5 Questions You Should Ask Your Team Members Every Month

Being a leader is about understanding what is going on around you.

In the military, it is called ‘Situational Awareness,’ Often, the people with the most pertinent information about the situation are those working for you.

Questions are powerful tools, and knowing how to wield them precisely is key to becoming a better leader.

How to ask?

If it’s about asking the questions, how do you ask the right questions in the right way?

  1. Ask these questions like you care & want to know the answers. You’re not reading from a script; ask with authenticity.
  2. You asked, so be prepared to hear answers that you may not like, but time to listen — openly and honestly.
  3. The answer you need may not happen the first time you try. But if you ask sincerely and humbly, you will build trust & confidence. So ask regularly, and the quality of the information you gather will improve.

Read about the six things you need to communicate

What to ask?

1. What is your biggest accomplishment this month?


  • This question provides a sense of forward motion and progress.
  • When workers relate positive information, it gives them a sense of personal accomplishment.
  • Answers give you both oversight and performance improvement potential.
  • You have a measure if people contribute in the ways you need them to.

2. What’s your biggest challenge right now?


  • You can begin to understand where the worker is struggling.
  • You can learn about pinch points in an employee’s process, work, or company culture.
  • It puts your conversation into problem-solving mode because when you know where your team member is struggling, you can do something about it.

Read how not to Eff Up talking to your people.

3. What things should we do differently, or what processes can we improve?


  • People understand that things can be done differently, so being open to feedback from ‘below’ can be invaluable.
  • When team members recognize that they can provide value beyond their job description, you can harness this power to improve the company.
  • You may not always act on every suggestion, but you’re going to discover some things that genuinely need to change.

4. What resources would be helpful to you right now?


  • By using the word “resources,” you’re opening the door beyond money.
  • What you might think employees need is often different from what they want.
  • Don’t assume the solution is more people or money, trust the people working on the project to understand what will solve the issue.

Read about how to listen.

5. Is there anything I can help you with?


  • It lets your employees know you’re a human and care about their success and well-being.
  • It allows you to understand any personal factors that may influence their work.
  • It demonstrates you’re a real human being.
  • You improve your working relationship with them by showing sincere interest in their life and improvement.