Split into two beautiful sections. First when you talk to people directly, second when you talk to people about other people (ie those you are trying to hire).
Talking to People
Maintain eye-contact.
What do you like to do?
What do you not like to do?
Tell me something that's truth that nobody agrees with you on.
What was the last thing you learned about yourself?
Follow up:
How did this learning came to you?
How do you apply this in your life?
What are you afraid off when you join a new social/work group?
What makes you come to work?
What is easy?
What challenges you?
How do you learn?
What are you most proud of in your life?
Follow up:
How about in your career?
What has been your biggest loss?
Follow up:
What was your biggest failure?
What is the biggest failure you have been a part of?
What kinds of people do you want to meet right now?
Follow up:
What's something you want to receive from the group?
And, what's something you can give to the group?
If you could meet anyone you wanted to who would it be?
What problems interest you? What problems are you looking to solve?
Follow up:
In here (were we to hire you)?
In your life?
What problems do you have?
Context: Understand what the person perceives as problems.
What do you want to have happen to the business?
Context: Useful for executive hires.
Talking to Co-Founder / Long-term Project Members
Setting up expectations with people you'll have to be tight like criminals in a shared cell.
Why do you want to do this startup?
What are your personal goals here, both financial and non-financial?
What are your long-term goals in life?
What is your overall life plan and how does this startup fit into it?
Are there pressures in your life that you’re dealing with now?
Who would you pick to start the company with if you could pick anyone in the world?
What makes you most excited about working with me?
What makes you concerned about working with me?
What’s the best way for me to give you feedback?
When you feel stressed, do you tend to want to talk about what’s going on or avoid talking about it?
What environment do you work best in?
What can we do to help you create it?
How will we divide responsibilities?
Who will be CEO?
What will our roles and titles be?
We should have a plan for what you’ll each work on for the first 6-12 months.
How will we split up equity?
Where will the company be based?
Where will we each live?
Will we work together in-person or remotely?
How do we pick the idea to work on?
If that idea doesn’t work out, are you willing to change the idea?
Are you only interested in working on ideas in certain areas?
What needs to happen for each of us to go full-time (quit other jobs or school commitments)?
ie: We’d have to raise at least $xx from investors, we’d need to validate the idea with a paying customer
What is your personal financial situation?
Are you willing to work for free and live on your savings? For how long?
If you'll need a salary to work on this full-time (either now or at some point), how much do you need to feel comfortable?
Will either of us put money into the company?
What will our typical working schedule be?
what days we work, what hours / day, etc?
How long do we want to keep that up?
Are there any things outside of work that are important to you to make time for?
What is important to you when building a team?
building an in-person vs remote company
having certain cultural values
having a particular approach to hiring or managing people
What will we do if we’re having trouble agreeing on an important decision?
What will happen if we decide we don’t want to work together anymore?
How would your friends or colleagues describe your strengths and weaknesses?
Do reference calls on each other.
Meet in person
Do a trial project
Meet friends / partner
What are you proud of having accomplished (can be work-related or not)?
What do you do with your free time?
What are your hobbies and interests?
One of the surprising things about successful co-founders is how consistently they have overlapping outside-of-work interests.
What are companies, founders, or products you really admire?
Are there any you want to model this company after?
What were your experiences like at your past jobs or past startups?
What did you like and not like about how the companies were run?
What lessons did you take away?
Have you worked with a co-founder previously? What was that experience like?
How have your experiences shaped your values?
What kind of work is so fun for you it doesn’t feel like work?
What kind of work do you avoid doing?
Talking to People about Other People
When doing due diligence. Apply before starting a business relationship. The higher the position, the more trust you need to have.
How does this person compare to the best you’ve ever seen in the role?
Follow up:
What is something that [candidate] is better at than anyone else you've worked with in this role
How many people have you worked with in [candidate’s] role/level?
How would you rank [candidate] among their peers?
What is something that [candidate] is better at than anyone else you've worked with in this role?
What type of advice would you go to [candidate] for?
On a scale of 1 - 5 (where 5 is absolutely perfect), how would you rank this person?
I stick by 1-5 rating, without half-sizes. Challenge an easy five by calling it "absolute perfect."
Follow up:
On a scale of 1 - 5, how do you rate XYZ on [specific trait or ability]?
What is the reason you did not rate XYZ (insert a number that is 1-2 points higher/lower)?
Can you tell me about a project that would have failed without [candidate]?
What is your most memorable experience working with this candidate?
Follow up:
How about when not working?
Tell me something about CANDIDATE that might not be listed on their resume or LinkedIn.
Would you rehire this person?
Look for enthusiasm when they talk about the candidate more than the answer itself.
Follow up:
On: "Yes." - Ok, why haven't you?
Would you rehire them for the same role? For a different role?
Would you invest your own personal money in this person? Why or why not?
What was the context of why you stopped working together?
Can you share an experience where [candidate] really blew your mind?
Follow up:
What is the candidate’s superpower?
What themes do you see in the candidate's feedback and 360 reviews?
What was an experience where you saw the candidate grow?
Follow up:
What might still be the candidate's growth areas?
If you were to design an ideal role for this person, what would it be?
Do you have any examples of times when the candidate demonstrated grit? Not giving up?
Explain the role at length and what success looks like in the first year. Do you think that [candidate] will thrive in that position?
Tell me about a time when you saw this leader build a new team.
Follow up:
They said they did it at the company. Can you tell me what you observed?
What was something unique about this candidate's team versus other teams?
Does [candidate] thrive as a team player or a lone wolf?
In which kinds of projects or work is [candidate] most effective?
Follow up:
Which situations are more challenging?
What causes the candidate stress or friction?
What environments do they thrive in, and where would they be less effective?
What "special treatment" helps [candidate] do their best work?
Can you tell me about a time that the candidate missed a deadline?
How does the candidate deal with giving and receiving criticism?
Follow up:
How does this person deal with differences in opinion?
Can you share someone who maybe doesn’t necessarily get along with [candidate] as well as you do? Why do you think they don’t mesh well?
What was [candidate’s] reputation within the organization or department?
Among customers?
How do you think I can best support this person to make sure they thrive here
Follow up:
How do you build trust with this person?
How would I know when [candidate] is unhappy?
What motivates this candidate?
Moving In - Moving Out
Finding a new place to live. Renting or buying, you want to ask a few questions of the owner or the current tenants.
