How to ask questions to strangers, part 3

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This article was originally published as part of the Pobox blog. Pobox was acquired by Fastmail in 2015.

Mark Dominus concludes his series of articles on how to send email to strangers asking for help. Read his previous entries about picking the right expert and using an informative subject.


In the past couple of articles, I covered the two most important rules of asking a stranger for help. There are also several minor-seeming mistakes you can make that will sink your chances of getting a reply.

Use correct spelling and grammar.

Yes, this is boring and tedious. And yes, I know you have heard it before. And yes, I know that only fussy old people care. But some of those people you are asking for help are as old and as fussy as I am. And some of those fussy old people will throw your message in the trash if it starts with:

i hope that u would be able to help me.

or ends with:

You wouldnt by any chance have any info on B+ & B* Trees would u ???

Maybe in another twenty years we’ll write everything in SMS abbreviations. Until then, the fussy old folks like me will still be alive, and the writer of a line like these will appear to be either:

  1. illiterate,
  2. too lazy to press the three extra keys required to get it right, or
  3. A GODDAMN JACKASS.

Excuse me, lost my patience there.

Related to this is that you should have your real name in the “From” line of the message, or at least a name that is not obviously a fake name. Seeing “Smoove B” in the header of a message is not going to help convince a stranger that you are worth emailing.

Don’t make the recipient do any work.

Of course, to answer a question, the recipient will have to do the work of answering the question. But your aim is to make them do as little work as possible. For example, I once got a message with the subject “your article” asking me “What is meant by ‘forkish’?” Huh? What article? Did I say “forkish”? How should I know what I meant?

I eventually dug up the article, which I had written several years earlier. If I had been a little busier that day, the question would have gone straight to the trash bin.
It would have been a big help if my correspondent had written something like this:

In your article “…” at URL http://… you said “Blah blah blah forkish.” What did you mean by “forkish”?

Then I would have known right away what I had meant, or at least I would have been able to look at the article easily.

Experts are busy people. The more work you ask them to do, the less likely you are to get a response. Try to provide all the relevant information that you can. Don’t ask them to look stuff up for you in books; say “I didn’t understand this thing I looked up in a book. Does it mean X or Y?”

Don’t appear impatient

I don’t know about other people, but when I get a message that says something like one of these:

Please respond ASAP!

I need the answer right away!

This is very important.

I want to unleash a torrent of sarcasm. “Gosh, I’ll be sure to clear my schedule to work on this important project for you!” You’re asking a stranger to do a favor for you, so it’s not appropriate for you to put conditions on when or how they do it. Here’s that “forkish” example in full:

what does forkish mean? this is very important. thank you. please respond.

“This is very important” spoils the effect of “please” and “thank you”. It says “please”, but it doesn’t mean “please”. Some time ago, I tried rewriting that message in a form I would have liked better, and came up with:

Could you take a moment to explain what you meant by ‘forkish’ here?

I didn’t notice until after I had written it that I had eliminated “please”. But the rewrite communicated “please” anyway, whereas the original one didn’t.
That’s all the advice I have. Good luck writing to strangers!


Thanks, Mark! I recently took his advice, and wrote to some experts on one of my favorite topics… Pobox! I asked them for tips and tricks that they use that they would like to share with other Pobox customers. If you’ve got something that you think other customers would be interested in, just drop me an email to pobox@pobox.com with the subject “blog tip”.

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