I figured out your next 19 posts

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Hey—It's Tim. 

Penfriend can help you with a lot of content things.
Write it. Research it. Score it. Structure it. Make it rank.

But we can't tell you what only you know. (Yet…)

• The insights from your sales calls.

• The objections prospects bring up every time.

• The win you got a customer last week.

That's the content that converts.

Not SEO templates. Not AI-generated fluff.

The stuff only you can write because only you lived it.

Here are 19 questions to get that out of your head and onto the page.

Use them for blogs. Long-form posts. Videos. LinkedIn. Whatever.

Just use them.

The 19 Questions

1. "What's the biggest objection prospects have before buying?"

Not features they're missing. The reason they don't pull the trigger.

Example: "It's too expensive" → Write about ROI calculation
Example: "We tried this before and it failed" → Write about why previous attempts fail

2. "How does someone actually work with you? What's the process?"

Walk through days 1-90. Most buyers have no idea what happens after they sign.

3. "What's one thing your customers can implement today?"

Not a 6-month strategy. Something they can do in 20 minutes that moves the needle.

4. "What's a mistake you made and the lesson you learned?"

Your failures are more interesting than your wins.

Bonus: Shows you're human.

5. "Who is your product for? Who is it NOT for?"

The second part is more valuable than the first.

Excluding people builds trust with the right people.

6. "Show a before/after transformation from a real customer."

Not a case study template. A story.

Where they started. What changed. What happened.

7. "What's the biggest win you've gotten a customer?"

Numbers. Specific outcomes. Real companies (with permission).

"Increased traffic" → "Went from 2K to 47K monthly organic visitors in 4 months"

8. "Why should someone choose you over your competitors?"

Not "we're better." Specific differentiation.

"We're the only ones who..." or "Unlike X, we..."

9. "What should buyers expect when evaluating your category?"

Educate them on what to look for. Even if it helps competitors.

You become the authority.

10. "What's a myth in your industry that everyone believes?"

"You need 10K followers to see ROI from content" (myth)
"SEO takes 6 months to work" (myth)
"AI content can't rank" (myth)

Bust it. With data.

11. "What's the biggest misconception prospects have about your product?"

They think it does X. It actually does Y.

Clear this up before they're on a sales call.

12. "What's a question you get on every single sales call?"

If you're answering it 10 times a week, write it once.

Then send the link.

13. "What's something you wish prospects knew before talking to you?"

Makes sales calls easier. Qualifies better. Saves everyone time.

14. "What's a contrarian opinion you have about your industry?"

Hot takes get attention. Backed-up hot takes get trust.

15. "What's a recent customer win?"

This week. This month. Recent = relevant.

16. "What do people need to know before they're ready to buy?"

Education content. Not selling. Just helping them understand the problem.

17. "What's an unpopular opinion you have about how to solve [problem]?"

Everyone says do X. You say do Y. Explain why.

18. "What's a question prospects asked you this week?"

Real questions from real calls. Answer it publicly.

Now it's SEO content.

19. "What's something nobody tells prospects but you will?"

The truth competitors won't say.

The ugly part of the process.

The thing that makes you trustworthy.

How to Use This

Step 1: Pick one question from the list above

Step 2: Record yourself answering those questions. Write them down. Film yourself.

Step 3: Add a real example (customer story, your experience, data)

Step 4: Publish it

Step 5: Repeat next week with a different question

You just solved "I don't know what to write" for the next 19 weeks.

Save this email.

Next time you're staring at a blank page, open it and pick one.

See you tomorrow.

✌️ Tim "I got 99 questions…" Hanson
CMO @Penfriend.ai

Same brain, different platforms: X, Threads, LinkedIn.

P.S. I use these questions to write a lot of the newsletters. And then I take those insights and put them into my blogs.

Really helps to build out the library of “what does Tim think about (topic)”

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