1. When you’re working on independent projects, how do you create structure and purpose? What places, routines, and interactions help you stay focused and on track?
2. When you’ve gotten stuck, have you ever tried self-distancing by reflecting on what advice you’d give to a friend or colleague in your position? How did it work?
3. How often do you work from home, and what do you see as the advantages and challenges?
4. How have you crafted your job? How would you like to craft it going forward—and how can you gain support from the people around you?
5. What would happen if your teammates all wrote out their projects for the year so everyone was on the same page?
6. What would it take to create a dynamic hierarchy in your team, where the person with the most expertise has the authority for a given meeting or task?
7. In your workplace, which people have earned status by demonstrating that they’re prototypical? What have they done to exemplify the group’s values?
8. How can you prevent the Peter Principle from trapping people at their level of incompetence?
9. If there are controlling bosses in your workplace, how can you convince them to give people more freedom?
10. Instead of waiting until exit interviews, have you ever tried conducting entry interviews to find out why people are joining your workplace and what their favorite projects have been in previous roles?