Every Monday morning at Nest, that’s how my management meetings started: Who are the great people we want to hire? Are we making our hiring goals or retention metrics? If not, what’s the problem? What are the roadblocks? And how is the team doing? What issues do people have? How are performance reviews going? Who needs a bonus? How are we going to celebrate these accomplishments so the team feels valued? And, most importantly, are people leaving? Why? How are we going to make this job more meaningful and fulfilling and exciting than anything else out there? How are we going to help our people grow?

Only after we got through this important subject could we move on to anything else—like what the hell we were building.

The managers on the team saw it was important to me, so that’s how they started structuring their weekly meetings with their teams. It became the Nest way. People first. Always.

What you’re building never matters as much as who you’re building it with.

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?

UNDERSTANDING YOUR CURRENT TEAM

• What are the first three adjectives that come to mind when describing the personality of your team?

• What moments made you feel most proud to be a part of your team? Why?

• What does your team do better than the majority of other teams out there?

• If you picked five random members of your team and individually asked each person, “What does our team value?” what would you hear?

• How similar is your team’s culture to the broader organization’s culture?

• Imagine a journalist scrutinizing your team. What would she say your team does well or not well?

• When people complain about how things work, what are the top three things that they bring up?

UNDERSTANDING YOUR ASPIRATIONS

• Describe the top five adjectives you’d want an external observer to use to describe your team’s culture. Why those?

• Now imagine those five adjectives sitting on a double-edged sword. What do you imagine are the pitfalls that come from ruthless adherence to those qualities? Are those acceptable to you?

• Make a list of the aspects of culture that you admire about other teams or organizations. Why do you admire them? What downsides does that team tolerate as a result?

• Make a list of the aspects of culture that you wouldn’t want to emulate from other teams or companies. Why not?

UNDERSTANDING THE DIFFERENCE

• On a scale from one to nine, with nine being “we’re 100 percent there” and one being “this is the opposite of our team,” how close is your current team from your aspirations?

• What shows up as both a strength of your team as well as a quality you value highly?

• Where are the biggest gaps between your current team culture and your aspirations?

• What are the obstacles that might get in the way of reaching your aspirations? How will you address them?

• Imagine how you want your team to work in a year’s time. How would you describe to a report what you hope will be different then compared to now?

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?

But are we missing something here? Is the separation we perceive between work and life helping or hindering us in our quest for the good life? What if the value of work—even work we dislike—lies not just in getting paid, but also in the moment-to-moment sensations of being alive in the workplace, and the feeling of vitality we get from being connected to others? What if even the most ordinary workday presents real opportunities for improving our lives and our sense of being connected to the broader world?