Here's the biggest mistake professionals make when beginning a project with a client or team: They don't ask enough questions.

You've been in the typical start-of-project meeting: Someone makes a presentation with dozens of slides and hundreds (well, it seems that way) of charts. Everyone nods . . . or nods off. And you leave the meeting not really understanding how the project will work or what's expected of you.

That's why you need to be the guy (or gal) who asks a lot of questions. As Jagdish Sheth and Andrew Sobel write in their book, Clients for Life, "The really good professionals ask great questions. Often they enable solutions rather than supply them."

Why don't professionals ask enough questions? Here's Mr. Sobel's take: "First, they are afraid. They lack boldness in asking questions because they don't want to come across as being aggressive or overly inquisitive. Second, they don't think enough before they speak. It takes time and investment to come up with really good questions to ask someone, until you get practiced at it. Finally--and this is the most important reason--in our culture we believe we impress others and demonstrate our worth by being "smart" and having all the answers."

Obviously, you should develop your own questions, tailored for the specific situation. But here are 15 great questions (or question sets) to get the party started:

  1. What are the objectives? How do you define success?
  2. If the project doesn't succeed, what are the implications?
  3. Why is this project so important? What is the case for change?
  4. What are the key milestones? What are the most important dates?
  5. What are the most important decisions that need to be made? What will prevent us from making those decisions?
  6. What are the biggest obstacles to getting this done?
  7. Who are the key stakeholders? Who's the owner/sponsor? Who influences but doesn't own? Who has the potential to be an obstacle?
  8. What are the project's greatest assets?
  9. How can we best leverage those assets?
  10. What are the most important areas we should always focus on?
  11. How much risk are you willing to take to accomplish this?
  12. What barriers have you encountered in the past about this issue?
  13. What keeps you up at night about this?
  14. What topics haven't we discussed? What topics would you rather not discuss?
  15. What is your personal passion about this project? What will this mean to you when we succeed?

Ready to ask great questions? (Oops, there's another one.)