1. What is the set of problems that will be resolved 90 days after your new hire comes on board?
2. Who are the most important internal and external customers for this role? What do each of them look to this person to deliver?
3. How will the new person in this role make your life easier?
4. What’s your story in this company? When did you arrive, and what has happened for you since then?
5. What are the biggest goals for the company this year?
6. What is this new person’s role in reaching those goals?
7. What are the biggest decisions that this new person will make on his or her own?
8. What is the story behind this job opening — is it a new role, or has someone been promoted or left the organization, or something else?
9. Apart from the formal responsibilities, what is the informal role of this person on the team? Some roles require an air traffic controller, some require a cheerleader and morale-booster, some require a drill sergeant. How would you describe this one?
10. What are the yardsticks your new hire will pay the most attention to? Why are those milestones important?