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Team questions

28 Strategic questions to ask to help you manage your team better

One of the main benefits of asking regular questions with your team is that you create an environment where the team is comfortable to share and discuss ideas and problems that affect both their performance and that of the team.

Arjun Rajkumar

November 19, 2024

  • Aim to understand Even though you are the manager, do not speak from a position of strength where you try to "win" the argument. Instead, aim to explain and understand the information.
  • Learn Assume everyone in your team has something to teach you, that you can learn from
  • Open ended Be open ended and invite pushback.
Before we get into the specific type of questions to ask, here are two important "rules" for getting better answers to your questions: 
1. People in your team should be allowed to and encouraged to question the status quo - i.e. just because something has been done a certain way, does not mean it cannot be questioned.
2. It should be easy for the team to give feedback - i.e. your team members should be able to answer your questions asynchronously without having to schedule a meeting.

Not all these questions will be applicable for you. Start by asking a few questions from each of these below to start managing your team better. Most of these questions will seem simple, but the answers you get from them will provide a lot of insight into what is working well, and what's been accomplished. Ideally aim to ask these questions one a week or once a month. It's also important to ask these questions asynchronously as you are giving them time to think before answering.

Questions for finding out what is working well:
1. What did you get done?
2. What work are you the most proud of?
3. Are there any accomplishments that you think were not celebrated properly?
4. Were there any unexpected wins? How did you get there?
5. What is the one thing you think our organization is doing well?
6. What challenges did we overcome that we should celebrate?
7. What's working better now than it was a month ago?
8. What changes have made the biggest positive impact?
9. What's an example of great teamwork you've seen?
10. Who helped you succeed this week and how?
11. What's something valuable you learnt from a recent project?
12. Which of our recent successes can we build on?

Questions for finding problems affecting your team:
1. What obstacles are slowing down your work right now?
2. Do you have all the tools and resources you need to do your job effectively?
3. Where do you feel we are spread too thin?
4. Which processes or meetings feel unnecessary or inefficient?
5. What bottlenecks do you keep running into?
6. What information do you wish you had earlier?
7. Are there any unclear expectations or responsibilities?
8. What is causing the most stress for you (or the team) right now?
9. Where do you feel you need more support?
10. What's holding you back from doing your best work?
11. Are there any skill gaps we need to address?
12. What training or resources will help you be more effective?

Questions for finding out upcoming work:
1. What are your goals for the next week/month?
2. What do you see as the most important priorities for the next week/month?
3. Which deadlines or milestones are you going to focus on next?
4. What support or resources will you need for accomplishing your upcoming goals?

Remember to give your team enough time to think while they answer these questions. 

Don't ask these questions in person, instead get them written down.
Select one or two questions from each of these groups and ask them regularly so that the team is aware of what is expected of them.

Automate status reports

2-3 days a week, or maybe once a week, depending on the schedule you choose, everyone on your team shares their status updates and any problems without wasting unnecessary time in a meeting.

Your team members will appreciate starting their week seeing everyone else’s accomplishments and goals, and ending it with sharing their own - and everyone in your team starts to see the bigger picture of what's happening.