Guide to interviewing your future manager before deciding where to work

“Can you tell me what resources you’ve used to learn to become a better manager?”

“Why did you join this company?”

“What will be the worst thing about being managed by you?”

“What do you want from life and what are you doing to get it?”

“What companies were you deciding between when you joined this company? Why did you pick this company? How do you feel about the decision?”

“What is one thing that makes you think this company is going to do really well?”

“Can you tell me about a time when you were impressed by the CEO?” (The earlier stage the company the more relevant this is, in later stages the CEOs skill will be evident in the company’s performance)

At the end of your interview process, you need to know the answers to the following questions:

• Are there people in this group that I want to be working with in 20 years? (Before asking this question, make sure you give people a chance to show their interestingness, either by looking up their profiles/websites online, or asking them many questions when you meet them)
• Do I respect and admire the people I’d be working with/for? (Charlie Munger)
• Added December 20 2015: As an example, a large factor of this for me would be assessing how much and how quickly the person is learning. One simple instantiation of this is to ask both the CEO and your future manager what books they’ve read in the past 6 months, and who they receive advice/mentorship from.
• Does the world/people want this, and will they continue to want it over the next 10+ years? (Big difference between what is valuable and what people want. i.e. perhaps reading for two hours a day is more valuable than spending two hours on Facebook, but looking at the numbers would indicate most people ‘want’ the latter more)
• etc.

Practically, that means looking up the bios of the people who are interviewing you, and seeing what you might admire about them. Then, give them a chance to talk about these things by asking about them!

This is especially true for the CEO in early stage, pre-product market fit companies. If you’re bold enough, ask the CEO to see their calendar for the past week. Perhaps even ask to talk to one of their investors, and then use the following guide to evaluate the person: http://blog.eladgil.com/2013/03/reference-check-candidates.html (e.g. How would you rank Sarah relative to other people you have worked with in terms of raw productivity? What percentile would she fall under? → How would you rank CEO relative to the other CEOs you’ve worked with in terms of XYZ? What percentile would they fall under?)

Is this awkward? Yes.

Will it help you make a better decision on how you spend ~50% of your waking hours over the next X years? Yes.

Something to avoid: Not getting enough information
Let’s say that you know your #1 factor on how you are going to make your decision.
It’s “which company has the people that I want to be working with for the next 20 years.”

For each of your company options, don’t stop asking/researching until you have the data!
Either 1) they don’t convince you, so you shouldn’t join or 2) they do convince you, so it remains an option. Avoid outcome 3) you don’t ask, and you don’t know!
In fact, if you think your hiring manager/contact is nice and rational and doesn’t mind questions, you can consider telling them what you are trying to optimize for, directly!

A bad outcome is one where you get 4 offers, but none of the companies knew that you weren’t thinking of doing something else, so they didn’t help you realize why they were your best option, and so you make the wrong choice.