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How to ask so that people can follow through

August 14, 2026 by Jenny Morse

Asking questions is important in our writing at work. We are typically writing messages in order to get other people to do something. Whether it’s update a client’s file or sign a contract or schedule a meeting, there’s something that we want to happen in the real world as a result of our message.

Often, we write messages where the ask is framed as an I-statement: 

I was wondering if you had updated the client file yet.

I was checking to see if we could meet on Tuesday at 2pm.

I was hoping you’d get that contract back to me by Friday.

All of those sentences have an ask, but the ask is hard to see inside of a bigger message. And it’s framed from the “I” point of view, so the reader is more likely to skim it.

When we use a question mark, we actually make it easier for the reader to see the question. And we shift the language from “I”-focused to “you”-focused.

Have you updated the client file yet?

Are you available to meet on Tuesday at 2pm?

Will you get the contract back to me by Friday?

These questions are more effective than the statements because they are easier for the skimming reader to see—the question mark draws the reader’s eye. And when the reader sees the question mark, they are more likely to read the ask and know what they should do and how they should respond.

Keep in mind that these questions are all yes/no, meaning the possible answers are either yes I have/can/will or no I haven’t/can’t/won’t.

Sometimes, asking yes/no questions is valuable. Other times, we want to ask an open-ended question instead which often presumes the person will do what we ask but reframes the request as part of a larger conversation:

How are the updates to the client file going?

When would you be available to meet? Here are some possibilities:

  • Tuesday at 2pm

  • Wednesday at 10am

  • Thursday at 3:30pm

What do you need to return the contract to me by Friday?

These open-ended questions invite more conversation from the reader with more possible answers. Notice that these questions imply that these things are going to happen–so they presume that if the writer had asked a yes/no question, the answer would have been “yes”. This presumption makes it more likely that the reader will follow through because the message assumes the positive response and moves into support. 

Our writing for work should ask one clear, specific question of the reader using a question mark so that the reader can easily find the ask in our message, they are more likely to read the request, and they if they can see it and read, they are more likely to do it. 

Make sure to think about whether to ask yes/no or open-ended questions. Typically, we want to ask yes/no questions to confirm information that was already established and ask open-ended questions when we don’t know what the outcome will be or if the outcome is possible.

Note: Please don’t ask more than one question in a message (or a maximum of 3 questions in bullets). Asking one question improves the message’s effectiveness, but asking too many makes it hard for the reader to see any particular question or understand what to focus on in the message and meet the requests.

August 14, 2026 /Jenny Morse
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