Questions are an essential part of the workday. Through our questions, we surface concerns, misunderstandings, incomplete information, and more. They are, however, inherently interruptive. They can also be uncomfortable as the asker; it can feel like you are admitting inadequacy or annoying your co-workers. Unfortunately, the only way to get better at asking questions is practice. Fortunately, there are a few guidelines you can follow to help make your questions more effective for all parties.
Respect others' time
Remember that not everyone's down-time coincides with yours. Especially at a remote company – where you cannot walk over to someone's office and see if they are busy – you may need to prepare yourself for a delay. We tend to encourage asking questions in public channels. It increases the likelihood someone will be free to answer your question at any given time. That said, if you're asking questions in a messaging platform like Semaphor your question may get buried in a public channel. If you don't get a timely response in the public channel, consider also sending a DM with clear context to someone you think may be able to help.
Research your questions
In general, you'll find people are happy to help out and get you oriented (especially when you're new and the most afraid of having questions!). However, no one welcomes a question that could be solved by a quick glance at the company wiki, or even a web search.
Researching your questions will allow you to arm yourself with an impactful question. You'll be able to ask in a clear, actionable way and you'll avoid the question spiral that can happen if you ask a vague question and the answer confuses you even more.
If you aren't even sure how to begin researching a question, try highlighting your desire to be self sufficient in your question format. Let your target know what you are trying to learn, and what you've already tried. "What is blockchain" will be received less favorably than, "Can you point me towards some high level information on blockchain? I searched the wiki, but there's so much information I'm not sure where to begin".
Set Clear Expectations
When you're starting a new project and you feel out of your depth, it can be hard to know whether you ought to research alone for 10 minutes or 10 days before calling in help. Work with the other project stakeholders to get a sense of how long you should struggle before surfacing questions. What's the overall project timeline? If your stakeholders are expecting results by end of day, you probably don't want to wait until 4pm to ask questions. If the project isn't due for another month, you can probably struggle on your own for a little longer. Can you find out from the outset when the other stakeholders or subject matter experts are most comfortable setting aside time for questions? The more clearly you can set expectations regarding your comfort level with the material, your resources availability, and the timeline available the less friction you should have when questions arise.
Record the Answer
Write down or repeat back the answer in your own words. This will not only solidify the answer in your memory, but will also allow for corrections if anything got lost in translation. If you're writing down answers, you can reference your notes before asking again the next time it comes up. Your cleaned-up notes may even serve as training and reference materials for folks who come after you. (As an added bonus – hand-written notes have been linked to better conceptual learning and synthesis of information!)
Everyone learns (and explains) differently. If you're still struggling after you've gotten a response, feel free to ask again but challenge yourself to ask a different person. This reduces friction caused by repeat questions and increased the likelihood a new way of explaining will cause the answer to click this time.
If you've got more than a couple minutes, I highly recommend checking out Eric Steven Raymond's How To Ask Questions the Smart Way. He goes into much greater detail.