I’m in the business of asking the right questions. In fact, in college I actually got kicked out of class for asking too many questions. But that’s another story. 

Drawing information out of people can be challenging. 

Once you do, you’ll see that there are endless possibilities for turning those conversations into meaningful content, whether it’s a podcast or blog or social media post. If the conversations spark something in both the one who asks and the one who answers, the chances are high that the insights will be meaningful to a broader audience.  

So, I keep the prompts I’ve listed below in a document within arm’s reach. They are intentionally open-ended and unusual enough to give my clients pause, and that circumspection is what you want. To illustrate the many possibilities, I’ve also added answers to them as well as some self-reflection questions.

The most important aspect of this tactic is NOT to judge the answers to the questions or devise a plan for executing them. Simply ask, listen to the answer and memorialize it somewhere. Once you notice that an answer reoccurs, it’s time to address it in content.

You can use the answers to these questions anywhere in your business from obvious places like your blog, social media, YouTube, email newsletters and sequences to improving sales processes and customer service. 

11 Deceptively Simple Content Prompts

Below I’ve listed 11 simple questions along with a few examples of answers for each one. Ask yourself and your team these questions to create an endless amount of compelling content. 

1. What questions do clients ask you the most?

• Can you jump on a quick call?
• Whom do I ask about…..??
• Where do I find….?
• How long will it take to….?

2. What questions do prospects ask you the most?

• Why are your services so expensive?
• Do you think we could do some kind of barter arrangement?
• How are you different from X competitor?
• Is there a guarantee?

3. What questions do you wish prospects would ask you?

• Is there one story that sticks with you about building this product/service?
• What’s the most challenging part about adopting this service/product?
• How does your company give back to the community?
• How many women are in leadership positions in your company?

4. What do your prospects need to understand/learn/know before becoming a client?

• We don’t take ourselves too seriously.
• We believe in ourselves and our company, but we’re not overconfident jerks. 
• The learning curve is steep with our product, but we’ll support you if you put in the work.
• We’re committed to social justice and support under-represented populations first. 
• We have no opinions on outside issues; we just want to sell software. 

5. What do you do differently than anyone else in your industry?

• We don’t interrupt our clients in meetings.
• We limit our membership and don’t invite anyone new until someone drops out (which is rare). 
• We communicate with our clients via phone. No auto-responders. No chatbots.
• We create content from 1on1 interviews with our clients, not just content briefs.

6. Why did you start doing what you’re doing? What got you into it? What keeps you doing it?

• I started this business because my son was frustrated by how many textbooks he had to carry in his backpack every day. 
• My work makes me laugh all the time. I can’t imagine doing anything else. 
• My Mom raised eight kids by herself. She showed me what leadership is about. 

7. What are some of the most common objections you get from your target prospects?

• It costs too much.
• I don’t see the value.
• I don’t know anyone who uses this.
• It seems like a huge commitment.

8. What’s something your prospects assume that’s almost always wrong?

• That we get it right a lot more than we don’t.
• That we will do the work for them, not with them.
• That the customer is always right. 
• That their investment alone guarantees success, it doesn’t. 

9. What barriers do your best prospects often have to converting?

• It’s never the right time.
• It’s always too much.
• It’s not a priority.

10. What are your best prospects thinking about, worried about, and researching?

• They want more human interaction. 
• They doom scroll pretty much 24/7.
• They’re trying to figure out what to do next. 

11. What are the things you find yourself telling your clients the most?

• It can be anything—advice, a helpful analogy, a visual, a story, a stat, etc.
• These are the things you usually repeat on autopilot, but your client leans forward in her chair when you say them.

Capturing these exchanges will pay dividends in meaningful insights, identifying emerging trends and sincere, on-brand content ideas. 

Your only job is to become a better listener. Heed the words of Mr. Rogers, who had a piece of paper on his desk that read, “WAIT.” Someone asked him what it meant. He answered, “Why Am I Talking?”