, but I think it's more complicated than that. So I think we should differentiate between two types of flexibility: generative flexibility and extractive flexibility.

Generative flexibility focuses on the other—be it a customer, team member, business partner, colleague, etc. Generative flexibility offers well-considered structure with space to adapt to the other's needs. The structure provides a sense of comfort or safety, while openness empowers the other to express their curiosity.

Generative flexibility doesn't cut any corners. It's actually more work, not less. It anticipates questions, factors in friction, and communicates thoroughly.

Extractive flexibility, on the other hand, is about flying by the seat of your pants. It's about doing less beforehand and trusting your instincts when it counts. This kind of flexibility is extractive because it's not an equitable transaction. It disproportionately draws on the resources of the other.

By that, I mean your customers or team members have to put in extra work to follow along, to make sense of what you're sharing. They can't fully participate because they're spending so much of that energy on figuring out what's going on.

Extractive flexibility might feel comfy for you, but it's chaos for everyone else.

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