How to ask

As always, my writing is influenced by my learning. Recently, I was revisiting a blog post from around 2014 about hacker culture and the art of asking smart questions in technical open forums. I’ve taken the ideas from that post and applied them to a wider range of situations. You should read this guide to improve your question skills and increase your chances of receiving a satisfactory answer.

Before You Ask

In general, the kind of answers you get to your questions depends as much on the way you ask them as on the difficulty of developing the answer.

Real creators like hard problems and good, thought-provoking questions about them. If we didn’t, we wouldn’t be here. When you present us with an engaging question, we appreciate it; well-crafted questions are a precious gift. They help us refine our understanding and often bring to light issues we might otherwise overlook. Among problem solvers, “Good question!” is a sincere compliment.

Despite this, we often have a reputation for responding to simple questions with what may appear as hostility or arrogance. This can sometimes come across as rudeness towards newcomers and those who are less knowledgeable. Yet, the reality is different.

What we are, is hostile to people who seem unwilling to invest the effort in thinking or conducting their own homework before asking questions. People like that are time sinks — they take without giving back, and they waste time we could have spent on another question more interesting and another person more worthy of an answer.

Still, our style of answering questions is tuned for people who do take an active interest in problem-solving and are willing to be active participants in the process. That’s not going to change. Nor should it; if it did, we would become less effective at the things we do best.

If you find our attitude condescending or arrogant, check your assumptions. We don’t expect you to defer to us— in fact, most of us would love to engage with you as equals and welcome you into our culture if you put in the effort required to make that possible. However, it’s not efficient for us to try to help those who are not willing to help themselves.

Therefore, while competence isn’t a prerequisite for receiving attention from us, demonstrating the attitude that leads to competence—being thoughtful, observant, and willing to actively collaborate on finding solutions—is essential.

How to Ask

Proficient creators blow off questions that are improperly targeted to try to protect their communications channels from being drowned in irrelevance. They are already receiving more than their fair share of mistargeted messages. Also, reaching out to someone you aren’t familiar with is risky at best. For instance, don’t assume that the founder of raising startup wants to be your free consultant. If you want a responsive answer, approach your question like someone who possesses intelligence, confidence, and some clues but simply needs assistance with a specific problem.

Before asking a question, do the following:

  1. Describe the symptoms of your problem.
  2. Describe the context in which it occurs.
  3. Describe the research you did to try and understand the problem before you asked the question.
  4. Try to find an answer by yourself.

When you ask your question, show that you’ve taken these initial steps. This will help establish that you’re not being a lazy sponge and wasting people’s time. Even better, display what you’ve learned from doing those things. We appreciate answering questions for people who have demonstrated they can learn from the answers. Making it clear that you are able and willing to participate in developing a solution is a very good start.

Take your time. Complex problems take time. Pause, think, and give the problem some thought before approaching experts. Trust us, we will be able to tell from your questions how much reading and thinking you did, and will be more willing to help if you come prepared. Don’t fire your whole arsenal of questions because your initial search didn’t yield results, or provided too many.

Prepare your question. Think it through. Hasty-sounding questions get hasty answers, or none at all. The more you demonstrate that you’ve put genuine thought and effort into solving the problem before seeking help, the more likely you are to actually, get help.

When You Ask

Avoid making optimistic guesses about whether your question will be well-received. If you’re unsure, send it elsewhere, or refrain from sending it at all. Never assume you are entitled to an answer. You aren’t. You will earn an answer, if you earn it, by asking an engaging and thought-provoking question — one that adds value to the community rather than demanding knowledge from others.

In general, questions to a well-selected public are more likely to get useful responses than equal questions to a private individual. There are several reasons for this. One is the larger pool of potential respondents. Another is the size of the audience; creators would rather answer questions that educate many people than those that benefit only a few.

Make it easy to reply

Use specific subject headers

Make your subject line accurately reflect your question. One good convention for subject headers is “objectdeviation”, where “object” specifies what is having a problem, and the “deviation” describes the deviation from expected behavior.

Stupid: “Help me find a co-founder”

Smart: “Tech startup co-founder search - I need guidance”

Smarter: “Tech startup co-founder search - I need strategies for networking experienced ed-tech founders”

Volume is not precision

I’ve found by experience that people who are sloppy writers are also sloppy at thinking. Answering questions from careless thinkers is not rewarding; we’d rather spend our time elsewhere. Thus, expressing your question clearly is important. If you can’t be bothered to do that, we can’t be bothered to pay attention.

Spend the extra effort to polish your language. It doesn’t have to be formal—in fact, we value informal humorous language used with precision. But it has to be precise; there has to be some sign that you’re thinking and paying attention. This end isn’t served by dumping your question with a massive amount of data. If you have a large, complex problem, aim to trim it as small as possible. This is useful for at least two reasons. First, simplifying the question makes it more likely you’ll get a useful answer. Second, during the process of refining your problem, you may discover a solution or workaround yourself

Groveling is not a substitute for doing your homework

Some people who get that they shouldn’t behave rudely, demanding an answer, retreat to the opposite extreme of groveling. “I know I’m just a newbie, but…”. This is distracting and unhelpful. It’s especially annoying when it’s coupled with vagueness about the actual problem.

Don’t waste your time, or ours, on politics. Instead, present the background facts and your question as clearly as you can. That is a better way to position yourself than by groveling.

Describe the problem’s symptoms, not your guesses

Often, people who need help have a high-level goal in mind and get stuck on what they think is one path toward the goal. They come for help with the step, but don’t realize that the path is wrong. It can take substantial effort to get past this. See the XY problem. If you are trying to find out how to do something, begin by describing the goal. Only then describe the particular step towards it that you are blocked on.

Also, it’s not useful to tell what you think is causing your problem. If you were confident about your diagnostic, would you be consulting others for help? So, make sure you’re telling the raw symptoms of what goes wrong, rather than your interpretations. Let them do the interpretation and diagnosis. If you feel it’s important to state your guess, label it as such and describe why that answer isn’t working for you.

Stupid: How do I use this specific library to generate PDFs from my data in Python?

Smart: I want to create PDF documents from data in Python, and I’m currently exploring different libraries to achieve this. While I’ve been looking into using Library X, I’m open to other suggestions or approaches that might be more suitable for this task.

Be explicit about your question

Open-ended questions tend to be perceived as open-ended time sinks. Those people most likely to be able to give you a useful answer are also the busiest people (if only because they take on the most work themselves). People like that are allergic to open-ended time sinks, thus they tend to be allergic to open-ended questions.

You are more likely to get a useful response if you are explicit about what you want respondents to do. This will focus their effort and implicitly put an upper bound on the time and energy a respondent must allocate to helping you. This is good.

To understand the world the experts live in, think of expertise as an abundant resource and time to respond as a scarce one. The less of a time commitment you implicitly ask for, the more likely you are to get an answer from someone really good and really busy. So it is useful to frame your question to minimize the time commitment required for an expert to field it — but this is often not the same thing as simplifying the question.

Prune pointless queries

Resist the temptation to close your request for help with null questions like “Can anyone help me?” or “Is there an answer?”. First, if you’ve written your problem description halfway, such tacked-on questions are at best superfluous. Second, because they are superfluous, creators find them annoying.

How To Interpret Answers

If you don’t understand the answer

Much of what looks like rudeness in creators’ circles is not intended to give offense. Rather, it’s the product of the direct, cut-through-the-bullshit communications style that is natural to people who are more concerned about solving problems than making others feel warm and fuzzy. So, if you don’t understand the answer, do not immediately bounce back a demand for clarification. Use the same tools that you used to try and answer your original question to understand the answer. Then, if you still need to ask for clarification, exhibit what you have learned.

If You Can’t Get An Answer

If you can’t get an answer, please don’t take it personally that we don’t feel we can help you. Sometimes we may not know the answer. No response is not the same as being ignored, though it’s hard to spot the difference from the outside. In general, re-posting your question is a bad idea. This will be seen as annoying. Have patience. Remember that the busy expert with your answer is solving more important problems, or it may be that your question wasn’t well-formed, to begin with.

How To Answer Questions

Be gentle. Problem-related stress can make people seem rude or stupid even when they’re not.

If you don’t know for sure, say so! A wrong but authoritative-sounding answer is worse than none at all. Don’t point anyone down a wrong path because it’s fun to sound like an expert. Be humble and honest; set a good example.

If you can’t help, don’t hinder. Don’t make jokes about initiatives that could deviate the querent away from the truth — the poor sap might interpret these as instructions.

Ask probing questions to elicit more details. If you’re good at this, the querent will learn something — and so might you. Try to turn the bad question into a good one; remember we were all newbies once. Reframe the question.

If you’re going to answer the question, give good value. Don’t suggest kludgy workarounds when somebody is using the wrong approach. Suggest good frameworks.

Help your community learn from the question. When you field a good question, ask yourself “What do I need to change so that nobody has to answer this again?”. One simple answer to this is to write a blog post about it, like this one!

Demonstrate your research skills rather than writing as though you pulled the answer out of your butt. Answering one good question is like feeding a hungry person one meal, but teaching them research skills by example is showing them how to grow food for a lifetime.