Don’t breathe down my neck!

  1. “Is there anything you’d like me to know about how this will get used?” (This reassures the boss that you understand the bigger picture of how the assignment fits into the overall strategy).
  2. “What’s your deadline?” (This one is pretty obvious but it’s always good to confirm it).
  3. “What’s the format that would be best for you?” (You can spare you and your boss unnecessary headaches by making sure your work gets delivered in the proper way).
  4. “Who/what resources should I approach with this?” (Let the boss know you can handle boundaries and political sensitivities and that you are thinking as strategically as they are).
  5. “Are there other precedents/models/prototypes for this you’d like me to build on?” (Sometimes the boss has done a project like this before, and if you build on, or at least reference their prior work, their anxiety will decrease immediately).
  6. “How long do you envision this taking?” (Sometimes the boss will tell you the deadline is Friday but they’re thinking to themselves that they would have it done by Tuesday. This question helps you discover that gap and gives you the chance to meet, or exceed, the boss’ expectations).
  7. “Given your other assignments for me, where should this one fit?” (This tells you the relative priority of the assignment and tells the boss that you understand where this assignment fits).
  8. “What should I make sure that I absolutely do (and do not do) on this project?” (This gives the boss confidence that you’re not going to step on any major land mines or miss something critical).



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Jonathan Mills

Jonathan Mills


Jonathan has spent over 30 years focusing his efforts on developing people throughout the world. He believes that people have the most impact when stretched.