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Mike Wagner / May 8, 2018

Five Questions Every Leader Needs In Their Toolbox

Here’s a “big something” I have learned working with leaders – when you start getting serious about the power of questions, you start getting serious about leading others.

I have observed many leaders who struggle to connect with their reports and lead them effectively. (You can probably think of that one report right now that you can’t seem to connect with.)

But what you might not expect is this; the breakthrough for these leaders occurred when they stopped thinking they had to be the answer person.

They stopped defining their value as needing to have the “right answer” for every situation.

Instead, they came to prize how the “right question” leads to deeper connection and improved performance.

When you ask the right question it changes the dynamic between you, the leader, and your report. Your report begins to feel their contribution and ideas matter.

To get started switching from being a “right answer” leader to a “right question” leader, here are five questions to put in your leadership toolbox.

1. What Do You Have for Me?

This is the “universal solvent” of questions. Use this questions to open up the biggest possible conversation with your reports.

During 1:1 sessions this can serve as your habitual “first” question.

At first, your report might be slow to respond, but they will learn that you expect them to come prepared to discuss the issues they are facing. Creating a more engaged report.

As your connection with your report deepens, this question only becomes more effective.

2. What Roadblocks are You Facing?

This question is about “improved performance” for each contributor on your team. But it will teach you much more!

You learn what processes aren’t working, what teams aren’t clicking, and what silos need busting!

You may hear about personal and family issues that are roadblocks facing your colleague. So, don’t be surprised.

This only means your connection is deepening with your report.

3. What Subject are You Afraid to Bring Up?

This is an “honesty” question. You want your report to speak truthfully about what they are seeing.

Asking this question early and often is important to developing a connection with your reports.

Your reports are already bringing up the subject in the “parking lot”. It’s your job to create an environment where your reports are willing to bring up any subject with you.

Ask this question, mean it, and get even more connected to your people!

4. What Skills Would you Like to Add?

This is the “personal development” question. It shows you want to see your report improve and grow.

When you ask this question you might get a quizzical look from your report. They’ve never had a boss ask how they would like to improve themselves.

So be prepared with categories of skills to prime their thinking. Here are the three big categories of skills I offer up when there seems to be confusion.

  • Operational/Technical Skills – like “using Excel Spreadsheets for reporting”.
  • Collaborative/Team Skills – like “active listening skills and note taking”.
  • Personal/Self-leadership Skills – like “how to manage time more effectively”.

Regardless of the response you get, this question sends the right message – you want to see them improve themselves.

5. Where Do You Want to Be in Three Years?

This is the “future” conversation. It shows your report you care about their career.

This question takes discipline to ask. Why? Because most of us live in the present both leader and follower.

Step away from the pressure of today’s drama and fire’s you’re fighting.

Instead, spend time discussing where your reports want to be. Show them you care about their future even if they have no idea how to answer this question.

Your reports have goals, be sure you are helping them achieve them.

So what questions do have in your toolbox?

If your toolbox is looking a little empty. Why not take these and use at least one of them every week for five weeks.

You might be surprised what you learn from your reports.

Filed Under: Connected Leader

Mike Wagner

I'm the Founder and President of White Rabbit. As a Speaker, Trainer, and Facilitator I strive to release the creative wisdom and capacity of everyone I serve. Keep Creating!

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