Anti-process leads to Sprezzatura

One common thing that happens in startups is founders renounce the whole idea of planning and process. I’m not sure if this is because coordination isn’t needed when startups are very small or if it’s because planning so often fails.

It turns out that renouncing process creates a new set of problems.

If a founder has renounced process, but getting to some kind of answer (product, data, strategy, etc) requires it, what happens? The person responsible for that thing doesn’t want the founder to know what’s going on behind the scenes to come up with a good answer, because the founder announced that process is bad. So their response has to look spontaneous while also being rigorous, well-reasoned, and cogent.

What’s happening is sprezzatura.

Sprezzatura is an italian word that refers to the work and effort it takes to appear nonchalant or carefree in the moment, while also being excellent. It’s the work it takes to appear both excellent and effortless. The latter is what makes sprezzatura different than other forms of preparation.

Sprezzatura is found in fine dining, hotel hospitality, fashion, and originally fine art. It’s attention to detail that’s so refined the creator introduces a bit of mess, and it presents as ease or grace. And that little bit of mess is what sets the other party at ease. Their need is not a burden; it’s weightless. This is how a host at a 3-star Michelin restaurant is striving to make their guests feel. Startup leaders are striving to make their zero-planning founders feel the same way about planning. The right answer appeared effortlessly out of nowhere.

The part about sprezzatura that’s confounding is that the work to appear effortless increases the total amount of work enormously. Introducing the right mess requires a high level of mastery.

One obvious component of sprezzatura is secrecy. Hiding work is more effort than doing something transparently, because you have to remember when and where to say or not say things, and who can and can’t be included. It’s an increase in cognitive overhead, which distracts from more useful, company-building tasks.

One tip off that this dynamic might be happening is when a leader asks a founder, “hey, can I have a little more time to prepare xyz thing, so I can talk to my teams about it?” The telling part is actually the response: “No. Just don’t do anything to prepare.”There are obviously countless reasons that meeting urgently could be the right thing to do. The point here is the founder is ignoring signs of sprezzatura.

What that really means is: prepare a lot, because you are representing tens or hundreds of people and their work as it relates to the new, top priority of the company. But then, spend extra effort to appear careless and ruffled, just enough so that it convinces me that you haven’t worked hard, even though what you show me still has to be excellent.

That’s sprezzatura.

It’s a lot of pantomime and pageantry to avoid reality. And it’s not worth it.

Thanks to CR, Chris, Perry, Ami, Rob, and Dimitri for reading drafts of this essay. And thanks to Sanjay for teaching me the word sprezzatura years and years ago. It’s a good one.