How to write an email that generates a useful response

Most people who are on top of their game respond to most emails within 48 hours. However some emails are so terribly written that it's actually impossible to send an answer. Other emails are so terribly written that the amount of time it would take to figure out what to answer is simply not worth it.

In order to get the response you're looking for, you need to ask a very good question. Here are five ways to do that:

1. Don't send an essay. Your whole email should not exceed five sentences. If you need to give the person a lot of information in order to help you, send them an email asking if you can send more information. But here's a tip: You're most likely to get a response if you don't need to send more information. A direct question is easiest to answer, and it doesn't take a lot of space.

2. Don't be vague. Here's an interesting question: “Is there a god?” But it's not a question for email, because any answer would be very long and philosophical. For this question, go buy a book. But that’s not even the worst type of offender. At least “Is there a god” is a short, direct question. Emails that call loudest for the delete button are those with vague requests for help followed by a long-winded personal introduction and no real question. Test yourself: Write a concise subject line, and then go back to the email and delete anything not directly related to that.

3. Do heavy lifting in the self-knowledge arena before you ask for help. Most people who are lost have huge questions: Should I start a company? Should I quit my job. If you are really, really lost, don't approach someone who is really, really in demand. You need a specific, high-payoff question for the person you are approaching. Which means you really need ask a lot of questions to get to the good question.

For example, the question, Should I quit my job? is usually about Does my job really suck? or Could I get a better job? And then there are specific questions related to that. Once you drill down to the core question, for example, is Phoenix a good place to raise kids or should I get a job somewhere else before I have kids? Then you can ask a child-rearing expert who lives in Phoenix. But no one can answer the broad question, should I quit my job?

4. Ask the right question of the right person. The best type of question is a very specific question in the exact sweet spot of this person's expertise. I know this because I field a lot of terrible career questions.

Last week someone I barely know asked me what she should get her boyfriend for a gift. Of course, I have no idea. But a good question for me would be what to get her boyfriend a gift if her boyfriend is her boss and there is company-wide public gift-giving. That's an office politics question, and it's specific, and I write a lot about topics like this. So I'd take some time to answer the question. (If you're wondering: buy a gift certificate to a bookstore. Totally impersonal and appropriate. It'll throw everyone off.)

5. Admit when you don't have a good question. It's hard to ask a question that meets all this criteria. That's because good questions come from good thinking, and it's easier to fire off an email than to sit on your sofa and think. But most answers to most tough questions are either in your heart or in Google. So try those avenues first. Then ask an expert. Because by the time you've exhausted your heart and Google, you'll probably ask a good question, because you'll an expert as well.

Posted in Knowing yourself, Networking, No image
32 comments on “How to write an email that generates a useful response
  1. Brandon says:

    PT – I am glad that you wrote this article if for no other reason that it tells me you’ve turned a new leaf. Nothing was more painful than reading those long meandering posts of yours, replete with dialogue that no one cared about. Welcome back.

    • Jennifer says:

      Some of us did care about that dialogue because we see PT as more than just a fierce professional, we see her as a human being. And frankly, PT I read your blog because you give good life advice too. I’m glad you show your person side occasionally.

  2. John at voyagers.typepad.com says:

    Absolutely!

    My rule of thumb is that unless I’m chatting with my friends or mother via email, I keep it under five sentences and add a memo, report or briefing if I need to. (And that shouldn’t be more than two pages as a rule.) I like http://five.sentenc.es as a site to explain it to people, too.

    See? Five-sentence comment.

    –John at voyagers.typepad.com

  3. Mark W. says:

    “However some emails are so terribly written that it's actually impossible to send an answer. Other emails are so terribly written that the amount of time it would take to figure out what to answer is simply not worth it.”
    This statement also applies to voice communications. I heard someone ask Guy Kawasaki a question on this past weekend’s Coast to Coast AM radio talk show while Guy was trying to promote his new book. It was either Guy or the host of the show that asked the caller to repeat his question since it was so convoluted. It was one of those real head scratchers that had me by this time wide awake even though it was like 4:30 AM! Somehow the host of the show was able to ask Guy a question somewhat related to the caller’s question.
    The bottom line on any kind of communication (especially email when all you’ve got is the printed word and emoticons) is 1) you have only a limited time frame to grab the attention of your reader and convey your message and 2) you will generally only get out of your question or message what thought you put into it. The more thought you put into the question, the more value you will receive from the answer. You’ll know what to look for in the answer and be better able to take those parts of the answer that apply to you.
    Now, five sentences, what do we do with those run-on, hyphenated monsters that stretch on endlessly? :)

  4. kevin says:

    Great advice! I agree with everything – I’d also love to see concrete examples of what to do and what not to do. And for the record, I disagree with Brandon’s comment – keep writing about everything, Penelope! :)

  5. Jason Alba says:

    Totally agree. I was recently at Inbox=0 but now I’m at around 250 messages… these are the ones where I have to do the heavy lifting… so they sit until I have some time, which doesn’t come often.

  6. Alex says:

    Another little email trick:

    I write the answer/question in the subject line with EOM (end of message)

    That way, the receiver doesn’t have to “open” the email to get the message.

    • Ken Girard says:

      Unless the question is real short (Free for lunch?) this type of thing annoys me. I’ve got people who send me 25+ word questions in the subject line.

      Also when saying it in 5 or fewer sentences, you should try covering the 5Ws. Who, What, Where, When, Why and How will give the reader all the info they need to answer your question. Oh, and actual names are also a good thing. I get tons of e-mails that are so vauge (“Did the customer call back?” being asked on Monday morning leaves one clueless unless you only deal with two or three customers) they just lead to re: e-mails asking for details.

  7. Carla says:

    Great column, and I love the meandering too.

    I’ve been wondering today about another email etiquette question: When do you stop the back and forth? I’m in PR , and today I pitched a reporter, and she bit and wrote back, so I sent her a document, and later she emailed to tell me she posted it on her paper’s blog, so I wrote back to say thanks and happy holidays, and she wrote back to say me too. I’ve stopped the back and forth now, but who should have the last word, and when do you stop thanking someone for an email greeting?

    Any ideas?

    Carla

    • Penelope Trunk says:

      I think you ended it just right. And, here’s a little tip that I picked up from my days at the Boston Globe: I was much more likely to pick up a story from someone in PR if they emailed me about something else I wrote (just a friendly comment) in between the times they pitched me.

      -Penelope

  8. Marsha Keeffer says:

    This post is helpful on all counts. And I agree with Jason – more than anything, I make my subject lines immediately understandable. We all have lots of saved email and it can be tough to find the right email when generic topics like ‘Acme Widget’ is used. Better to use ‘Acme Contract Issues December 2008.’

  9. Peter Abelard says:

    Interesting post. Don’t have time to think it through so I will send you a lengthy email covering some of the high points so we can sort all this out. I thank you in advance for your time.

  10. Tiffany Monhollon says:

    I love this advice, but I’ll just be honest and say I have a very hard time doing it.

    It’s usually the worst when I’m communicating with someone I don’t know well enough to contact in any other way. Is that typical?

    I think it’s because I know if an e-mail really needs to be over 5 sentences, I should pick up the phone or have a quick meeting. But if it’s someone whose number I don’t have or have never met in person, e-mail feels like the one and only shot. And I get too wordy, giving too much context, or even apologizing. Which is horrible, because people you don’t know that well are the ones you should really not abuse with long e-mails.

    • Ken Girard says:

      Can I suggest sending them an e-mail giving a brief intro and what you need to talk to them about, and ask that they call you or send you contact info and preferred times so that you can call them?

  11. Aneevarp says:

    Most times email is the slowest way to get the answer, call instead and I am sure you will have an instant response.

    The best use of email in my view is for summarizing a discussion or when there are some points that need to be documented for future reference.

  12. Neil C. says:

    Good advice on a very useful subject. This should apply to blog comments as well. Some people like to write a blog response to Penelope’s blog which can be long winded & often times it looks even worse because it is 15 sentences but only one paragraph.

    In reponse to Brandon’s crackback (note I started a new paragraph John) I agree that some of your posts digress into too many diffent directions & lose focus but some of these digressions open up whole new interesting topics. Sometimes I could do without certain details (shaving in the nether regions, frequency of oral, etc.) but other times it is interesting so I can’t really ask you to reign it in too much. Just expect my sarcastic comments when you go too far. :)

  13. Angie says:

    Other email tips: ask for a response by a specific time (applies more to internal company communications), don’t copy people who don’t need to be copied (please!), don’t be afraid to use a few bullets if listing criteria, process steps, requesting specific pieces of information, etc.

  14. Chandlee Bryan says:

    Great post.

    A friend who is a Marketing exec at Google has another piece of advice for e-mailing: If the issue at hand or question is going to involve more than three e-mails of back-and-forth communication, avoid e-mail altogether and pick up the phone or go face-to-face.

    Thanks for continuing to provide such thought-provoking content.

  15. prklypr says:

    Great post!
    A small punctuation omission (3. Should I quit my job?)made me think about the biggest issue I have with emails: punctuation (or lack thereof). Seems like no one proofreads emails to make sure (a) there is punctuation and (b) it is placed properly so that the sentence reads they way you want it to :)

  16. prklypr says:

    oops – guess I didn’t proofread! Last line should read “…sentence reads THE way you want it to.”

  17. Angie says:

    Great point from Chandlee – sometimes the phone really is the more efficient option.

  18. The Office Newb says:

    Iwork with a girl who is a constant failure at rule #1. Her emails are about 5 paragraphs on average and meander through her thoughts/feelings/musings until she gets to the semblance of a question midway through.

    After getting complaints from others in the company that her emails were negatively impacting productivity (yes this is how bad they were!), my boss and I tried talking with her giving her the “who, what, where, when, why” guidelines but she still cannot get to the point to save her life. I have literally stood next to her and showed her line by line what to take out but she still can’t seem to grasp the concept of brevity.

    Anyone have any suggestions?

    • Mark W. says:

      I didn’t come up with this one myself but I came across it when I did the infamous Google search – email brevity. It’s referred to as the ‘email brevity policy’ and is merely a short and clever ‘policy’ written up in the email signature of your emails extolling the virtues of brevity. All of your emails to this person or everyone for that matter could have this signature and be a constant reminder.

  19. dailyfill says:

    Great post! I get at least one email a week from people basically asking me “how do I copy your business?” I’d be happy to answer one (or five) specific questions, but not vague ones.

    Another email tip: one email per subject or concept. (Don’t ask a business question and include a party invite.) Especially since people are GTD’ing their inboxes.

    (And I like the meandering. ;-)

  20. Peter says:

    @Angie – I’d just call her straight away or reply “call me/what is it you need?”. The same goes for any unclear message, which are usually from the engineers :)

    In my office there are those who respond quickly everytime. There are those who just don’t. I email those that usually respond, I call those that usually don’t. After I’ve called, I email with a short summary/reminder, as the phonecall is quickly forgotten.

  21. Dale says:

    I find that many people already know the answer to the question that they are asking in emails (this does not apply to technical inquires). In fact, the majority of the time, people typically send long emails for two reasons:
    First, to get another alternative when the real/obvious/most appropriate option is unsavory to them, or when they lack self confidence.

    Second, to connect with someone… anyone. There are many, many lonely people out there, and sometimes this is apparent in the long meandering email that initially asks a question, but then goes off into alternate unrelated directions.

    I guess the answer in both cases (for me) is kindness. I’m not saying to waste your time addressing every point, but at least recognise that the other party is in need, and treat them with respect, kindness, and honesty.

    My2centsworth.

  22. The Office Newb says:

    Dale,

    That’s exactly how I feel about my trolls. What a nice sentiment, very in the spirit of the holidays.

  23. Shawn says:

    Vague questions are the worst. “Can you send me some employment data?” Sure…but what specifically are you looking for(industry, function, geographic location, etc.) and from what time period?

    On the flip side, incredibly detailed questions are equally as bad. Although technically they always seem to be one “question” with 17 “sub questions.”

  24. Emma says:

    The first point about emails not being longer than 5 sentences does not reflect the current reality of the global market and feels a little too Gen X. There is no way I am going to email a vendor in India and ask if I should send more information, wait until I get a “yes” response 12 hours later and then respond when I am back in the office 12 hours after that. I send all the information right away, in my first email, but TOTALLY AGREE that I have to do heavy-lifting in the self knowledge arena before I send it or risk wasting additional time. When I send an email to someone in the US, I usually re-read it once before I send it. International emails get re-read at least 3 times to make sure they are clear and I have done my due diligence to find out everything I can on my own first.

  25. Tiffani Bell says:

    Yeah, I really have learned something important from this post. I’m notorious for writing essays as emails and then wondering why nobody ever writes back. Or when they do, it’s like “Ok.” or “Will call later…”. I’ll just stop being so long-winded now. lol.

  26. chaney says:

    Good advice on a very useful subject. This should apply to blog comments as well. Some people like to write a blog response to Penelope’s blog which can be long winded & often times it looks even worse because it is 15 sentences but only one paragraph.

    In reponse to Brandon’s crackback (note I started a new paragraph John) I agree that some of your posts digress into too many diffent directions & lose focus but some of these digressions open up whole new interesting topics. Sometimes I could do without certain details (shaving in the nether regions, frequency of oral, etc.) but other times it is interesting so I can’t really ask you to reign it in too much.

  27. Mike of Hypnosis Norwich says:

    I think that something like “Is there a god?” is a great question. It attracted my attention, just because I can write loads in response to it. If I were religious, I would want to put my view forward, and as I’m not, I could explain my reasons – or perhaps just put a short comment there. Either way, it is a compelling subject.

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