Brian Bailey Preface to the Revised Edition

Clarity and Freedom

On a recent weekend, I watched two documentaries, Jiro Dreams of Sushi and Woody Allen. They were oddly similar — two stories of men pursuing their craft with incredible persistence. The films are interesting bookends; both men chase perfection in different ways. Whereas Jiro controls every step of the process and holds each person to the highest of standard, Allen appears resigned to the unreliability of the creative process. Each year, he creates a new movie. The moment it’s finished, he begins the next. Some of them work, some don’t. Some are very successful, most aren’t. Allen hopes to improve as a filmmaker each time, but knows he will always fall short.

There was one moment in the Woody Allen film that stood out. Naomi Watts was talking about what it’s like to work with Allen and said:

While he’s giving us a lot of free rein, he’s still going for something very specific.

I love this. In my experience, it’s how the best people lead and how most of us want to be led; clarity as to the goal and freedom in how to achieve it.

By goal, I’m referring to both the end result (increase sales by 20%, design a page where someone can create a playlist, write an article on the latest feature) and the broader, “Here’s what I’m looking for.” It’s the “he’s still going for something very specific” part. The actors clearly know what Allen expects from them; they aren’t guessing.

The combination of clarity and freedom is what makes work a joy; one without the other is where you find frustration. When you have great freedom, but an incomplete understanding of the goal, you’re likely to invest hours of effort in a futile attempt to hit a target you can’t see. You know this is the case when you see revisions requested again and again, or products that are perpetually delayed.

On the other hand, a clear goal with little freedom in how to achieve it produces uninspired work by dispirited people. The lack of freedom is experienced as a lack of trust and confidence. People in these environments will eventually seek out new places to work.

The freedom Allen gives his actors is possible because he has chosen people he trusts. Earlier, the film discusses how he casts his films. For the main roles, Allen typically has a single person in mind. He sends a hand-written note to the actor asking if they would consider appearing in his film, along with a copy of the script, which they must return the next day. Most say yes immediately, not only because of his status as a filmmaker, but because of the quality of work they see other actors do for and with him.

It’s the same in our companies. The way to attract the best people is to develop a reputation for talented people doing amazing work.

Hire great people, be clear about the goal, and provide the freedom to achieve it.