Catch Up Questions

What is one thing you would recommend I do to be a better communicator?
What do you need most from me right now?
In which areas of your work would you like more or less direction from me?
At what point in the past week were you most frustrated with or discouraged by your work? What can I do to help you manage that?
In what ways, if any, can I provide better or more feedback to help you succeed?
As your manager, what would you like me to stop, start, or continue doing?
What would you like to see change about these discussions? How could we make them more useful for you?
As your manager, what could I do more of to help you make progress toward your goals?

What aspects of a given project make you excited and motivated to work on it? What aspects are less interesting for you?
A year from now, what do you hope to have accomplished that will help advance your career?
Are there any projects you’d really like to work on if you were given the opportunity?
What can I do to help you grow in your career?
Who in the company would you like to learn from? What do you want to learn?
What is one aspect of your job you would like more help or coaching with?
What are the new things you learned at work lately? What are the areas you want to learn about?
In what ways is your current work helping to advance your career? In what ways is it hindering advancement?
Which of your career or development goals is it hardest for you to focus on right now?

What are three things that might make your job more enjoyable? How might we experiment to try to make at least one of these a reality?
What sorts of behavior shifts might help us improve team dynamics?
What part of your job do you wish you didn’t have to do?
Do you feel over-worked, under-worked, or just the right workload?
Which of your recent accomplishments are you most proud of? Do you feel appreciated for it?
What is your least favorite part of your role? How might that affect your overall performance?
What’s a recent situation you wish you handled differently? What would you change?
What has either been helping you, or preventing you from doing your best work lately?
What aspect of your current work is most interesting to you? Why?
What’s an area of your work you want to improve? How can we work together on that?
What might be holding you back from growing in your role?
What’s your No. 1 problem right now? How are you feeling about it?
What aspect of your role keeps you learning and feeling challenged at work?
What do you want to do but don't feel like you have the time for?
What are your biggest concerns about your current project(s)?
How would you characterize the dynamics and working relationships on our team? What works well and what doesn't?
How does your work align with your personal purpose?

How can I improve the situation without putting myself at the center?
Do you have any advice on how I can manage my relationship with XYZ?
Does XYZ get along well with others? Wondering if the problem is really with them or if it’s really with me.

What's one thing that would be outrageous not to do in the next quarter, as a team or as a company?
Which of your peers are you least comfortable giving feedback to? Why do you think that might be?
How would you say we're working together as team? What makes you say that?
Are there any aspects to how work gets divided among team members that you would change?
Which areas would like more feedback on?
Are there any meetings or discussions you feel you should be a part of that you’re not? Are you included in any you don’t want to be a part of?
What kinds of resources do you wish you had access to, that you don't have right now?
Who on the team inspires you? Whose opinions do you respect? What have they done?
What are we not doing that we should be doing, as a team or a company?
What kind of communication or information do you wish you had more of?
What's the biggest opportunity that we aren't thinking about, as a team or as a company?
How would you describe our team's communication style? What could we do to improve it?

Have you noticed any changes to your stress or energy levels lately?
How have you been maintaining meaningful connections with your work friends and colleagues while working remotely?
What changes should we make to improve how our team is communicating and collaborating?
What new challenges have come up from working remotely that you didn't face while working in the office?
What projects or tasks are being blocked or impacted by working remotely?
Do you have all of the access and equipment you need to work effectively from home?
What new challenges have come up from working remotely that you didn't face while working in the office?

Stepping back, what aspects of your work routine do you think are working best? What aspects could use rethinking?
What does an ideal day of work look like to you? What's blocking you from having more of those?
What were your biggest time-wasters or roadblocks since we last met?
How can we better connect your work to your personal purpose?
What should we change to make these check-ins most useful for you?
What do you do when you feel low energy or unmotivated?
What's one thing you would change about your work that would positively impact your well-being?
What are the most important things you will focus on before we meet next?