As I’ve grown my agency, I’ve learned that it’s no longer about ‘how’, but ‘who’ to hire.
Here’s a list of questions that I’ve compiled over the years. These are taken from people such as Vinod Khosla, Chamath, various hiring books and more.
One that I just picked up recently:
‘Can this person become a top 3 player in the organization?’
Feel free to swipe what you like and comment with your favorite questions below:
APPENDIX: LIST OF KEY QUESTIONS TO ASK DURING AN INTERVIEW
A.) Are they HUMBLE, HUNGRY and SMART? (note: you can only really see ‘humble’ through their reference checks and how excited they are)
Sam Ovens/elon musk question: tell me youe story Tell me all the key milestones in your life and each decision you had to make and why you chos ethat path - give them 5 minutes and ask 'why?'.
whats the most impressive thing youve done in your career?
What are your 3 best ideas in relation to [JOB]?
Chamath question: Think about something you deeply love. Take a few minutes to prepare and then teach it to me in a few minutes. <-- shows if they are learners/thinkers/teachers
Have you worked for a startup before?
What are your daily habits? (leveling up/discipline)
What is that you do to practice your craft daily? (leveling up)
What do you do on the weekends? (show me leadership potential and true motivations)
What are they passionate about - teach me
If they had $100M and charity and family are taken care of, what would they do w the money
If they had $10M and they had to invest it into one company, whath would it be?
What's the kindest thing this person has done? (humility)
Is this person a bar raiser?
Do I think this person is smarter than me?
Would I work for this person?
What's the most impressive thing this person has done in their career?
Would I hang out with this person?
what’s most imporant to you
why single grain?
Pick a project you’re proud of that took 3-9 months. Walk me through it from beginning to end. I’ll ask questions along the way.
Tell me about your favorite marketing campaign. Walk me through your strategy for it.
How would you improve our marketing?
Management - tell me about someone who you were NOT able to reach their fullest potential?
Does this person have a track record of staying?
Has this person been promoted multiple times at their current job? Previous jobs?
What things do you think are important to do every day? What are your habits?
focus on 2-3 topics but go deep, starting with what professional achievement are you most proud of? Challenges? Why are you proud of this? // biggest professional regret
Tell me about a time where you [SOLVED KEY NEED WE HAVE]? *keep asking for all these needs*
Give me an example of adversity you’ve had to overcome and how you pushed through?
What's your story? Then tell mine
If more ambigious: What do you currently do for your company? Want to do that for us?
What's your most impressive win?
List of key questions to ask during an interview
What's one thing people commonly misunderstand about you?
What's your greatest strength? What's your greatest area for improvement?
What's an epic hiring close you made recently?
Will people follow you here?
What do you like about [COMPANY]?
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?