Writing Better Emails and Texts: Asking Multiple Questions
The Problem
Has this ever happened to you? You send an email or text message to someone asking two or three questions, but when the other person replies, they only answer one of them.
And, depending on how they responded (e.g., “Yes” or “No” or “Ok”), you might not even be able to tell which one of your questions they were answering.
The simple change that you can make
If possible, I recommend only asking one question at a time when messaging with someone who is likely to respond like that.
This approach has some pros and cons.
On the one hand:
- This will probably take more than one message to get all of your questions answered,
- and it will take more effort on your part to keep track of the remaining questions at each stage.
On the other hand:
- This will make your overall conversation easier and simpler for the other person,
- each of your messages will be quicker to answer,
- you will be more likely to get all of your questions answered without having to repeat yourself,
- and if any of your questions are interconnected (for example, the answer to Question 1 might change or even eliminate Question 2), this will save you the trouble of explaining those interdependencies.
Additional advice
- Begin your first message with something positive and friendly, e.g., “Hi Mary-- I’m so glad I could help the other day,” “Hi Bob, Thanks for your time on the phone last week explaining your situation to me,” etc.
- If you’re not in a hurry to get answers to your questions, I suggest that you write, “When you have a moment, it would be helpful for me to know,” “I’m wondering,” etc., and put that phrase before your first question.
- If you do have a target date in mind, consider writing “It would be helpful for me to hear back from you by Friday May 31st” or “I will need this information by...” so the other person will have a clear idea of your timeframe.
- Mention that you’ll probably have some follow-up questions so they’ll know to expect additional messages from you.
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Proofread each question you send to eliminate any assumptions or unclear pronouns on your part. It’s better to be a little repetitive than to assume that they remember the entire context like you do.
- If you’re offering a number of choices (back up to an external drive vs. online, inkjet vs. laser printer, Italian vs. Thai vs. Chinese food, etc.), consider adding one more choice to your conversation: “...Or something else that I haven’t thought of.” The other person may have another alternative in mind that’s not on your list, or they may not be ready to make a decision yet and they may feel limited or pressured by the list of choices that you’re offering.
- At the end of your first message, include your fallback position if appropriate, e.g., “If I don’t hear back from you by Monday June 3rd, I’ll check in with you again in July,” “...I’ll offer that appointment time to someone else,” etc.
- As you get each response, start positively again with “Thanks for this, here’s my follow-up:” or “Thanks for this, I’m not sure what you meant when you wrote....”
- When you’ve got all of your questions answered, send “This is great, I’ve got what I need, thanks for your help!” or something equivalent to indicate that you’re done and to thank them.
- However, at any point in the process be prepared to get no response at all. It’s possible that they have other things going on in their work or personal life that are far more important to them than your questions. After sending each message, put “Check in with Mary if I haven’t heard back” on your calendar or to-do list at an appropriate future date, e.g., a week or a month from now. That will make it easier for you to follow up with them in a timely manner.
Where to go from here
As always, if this seems too difficult to achieve on your own, I recommend that you find someone you know and trust to help you, especially if you feel you need feedback on what you’re writing before you send it.
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