People Hacking 101: Questions to Ask to Help You Guestimate a Person's Personality Type

Want to know if you and your date are compatible?  Looking to build a rapport with a potential client?  Wouldn’t it be amazing  if you could “hack “ into the personalities of people you meet? Well, this is actually possible.  The secret is having an understanding of  the basics of Jungian personality theory, and recognizing clues in a person’s behaviors,  physical environment, appearance, and communication.   So how do you go about “hacking” people?   Today I’ll share questions  that you can ask that help you guestimate the type of a person you’re just meeting.  

Personality Basics

Based on Jungian personality theory, there are four dimensions of human personality. They are as followed:

Extroversion (E) vs. Introversion (I)

This dichotomy describes how a person prefers to "recharge"  People who prefer Extroversion (E) recharge by being around others. Socialization gives them energy, hence they typically seek out social interactions and develop a large circle of friends and interests.  On the other hand, people with a preference for Introversion (I)  are drained by socialization.  They seek alone time to "recharge" after prolonged social engagement.  They tend to have a smaller amount of hobbies and friends,  but have a greater depth in their interests and relationships.  

Questions to Ask that Hack E vs. I: You want to ask questions that center around how the person you’re hacking recharges.  Ask variations of the following questions during the flow of conversation.  Be sure not to make it look too obvious.

  • Do you prefer to work alone or with others?
  • So, after a long week would you rather chill at home, or spend time with friends?
  • What’s some of your hobbies? (An extrovert has tons of hobbies. Introverts have fewer hobbies, but have more in depth knowledge of them than extroverts)?
  • Do like going to parties? 


Sensing (S) vs. Intuition (N)

This dichotomy dictates what type of information a person prefers.  People with a Sensing (S) preference favor information that is concrete and tangible. Information holds less value if they can't experience it with their five senses, or if it isn't tried, true and proven.   They live in the present moment and speak in a concrete manner.   People who prefer Intuition (N) are more speculative, abstract, and theoretical.   They make inferences based on what they experience, and like to "read in between the lines".  They communicate using concepts and symbols, and often speak in metaphor.

Questions to Ask that Hack S vs. N: You want to ask questions that center around how the person you’re hacking processes information.  Also, pay attention to HOW the person answers the question.  If they use a lot of collegiate level words and/or a lot of  metaphor in their answers, they likely prefer Intuition.  If they use real world examples and provide straight forward answers, they likely prefer Sensing.

  • What type of books do you like to read?
  •  Do you like to try new ways of doing things, or do you like a tried and true approach?
  • Do you consider yourself more detailed or big picture oriented?
  •  Would you consider yourself traditional or eclectic?

Thinking (T) vs. Feeling (F)

These letters describe how people prefer to make decisions.  People who prefer Thinking (T) make decisions on what they perceive to be a set of logical principles. They do not consider their feelings or the feelings of others as much as they do the facts.  They strive for consistency in decision making, and often make decisions in new situations based on how they handled previous ones.   People with a Feeling (F) preference make decisions based on their own values. They strive for win-win situations and consider the human element an important (if not the most important) aspect of the decision making process.  

Questions to Ask that Hack T vs. F: You want to ask questions that gauge whether a person prefers logic or “the human element” when making decisions.  Again, pay attention to HOW the person answers the question.  People who prefer Feeling tend to have more of a warm essence, and are complimentary and kind.   People who prefer Thinking  tend to be more stern, direct, and assertive.

  • Would you consider yourself a sensitive person?
  • (Suggestion) Ask for the person for their advice about a situation that contrasts between facts vs. peoples’ feelings.  The advice they give can help you hack their preference.
  • Are you affectionate?
  •  Do you trust your gut? Or are you more analytical?

Judging (J) vs. Perceiving (P)

This last dichotomy governs how people prefer to structure their lifestyle.  People with a Judging preference like organization, structure, and to have things resolved. They tend to meet deadlines, keep a schedule, arrive on time for appointments, and keep their work space and home environment organized.  People with a Perceiving preference tend to take a more flexible approach to life and like to stay open to information.  They tend to prefer deadlines that can be easily changed, prefer to go with the flow, are comfortable with unexpected changes of plans and occurrences, and keep messy work spaces.

Questions to Ask that Hack J vs. P: You want to ask questions that will give you clues on how the person structures their life. People with a Judging preference will prefer order, and people with a Perceiving preference will prefer flexibility and spontaneity.  

  • Are you a spontaneous person?
  • What do you have on your calendar coming up?  (People who prefer Perceiving will be more likely to guess, while people who prefer Judging will pull their calendar out and tell you verbatim).
  •  Do you consider yourself organized?
  • What do you want to do/go next?  (A person with a Perceiving preference is more likely to reply “I don’t care, it’s up to you”. A person who prefers judging is more likely to have a suggestion in mind).


You’ve Guestimated Their Personality Type, Now What?


You have the person’s four letter code (i.e. ISTP), now what?   Tell the person that you are hacking that you have to run to the bathroom. Then, while in the bathroom, Google their personality code. has excellent descriptions of each type, and these descriptions are usually first or second in the Google search results. Read up on the person you’re hacking, and then use this information to communicate more effectively with him/her.   In the upcoming weeks, I’ll share additional People Hacking tips.    Stay tuned.