1. What’s the biggest change your group has gone through in the last year? Does your group feel like the tough times are over and things are getting better, or are things still pretty tough? What’s the plan to handle to either scenario?
2. If I get the job, how do I earn a “gold star” on my performance review? What are the key accomplishments you’d like to see in this role over the next year?
3. What’s your (or my future boss’) leadership style?
4. About which competitor are you most worried?
5. How does sales / operations / technology / marketing / finance / customer service statistics work around here? (I.e., groups other than the one you’re interviewing for.)
6. What type of people are successful here? What type of people are not?
7. What’s one thing that’s key to this company’s success that somebody from outside the company wouldn’t know about?
8. How did you get your start in this industry? Why do you stay?
9. What are your group’s best and worst working relationships with other groups in the company? What are the pain points you have to deal with day-to-day?
10. What keeps you up at night? What’s your biggest worry these days?
11. What’s the timeline for making a decision on this position? When should I get back in touch with you?
12. It’s been tough economic times, and every position is precious when it comes to the budget. Why did you decide to hire somebody for this position instead of the many other roles / jobs you could have hired for? What about this position made you prioritize it over others?
13. What is your reward system? Is it a star system / team-oriented / equity-based / bonus-based / “attaboy!”-based? Why is that your reward system? What do you guys hope to get out of it, and what actually happens when you put it into practice? What are the positives and the negatives of your reward system? If you could change any one thing, what would it be?
14. What information is shared with the employees (revenues, costs, operating metrics)? Is this an “open book” shop, or do you play it closer to the vest? How is information shared? How do I get access to the information I need to be successful in this job?
15. If we are going to have a very successful year in 2016, what will that look like? What will we have done over the next 12 months to make it successful? How does this position help achieve those goals? (This question helps show your ability to look beyond today’s duties to the future more than a year away.)
16. How does the company / my future boss do performance reviews? How do I make the most of the performance review process to ensure that I’m doing the best I can for the company?
17. What is the rhythm to the work around here? Is there a time of year that it’s “all hands on deck” and we’re pulling all-nighters, or is it pretty consistent throughout the year? How about during the week / month? Is it pretty evenly spread throughout the week / month, or are there crunch days?
18. What type of industry / functional / skills-based experience and background are you looking for in the person who will fill this position? What would the “perfect” candidate look like? How do you assess my experience in comparison? What gaps do you see?
19. What is your (or my future boss’) hiring philosophy? Is it “hire the attitude / teach the skills” or are you primarily looking to add people with domain expertise first and foremost?
20. In my career, I’ve primarily enjoyed working with big / small / growing / independent / private / public / family-run companies. If that’s the case, how successful will I be at your firm?
21. Who are the heroes at your company? What characteristics do the people who are most celebrated have in common with each other? Conversely, what are the characteristics that are common to the promising people you hired, but who then flamed out and failed or left? As I’m considering whether or not I’d be successful here, how should I think about the experiences of the heroes and of the flame-outs?
(from email by Marc Cenedella)