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Monday, January 6, 2025
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Uncomfortable Questions

Asking questions is part of a leader’s job in church, politics, schools, or business.

Much is written in books, blog posts, and magazines about being a leader who asks and keeps asking questions. Hopefully, that’s you.

But you also want people in your organization who ask challenging, even annoying questions, and you better lis­ten.

After thoughtful consider­ation, you’re beginning a new customer service policy, tech­nology, or compensation plan. The county board you’re serv­ing on is looking at projects that will cost significant sums.

You’ve consulted your ad­visers, who tell you it’s a great idea.

Your management team, for not all the right reasons, per­haps, says you’re on the right track.

You believe you looked at all the alternatives, and your deci­sion is rock solid.

As the leader, you are brim­ming with confidence that the folks on the front line, along with your customers and con­stituents, will immediately see the benefits of your wise decision. And then…someone asks, “Why are we doing this again?”

It is a challenging and un­comfortable question at any time, 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 are, they can’t know all the questions they must answer. But they know you and how far they can go in challenging your assump­tions. Did they challenge you enough?

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

The people closest to your customers and business pro­cesses see things 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 (amid some nonsense), they will do so. And they’ll get better at it with time.

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

One tactic to encourage your people to ask questions be­fore making decisions is fre­quently conducting “Question Storms.” For example, what are 50 questions that need to be answered before we move forward with this project?

Steve Fernlund
Steve Fernlund
Typically these “about me” pages include a list of academic achievements (I have none) and positions held (I have had many, but who really cares about those?) So, in the words of the late Admiral James Stockwell, “Who am I? Why am I here?” I’m well into my seventh decade on this blue planet we call home. I’m a pretty successful husband, father, and grandfather, at least in my humble opinion. My progeny may disagree. We have four children and five grandchildren. I spent most of my professional life in the freight business. At the tender age of 40, early retirement beckoned and we moved to Grand Marais. A year after we got here, we bought and operated the Cook County News Herald, a weekly newspaper in Grand Marais. A sharp learning curve for a dumb freight broker to become a newspaper editor and publisher. By 1999 the News Herald was an acquisition target for a rapidly consolidating media market. We sold our businesses and “retired” again, buying a winter retreat in Nevada. In the fall of 2016, we returned to Grand Marais and bought a house from old friends of ours on the ridge overlooking Lake Superior. They were able to move closer to family and their Mexico winter home. And we came home to what we say is our last house. I’m a strong believer in the value of local newspapers--both online and those you can wrap a fish in. I write a weekly column and a couple of feature stories for the Northshore Journal. I’m most interested in writing about the everyday lives of local people and reporting on issues of importance to them.
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