"Questioning", When the Team needs a Check-up

The goal of conversations like these is to understand the health of your team. As a leader, it is important to understand the expectations and goals of each team member and steward their time in the most effective way. When asking these questions it’s important to understand why you are asking each question. Asking follow-up questions to dig deeper is going to be important in understanding each individual. It is about having a conversation and listening intently.

Taking thorough notes in each conversation for later review is going to be key. These conversations may have to happen multiple times to get a full grasp of the true expectations and goals of each team member. gathering this information from new team members and keeping this information up to date and is going to be critical to maintaining a healthy balance for the team. Once this information is gathered from each team member, leadership can begin to make more informed decisions about the team. 

1. What is the most enjoyable thing about your role on the team? And, What is the least enjoyable thing about your role on the team?

Follow up: What is one thing you get to do every day that makes you happy? What is one thing you have to do at work that adds stress to your job? Where would you prefer to invest your time at work? What is something you wish you could do more of at work? What is something you wish you got to do less of at work?

This question is about figuring out what motivates each team player. You are trying to discover what gets them out of bed and into work every day. You are also trying to learn what about their job adds stress and what about their job adds joy. The answers to this question will inform how responsibility and tasks can be delegated to individuals on the team. 

2. What does a healthy work-life balance look like to you in the form of time commitment?

Follow up: What do you enjoy doing outside of work to feel rested and recharged? What ratio of travel do you prefer? What hours are you looking to work? How have you seen sustainability manifested on a team? How often do you like to see your family? How long does it take for you to recover physically and mentally from being on the road? What do you do to allow your mind and body to recover from a difficult work week?

This question is about gaining clear expectations from each team member. You are looking for a number in the form of desired time on the road and hours worked. Beyond that, you are trying to figure out how each person recharges so we can make space as a team for them to be able to do those things that give them energy. Diving into the specifics of activities, future trips, and desired time with family is key to understanding the unique needs of the team.

3. Tell me about the conditions you currently face at work, on job-sites, or in the office. Explain how you feel you fit in, or don’t fit in on the team. Describe a specific challenge or two you have faced recently and how you and your teammates navigated it.

Follow up: How have you overcome this challenge? What do you think made that challenge arise in the first place? What about your personality contributes to your strengths on the team? In what situation do you feel like you are the most effective at work? In what situation do you feel you are the least effective at work?

This question is the team’s oil check. This is a “TED” question: Tell, Explain, Describe. It is important to ask each part of this question to gain a rounded understanding. This is about understanding team culture through personal experience. You are attempting to understand how each team member sees themselves, their team members, and the team and a whole. You are looking for any personal pain or stress points. You are looking for any interpersonal or organizational conflict so it can be resolved. You are looking for any broken processes or damaged lines of communication that need repair. You are trying to understand how they currently operate on the team and if any adjustments need to be made so we operate more effectively individually and as a team.

4. What is a goal you would like the team to help you achieve this year? What is a goal you would like to help the team achieve this year?

Follow Up: Is there any sort of further education or certification you are pursuing? Is there something about what we do you would like to learn more about? Is there a personal goal that you would like professional support in? Are there any practical ways the team can support you? What is an area of the team you personally would like to do something about improving? What is something you would like to be empowered to do on the team?

This question is about goals and support. You are trying to find any practical ways the team can support individuals and the individuals can support the team. Getting a team to write their own goals is an effective way to have buy-in from everyone. Allowing the team to be a part of individual growth cultivates a spirit of collaboration and builds the trust needed for accountability. We are trying to understand what makes each individual tick in the long run. What are they pursuing? And if they are not pursuing anything, this is a good opportunity to figure out what can be delegated based on the desires and skillsets of the individual.