Askers and Guessers: Who Are You?

We’ve probably all heard at least a handful of sayings starting with the words: “There are two types of people in the world.” Robert Benchley humorously captured the distrust that many of us feel with “two types of people” distinctions when he wrote, “There are two kinds of people in the world: Those who believe there are two kinds of people in the world and those who don't."

I’m definitely in the latter of Benchley’s categories (as probably most of us are), believing not only that humans are much too complicated to fit into neat boxes, but also that dividing people into different groups—us and them—promotes conflict and unnecessary division. However, I do often find models for understanding personality, ones that divide people into types and groups, very helpful for self-understanding and personal growth. One model that recently caught my attention is the “Askers versus Guessers” model. 

In a response to a 2007 AskMetaFilter post, writer Andrea Donderi proposes that the world is divided between Askers and Guessers. Askers believe that it is okay to ask for anything at all, as long as you are willing to accept “no” for an answer. Askers are comfortable requesting anything from getting a raise from the boss to borrowing a friend’s car for a week, and they aren’t offended or ashamed when their requests are denied. Likewise, they don’t mind being asked for things and are comfortable giving “yes” or “no” for an answer.

Guessers, on the other hand, resist making outright requests, opting instead to put out delicate feelers, perhaps hinting at their desire, with the hope that their companion will deduce their desire and make an offer. They hate being told “no,” so they avoid asking for things until they are near certain that the answer will be “yes.” Because of their aversion to hearing “no,” they feel guilty and uncomfortable saying no to others. Guessers, as you may imagine, are often put off by the forthrightness of Askers—considering them pushy—and Askers often find Guessers passive and confusing.

Whether by nature or nurture, I am a Guesser. In some cases, this serves me well. I am very sensitive to the feelings and needs of others, and I am able to delicately handle complicated social situations. But as a woman in a leadership role requiring the cooperation and support of countless individuals, I can see that my Guess-proclivities often hinder me as well.   notice the needs of others, but I have a hard time asking for what I need—whether that be for something personal, like a raise or more flexibility, or something relating to my projects at work, like extra volunteer hands or a higher level of commitment from my team. 

This model for understanding personality caught my attention because it helped me notice a growing edge of mine and it also helped me identify a way that I can develop myself. Asking outright doesn’t come naturally to me, but I’m not incapable of doing it. This year, I’m resolving to ask more and say no more—qualities of Askers that don’t come naturally to me, but that I believe will help me grow as a leader and as a person.      

Are you an Asker or a Guesser? How do the traits associated with your type help you in your work and personal lives? How might you adopt traits of the other to enhance your work?

Teresa lives in Providence, Rhode Island, where she works as a Director of Faith Formation at a Catholic Church and dabbles in hospital chaplaincy. She has a BA in English, a Master’s in Divinity, and a passion for thinking about the intersection of spirituality, self-improvement, and well-being. Her perfect day includes slowly savoring a morning cup of coffee, reading for work and for fun, and receiving snail mail.