Making Bets

Sometimes your bets don't pay off ... but success or failure might be in how you executed the decision. This newsletter first appeared on the Duha One substack .

Leadership Moment: Snowmageddon? Or is that NOmageddon?

While I’m now enjoying the lovely weather in Tel Aviv, last week I was home outside Boston, prepping to leave, when I was joined by my whole family, since school was closed for the impending snow storm. The storm was a dud, however. rain, wintry mix, and a bunch of snow that didn’t stick. My social media feeds were filled with gentle (and not-so-gentle) mockery of the decisions to shut everything down.

There is some fair criticism - some models were already forecasting less snow by the day before. Schools announced closures at 4 pm, and there was an updated model coming out at 6 pm. Certainly, these are items that decision makers should evaluate before next time.

At the same time, we should be wary of resultism – the practice of criticism a decision only after the outcome of a gamble is known. Organizations who wait too long to make a decision leave their constituents in limbo for too long, or fail to make a decision at all (Bostonians have often seen snow storms with no closures that hit midday, stranding drivers away from their home).

It’s fair to critique how a decision was made, but be careful about justifying your criticism with the outcome. We often want people to make “risky” choices (in this case, the “conservative” choice is the risky one), and we should avoid creating aversion to risk.

One Minute Pro Tip: Pick Your Success Metrics First

When you’ve finished an activity, it’s easy to cherrypick the best outcomes and assert that the activity was a success. Since many activities have mixed positive and negative outcomes, only highlighting the positives makes it easy to not learn from the negatives (and might feel disingenuous to participants who might have a less rosy view).

Instead, try to define what success should look like before you begin. It’s okay to also think about the worst-case (“well, at least we’ll get team bonding, even if we don’t produce a roadmap”), but think about how you’ll measure your successes (or failures). This’ll help you be honest about the outcomes, and perhaps think about how to more effectively achieve success in the future.

Appearances

Feb 13: The CISO Series: It’s Like a Trust Fall, But We Know You’ll Hit the Floor

Upcoming Appearances

Feb 21: RSAC Innovation Showcase: Cloud Native Remediation

March 5: Cloud Control Newsletter

March 19: Crestron Modern Work Summit , Orlando: AI-Driven Hospitality in the Modern Workplace

May 5: BsidesSF : Live CISO Series recording

May 8, 2:55 Pacific: You Can’t Measure Risk, RSAC

September 24: HOU.SEC.CON

1% Leadership Chapter Cameo: There is no perfect plan – there is only the best plan so far.

You’ll make a lot of mistakes in your career, but one of the worst of them can be refusing to make decisions until they’re mistake-free. Punishing people for failures can lead to decision avoidance; so recognize that you and others need to make the best plan they can, and then go execute on that plan. It may be that a better plan shows up the next day, which you mar or may not be able to take … but more often you need to act before you can define ideal.