Are You an “Asker” or a “Guesser” at Work?

The concept of “ask culture” and “guess culture” has fascinated me for years. Andrea Donderi named the phenomenon in a 2007 MetaFilter post. Many thoughtprovoking essays have explored the idea’s role in fouling up interpersonal relationships since.

The concept is that there are two types of people in the world: guessers and askers.

Guessers are prone to perceiving needs around them and proactively addressing those needs before an “ask” is made of them. Askers, by contrast, wait until something is asked of them to act. While guessers live in fear of making a request that might be denied, askers are happy to ask for what they want and need and don’t think anything of being turned down.

Are you a professional asker or a guesser?

This isn’t a science-backed typology. I’ve not engaged in any formal study of asking and guessing and how it applies to the workplace. But I do think the concept is fun to play with and can be illuminating around interpersonal tension—which, of course, occurs at work.

Signs You Might Be an Asker at Work

You might be an asker if you…

  • Find it easier than your peers to ask for raises, promotions, and other growth opportunities.
  • Feel comfortable turning down projects in which you’re not interested.
  • Err on the side of efficiency and direct communication rather than tuning into the emotional environment.
  • Find it difficult to read into subtle information; e.g., you might be surprised by un-communicated changes like reorganizations.
  • Respond to critique less defensively — maybe even expect it.
  • Are less able to parse vague feedback.
  • Are seen as having a more transactional relationship with work — not because you don’t care, just because you tend not to act when unprompted.

Signs You Might Be a Guesser at Work

You might be a guesser if you…

  • Get more burned out than others around you; take on more glue work.
  • Are often the one to perceive changes before they happen; are good at reading the tea leaves.
  • Find yourself feeling occasionally resentful about completing work you’ve agreed to take on.
  • Feel passed up for opportunities you think you deserve.
  • Have a harder time than your peers in giving direct feedback.
  • Tend to think you’ve gotten a message across and later learn you haven’t.
  • Feel sensitive about receiving feedback about performance because you work so hard to preempt it.
  • Are frequently referred to as a team player.

How to Cross the Communication Chasm

As a guesser myself, I find this guesser/asker construct especially helpful to infuse a little more curiosity and empathy into interpersonal conflict. At work, this is an especially valuable lens to bring to bear.

Do you hear yourself muttering, “She is always taking advantage of me and doesn’t appreciate anything I do”? Or, “Why can’t he just say what he means instead of embarrassing me after the fact?” That can be a good moment to consider whether you two might be on opposite sides of the asking/guessing divide.

When trying to improve relationships with askers, guessers need to push a little beyond their comfort zone to communicate more directly. They’ll get to benefit from doing fewer mental gymnastics.  On the flip side, askers trying to accommodate the needs of guessers might need to stretch their powers of inference.

Advice for Guessers Working with Askers

Guessers are likely spending too much time in their heads and too little time stating what they want and need as simply as possible.

Consider a recent work conflict with someone you presume is an asker. Ask yourself, “Did I ever really say plainly what I wanted to the person?” and answer honestly. This is different from, “Did I spend a lot of time thinking about what I wanted and wishing they could pick up on that through subtlety? Was I hoping they would read between the lines, even if my hints seemed obvious to me?”

If you can master speaking up for your preferences in plain, unemotional language with askers, you might find the result pleasantly surprising.

Often, guessers live in personal fear of failing to perceive and meet someone else’s needs. For them, the idea of the person they are trying to accommodate asking them for something they need is akin to deep embarrassment. This is not how askers see social interactions. They are not paying attention to what you might need; they are waiting for you to advocate for yourself.

If your boss asks you to complete a project under a tight deadline, you might not think you have a choice besides saying yes. Your asker boss might just be throwing out an idea, waiting for you to counter if you have a constraint. He may easily accept a suggestion for a later deadline.

Next time there’s interpersonal work tension with an asker, see what experimenting on the side of what you might consider bluntness bordering on rudeness gets you. You’re likely putting too much energy into what you think of as tact or diplomacy, and it’s going over the asker’s head.

Advice for Askers Working with Guessers

Askers trying to get their minds into a guesser headspace will need to get more comfortable interpreting the subtle or unsaid.

When working with a guesser, it helps to run through a series of internal questions before and after you make decisions together. These might include something like, “What do I know about what is going on in this person’s work life that might add context to the decision?” or, “When this person offers to make an additional effort, is that a subtle sign to encourage me to make a similar offer?” or “Does the distribution of work we agreed to seem fair and equitable?”

While you’re in the interaction with the guesser, use your powers of active listening. Broaden your awareness beyond just what they say. Also look for subtle clues around body language, tone of voice, eye contact, and word choice to see what’s below the surface. If you think you’ve caught an implication, try asking probing questions like, “It occurs to me that you might be feeling a little stressed about what’s on your plate right now. Do you think this plan is coming together in a sustainable way for you?” This gives them an invitation to verbalize what they may haven’t felt safe to say.

Similarly, wield your direct asks carefully when you’re working with guessers. It’s not safe to assume, especially if you have greater institutional power, that your colleague will interpret the request with the optionality you intend. Instead of asking in your natural phrasing, try peppering in softeners to create room for freer dialog. That might look like the difference between, “Can you get this done by Monday?” vs. “I don’t assume you have the capacity, but if you do, would it be feasible to complete this project by Monday?”

Making Peace with Communication Compromise

As a guesser writing out advice for how askers can deal with my type, I can hear the accusations of catering to passive aggressive behavior mount. I have empathy for askers trying to flex into the world of guessers: Wouldn’t it be easier if we lived in a world where people just said what they meant?

I also understand guessers’ wish that we all lived in a world where people focused more on the needs of others and tried to resolve problems before they started.

Like in any dichotomy, I think moving toward the happy medium is the right move. Askers and guessers need not abandon their strengths to better communicate with those on the other side of the divide. Once we see and name these dynamics, we can be less bewildered or frustrated—and more effective at navigating interpersonal conflict at work.

How have you seen these dynamics shape your work experience? Do you have advice for colleagues communicating across ask/guess differences?


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