Entrepreneurial teaching and the gift of failure

I was a late bloomer in recognizing many of my own most effective leadership skills.   It wasn’t until I worked for the single most inspiring leader I’ve ever known — Howard Anderson, who was at the time the head of the Cathedral College of Washington National Cathedral – that I came to appreciate one of them.

As Howard shocked me by saying out of the blue one day, “I just love your entrepreneurial spirit as a teacher!”

I had never heard entrepreneur and teacher used in the same sentence.  Then I realized he was right: way more important than any information I had ever known (even when I was young and still remembered far more than I have now forgotten) was the fact that classroom teaching had taught me to think on my feet.

It’s not that knowledge and expertise aren’t important in teaching; it’s just that it turns out they’re more often means to the end of learning, rather than ends in themselves.   It helps to know something worth teaching someone; but until learning becomes the goal – which is different from conveying information — simply having the teacher know a lot can be a boring thing.   Pedagogy matters, but it’s got to be able to change and adapt as students respond, or fail to respond, to what you’re trying to teach. You try one thing, when it doesn’t work you just try something else; you’re entirely on your own and you just keep building the airplane as you fly it – and now and then you crash and burn.

You go into a room of freshmen with three things up your sleeve for the day, and ten minutes into class, they’ve already yawned at the first seven things you could pull out of your ear.  And then the fun begins, when the dance between a few successes and a lot of failures gets everyone’s juices flowing with learning that just seems to emerge like dust from an old carpet – stomp on a teacher’s over-confidence squarely enough, and a cloud of tidbits gets stirred up and then coalesces into “something important” like a genie from a bottle.

I couldn’t plan it, but failure just brought out the best in me.  Failure isn’t always fun, or fair, or life-affirming in any way.  But it really was in the best of the entrepreneurial spirit that if I could stay nimble and respond to each new challenge with at least outward equanimity, more often than not I would get totally surprised when the lights came on, and Voila! Learning happened.  At least I went home smarter, and my students couldn’t wait to come back for the next round.

The trick is in managing people’s expectations.  Students who came into class expecting to be dazzled by instantaneous mastery, expertise, and wisdom from on high were most often sorely disappointed with the initial results of an hour of class.

But if I could just, as Ronald Heifetz puts it, “fail their expectations at a rate they could stand,” I could ride the wave until it crested and everyone would go home saying, “Wow!  Every class should be like that!”  Which it should.