20 Prompts
To Make Your Marketing More Comfortable
First – some context
I answer dozens of questions every week during mentoring client Q&A Voxer sessions.
And I’ve started offering monthly Q&A sessions to All Access Passholders.
I wanted to create a short guide for anyone who wanted to chat with me during a Q&A day but didn’t know what to ask me or how to start the conversation.
So I copy and pasted a big, long list of previous questions into ChatGPT and asked for help analyzing them so I could come up with a list of prompts to inspire clients/Passholders.
Once I’d tweaked the list, I realized this was actually a pretty solid set of questions for anyone wondering how they could make their marketing (or business) more comfortable.
So here you go.
You can use this list of questions to come up with ideas you’d like to try out in your business, or identify areas you need to focus on.
Or you can use the prompts to come up with a question to ask me at the next Passholder Q&A day (usually the last Tuesday every month).

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Prompts About Direction and Strategy
1. What feels unclear or confusing about where you’re heading next?
2. Where are you hesitating or second-guessing yourself?
3. What decision keeps circling in your head, but you haven’t made it yet?
4. What’s working fine, but could probably work harder for you/your business?
Prompts About Offers and Sales
5. What offer feels misaligned, too much effort, too little return, or just not fun anymore?
6. Do you sense a mismatch between interest/enthusiasm and sales? Example: Having a good flow of new subscribers but they don’t buy.
7. What’s one way you’d love to earn money that currently feels out of reach?
8. What part of your sales process feels awkward or forced?
Prompts About Marketing and Messaging
9. Which part of your online marketing isn’t pulling its weight? (email, social media, blog, podcast, website, sales pages, funnels)
10. Are you struggling to say clearly who you help, what you do, or why it matters?
11. What are you doing to get in front of new people, and is that working for you?
12. What story, idea, or update would you like to share but don’t know how to frame?
Prompts About Systems and Structure
13. What feels like to takes up a disproportionate amount of your time, energy or headspace each week?
14. Which tools, tech, or systems are you unsure whether to stick with or change?
15. Where do you feel scattered or overloaded in your marketing or workload planning?
16. What was your most ‘I don’t wanna’ moment in the last 7 days?
Prompts About Opportunities and Experiments
17. What new opportunity or idea feels exciting but also a bit risky or confusing?
18. Is there something you’d like to try but it feels like too much of a commitment? Want my help making that more manageable?
19. What’s something you’d like an outside perspective on before you say yes or no?
20. What is something that used to work well for you, but has unintentionally fallen by the wayside (been forgotten)?
Ways to make the most of this list
You only need to use it a few times each year, or when you feel totally stuck and not sure what to focus on.
You don’t need to act on every problem/opportunity it identifies – pick what feels the most impactful and/or exciting to you.
This could be a fun thing to do with another business owner – complete the questions separately, then get together to discuss the results and make a plan of action.
For the opportunity to…
Ask me anything on the monthly Voxer Passholders Q&A day – join the All Access Pass here.
Work with me 1-1 for 3 months to make your marketing more comfortable and effective – join Marketing On Purpose waitlist here.

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