My favorite leadership moments have come when people who worked for me disagreed with me, chose their way and proved me wrong. These happened when we had the right people in the right roles with clear direction and guardrails and different perspectives who learned through practice.

“Remember how we disagreed on this and we chose to do it your way? Turns out you were right. Good for you. Do it again.”


Right People In Right Roles

Not everyone has the two-way confidence to disagree with his or her boss successfully. The people that do have the talent, knowledge and skills required to their jobs well and have built a trusting relationship with their bosses. They have confidence in themselves, in their relationship with their bosses; and their bosses have confidence in them.

This is a prerequisite for disagreeing. If your people can’t get to this point relatively quickly, you probably don’t have the right people in the right roles. The number one regret experienced leaders have looking back on their careers is not moving fast enough on their people. If you don’t have the right people in the right roles, shame on you.

Note to people thinking about disagreeing with your boss. You should check by asking your boss how he or she likes to be disagreed with. There tend to be five modes:

1. Don’t disagree with me. I’m the boss. Therefore I’m right.

2. Disagree with me one-on-one in private.

3. Disagree with me in small groups (and never let anyone outside the family know we disagree)

4. Disagree with me in public – but politely.

5. Disagree with me in public, gloves off, brutal honesty to set an example.

Ask your boss which level he or she prefers. Then don’t believe them. Most people over-estimated their appetite for disagreement by at least one click. So ask and then watch to see what happens to others that disagree first.


Clear Direction And Guardrails

You shouldn’t give people the right to be wrong without giving them a picture of the end in mind and guardrails. Per my earlier article, often the difference between good and bad mistakes goes to intent and risk. If you’ll forgive the mixed metaphors, proper guardrails can keep people from taking unintentional below the waterline risks.

In other words, make sure everyone is clear on the mission and their role in moving the organization towards that mission. Then give people the appropriate freedom to try new things – and no more freedom than appropriate.


Different Perspectives

It’s often said that if everyone in a meeting agrees, the meeting is probably a waste of time. New ideas are born out of creative tension. You want the people around you to bring their different perspectives to the game. It’s not that they are necessarily smarter or less smart than you. It’s that they see things differently.


Learn Through Practice

There are two parts to this: practice leading up to disagreeing with you and practice afterwards. Those who have tried different things and made them work in the past will be more likely to try different things going forward.

Separately, and even more importantly, is positively reinforcing behaviors you want your people to repeat. And you most definitely want the right people in the right roles to disagree with you in ways that reinforce the mission, are within the guardrails and help develop valuable skills.

That’s why the opening quote is so valuable.

“Remember how we disagreed on this and we chose to do it your way? Turns out you were right. Good for you. Do it again.”

This quote calls out the original disagreement. It highlights your choice to back the other person. It credits the other person with being right. It offers praise. And, finally, it proffers an invitation to “do it again.” This is where you will find the joy of being wrong.