Ask vs guess culture in the office

A new way of looking at interpersonal dynamics

people thinking

You know when you ask someone for a favor, but it feels weird, especially if you barely know them? Or when someone asks for something in a light-hearted manner that’d be seriously cumbersome if you agreed to do it? Those feelings were summed up perfectly by keen observer Andrea Donderi way back in 2007. Her explanation of “ask culture versus guess culture” is a quick read that may just blow your mind and alter the way you relate to others.

In it, she describes two personality types that dominate our personal relationships. The first is an “Asker”; someone who frequently makes requests of others, regardless of how well they know them, knowing full well that they’ll often get a “no” in return. If you’ve ever felt put off by someone’s request for a favor, rebuked them, and got a cheerful “well, it never hurts to ask!” in reply, you’ve met a quintessential Asker.

The flip side is a “Guesser.” In guess culture, you hold off on asking someone a favor until you know the answer is almost assuredly yes. This requires deep knowledge of the people you’re about to ask favors of, and entails putting out subtle feelers first to gauge their response. In the Guesser’s ideal world, if they play their interactions right, they’ll be offered what they need without ever having to ask.

It’s important to note neither one is “correct” — rather, people have personality types that tend to one or the other, and knowing that can help guide your future interactions with everyone.

But how does this work at… work?

Naturally, thinking about how you and your family or friends fit into the Ask vs. Guess dichotomy works wonders for learning how to deal with others, but what about when you’re at work?

I went directly to the source to ask. Andrea was nice enough to answer questions about the way this philosophy plays out in a workplace, and how it varies from typical interpersonal situations. My questions and her answers follow.

How do you think the Ask vs. Guess culture might play out in our day jobs? What’s different about the office environment specifically?

I’ve often worked in tightly knit settings, where a significant chunk of people have known each other well (often inside and outside of work) for a long time. That’s true where I work now. In environments with a lot of shared context, people find themselves Guessing almost in spite of themselves. In principle, if you asked each of us where we stood on the Ask/Guess spectrum, I bet about two-thirds of us would claim to sit on the Ask side. But in practice, when we have requests for each other, we use what we know. Not only who knows what, but who usually likes to talk about things in person, who’d prefer Slack, who’d prefer email; who’s good early, and who is good late. Maybe someone’s moving, going through tough personal times, dealing with a health problem. Obviously those things temper our expectations and approaches.

Are there any situations where that changes?

If you’re the new person, you don’t have much choice. You just have to jump in and do lots of low-context Asking. The rest of us know that new people don’t share that context, and that gets factored in too.
But this is all on the request side.

“Ideally, wherever you sit along Ask/Guess, at work or elsewhere, requests are all about having the intelligence and perception to recognize what you need, the courage to ask for it, and the tact to do it gracefully.”—Andrea Donderi


What are the dynamics at play on the response side? How does this play out in your experience (Ignoring that people in positions of power may ask a lot of employees)?

It’s only when somebody says “no” that things get complicated. The biggest difference between mostly Askers and mostly Guessers is how much tension they feel about “no”. That goes for saying it and/or hearing it.

“No” can be especially complicated at work. There may be situations in which it feels almost impossible to say no. I’m not so much talking about lines of authority, because your question takes that off the table. But at work, the organization itself is pursuing shared goals, and each team in that organization is responsible for different aspects of that goal. Accepting or denying a request is likely to involve some calculations about priorities.

What can we do with this knowledge?

Now that you’re aware of Ask vs. Guess culture, keep these lessons in mind in both personal and professional settings. Try to identify and empathize with people close to you, who may be the opposite kind of person, so you can better meet each other’s needs.

Matt Haughey is 100% guesser, but emailing Andrea out of the blue for this piece was total asker behavior.

Slack is the collaboration hub, where the right people are always in the loop and key information is always at their fingertips. Teamwork in Slack happens in channels — searchable conversations that keep work organized and teams better connected.