The Restless Executive


I had a lot of fun with this one, especially the interview questions. Most of them would make me squirm a bit which is probably a good sign :)


Goal, Motivation, and Conflict

Goal: To take over as CEO of the pet care company

Motivation: To be adored and respected

Conflict: Current CEO and his old mentor is beloved by the board and has no intention of retiring


Character Attributes

Age: 56

Family: Wife and three daughters, mom and dad are deceased   

Ethnicity: White

Orientation: Gay, but closeted

Gender: Male

Socioeconomic: Wealthy, but struggling to maintain high-end lifestyle

Appearance: Tall, thin build, bright blue eyes, boyish smile with plenty of smile lines, white/blonde hair, voice that carries   

Education: BA in History, MBA


Setting Up Your Character Interview


  1. Where did you grow up? What was it like there?
  2. Do you look back on your childhood a lot? What stands out?
  3. How did your mom and dad get along? Did they love each other?
  4. What made your parents proud?
  5. Do feel your parents did a good job raising you? What was their parenting style like?

Daily Life

  1. What would your peers say about you?
  2. How’s your relationship with your wife? What about your kids?
  3. How do you spend your time at work?
  4. What are your goals for the company?
  5. What keeps you up at night?
  6. What’s your ideal weekend?
  7. What do you wish you spent more time on?


  1. What do you like about yourself most? Why?
  2. Do you think you're funny?
  3. What makes you laugh?
  4. Do you enjoy presenting to people?
  5. Do you have any ice breakers?
  6. Do you entertain a lot? What does that look like?


Dig Deep

  1. Do you feel you should be promoted? Why?
  2. What do you think about the current CEO? Do you feel like he’s doing a good job?
  3. Tell me about the last major relationship before you met your wife. Why did you break up?
  4. What’s your ideal vacation?


  1. Tell me a memory you wish you could get rid of?
  2. What’s one thing you regret?
  3. What’s the last lie you told?
  4. What’s your greatest fear?
  5. What’s something that embarrassed you recently?
Jack Pollock
Partnerships at Skillshare