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.”


  • Kevin Crosthwaite

    I enjoyed reading about your lunch experience, a lesson for us all. I was a CEO of a group of underperforming public companies with the responsibility to return those companies to profitability, increase market share to dominant proportions then sell the portfolio. It takes laser focus, insatiable drive, high standards and a clearly articulated plan. Successful people are successful because they are willing to do the things that unsuccessful people aren’t willing to do. This should be everyone’s credo today to compete in the world we live in.

    Redfin has done an incredible job in re-shaping the Real Estate industry to meet the needs of the 21st Century consumer. Keep up the good work!

  • Glenn Kelman

    Kevin, what an amazing journey you must have had! Thanks for the words of support. It really means a lot to us…

  • Ross

    “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.”

    How did he express the difference? The one thing I’ve really hit upon is to genuine care. To want the absolute best – product, practice, result – and express that as expectation or feedback in my project reviews.

    I figure I only get it right 75% of the time. The other 25% I’m a demanding jerk.

  • Ben Elowitz

    In my role at Wetpaint, it feels like setting direction is only about 10% of what I do. So much more of my time goes to working with the other leaders to make that vision a reality. For me, at least, the place I tend to spend time is being open right along with the others in my company to how can we each do better.
    –Ben (@elowitz)

  • Glenn Kelman

    @Ross: it helps to care, but mostly to keep your cool; it’s nearly impossible but necessary to do both. I am quite sure you’re not a jerk 75% of the time, or even 25%.

    @Ben: I must copy your every move… you’ve got it down!

  • JanelleS

    Glenn, you hate praise, and sweetly “promise” to demote anyone who throws compliments your way at company meetings or in the kitchen at HQ. But, as a Redfin employee of three years now; and having worked at other establishments over the years, what I admire about you (and Redfin), is you expect even more from yourself than we do. Imagine folks, an approachable CEO that actually returns emails with lengthy, thoughtful responses.

    Or, perhaps I should put it this way: You are the most humble b*ll buster I’ve ever known.

  • Glenn Kelman

    Ah Janelle, you are too kind, you embarrass me.

  • jason

    I love reading about tech Ceos and read a lot of their blogs, books etc looking for advice but often they seem to be missing some of the experienced older non-tech Ceos have.

    great post

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