From 2015

Much is written about being a leader who asks, and keeps asking the right questions. Hopefully that’s you—100%.

But you want people in your organization who will ask questions too. Tough, even annoying questions. And you better listen.

After thoughtful consideration, you’re beginning a new customer service policy, technology, or compensation plan.

You’ve consulted your advisers and they tell you it’s a great idea.

Your management team says you’re on the right track.

You think you looked at all the alternatives.

As the boss, you are filled with confidence that the folks on the front line with your customers will immediately see the benefits of your wise decision too. And then…

“Why are we doing this again?”

A challenging and uncomfortable question anytime, but especially when it comes from one of your front line employees as you begin a new initiative. How dare they question you, the leader of this organization?

Why are people questioning you now?

Because you didn’t gather all the input that was there, despite what you believe.

No matter how good your outside advisers, they can’t know all the questions they need to ask. But they know you, and they know how far they can go in challenging your assumptions. Did they challenge you enough?

Your management team may love you or loathe you, but they always know how far they can go in questioning your decisions. Too often, that will not be far enough. Keeping the boss happy may mean not asking the hard questions that are pressing on their mind.

The people closest to your customers and business processes see things that you don’t. But like your management team, they might think that you don’t want to hear the hard questions—likely because you’ve made that clear to them in some way at some point in the past.

As you add and develop staff, seek out those who ask a seemingly endless stream of questions. Assure them that you’ll consider every question and explain every decision. With the freedom to ask the hard ones (in the midst of some nonsense) they will do so. And they’ll get better at it with time.

Thus empowered, they’ll be valuable collaborators in building a successful organization. And you will be a better leader.