The art, science, and labor of recruiting: Appendix

List of key questions to ask during an interview


Job performance:

  • What were their key contributions?
  • Where have they made the most difference in each job?
  • What would they do over again?


Feedback from others:

  • What did their boss think of their job performance?
  • What did peers think?
  • What did direct reports think of the job they did?
  • What are their strengths and weaknesses?
  • What would others say about you?


Domain Knowledge

  • What do they think of other companies’ strategy in the industry?
  • What do they think of other great companies outside the industry?
  • What magazines/blogs /news sources do you read regularly?
  • Describe a problem in their functional area of expertise: What would they do? When? How long do they take to get to decide? Who would they ask for help?
  • How much do they know areas that they did not directly work on?
  • If they could have any job, which startup would they work for? Why?
  • What business opportunity would you pursue if you got $10 MM to invest in one startup?
  • In which business opportunities, if any, would you defy conventional wisdom and stay away from investing?
  • What would be a game changer in their business?


Hiring and Building Teams

  • Who is the best manager they have worked with and why?
  • Who is the best technologist that they have worked with?
  • What do they look for in a potential new hire for these types of positions or prioritize in key hires?
  • What is their “model” hire for a position?
  • What do they look for or prioritize in a candidate or in each job they had?
  • Who was their best hire in each job?
  • Who was the most difficult hire they made?
  • How much new hiring did they do?
  • What kinds of questions do they ask potential new hires when they are recruiting?
  • What kind of recruiter are they? Maniacal (good)? Creative (good)? Is their style of hiring similar to your own or different? Are they process-oriented? Do they depend on HR or recruiters (bad)? Are they aggressive? How good a salesman are they for new hires? How aggressive, persistent or imaginative is the candidate?


Motivation, Thoughtfulness and Critical Thinking

  • What do they look for and what do they worry about in various direct and related businesses?
  • What are they most proud of in each job they had?
  • Have they jumped to new areas? New companies? How risk-averse are they?


What they value in a position

  • If this role wasn’t around what would they ideally look for?
  • What other jobs are they considering? Why?
  • What other roles are they / have they considered? Which ones did they like? Why?
  • Which roles did they turn down? Why?


Performance in new role

  • What would they do in the first 90/180 days of this job?


Work Style

  • What is the hardest they’ve ever worked? Hardest job? Do they fire people when they need to? How much do they care about the firings?
  • How do they handle a crisis? What crisis or difficult situations have they been in? What did they do?
  • When have they fired people or motivated people, and what are the stories behind them? What are their greatest achievements in each job?
  • Describe a problem they’ve had. What did they do? What would they choose as a do-over in each job? How long did they take to get to a decision? Who did they / would they ask for help?
  • How would they define the job they would pursue if the current position was not open? What if their position was open at their favorite startup?
  • How do they answer questions they don’t know answers to?
  • How well do they think on the fly in new areas?
  • How do they make decisions? How do they make critical decisions in each job?
  • Ask them to describe a time they took responsibility for a failure? Why did it happen?
  • When have they shown leadership in a non-obvious situation?
  • How did they work with “hard to handle” people?
  • When did they make a bold decision? What do they consider bold?
  • Are they driven by gut instinct or process? Do they know when to use each?
  • Are they able to make both process-oriented and rapid-fire decisions?
  • Who is the best person they have worked with at a variety of levels (e.g., CEO, CFO)? Why?
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