Ask vs Guess - MAC015

Managing A Career

The other day, I was reading a series of articles by Jean Hsu on Substack (link to part one). These articles outline how ask-culture and guess-culture can clash at work and how to navigate the differences.

Ask Culture is when members of the group are inclined to ask for something even when the chance of receiving a "yes" are low. Their belief is that people will say no unless they really want to say yes, so asking has no consequences.

Guess Culture is when members of the group are inclined to wait to ask for something until they guess that the chances of a "yes" are high. Their belief is that people will be offended if they have to say no, so asking has high consequences.

Which type of person you are, an asker or a guesser, can have a huge impact on how your career progresses. But it's not a single statement of "be a " because there are other factors that should be considered.

If you are an asker in a world of guessers, you could come across as aggressive or needy. If guessers have to continually say "no" to your requests, they'll be offended that you didn't understand the pain that they feel. Or if they say "yes" when they weren't fully ready to say yes, they will resent your request and the things that they had to put off in order to fulfill your request.

If you are a guesser in a world of askers, your needs will often be overlooked and the few instances when you do ask could still face a "no" that was easy to give but may have been a "yes" if you had asked again or pressed for more.

In reality, life is a spectrum and there is no one instance where a person or group is fully "asker" or fully "guesser" but having an understanding of the general mode that both you and your team operate in will reduce the opportunities for conflict. It's not quite as simple as telling the asker to "guess more" or the guesser to "ask more", but that's at least a good place to start.

If you are an asker, the key is understanding that the guesser sees being forced to say no as the greatest offense….so much so that they will sometimes say yes even when they don't want to do so but at a cost of increased resentment towards the asker. When you ask for something, ask in a softer manner so that saying "no" isn't uncomfortable…..just be careful that you don't ask in such a way that "no" is the default answer. Consider the difference between "Can I have a raise?" vs "Have I done everything necessary to be in position for a raise?".

If you are a guesser, you are often trying to read the person you are asking to ensure a "yes". Instead of trying to glean clues on your own, ask exploratory questions. These exploratory questions will express your interest without feeling like you are asking directly. It also prepares the askee for that "yes" when you finally ask. As with the asker, asking "Have I done everything necessary to be in position for a raise?" expresses your interest in a raise and allows you to ask "Can I have a raise?" when the answer to the previous question is yes.

In both instances, the softer question will still lead to your ultimate request but without raising the potential for conflict in ask vs guess styles.

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