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Let's say I want to ask my boss (or my boss' boss) two things but are on separate matters. I don't know which of the following is preferred:

  1. Send two e-mails asking one each. #teamseparate
  2. Collate the two questions into one e-mail containing both things. #teamcollate

Is there a general consensus of one being preferred over the other?

If so, which, why, and what are some counterexamples?

If not, why not, and what are some guidelines in deciding which to use?

Example:

Thing 1:

Asking about a possible mistake in a certain document

Thing 2:

Asking about possible exception for a rule for a certain customer

Now if the document has several possible mistakes, I would definitely send 1 e-mail for all the mistakes because sending separate e-mails would involve redundant file openings.

Finally, I have a feeling this may have something to do with the priority matrix/Eisenhower method. I guess urgent could be done through text/call if possible. Thus, we may assume that the two things have the same level of importance or urgency, whichever is helpful.

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4 Answers 4

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Is there a general consensus of one being preferred over the other?

Send at least two emails. Remember the first rule of bureaucracy: any message worth sending is worth sending in triplicate.

If so, which, why, and what are some counterexamples?

Today's workforce has such a low attention span that sending a single message with two questions has a much higher chance of getting no reply (TL;DR effect) or getting a reply to only one question.

Also, it is possible that the recipient doesn't know the answer to one of the questions, but knows whom to forward the question to. Having only one question per email greatly facilitates optimal routing.

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  • If anyone sends me something in triplicates I get rather annoyed and might put off handling the issue. I much prefer one (to the point) email covering all questions. If I have to forward it, i can still forward the email and take out the stuff not meant for the next recipient from the text. So, TL;DR: That depends on the people you are dealing with. Some don't read long emails, some don't read to many emails.
    – skymningen
    Commented Feb 21, 2017 at 8:51
  • @skymningen huh? But if you have to take out stuff if you forward it then it follows it is more convenient to separate? Or you mean the convenience there is balanced by inconvenience elsewhere? Also it is not triplicates. It is separating issues. For example if you plan to read a certain part of a long email later how will you remind yourself to read only the part you want to read (because the other parts don't need a second reading) ?
    – BCLC
    Commented Feb 21, 2017 at 12:43
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    @BCLC The triplicates referred to the given answer, not to you original question. I would rather have to take something out of a mail, than having to condense multiple mails to forward them. I just wanted to point out that people can have very different preferences.
    – skymningen
    Commented Feb 21, 2017 at 13:50
  • @skymningen Do you then disagree with DepressedDaniel, Philipp and corsiKa?
    – BCLC
    Commented Feb 22, 2017 at 9:06
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    @BCLC I do definitely agree with corsiKa in that the best is to ask the person about what style of communication they prefer.
    – skymningen
    Commented Feb 22, 2017 at 10:14
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Write separate emails for separate topics. When you write two emails they can be:

  • Separately titled. Descriptive email titles are important for the receiver to find the information they are looking for when reading through older email.
  • Separately categorized and archived by the receiver. Many people have a personal filing system for their mail. When you send one mail about two completely different topics, you make it much harder for them to keep their inbox in order.
  • Separately forwarded to other people. When your receiver needs to forward the mail to A for the first question and to B for the second, they will have to remove the parts which don't concern them. When you already pre-separate these two inquiries, you already did that work for them.
  • Separately reacted to. One inquiry might have a higher priority than the other, or the receiver might be able to reply to one right away but require more research to reply to the other. In the worst case the receiver might only reply to one of your questions but forget to also answer the second.
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  • you worded my points a lot better than me - deleting my answer
    – Kate Gregory
    Commented Feb 21, 2017 at 13:52
  • THANKS. I think I'm gonna link this a lot because I know more than a few on teamcollate. Go #teamseparate ! Also Philipp what do you think about corsiKa's 'If you're concerned about it being spammy, then pick which one is most time critical and send that alone. Then, in a few hours, send the second' (Thank God for Boomerang) ?
    – BCLC
    Commented Feb 22, 2017 at 9:07
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It really depends on who you're talking to. The obvious solution is to ask.

If you can't ask, or are afraid to, send two separate ones. If you're concerned about it being spammy, then pick which one is most time critical and send that alone. Then, in a few hours, send the second.

But nothing beats getting it from the source. Asking your manager also shows you're aware the effects your communication has and are doing what is necessary to make your communication effective. Every manager loves that.

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  • 'Then, in a few hours, send the second.' --> GREAT IDEA! Thank God for boomerang. Thanks corsiKa! ^-^
    – BCLC
    Commented Feb 22, 2017 at 9:05
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Send one email: a request to meet in person/over the phone/via Skype or another method of live interaction.

With this many topics to discuss, you really need to get your boss's undivided attention for the length of time that it will take to get all of the topics resolved.

The best way to do this is talking in person face-to-face, but if you're not collocated, then the next best thing is a Skype meeting or phone call. Otherwise you'll end up going back and forth for days over email.

Your one email should say something like:

Boss, I've got a few small things I'd like to talk to you about. I won't go into details in this email, but in general the topics are:

  • a personnel matter with the team
  • our schedule for the next release
  • my planned vacation this summer

Is there a good time [today, tomorrow, next week] when I can get you for about [10, 20, 30] minutes?

Don't stack up too many items in one conversation, and don't take too much of the boss's time.

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    One problem with this approach is that it gives the other person no way to prepare. It's the equivalent to sending your boss a blank meeting invitation, except now your boss needs to add that invitation to their calendar themselves, too. By actually asking the question you want answered to begin with, the worst possible outcome is that you will receive a meeting request in response. By not asking the question that you want answered, the best possible outcome is to be told at what time you can ask your question.
    – user
    Commented Feb 21, 2017 at 16:22
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    I disagree, personally. I'd only do this if we've exchanged a few emails and deadlines are approaching.
    – corsiKa
    Commented Feb 21, 2017 at 16:38
  • Thanks shoover. Gave an upvote for effort, but I think I neither agree nor disagree because I think we're talking about different things. I agree that there are some situations that require such e-mails, and I'm not sure the alternatives in those situations are much better, but I'm not sure that the situations you have in mind are the same as the situations I have in mind. Perhaps my question was not so well-defined. Let's say there are two things to ask wherein these are very short individually but together, well, are still short but seem long when put together.
    – BCLC
    Commented Feb 22, 2017 at 9:01

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