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How to Email Busy People (humbledmba.com)
221 points by jaf12duke on May 10, 2011 | hide | past | favorite | 60 comments

Be brief and say what you want.

I think this should apply for any kind of email, not just for busy people. Actually, this applies to most kinds of writing too.

It'll come off much better if it's well-worded but simple and to-the-point. The more fluffy sentences you add to your email, blog post, internet comment or product copy, the less professional it starts to sound.

True, but long copy sales letters have been shown to be effective. It all depends on the audience.

long copy sales letters tend to be aimed at the bottom 1 percent.

Balance the two.

Be direct in your requests, include enough details (pick the right ones!), say thank you, and cut out everything else.

To quote the Bard: Brevity is the soul of wit.

Therefore, be brief when you can, but always..be polite.

I wish I could upvote this more than once. I'm a professional so I don't need requests to be sugar coated. I also don't need lots of detail in the first email. If I'm interested then I will get back to you!

This comment is all the better for being both a description and instance of the advice.

"Write tight."

Here's something I learned: don't be wishy washy. Avoid pandering to the person you're emailing - it takes up words and sounds pathetic.

I've done this in the past and been the recipient. It just goes bad.

Busy people work on short terse communication, unless they are actively in a conversation with you. And, in general, they will appreciate the first few emails you send them being of the same - condensed and full of content.

Never worry about being rude by not saying please every other word.

On another note, I mildly dislike this one:

Show your target respect by responding to everything immediately. Just because the VC you're emailing might not get back to you immediately, doesn't mean that you have the same privilege. Ron Conway famously makes immediately email responses a pre-condition for investment.

I'm a busy guy, I get a LOT of work email each day. And yet the people we work for seem to see slow response as an indication of laziness :S Even though it takes them a week to respond. Yes, you're important to me, you are potentially worth a lot of money to me and I really want to keep you happy. But give me a fracking chance!

So, investors, cut founders a bit of slack :)

I doubt Conway is that stupid to correlate email responsiveness with entrepreneurial ability, but on the other hand he probably appreciates prompt responses so he lets people believe that.

Also, there's a pecking order. If you are some unknown founder who really needs Conway you should respond as fast as humanly possible. On the other hand, if Conway wants something from Steve Jobs he probably should respond quickly.

It was a copy/paste error to include the reference to Conway; from what I have read about him I very much doubt he expects instant, the next second, replies. Just reasonably prompt replies.

Which is not really what that point was saying.

I just think that the time between sending and email and a reply is not a good measure of how important you are to that person. Certainly, if someone replied within a few seconds of my email to them I'd have to pause and question why they responded so fast. Are they literally desperate for my input? Why? (of course, usually being desperate for that input is fine, and part of being excited to have a chance with someone who can really help you - but occasionally it is a marker of someone dodgy).

Basically: it seems something of a shallow way to judge things.

"Don't be wishy washy" he said and than goes on writing 1000 more words about that topic.

The idea is simple, but the execution is tricky, and more words were required to elucidate it. I would not have found it nearly as helpful if he just stopped with "don't be wishy washy."

i think responding immediately makes sense: the other party is at the computer/by the smartphone. they tend to read the freshest emails that come, and if they have thought on the topic just a few minutes ago, they may jump to your letter and respond to you with more useful info.

wait half an hour, and the emailing session of your potential investor could be over, and your response would be buried under other important bullshit in their inbox.

I've had some success with sending email that has a short and long version (or if you include the subject itself, 3 levels). Ask your main question in the first sentence or two, enough to provide context, detail, and what you want.

At the end say "[more detail below if needed]". Draw a line in the email ===== and include more detail below that they can dip into if necessary.

It's nice to see that a journalism degree is universally applicable.

What you describe is basically an inverse pyramid news article.

Hook Lead Background News

Putting it into 5 sentences is where the art comes in...

I do this too, especially when emailing people who I believe are unable or unwilling to read a long email. It feels weird and unnatural. I'm not sure if the people I'm sending to appreciate it, but I know I can very easily become very verbose, and which details are important is very context sensitive and sometimes non-obvious.

i get a ton of email from people who want stuff. i try to reply but it's a barrage.

Some stuff that makes it easier:

- understand that I am likely to read your email on an iPhone. keep it brief, don't write an essay.

- if i reply and say something like "interesting, please send an executive summary" or "i'd love to see a demo" then do that or offer something equivalent/better. i do not want to meet you to see your demo, etc etc etc.

- don't ask for extremely unlikely things and expect a reply

- it takes me a week or two to get to low-priority stuff. don't email me and ask for a detailed response within an hour. if you do have a deadline, tell me so, so i can prioritize appropriately. i'm looking at you, journalists.

- if you are pitching a startup, don't pitch investors who have clear and obvious conflicts.

- if you are offering an advisory role, be up front about offering equity or something.

that said, i try my best. that guy who had acquisition questions a few months ago on Ask HN? i got him to someone who got the deal done.

As a former founder and now VC, I am thrilled about this post. It's so true. There is nothing I like more than learning about startups and helping entrepreneurs and founders. If that wasn't the case I would find some other line of work.

That's why I'm so sad when people view my inability to get to email in a timely fashion as a proxy for my interest or the type of person I am.

I just get a ton of email and it's impossible to respond to it all, much less in a timely fashion. I'll try my best to get to it all, but if for some reason you haven't heard back in awhile try again and again. If nothing else I'll notice your determination and provide some feedback.

Could You please specify if there are undesirable mails in the ton of mails you get or if you are just saturated of information ? Suggesting as a solution to retry sending mail again and again will worsen the problem. You'll get echos in addition to signal.

Maybe people in your situation should use a pull method (~on demand messages) using a web service for this purpose. People who want to get in touch with you see the number of messages in the queue and you may pushback (temporarily suspending message submission) and provide priority to users. They'll see their queue position and eventully some feedback once processed tldr, not understood, contact me @xxx, ...

if it's undesirable email that keeps getting sent then I'll either ignore it forever (unlikely) or more likely respond with a reason I'd rather not get your email.

If someone repeatedly puts effort into emails to me then I will respond because they deserve that much for taking the time.

I agree this advice does not only apply to emailing VC's. It applies to emailing ANYONE in the course of doing your job: interns to CEO's.

5 sentences often is too much. If you can get it down to 3 sentences (or even 1 or 2 with judicious subject line) that is better. Just state the situation and what action you request.

For christ's sake, above all, don't resort to voicemail.

Many people are really bad writers. Further, many people are really bad readers. Restricting yourself to email with someone who functions better on the phone or in person is just asking that relationship to collapse. At some point one of you will take something the wrong way, or write something the wrong way, and you'll just get deeper and deeper resentment and other fundamental causes of relationship dissolution.

If you're working with someone who doesn't "get" email, even if they think they do, you do everyone a favor by manning up and calling when you have to and meeting in person when possible.

I agree on the voice mail, although I've come to realize that some people avoid email and online communication altogether and if you don't call them, you won't talk to them.

Many people do this to avoid a papertrail. Sometimes its a good idea to followup with an email summarizing the conversation when working with these types.

and some people avoid phone communication entirely; For me, the phone is essentially a pager; If you call me and nothing is on fire, generally speaking, I won't be particularly happy.

Include a Short, Professional Signature My standard signature includes my name, company, blog, Twitter, and LinkedIn. If I want a phone call or fax or meeting, it'll include phone number, fax, address.

Four lines is not short. Nobody cares about your blog, Twitter, or LinkedIn.

I sign my emails either "--Jon" or "Regards, Jonathan Rockway" depending on who the intended recipient is. If you want to read my blog, just type my name into the nearest search engine.

This is an example of where the person who came up with a term screwed up. You're talking about how you sign your email, but the post is talking about the signature line (or lines), which are not a substitute for signing your message.

For personal emails I don't use a signature, I just sign it. For business emails I sign the email and have a signature line with my name, title, business group, phone numbers, and group website. --This information fits on one line and is easy to refer to or ignore as per the recipient's needs.

Question, relating to email etiquette.

Do people send "thanks" emails at the end of a discussion? Sometimes I'll have a discussion with someone online. Sometimes there's no more to say, and I always wonder if I should send a "thanks" email. No content, but just something to close the loop and a minor show of gratitude. But it seems wasteful. In a verbal converation it's a no-brainer to just say, "thanks for the time", but in email its not clear if its better to do it or to just end the convo by not sending another.

I just weighed in on this in a slightly different way... how to email people for the first time: http://chriscoyier.net/2011/05/04/how-to-write-an-email-to-s...

As I said in the comments, isn't there a little irony in an essay on concise communication that opens with seven mostly content-free paragraphs? Much more effective, I suspect, would be to rely on the title as a hook, launch right into the prescribed methods, and argue the case in each one.

As it is, how to actually email busy people is an entire window scroll away.

These are some good advices, and they're not limited to VC. In the academic domain researchers and professors also have a lots of email to deal with, maybe not as much but we also have to consider that reading email is even less their job than a VC (and they have enough freakin administrative tasks that take on their working time). As a matter of fact, I've always had quicker (and often better) responses when I wrote email that more or less follow the rules described in the linked post, for instance when looking for an internship, or requesting a specific paper.

>If you can fit the entire question into the header, just do it and include #eom at the end, which means 'end of message'. Yes, it feels weird. Do it anyways.

This I cannot agree with, however. I receive a fair amount of email, and I just cannot stand when people do this. It annoys me to no end and will most likely earn an instant-delete to the email.

Any reason? Or just a pet-peeve?

Mostly a pet peeve, I guess. The subject should describe what the message is about, the body is the message. After opening the message, I automatically look down to read or skim the body. When there's nothing there, it annoys me to no end.

Worst case… at least repeat the subject in the body. Also it annoys me to no end when messages aren't formulated in correct english. (Text-speak is a big no-no.)

If it doesn't all fit in the subject line, put what you're asking for in the first sentence. This makes the purpose of your email immediately clear, and if the recipient is interested in the details they can read the next four lines. A busy person will appreciate you getting to the point and not beating around the bush.

The message body should stand on its own, even if it means repeating information from the subject line. I hate long, rambling subjects only to find something like "So how about it?" in the message itself. Like the contents, the subject line should be short, concise and to the point, only moreso. This is especially important if I'm reading the email on my phone, where a long subject will be mercilessly truncated.

I've found that sending emails when you know they'll be at work (so they'll notice it) is tremendously useful -- say 9am, 2pm, 5pm. People will tend to answer immediately incoming messages before a long queue of messages from the previous day that need attention.

A little shameless self-promotion, that's exactly one of the use-cases we envisioned for our company's product, Momentomail ( http://www.momentomail.com ).

My co-founder and I actually do this with each other, schedule messages so they'll be received sometime in the morning when we're both likely to be working through our mail queue from the end of the day and night before.

I actually almost invariably use the same template for all my communications; 3 straight to the point paragraphs, leaving the details to further discussion (if need there is). Start with the context, followed by the matter at hand and finally the expose the solution, proposal or action required by the recipient. Work in most cases.

I also use the Boomerang plugin for Gmail to schedule my emails to be sent at 9:30 AM, local time of the recipient (you want to be at the top of the inbox when he grabbed his coffee and starts going through his emails).

Sometimes, if you've recently met the person, it's just good to send a "nice to meet you" follow-up with no ask at all. You're very likely to get a response, and once the response has been made, you can make the simple ask (once they've responded once, they're probably more likely to respond again).

This is akin to the "one-line hook" in online dating: http://www.onlinedatingmatchmaker.com/match-messages/

I'm trying to work out emailing for sponsorships for projects that we're running. It's generally cold-calling, but not a shotgun approach - we work pretty hard to come up with companies who would have something to gain from the project.

I'm going to try some of these tips, but would an email with 'Seeking Sponsorship' in the subject get caught in your personal spam filter?

I suggest being as specific as possible. Seeking Sponsorship for [whatever]. Otherwise, it seems to comes off as an impersonal, mass-bcc'ed email, spammed to like a thousand email addresses.

That's not very accurate or descriptive, unless I know you and what you were doing.

Here's my tip: give me something actionable. The e-mails that sit around unanswered are those with wishy-washy requests that require me to think about what the person really wants. The ones that get fast, useful answers are direct and obvious. The "five sentences or fewer" item will get you most of the way there.

People often ask me for writing advice. The number-one tip is always brevity. Cut, cut, cut!

For someone just getting involved with this space, these tips definitely seem helpful. Seems like this is a bit contingent on prior contact and not first-time intro. Should it be in person > then e-mail? A bit confused...

I find it works best to keep each email short and direct. Provide a title which has real content. Keep on topic. NEVER mix two topics in an email; inevitably all but one of the topics will be ignored.

One of the reasons i keep it to 5 lines mails is that most of the top shots I know are reading their emails on devices like the blackberry. Short and simple, even telegraphic gets you responses.

How do you pitch someone while seeking a job/project in 5-6 lines of email? Especially when you are going in as a team rather than sending individual resumes!

The same way you pitch your company in a 60 second elevator ride. Pare it down to the simplest possible (and most compelling) idea.

This advice more or less matches my experience with busy people, although there are some people who just won't read your email no matter how you write it.

i used to use http://five.sentenc.es/ as a guideline.

i tried to use http://three.sentenc.es/, but as i am not a native english speaker, it's hard for me to be compact AND understandable at the same time.

I'm curious what your experience has been using the (two|three|four|five).sentenc.es guides? Do people respond better/worse when you've got that in your email? My thought is most people receiving this message would view it negatively...

i can't say.

i noticed that busy people themselves tend to write very short letters: a pair of questions, no hello/goodbye, nothing personal. seeing that, i started to think that writing five sentences is a respect for their attention and time; i include the disclaimer (signature) to the bottom to indicate that i am not just a dumb, but trying to be short for the recipient's sake.

if they ask specific questions, i elaborate in many sentences (just like i do now :), and then they sometimes don't respond (if we didn't met) or respond after a month (if a person knows me personally). i right imagine how they see the Tolstoy's War and Peace novel, get upset, but as they generally like me, move my lame english masterpiece to some Later folder and move on.

the initial cold emails of any number of sentences stay 90% unanswered.

thrice i shot messages on facebook to the complete strangers that i read about in press (3 sentences: "cograts with new post, would you consider project like ours, if would, i'd be glad to blah blah blah"). and once i got a respond, which forced me to write a long letter which was also answered...

so i dont know if it really works (cold emails are unlucky by nature), but i like to think that being short is a new form of politeness.

(i even tend not to write cold emails at all now! zero sentences, hehe)

I think most of the points are important for every way of communicating. You can exercise them every day.

the shortness is very important...before I used to spell everything out thinking it'd help them make their decision...and my response rate was horrible.

now it's just a simple...would your company be interested in X...and if they say yes...thats when I send the rest of the details

in cases like this, i always tell people to write like a news article: open with your conclusion!

nobody wants to read through as you try to explain all the reasons for your conclusion. if you can't draw them in in the first line, you've lost them

My best advice: read "Made to stick". Not just once - at least once per year.

You can't explain it in 30 seconds, so they'll ignore it

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