How Being Humble Can Help You Be Wrong Less Often

Greetings friends!

Let me teach you how to disagree with yourself. That is, if you want to improve the quality of your thinking and decision-making. One way to do so is to regularly challenge your thinking.

I assume no one wants to fail at what they set out to do. I also understand that few people like to be reminded of their failures. But, if by studying our failures we can improve our odds of future success, I say the study is well worth the discomfort.

Even better, when we get into the habit of considering what could go wrong before we act, we can improve our odds of future success without having to first personally experience failure. Today’s post explores how being humble can lead us to make better decisions. (For more on the actual humility aspect, see Why You Should Doubt Yourself.)

Shooting from the hip is for the foolhardy

Johnny Mercer wrote the lyrics in 1940 to what could be the unofficial decision-maker’s anthem: Fools Rush In (Where Angels Fear to Tread).

But I prefer the earlier formulation by Alexander Pope in An Essay on Criticism: "Foolish people are often reckless, attempting feats that the wise avoid."

N.B. This could also serve as the rallying cry for every technical writer preparing warning labels for consumer goods products.

While avoiding reckless behavior is a worthy goal, inaction is no answer. To make progress in business, relationships, and life, we must act.

I recall our CEO frequently exhorting us to have a “bias for action.” Analyze as necessary, but make sure not to be paralyzed by wanting to perfect your analysis. Sooner than you feel ready, plan to take concrete action. Even if the original plan is not perfect, we can also make corrections while we’re implementing it.

The ideal mix of analysis and action comes about when we plan to increase our odds of success while simultaneously contemplating how our plans could be frustrated. That is, identifying what are the things that could go wrong and derail us.

Planning for success while also contemplating failure is not intuitive, and most people can’t do it reliably. In my experience, we like to focus on the pleasant daydreams of success rather than the ways we might flop.

Daydreaming of success is necessary and healthy, to a point. Taken too far, we risk falling into cognitive dissonance.

We fall in love with our plan and see all the ways that it will be great. But then we tend to filter new information to fit our view of the world. We easily disregard contrary indications and ignore warning signs.

We have two potential countermeasures to this blindness:

1. Conduct a pre-mortem

When working alone, we can ensure our personal project plans include a “pre-mortem” step. It’s usually helpful to do this sometime after starting your planning, but before you get too near the end. Say halfway through your planning as a good rule of thumb.

The purpose of the pre-mortem is to daydream again, but this time you imagine all the ways your project could be frustrated. Nothing goes according to plan. Why is that?

Be broad in spinning out your disaster scenarios and try to come up with a lengthy list. Only once you’ve prepared a good list, rank your future obstacles in terms of likelihood, magnitude, and addressability.

• Focus some of your planning attention on more likely risks of consequence that you can pragmatically do something about.
• Ignore small risks, unlikely risks, and risks that you cannot reasonably plan around.
• But be creative in considering potential mitigation before dismissing a risk as too hard to plan around. Even if you can’t think of a solution, if the risk is real and not unlikely, you might get some advice from others before moving on.

2. Make sure to invite a spoiler to the team

Our second countermeasure is available when we are working in teams: Assign a person specifically to think of the various spoiler scenarios while the rest of the team does its work.

When the spoiler has a good list, bring the team together for a brainstorming session. This serves to review and expand the list and then discuss possible countermeasures.

The benefits of the pre-mortem review go beyond identifying weaknesses and improving your plan. A good pre-mortem includes asking “How will we know if things are starting to go badly? What types of information will we collect, and who will review it?” This helps shield you from ignoring negative data after you’ve started to implement your plan.

We improve our vision by remembering our fallibility

We humans value the things we invest time and effort into. The harder you and your team work on a project, the more difficult it is for you to objectively identify and assess warning signs.

Knowing this, you can get help from people who are close to, but not directly involved in, your project. Have them monitor the data and assess for you whether you are on track or need to correct course.

A person can be smart, well-intentioned, and sincere while also being dangerously wrong. Relying on your good intentions to confirm the validity of your actions is risky indeed.

One way to improve our chances of being wrong less often is to be humbler.

When planning our initiatives and implementing them, use the pre-mortem process to identify how our plans might go awry. This includes designing processes for collecting good data, objectively reviewing that data, and adjusting course if results aren’t coming in as hoped.

Doing so is no guarantee against being a fool rushing in, attempting feats the wise avoid, but it will make you more effective than most.

Be well.

Don’t miss a vital piece of advice. Click here to get all my stories.

I published a version of this article in the ACC Docket, the global magazine for the Association of Corporate Counsel.