When I talk to people about my work, they often ask how I know what to write when dealing with industries, companies, products, and services I initially know very little about. My response is, “I ask a lot of questions.” The follow-up response is typically, “Yes, but how do you know what questions to ask?”
Last year I wrote a blog post on just that topic: How to Ask the Right Questions. Since writing it, and talking to several people lately about the art of asking questions, I have come up with some additional tips worthy of their own post. Here they are:
Begin With the End in Mind
When starting a writing assignment, you usually know what type of document you want to end up with: a blog post, a brochure, a case study. Right there, the questions you ask can be narrowed. For example, with a blog post, you will want to ask something like, “What is the most important thing readers will want to know about this topic?” or “What do readers have difficulty with regarding this topic?” While a blog post is meant to narrow a topic, something like a white paper is meant to expand on it, so you might ask your subject matter expert (SME) to give you an overview of the topic.
Review Previous Documents
Try to find a document already developed, by you or someone else, that looks close to what you want. Write down the qualities you like: “to the point,” “nice rhythm,” “does a good job of outlining benefits,” “strong call to action.”
You now know what qualities you’re going for. Direct your questions to subject matter experts in ways that will produce answers to help you achieve them. For example, if your target document is a website with a strong call to action, ask the website owner, “What would you like readers to do after viewing your website?”
Analyze Previous Documents
Just because you have the end in mind doesn’t mean you know how to get there. The next step is to take out your red pen and go through the document, section by section (line by line if necessary) to analyze just what the author did to make it so brilliant. I find this exercise particularly useful when I’m dealing with a type of document I haven’t written before, or when a client provides vague instructions.
You should notice things like the type of information (e.g. description, benefits, ordering info), the order of the information, the tone, use of certain terms or phrases, styling and position of subtitles, paragraph length, and level of detail.
Now you have even more questions to ask. For example, if the sample document offers a detailed description of each product, ask your interviewee, “What are the exact measurements of the Deluxe Widget X-347?”
Draw on Past Experience
No one has experience in every industry. But, the professional and personal experiences you have had can help you develop insightful questions. For example, one of my current website clients initially told me that he repairs digital signs. I know nothing about digital signs, but I do know from experience with other technician types that when they can repair, they can also typically install; so one of the questions I asked him is, “Do you also do digital sign installations?” And, while I don’t know much about what goes on in a digital sign repair session, based on my professional experience, I know that the process of each service provider is unique; so I also asked this client, “Can you describe a typical engagement, from start to finish?”
Listen Carefully
Part of mastering the art of asking questions is good listening. Often, the answers a content owner or SME gives you can lead to additional questions. For example, say you are interviewing the owner of a business to put together a brochure. You ask: “What are the primary services you provide?” She responds: “Well, on the software side, we provide consulting, training, and educational video development.” You, being the savvy interviewer, think, “Hm, she said ‘software side.’ That must mean there is another side.” You ask: “What is the other side of your business and what services do you offer there?”
How have you cultivated the art of asking questions? Please tell us in the comments.
About the Author: Karen Marcus, M.A. is a Northern Colorado copywriter who has been helping clients in a wide range of industries to put their best word forward for 13 years.
Need assistance developing great questions? Karen can help! Click here for contact info.



Very useful tips. Really helps to narrow things down and focus the information. Even though sometimes we already know the answers, asking the right questions helps to sort out the info. Thanks alot!
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Thank you for the tips, it helps a lot. Ive been pretty much interested in the art of asking the right questions, and i totally agree with you on the “Listen Carefully” part. Sometimes we just have to listen carefully because there are things that we already know the answer about surprisingly
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