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

Pobox is proud to have several very active members of the open source community as staff or alumni, which means they get many questions about how their software works (and not just from me!) Today, Mark Jason Dominus, Perl expert, noted author and Pobox staffer, offers his thoughts on how to ask a good question.

I once emailed Dr. Mark Norman, one of the world's foremost experts on octopuses, to ask some questions about octopus anatomy. I once wrote to a well-known writer of computer programming books asking for advice on how to choose a publisher for my own book. I once bugged one of the inventors of the Unix operating system for information about the early technical details of Unix. Last month I wrote to a famous mathematician to ask for a copy of a paper he had written that was too old to be available on the web.

Maybe you're not interested in octopus anatomy or in digging up copies of obscure mathematics papers. But I know some of you are interested in emailing some sort of questions to well-known experts on something, because I'm a well-known expert on computer programing, I get email from strangers all the time, and I know I can't be the only one who does. Someone must be sending those messages. Maybe it was you.

Sometimes I'm really happy to get the messages, and I answer quickly and at length. Other times, I snort and throw the message away, or save it to chuckle over with my friends — or worse, I save it to ridicule in a blog post years later. Here are some easy rules to follow if you want to know how to send the first kind of email, the kind that gets a reply, and not the second.

The rules are pretty simple. Probably the biggest one is:

Pick the right expert for your question.

Only ask the expert questions about an area in which they actually have expertise. If you write to the octopus expert with a question about advanced mathematics, or to the mathematician for advice about octopus behavior, you'll look like a fool, a lunatic, or both. And even if the mathematician is feeling indulgent and is willing to help you, she can't, because she doesn't know the answer to your question anyway.

Does that seem obvious? About ten years ago I received this awesome specimen:

I am a student of Romance and Germanic philology faculty,
I am getting my Master's degree, so I have to write a thesis.
The theme I have chosen is "Lexico-grammatical peculiarities of
the language of constitution" I have to compare the UK(magna
karta)and US Constitution. . ... Will you provide me with the
information, or give a hint about those sources where I can read
about my topic?

I didn't bother replying to this message. I'm a computer programmer. What do I know about lexico-grammatical peculiarities?

But really, there was nothing wrong with the request itself; the only problem was that it was sent to the wrong person. Somewhere out there is a professor of linguistics who specializes in the study of legal documents. That professor would probably have been delighted to offer this poor schmuck some pointers.

People I meet often worry that the expert will be annoyed that a member of the general public is taking up their time. But if you observe this rule, you won't have to worry. I promise you that the expert on the history of knitting would love to get your email inquiring about the origin of the slip stitch. The education expert who wrote about penmanship education in last week's local paper will be thrilled to hear from you. People become experts because they are interested in their topics. Getting email from another interested person brightens their day. People write papers and articles because they want other people to read them attentively. Their great fear is that nobody is listening. Hearing from someone who not only read their article but who cared enough to follow up is a shining joy.

But even if you send your question to the right person, there are still a few ways to go wrong. Next week, I'll discuss some of the other mistakes people have made in asking me for help.