107: The Simple Hack for Answering Tricky Emails

Ever received a customer email that left you staring at the screen, completely stumped on how to respond? As the owner of two businesses, Heather knows that feeling all too well!
In this episode, she shares her simple hack for handling those tricky emails with ease, including how she uses ChatGPT to craft replies in minutes. You’ll hear how she collaborates with her team to stay on top of her inbox, why setting clear communication boundaries makes a big difference, and how screenshots + AI = a total game-changer.
Plus, Heather shares how she uses ChatGPT beyond email, like outlining sales pages and saving time on content creation.
Key Takeaways:
- (02:50) The struggle of responding to tricky customer emails
- (04:25) How ChatGPT helps craft thoughtful, professional replies
- (06:00) Setting communication boundaries and why it matters
- (08:40) Other ways Heather uses ChatGPT to boost productivity
Listen to Episode 104:
Using Graphics to Build Trust and Increase Conversions with Mauri King
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Turning Tricky Customer Emails into Opportunities: Tech Tips & Teacher Biz Wisdom
Practical strategies for handling customer communication, setting business boundaries, and leveraging AI tools
Facing the Fear: You Don’t Need All the Answers
It’s easy to assume that business owners have it all figured out. The reality? Heather reminds us that no one hands you an owner’s manual when you start a biz.
Many entrepreneurs—teachers included—encounter tricky customer emails that leave them stumped. Sometimes, your team might not know how to respond and turning to each other doesn’t always yield the perfect answer.
Whether you’re fielding offbeat requests or trying to untangle unclear customer complaints, you’re not alone in feeling unsure of what to do next.
Harnessing AI: ChatGPT as Your “Kind but Firm” Email Partner
Heather’s favorite hack for handling “bizarre” or challenging customer emails is leveraging ChatGPT (affectionately dubbed “Chatty G”). Here’s her process:
- Screenshot the email: Capture the confusing or tough message.
- Upload to ChatGPT: Input the screenshot with a prompt like “Give me a kind but firm no response to this email” or ask for help clarifying what a customer means.
- Refine and personalize: Copy, paste, and tweak the suggestion as needed. If you upload the actual screenshot, the tool can personalize the response using the customer’s name.
AI isn’t just a time-saver—it can help you strike just the right tone, keeping communications kind but clear, especially for situations where you need to say “no,” or clarify without coming across as harsh.
Setting Boundaries: Defining How You Do Business
As Heather puts it, just because you have a business doesn’t mean you have to let customers into every corner of your life. She underscores the importance of setting boundaries, especially as a small online business owner:
- No phone calls, please: Establish that all customer service happens over email—no need to share your personal number or chat on the phone.
- Redirect social media requests: If a customer tries to use direct messages for support, gently guide them to your business email with a pre-written, canned response.
- Tech tips: If you do end up needing a public-facing phone number, tools like Google Voice let you create one for free, so you never have to give out your private number.
These boundaries create a more manageable and less stressful customer service experience, and they set healthy expectations for your clients from the get-go.
AI Beyond Email: Brainstorming, Content, and Scaling Smarter
AI isn’t just for email.
As Heather and her podcast guest Maury King discussed in episode 104, ChatGPT can help you outline sales pages, rewrite content, and repurpose materials to fit different products or audiences.
Just input a piece you’ve already written, and let ChatGPT adapt it for the next project—an enormous time-saver for any solopreneur.
Your teaching skills go far beyond the classroom. Heather proves you can build a profitable, flexible business that fits your life. Start small with her free guide and see where it takes you!