How to send anonymous questions that get answered: tips for senders

Sending questions is a skill too

When people talk about how to use a question box, it tends to be from the point of view of the person receiving the questions (the owner). But the question box experience is a joint effort between the sender and the receiver. Good questions lead to good answers, and when good answers are published, even better questions tend to come in. The starting point of this good cycle is the quality of the questions.

You might think, "It's anonymous, so I can send whatever I want." It's true that on this service, the sender's name isn't shown to the other person. But as long as the owner has the right to choose which questions to answer, whether your question gets answered depends on its quality.

Sending a question to a question box is like writing a letter to someone you don't know. Even when it's anonymous, you're still asking them to spend their time on you. The skill of writing questions that make the other person want to answer shapes the quality of anonymous communication.

3 patterns of questions that get skipped

The questions that question box owners tend to skip follow some common patterns.

Pattern 1: questions that are too short. "What's your favorite food?" "What are your hobbies?" "Do you have a boyfriend?" These are more like survey items than questions. The answers also end in a word or two, so they aren't interesting as a Q&A. The owner may decide, "Even if I answer this, it won't be interesting for people reading," and skip it.

Pattern 2: questions that are impossible to answer. "What do you think life is?" "Can world peace be achieved?" Philosophical questions look deep at first glance, but they're so abstract that there's nothing to grab onto. The owner feels, "Anything I say will sound shallow," puts it off, and it tends to get buried.

Pattern 3: questions that are risky to answer. Questions involving personal information, questions that try to get the owner to badmouth others, and questions on topics likely to cause backlash. The owner may decide, "Answering this will probably cause trouble," and delete it. The sender can send without giving their name, but the owner who answers publishes it in their own question box, so the weight of the risk is different.

How to write questions people want to answer

Questions that tend to get answered have a few things in common.

They're specific. Rather than "Any book recommendations?", something like "I've hit a wall at work lately, so if you know a book that might change how I think, I'd love to hear about it" makes it easier for the owner to put together an answer. When a question has context, the answer becomes specific and fits that context, which should make the Q&A more valuable.

They include the sender's own thoughts or situation. Rather than "Should I change jobs?", something like "I've been at my current company for 5 years, and I feel like I've stopped growing. But I don't have the courage to give up the stability. X, what was the deciding factor when you decided to change jobs?" lets the owner answer by connecting it to their own experience. When the owner can see the sender's situation, the answer becomes more accurate, and the sender may get back an answer that's useful to them too.

They leave room to answer. Rather than questions that end with yes or no, questions that leave the owner room to talk in their own words will likely lead to fuller answers. Rather than "Do you like X?", questions like "What do you think about X?" or "What do you think makes X appealing?" can draw out answers that show the owner's personality.

Manners to keep precisely because it's anonymous

Being anonymous isn't a reason to throw away your manners. In fact, if you make a point of keeping your manners because you're anonymous, the quality of your questions should go up too.

Avoiding aggressive language is the bare minimum, of course. But even more important is respecting the other person's time. Question box owners answer questions without being paid. Whether respect for that time and effort shows through in the wording of your question may change how motivated the owner is to answer.

Opening lines like "Sorry to bother you when you're busy" or "I always enjoy reading your answers" aren't empty formalities. They show consideration for the other person. Even when you're anonymous, just adding this one line tends to make the owner feel, "I'll answer this person's question carefully."

If you send a critical question, draw a clear line between attacking and criticizing. "That comment was the worst" is an attack. "I had doubts about that comment from the point of view of X. Could you tell me what you meant by it?" is constructive criticism. The latter also gives the owner a chance to sort out their own thoughts, and it's more likely to get answered.

The value of sending questions

Sending a question to a question box is active communication that takes a step beyond passive social media use. A relationship where you just scroll your timeline and hit "like" and one where you send questions, even anonymously, and get answers back give you different depths of experience as a follower.

When you send a good question, you may gain new perspectives and knowledge through the owner's answer. You may come across ways of thinking you'd never have come up with yourself, or get concrete hints for vague worries. This is the value that only conversation offers, and it's hard to get from passively taking in information by reading articles or watching videos.

On top of that, the process of putting a question into words is valuable in itself. To make clear what you want to ask, you have to sort out your own interests and worries. Sometimes you even find the answer yourself while writing the question. A question box is a tool for organizing your thoughts for the sender, too.

An anonymous question box is a form of communication where both the sender and the receiver gain something. Sharpening your skill at sending good questions is an investment that adds to that value.