Managers: Are You Asking the Right Questions?

BY C. Lee Smith
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Are the managers in your organization expected to have all the right answers? Dave McKeown’s research shows managers can do a better job when they ask the right questions. To explain his thinking, McKeown spoke with us during a Manage Smarter podcast and outlined the principles of his book, "The Self-​Evolved Leader."

The Management Disconnect

If you’ve had management training during the past few years, the curriculum might have left out some critical details. I’m talking about how to handle the situation when a staff member comes to you for help. Maybe they can’t remember their password to get into a specific database. Or they’re trying to find an email you sent them a few months ago. In both of these cases, the employee could easily find the information by themselves. Their behavior indicates they’ve come to rely on you as the answer person.

By continuing to answer questions, instead of training them to look for information on their own, you’re also defining your role. And that role is all about letting them believe they can’t make decisions on their own.

Your Team Members Are Your Co-Conspirators

You can turn around your management style by understanding one key principle. “Your value comes in building better people and leaders underneath you,” says McKeown. If you’re familiar with the old saying from Moses Maimonides, “Give a man a fish and you feed him for a day; teach a man to fish and you feed him for a lifetime,” you’ll know what I mean. One of the first steps you should take is asking the right questions about how you’re responding to employee requests for help. Do you feel yourself getting pulled into the weeds by questions involving administrative minutiae? Sure, you can usually answer the questions quickly. Sometimes you can even do the work more quickly than your team members can. Good for you. But what are you really accomplishing? Are you trying to come off as a superhero who has all the answers?

That strategy doesn’t help the team members meet their goals, especially not in the long run. And if they don’t all succeed at what you’ve asked them to do, then you’ve failed.

So, when people keep coming to you with the same simple questions, step back and look at the big picture. It could be time to audit your team members and the responsibilities you’ve given them. Then, talk with your team about how you want to shift your management style. Instead of being the person who knows everything, explain that your role should be one of facilitation. And describe the new roles you envision for your team members.


You shouldn’t expect this to be a one-​and-​done conversation. Your team members will be confused, and some may push back. They’ll continue to come to you with the same old questions because they have a learned pattern of behavior.

When this happens, remind them that things are changing. Then, ask them the right questions. If they are having trouble handling a new responsibility, find out exactly what is in their way. Do they need to work more efficiently at completing their old tasks so they can take on the new ones? Perhaps there is a task they’ve been doing forever that they enjoy. If it’s not contributing to the bottom line, shut it down. Similarly, if the task is easy for them, but necessary for the organization, maybe it’s time to turn it over to a team member with less experience. Regardless of the types of changes you’re making in the department, take the time to ensure that everyone understands your role.

How the Right Questions Can Improve a Difficult Conversation

These kinds of conversations can be challenging for you and your employee to have. Whether you are initiating the conversation or responding to what the employee has said, slow down and think about what’s going on. Conversational control requires you to think ahead, especially since you’ll want to steer toward a satisfactory conclusion.

If an employee has come to your office complaining that they can’t possibly get all their work done in the allotted time, you must first acknowledge their struggle. Try to understand where they are coming from. If you don’t come across with empathy, they’ll figure you don’t care and that you don’t get their issue. And they may give up.

The key step in these conversations, McKeown says, is to envision the outcome you want. What will success look like? Will the employee try to improve their focus on tasks? Develop specific questions to ask them that will lead them to come to this conclusion on their own.

When you need to initiate a difficult conversation, remind yourself of the one characteristic you must bring forth: courage. Kaila Colbin summarizes the importance of this characteristic for leaders: “The single biggest indicator of a lack of courage is the inability to have difficult conversations.” Her comments are based on training she took through Dr. Brene Brown’s Dare to Lead facilitator program.

It’s not easy to sit an employee down and ask them challenging questions about their performance. But when you do, you are helping them improve their outcomes. You’re also developing your management skills. If these conversations don’t go well at the first time or two, McKeown tells us not to beat ourselves up. Learn from them and do better each time.