45 Pre-Interview Questions from Brad Jacobs

One of my favorite hobbies is reading autobiographies of entrepreneurs. The most recent one I read is by Brad Jacobs, the founder of United Rentals, United Waste Systems, and XPO Logistics. Brad’s style and journey differ from the ones I’m accustomed to reading, where the entrepreneur invents a new product and shares the stories of building a huge business. In Brad’s case, his specialty lies in identifying large markets that need consolidation and technology. He focuses on building great teams, raising tremendous amounts of capital, and rolling up the market.

His strategy and approach resemble a mega search fund, where the idea is to secure a pool of capital and then enter a market by acquiring existing businesses. One of my favorite takeaways from the book is where he talks about the importance of hiring executives. His process involves spending 8 to 10 hours with each candidate and gaining buy-in from the rest of the executive team through interviews and exercises. As part of this process, he has candidates fill out 45 questions before the interview.

After reading these questions, I realized they are ones every entrepreneur should consider incorporating into their recruiting process. Here are the 45 pre-interview questions from Brad Jacobs.

Strengths

1. List some adjectives or phrases that sum you up, that get to your essence.
2. When you look at your professional self in the mirror, what do you see?
3. What motivates you? What are you trying to accomplish at this point in your career?
4. What do you consider to be your biggest career accomplishment(s) so far?
5. What are your biggest professional strengths?
6. What’s been the high point of your career so far?
7. What parts of your jobs have you liked the most?
8. What’s your favorite professional activity?
9. Name five reasons for your professional success.
10. What do your subordinates think are your strengths?
11. Who was your favorite boss and why?
12. What positive things might your bosses and colleagues say about you?
13. What’s the most significant praise you’ve received in a performance appraisal in the last five years?

Areas for Improvement 

1. What are some of your biggest professional weaknesses or areas for improvement?
2. What’s been the low point of your career so far?
3. What have been some of the biggest mistakes you’ve made, and what did you learn from them?
4. What’s the most significant criticism you’ve received in a performance appraisal in the last five years?
5. Who was your least favorite boss and why?
6. What negative things might your bosses and colleagues say about you?
7. What do your subordinates think are your weaknesses?
8. What have been the biggest frustrations or failures in your career?
9. If you could change on thing about yourself, what would it be?

Miscellaneous

1. Describe your character.
2. What quality do you admire most in people?
3. What parts of your jobs have you enjoyed the least?
4. What was the toughest decision you’ve ever had to make in business? How did you handle it? What did you learn from it?
5. What was your favorite job and why?
6. What was your least favorite job and why?
7. What defect should a professional never allow themself to have?
8. How do you manage your personal/professional balance?
9. Who in the business world do you admire and why?
10. Explain the reason for your separation from each one of your jobs.
11. In an ideal world, describe your perfect job.
12. Name three of your biases.
13. What your working habits (a typical day and week)? How many hours do you usually work? How much do you travel for work?
14. What do you think it takes to be successful in the job you’re applying for?
15. On a scale of 1-10, how well do you think your skill set matches what’s required to succeed in this job?
16. What would it take to make your answer to the previous question a 10?
17. On a scale of 1-10, subject to acceptable compensation, how much do you want this job?
18. What would it take to make your answer to the previous question a 10?
19. What are the top three reasons why you’re interested in this position?
20. Would you accept this job if it were offered to you?
21. What more do you need to know in order to decide if this role is right for you?
22. What questions or comments do you have for us?
23. Why should we hire you?

Bonus ending question: What have been one or two of the happiest moments of your professional life so far?

As an entrepreneur, the next time you’re hiring for a key position, consider using some or all of these questions as part of your process. Entrepreneurs are wired to move fast and get things done, but hiring is one area where it pays to slow down just a bit and get it right.