- How much is this project going to cost when we are done?
- How long is it going to take to deliver all the promised outcomes from the project?
- How many people do you need to get the deliverable out the door for the estimated cost and estimated completion date?
- What is going to cause your project to get in trouble?
- How can you assure you are actually making progress in some way meaningful to the people funding the project?
Asking (and getting the answers) to these questions open up a series of smaller, more minute details about projects that people often overlook or forget about. They are larger questions which allow for the conversation to take place around the likelihood of project success.