Ask vs. Guess

Communication  Leadership
29 January, 2024

Understand these communication styles to manage your team more effectively.

Sometime back, one of the team members who had recently joined the company was asked to complete a challenging assignment. She was relatively inexperienced, and she spent a week trying to complete the work. Unfortunately, her output left a lot to be desired. When I asked her why she had not reached out to her peers or her boss to assist her, she said that “I thought that people would think less of me. I also wasn’t sure how to ask for help. And what if they said no?”.

This is not unusual. If you pay close attention to the way people communicate, you will notice the daily skirmishes between Ask and Guess culture. The tension between the two styles can lead to ruffled feathers, crossed wires, and immense frustration.

The “Ask” approach favours a clear, straightforward communication style. It can be summed up as “it can’t hurt to ask”. People in this group aren’t shy about asking for things, even if it’s something big or unrealistic. They expect direct answers and can handle being told no. They may be perceived as honest and straightforward — or as blunt and presumptuous.

The “Guess” approach is about communicating indirectly to avoid confrontation and rejection. It can be summed up as “ask only if the answer will be yes”. People in this group are more subtle and nuanced, using feelers, hints, and nudges. They prefer to be offered something without having to ask for it. They may be perceived as polite and considerate — or as passive-aggressive and manipulative.

If you’re a Guesser, encountering an Asker can feel like a punch in the face. You might find yourself thinking: “How can he be so rude? What an outrageous thing to ask for.”

And if you’re an Asker, interacting with a Guesser can feel like an exhausting game of chess. You might find yourself thinking: “She’s so passive-aggressive. Why doesn’t she just say what she wants?”

This week, my message focuses on the clash between Ask and Guess culture. Learning about both styles enables us to communicate and support our teams more effectively.

First things first: are you more of an Asker or a Guesser? To figure it out, see how you feel about the following dilemma shared sometime back by someone who posted on MetaFilter — which happens to be the origin of the entire conversation around Ask versus Guess!

An old friend of the poster’s wife had asked if she could stay with them while she was in town. The person and his wife wanted to decline but felt backed into a corner. They asked people for help with how to turn down the request.

Respondents were deeply divided on whether the friend’s request was acceptable or not. About half the people thought it was totally natural — what’s the big deal about asking if you can stay with a friend? The other half felt she was presumptuous — how can you just invite yourself over to someone’s place?

The most enlightening answer came from writer Andrea Donderi, who wrote that this was a classic clash between Ask and Guess culture. The way people responded to the situation gave a pretty good idea of which camp they were in! The original poster was definitely a Guesser, as you can easily deduce from their words:

It really annoys me when people just invite themselves over. This is something I strive never to do. If anything, I might “test the waters” by mentioning I’ll be in town, and see if an offer comes my way, but suggesting that you should allow me to stay in your apartment seems borderline if not downright rude.

So, how do you feel about the above scenario? Do you identify more with the Ask or Guess approach?

Ask vs. Guess

Most of us are moulded into Askers or Guessers in our early years. The norms of our families and communities tend to shape our personal communication style and etiquette. Certain cultures are more Ask dominant (think America), and others are more Guess dominant (think East Asia).

Neither Ask nor Guess is inherently right or wrong, better or worse. Each offers specific advantages, carries certain downsides, and holds its own appeal.

Being able to recognize the difference between these two styles is a great way to expand your perspective, foster empathy and raise your communication game. When people rub you the wrong way, you’re able to understand that they aren’t intentionally being rude or manipulative. Rather, they’re adhering to a set of unwritten rules they probably grew up with and believe to be the best way to communicate.

Detecting Ask vs. Guess

So, how do you figure out who is an Asker? And who is a Guesser? While it is unlikely that people are on the extremes of this spectrum, many of us will tend towards one side. Probe on the following to assess the default style of your team members:

  1. Listening: how do your team member express themselves? Are they direct in their language? Or do they use softer language? How about body language and facial expressions during communicating?
  2. Communications preference: Do they prefer straightforward, written communications? Or are they more comfortable with face-to-face interactions?
  3. Level of detail when making requests: do they ask for a lot of clarifications and specific instructions? Or do they want broad guidance for a task?
  4. Handling rejection: When told no, do they take it in their stride? Or do they feel discouraged or disappointed?
  5. Participating in meetings: Do they directly express their opinions and take a clear stand? Or do they prefer to lay out options and see what others think?
  6. Handling conflict: Do they address issues head-on? Or do they avoid direct confrontation?

Tailoring your style

Managers can leverage their know-how of Ask and Guess culture to tailor their communication style and support their teams more effectively. Here are three areas to consider:

1. High-value work assignments.

Since Askers have no problem requesting for what they want, they are at an advantage for securing plum projects. As managers, however, we must ensure growth opportunities for all team members. So, don’t instantly say yes when the Askers come calling. Pause and think about it. Are coveted assignments being distributed fairly between in your team?

Keep in mind that just because a Guesser doesn’t outright ask for something doesn’t mean they don’t want it. (Leaders who belong to Ask culture may not realize this at first.) Try to notice whether your team member is expressing their interest in more subtle ways — indirect questions, stories, tone of voice.

In her excellent article on this topic, Jean Hsu shares her personal experience as an Asian-American employee:

Being guess-culture in an ask-culture work environment looks like hoping someone will tap you to become a manager because you’re clearly the best person for the job.

It also looks like being frustrated when others loudly express enthusiasm about taking on a new project and are given the opportunity to lead it, when you were also interested in it and maybe dropped some hints about it being somewhat interesting.

When offering an above-and-beyond project to a Guesser, it’s also important to give them the option of saying no. Being averse to disagreement and conflict, they may feel reluctant to turn down the opportunity even if they don’t have the skills or bandwidth for it.

2. Low-value work assignments.

It’s also important to remember these differences when allocating more mundane yet necessary tasks. With Askers, dropping clues may not work; going direct is the best way. If they feel overwhelmed, they will likely share this with you (provided you have created a team culture of open communication, of course).

Guessers, on the other hand, might feel like they’ve been put in the spot. Even if they feel overworked or undervalued, they will be unable to express these feelings. To ensure these team members don’t handle a disproportionate amount of low-value work, managers must assign such tasks equitably and give Guessers enough room to push back gently.

3. Feedback and development.

In a piece published on Medium, leader Michelle Murphy explains how she tailors feedback sessions based on the individual’s preferred style:

For Askers, I am pretty blunt and direct with my feedback. I am kind and empathetic, but generally cut right to the chase. For Guessers, I use a much lighter touch. I use tools such as asking them to assess themselves up front before I jump into my feedback.

For Ask team members, it’s best to be clear about the skills and experience they need to build in order to achieve their goals. Veiled hints and nudges are unlikely to yield optimum results. For Guess team members, a softer approach works better. Ask open-ended questions and create a dialogue around the areas they need to work on to grow and succeed.

When we encounter different styles of communication, we often jump to the worst conclusion. Recognise and respect the differences. No matter what our personal style may be, we can use this knowledge to flex our empathy muscle and foster better communication within our teams.


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