Success and Failure are in the Beholder’s Eye

Leadership Moment: Plans Change

Last weekend, my wife and I had great plans. Her plan was scheduled hour-by-hour for a full week: she was going to a memorial service in Santa Fe, with days to tourist and vacation and catch up with old friends. My plan was loosely defined: I was going to drive out to Canton, Ohio, to watch the Boston Renegades win another championship. Our two teenage children would get a couple of days alone at home. And then, a few days before my wife was to leave, our daughter came down with whatever the summer respiratory bug is.

We didn’t really have to discuss whose plan was going to get tossed by the wayside (mine), because it was obvious to both of us (not just because my plan was more flexible, and hers involved a family obligation, but also because I travel a lot more than Gisele does). We shifted into a mode where that had now always been the plan; because we knew exactly what we wanted out of the week (besides healthy teenagers): a great week away for my wife. Her time away may have become a bit more expensive, but we still wanted to make it worth it.

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One Minute Pro Tip: Remember Your Failures

Whether you’re reviewing your performance annually or continuously with your boss, have a private review alongside it with yourself, where you evaluate and go over all of your failures in the prior year (hopefully, you have a great relationship with your boss and can also do this with them, but do it alone first). To do this, write them down as they happen. If you’re an agile leader, you can often turn a failure into at least a middling success, but you should write it down so you can later review how it didn’t meet your expectations.

If your list is too short, you’re not taking enough risks. For each failure, ask yourself if there were cheap things you could have done to reduce the risk. Ask yourself if there was information you had available but ignored that might have triggered a different choice. Your goal here isn’t to figure out how you could have not failed, but to learn more about how you made your decision, and to seek improvements in the process, not merely in a point outcome.



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Sep 20: SANS CISO Roundtable

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Chapter Cameo: Failed Bets

Chapter 52 of 1% Leadership begins with If organizations aren’t regularly failing at future bets, they aren’t taking enough risk. Whenever you’re making plans for the future, consider that you need to be willing to have plans that fail – like my roadtrip to Canton – when circumstances change. Maybe it’s a product launch, or a new initiative, but it’s important to make failure an option. Your best successes came not from perfect plans with no opportunity for failure, but from imperfect plans that you succeed through effort, innovation, and a bit of luck.

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Content: Ado

A bit of fiction for your enjoyment: the below work placed twelfth in its division in the NYC Midnight 1000-word Flash Fiction contest. And yes, there’s a leadership subtext in it.

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