How to Be

I just had lunch with a retired airline CEO, as part of a personal-training program Madrona’s Paul Goodrich put together to ensure Redfin folks learn how to build our little company into a juggernaut. It was fantastic.

Half an hour before the lunch, I decided to ride my bicycle home to change into nice pants. We met at a restaurant with bottles of wines in locked cabinets bearing the names of different patrons, and oil paintings, and dark-wood paneling, and a menagerie of mounted animals.

He came in talking about his African sightseeing safari — Masai warriors who were opening schools to teach their children a new way of life, a leopard who leaped into a tree “just like that.” We found ourselves discussing salmon who had swum from Russia into remote Alaskan plains, avoiding Chinese fishing nets and bears, only to be caught for sport a few miles from their final homecoming — and I suddenly felt an enormous affinity for him.

He told me that when he first took over a struggling airline, he drove from the office to the airfield, scraping fossilized Bubbalicious from airplanes seats between 8 pm – 2 am. He could still reel off his first-year’s top-three objectives: clean planes, arriving on time, with all their bags. Stabbing at his Caesar salad with raised eyebrows, he said: “Couldn’t do the bags.” He talked about canceling money-losing routes, and I thought how often the best decision isn’t to do something, but to stop doing something. He talked about CEO pay; he’d donated his multi-million-dollar bonus to charity.

Listening to him, it dawned on me that I had been looking for the best management mentors in only one place, high-tech, and that it wasn’t always the right place. Some of the best managers are from businesses that don’t have a technology rabbit to pull out of their hats, or stock options to pull from behind employees’ ears; they win through pure management guts.

Then my lunch companion told me what I had come to hear, the nitty-gritty of how he spent his days. Everyone wants to believe that the secret to a startup’s success is what you do — the bold strategic decisions — but you only make one or two of these every five years. The hardest part for most CEOs is how to be.

Many wise folks will tell you to let go: of responsibility, of details, of all the little things that you go crazy about late at night. It’s good advice. But almost every CEO I’ve met, even of some of the largest companies in the world, has a different emphasis: to dive in, to make your mark, to insist unapologetically on what you want. No one, my lunch companion told me, will have high standards if you don’t. No one will work hard if you don’t.

Most of us struggle to appreciate the difference between expecting more — of yourself and of others — and just being inexcusably mean or bossy. The person across from me made that distinction seem as plain as day. It made me feel hopeful and stern at the same time.

At the end of our lunch I asked if he missed it, being in the thick of things? Sometimes, he said. “But I don’t have to fire people anymore. And that’s a big relief.”