Project Management

25 Questions To Consider Before Starting A New Project

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You receive an email where you read that you've been put in charge of a project. Your boss wants to sit down with you to talk through the details tomorrow.


What questions should you ask that will help set you up for success?


Consider these:

  1. Is there a clear, tangible objective to this project? If so, what is it?  If not, how can we make it clear and tangible?

  2. What is the most essential part of this project?

  3. How will we know we've succeeded?

  4. What happens if this project is not successful?

  5. How is this project tied to the greater organization?

  6. When is this project due?

  7. What are the key milestones that must be met?

  8. What is it about me that led you to choose me to lead this project?

  9. What are your expectations of me?  The team?

  10. May I share how I work best?  May we talk about how my workstyle lines up with your expectations?

  11. Who is the actual client?

  12. Who is the point of contact?

  13. Who is RACI (Responsible, Accountable, Consulted & Informed)?

  14. How does each RACI want to be communicated with, to what level of detail, and when?

  15. How will I be held accountable for this project?  

  16. Has this project been done before?

  17. What things should I do immediately to set this project up for success?

  18. What obstacles should I expect to find in completing this project?

  19. How high does the project compare with the other projects I'm working on?

  20. What support will I have in completing this project?

  21. What skills are necessary to complete this project successfully?

  22. What are the strengths and weaknesses of the team who will be working with me on this?

  23. How can I gain each team member’s commitment to see the project through to successful completion?

  24. How will this project be delivered?

  25. What should I have asked you that I didn't ask you?


Chew On This:

  • Which questions above especially stand out to you?





Ryan C. Bailey is President and CEO of an organizational effectiveness company that supports leaders in developing in-demand high performing teams




*This blog is an amalgamation of a few different clients.  No one single client is being singled out.