Questions to Ask Michelle Obama

The questions

Open any question to see why it works.

1. 1

   What was the first job you had where you felt like an adult?

   An opener that skips the biography everybody already knows and asks for a moment instead. People almost always answer with a detail about money, a commute or a boss, and those specifics are where an interview starts to sound like a person talking rather than a subject being covered.

2. 2

   Who told you the truth when you were getting something wrong?

   It asks about the people around her rather than about her, which usually loosens the conversation. Notice whether the person named is family, a colleague or a friend, because that says more about how she makes decisions than a question about leadership style would.

3. 3

   What did practicing law teach you that you still use?

   This gets a craft answer, and craft answers are less rehearsed than legacy ones. Follow up on what she was good at, since lawyers usually distinguish between the parts they enjoyed and the parts they merely survived.

4. 4

   How did you know it was time to leave the law?

   Career changes get told as decisive stories after the fact, so push for the ordinary version: what the last months felt like, what she was afraid of, who she told first. That is the part listeners in the room will actually use.

5. 5

   When you moved into work that touched a whole city, what surprised you about how institutions really run?

   Ask about the machinery rather than the mission. People who have worked inside universities, hospitals and city government have concrete observations about budgets, turf and inertia that never make it into a keynote.

6. 6

   How did you choose what to work on once you were in the White House?

   The role has no job description, which makes the selection process interesting. Ask what she considered and set aside, since the rejected options reveal the constraints of the position better than the chosen ones do.

7. 7

   What did an ordinary Tuesday look like, hour by hour?

   Ask for the schedule rather than the feeling. The briefings, the travel, the moment the day stopped being hers: it is the part nobody outside that life can picture, and it produces details that no press answer covers.

8. 8

   What did you have to stop doing when you moved in?

   Driving, walking to a shop, standing in a queue. The lost ordinary things are the most concrete way to convey what that life costs, and they are usually the things people forget to ask about entirely.

9. 9

   How did you explain the cameras to your daughters?

   This is a parenting question rather than a political one, and it tends to get an unguarded answer. Follow up on what rules the family made for itself, because household rules are where abstract principles become practical.

10. 10

    What is hardest to explain to people who have never lived under that kind of attention?

    It invites her to describe a gap rather than defend a position. The answers people give to this are usually about time, about not being able to correct anything, or about other people's certainty, and any of the three opens a longer conversation.

11. 11

    What do you do with criticism aimed at how you look rather than what you said?

    Asked directly rather than sympathetically, this gets a method instead of a sentiment. Follow up on whether the method changed over the years, since most people describe an early response they later abandoned as too expensive.

12. 12

    How do two people with demanding careers decide whose turn it is?

    A question about logistics rather than romance, which is why it works. Ask for a specific negotiation they had, since couples remember particular arguments about moves and jobs far more clearly than they remember any general philosophy.

13. 13

    What do you say to someone who feels they do not belong in the room they are in?

    She has been asked versions of this before, so make it harder by asking for the sentence she actually says to one person rather than the advice she gives an audience. Advice for a crowd and advice for a friend are rarely the same.

14. 14

    What did you get wrong?

    Four words, no cushioning, asked once the conversation has warmed up. The temptation is to soften it with a preamble, which lets the answer soften too. What you want is one specific decision, not a category of regret.

15. 15

    Which of your projects did not go the way you wanted?

    Initiatives outlive the people who start them or they quietly do not, and the reasons are usually structural: funding, a successor, a change in the political weather. This is the question that gets you an honest account of how public work actually survives.

16. 16

    What is the difference between writing about your life and telling it out loud on a stage?

    Two crafts with different rules, and people who have done both are usually precise about it. Ask what a room lets her say that a page does not, and what she has to leave out of a live telling that a book could hold.

17. 17

    What did you cut from the book, and why?

    Every memoir has a discarded chapter, and the reason for cutting it is generally either that it involved somebody else or that it was not resolved yet. Either answer is more interesting than a question about the writing process.

18. 18

    Who are you protective of, and what does that cost you?

    Public figures build a boundary around a few people, and asking about it directly is more respectful than trying to cross it. The cost half of the question is what makes it worth asking, since the boundary usually means declining things she would otherwise say yes to.

19. 19

    What do you want to be doing in ten years that has nothing to do with politics?

    It moves the conversation forward instead of asking her to curate the past again. Ask for something small and concrete: a place, a skill, a routine. Big answers to this question are polite and empty.

20. 20

    What question are you tired of being asked?

    A closer that flatters nobody and usually gets a laugh plus a real answer. It also tells the room which of the evening's questions were the tired ones, which is useful information if you ever get to ask her again.