Here are some of my favorite questions to get the conversation moving:

• Identify: These questions focus on what really matters for your report and what topics are worth spending more time on.

What’s top of mind for you right now?

What priorities are you thinking about this week?

What’s the best use of our time today?

• Understand: Once you’ve identified a topic to discuss, these next questions get at the root of the problem and what can be done about it.

What does your ideal outcome look like?

What’s hard for you in getting to that outcome?

What do you really care about?

What do you think is the best course of action?

What’s the worst-case scenario you’re worried about?

• Support: These questions zero in on how you can be of greatest service to your report.

How can I help you?

What can I do to make you more successful?

What was the most useful part of our conversation today?

Much of our work is helping leadership teams formulate the right questions. Once they get the questions right, the answers tend to appear.

KEY QUESTION: Are the stakeholders (employees, customers, shareholders) happy and engaged in the business; and would you “rehire” all of them?

1. Who/Where are your (juicy red) core customers?

1. What are you really selling them?

1. What are your three Brand Promises?

1. What methods do you use to measure whether you’re keeping those promises? (We call these the Kept Promise Indicators, a play on the standard definition of KPIs.)

So often I’m called in to help lead conversations about mission, value, and purpose. When, really, the only questions that matter are those that tell us who we are and wish to be.

• How would our organization respond were we to hear all the things that are being said, regardless if they are being said with words or deeds? 

• What does it mean to be a leader at our organization? 

• What does it mean to be grown, a fully actualized adult? 

• How would we feel if our children were to work for the company we’ve created or the team we lead? 

• How has the unsorted baggage of what has happened to us shaped who we are as leaders? 

• When our employees and colleagues leave our sides and our company, what do we want them to say about our time together? 

• What do we believe to be true about the world? 

• What do we, as a community of people working toward a common goal, believe the world needs?