List of key questions to ask during an interview
- 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?
- 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?
- 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?