3 Questions To Ask To Understand What Keeps Your Prospect Up At Night

If you read any books about copywriting, you’ve probably heard how important it is to know what keeps your prospects awake at night. Powerful copy addresses issues prospects are already facing, problems that already exist, desires they already have, and shows how your solution is the natural answer. It’s critical to understand exactly what issues they’re facing - what is keeping them up at night.

Asking directly, “What is keeping you up at night” is a good start, but you can get much clearer and useful answers by following up with a series of other questions. In this post I’ll share three specific kinds of questions you can ask to get valuable insights into what is keeping your prospect awake at night. First, here’s a story for you.

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Back when I started writing freelance, I worked with a number of different trade publications. I’d interview world-class experts - everyone from NASA sleep researchers to vice presidents at Fortune 500 companies - and piece their insights into a journalistic style article. But interviewing was a challenge, since I wasn’t an expert in any of the topics I wrote about.

So I tried researching the topics, and tried to know enough about them to converse with the expert.

I tried listing out questions beforehand, hoping to overcome my nervousness by being prepared.

I studied the techniques master interviewers like Larry King use.

But all that resulted was being nerve-wracked during the interview, and feeling I didn’t get the best information I could’ve gotten.

Finally I found something that worked. I prepared for the interviews by reading up on the topic beforehand. Then I listed 5-7 brief topics to cover during the interview. And once the interview was underway, I listened closely to the expert, made notes, and highlighted anything that caught my curiosity. I let my curiosity guide the way, and I dug further and deeper on anything that seemed unclear or interesting. I asked open-ended questions like, “Is there anything else you thought I should ask about this topic that I didn’t?” that helped uncover new information I wouldn’t have thought to ask about.

And the result I got was golden. I learned all sorts of new angles and information I couldn’t have imagined before the interview. I dug inside my ithe expert’s head in a way that was otherwise impossible with a direct-style interview. My subjects complimented on my interviewing technique. And my editors were pleased with the results - at least enough to keep hiring me.

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You too can use a similar strategy to dig into what really keeps your prospect up at night. Start by interviewing your prospects, but instead of simply asking what keeps them up at night, create a list of questions to start the interview with, listen closely to their answers, and try to detect any part that seems interesting, or particularly powerful to them. Here are three steps to doing that:

1- Start with “what” questions

Ask your prospect “what” questions like: “What keeps you awake at night?” “What makes you angry about (the problem your solution solves)?” What is your top daily frustration? What do you see happening with this problem over the next 1-5 years? What have you tried doing to address this issue?

2- Listen closely to their answers, then follow up with “why” questions.

Once you’ve covered the “what” questions, listen closely and take notes on any answers they seem particularly passionate about, that catch your attention, or that seem to have any special importance to them. Use your gut feeling here. Then, ask why that issue is so important to them. Uncover the reason and meaning behind that particular problem. Learn how your prospect describes it, in their own words.

3- Ask outcome-related “what” questions

Part of effectively marketing a solution is creating a vision of what the outcome looks like. You’ll need to connect your solution to the positive resolution of the prospect’s issues. So it’s key to learn how your prospect envisions a successful resolution, and the words they use to describe it. So ask outcome-related “what” questions, like: “What would it look like if you were able to solve this issue once and for all?” Learn how they they see what a successful resolution looks like.

So: to learn what really keeps your prospect up at night, ask them directly what keeps them up at night. But follow that up with other “what” questions until you find the key challenge they’re facing. Then understand the “why” behind that challenge, and follow that up with an outcome-related “what” question so you can create a vision around the successful resolution of your prospect’s issue.

If you do this you’ll learn how your prospects describe their problem, in your own words. You’ll be able to relate to them in a way they resonate with. And you’ll likely gain intelligence you can feed back to product development so your solution more closely matches the exact challenges your ideal customer faces.

About Scott McKinney: I'm a freelance copywriter specializing in B2B software/SaaS. Unlike other writers, I come from a mathematics background, so I'm able to tackle technical topics and translate them to what the reader needs to know. Need a writer? Email me at [email protected]