In Praise of Doubt

We WANT to see confidence … but first we NEED healthy doubt.

While presenting decision disciplines at a Board of Directors conference I came to the point “Praise Uncertainty and Challenge Over-Confidence.” A powerful voice boomed from the audience “I don’t want to see uncertainty – I want to know the team believes in themselves!” The protester was retired military and I could sense where he was coming from, but in the context of decision-making, that attitude is destructive. The key is TIMING.

Taking The Hill

Let’s go with a military example: You’re a general and must take a hill. Your strategists studied the terrain, the enemy’s positions and strength were plotted, and a plan of attack approved. When we look into the eyes of the lieutenant tasked to take that hill we don’t want to see fear or uncertainty – those doubts slow decisions, poison the team’s morale, and may doom the mission to casualties and failure. The leader’s confidence inspires boldness and courage in troops. But let’s be clear – we want to see this confidence after the plan is approved.

During the study and planning, if you care about your troops you do not want an over-confident team leader brushing aside warnings and presenting you with an unfounded “Can Do!” act. You want the strategists agonizing over all the options, checking and rechecking intelligence reports, and delivering a sober analysis of the perils faced under the recommended solution option; you want the unvarnished assessment.

Our business culture, unfortunately, tends to reward confidence above candor. It has been noted that unfounded over-confidence is seen as leadership material while appropriate uncertainty is deemed weakness. So people put on false bravado (or truly delude themselves) to tell you that, in their hands, success is almost guaranteed. Think of past IT proposals: did they consistently give you full warning of the downside risks?

Making Your Job More Difficult

Hearing the uncertainties definitely makes decisions more difficult, but if you really want the truth, folks must know you value and reward candor. Simply saying so changes nothing at first, but you can transform the culture by supplementing words with actions:

  • Genuinely praise those who reveal their personal doubts about the recommended course of action.
  • Call out over-confidence. Make it clear that failing to appreciate risks (pre-approval) is recklessness, not courage.

Put these first two points on a Post-It Note® and place it with their risk analysis as a reminder to yourself during meetings. We’re predisposed to ascribe strength to those who appear confident so we need to change our own habits. Finally,

  • Follow-Up relentlessly. Only history’s feedback truly sharpens risk assessment skills.

Even with these tips, change will take time so determination and consistency on your part are imperative. Keep in mind that we are fighting our own deeply embedded instincts.

“Doubt is not always a sign that a man is wrong; it may be a sign that he is thinking.” Oswald Chambers

© Dave Wittenberg