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Pitch Incoming: How One Honest DM Outperformed 10,000 Automated Messages
This week, we’re diving into what AI can’t automate — authentic human connection.
When an unexpected “Pitch incoming 😎” message caught Kim’s attention, it sparked a bigger conversation: Why do some automated messages make us roll our eyes, while others make us reply?
Join Kim and Hal as they break down:
- The DM that did everything “wrong” — and yet worked brilliantly.
- Why automation without empathy kills trust.
- The “Handshake Clause” — how to make sure everysystem ends with a human touch.
- The H.E.A.R.T. Method — five simple principles that help you scale authenticity alongside efficiency.
You’ll learn how to design your AI systems to sound morelike you, keep your customers’ trust intact, and build automation that scales connection, not just communication.
Because in the end, authenticity isn’t soft — it’s strategic.
You’ll Learn:
- Why transparency is the new trust currency.
- How to design automation that feels human, not hollow.
- The 5-part H.E.A.R.T. Method for balancing empathy and efficiency.
The H.E.A.R.T. Method (Quick Reference):
- H – Honesty: Be upfront about automation. It builds credibility, not risk.
- E – Empathy: Program your AI to recognize emotion and respond with care.
- A – Authenticity: Feed your systems your real voice, tone, and phrasing.
- R – Reciprocity: Automate a gift before a demand. Lead with value.
- T – Transparency: Keep your human handoffs clear and your audit trail clean.
Ready to Take Action?
- Subscribe to Small Business Big AI on Spotify or your preferred platform, leave a review, and share this episode with a fellow entrepreneur who could benefit from AI insights.
- Join the AI Insiders Community for Exclusive Tips & Resources → Request to Join our Private Community
- Ask us about the IMPACT Framework course—a strategic way to communicate effectively with the AI → Email Howard & Howard Holdings, Inc.
- Ask us about the Small Business Transformation Model (SBTM)—a simple, step-by-step framework designed forbusiness owners → Email Howard & Howard Holdings, Inc.
- Have a question or an AI success story? DM us on LinkedIn or Facebook!
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Music Credit: “I Am with You” by Dream Cave; EpidemicSound via iStock.com
Sound Effects: https://pixabay.com/sound-effects/
View all episodes
By Kim Lewis HowardThis week, we’re diving into what AI can’t automate — authentic human connection.
When an unexpected “Pitch incoming 😎” message caught Kim’s attention, it sparked a bigger conversation: Why do some automated messages make us roll our eyes, while others make us reply?
Join Kim and Hal as they break down:
- The DM that did everything “wrong” — and yet worked brilliantly.
- Why automation without empathy kills trust.
- The “Handshake Clause” — how to make sure everysystem ends with a human touch.
- The H.E.A.R.T. Method — five simple principles that help you scale authenticity alongside efficiency.
You’ll learn how to design your AI systems to sound morelike you, keep your customers’ trust intact, and build automation that scales connection, not just communication.
Because in the end, authenticity isn’t soft — it’s strategic.
You’ll Learn:
- Why transparency is the new trust currency.
- How to design automation that feels human, not hollow.
- The 5-part H.E.A.R.T. Method for balancing empathy and efficiency.
The H.E.A.R.T. Method (Quick Reference):
- H – Honesty: Be upfront about automation. It builds credibility, not risk.
- E – Empathy: Program your AI to recognize emotion and respond with care.
- A – Authenticity: Feed your systems your real voice, tone, and phrasing.
- R – Reciprocity: Automate a gift before a demand. Lead with value.
- T – Transparency: Keep your human handoffs clear and your audit trail clean.
Ready to Take Action?
- Subscribe to Small Business Big AI on Spotify or your preferred platform, leave a review, and share this episode with a fellow entrepreneur who could benefit from AI insights.
- Join the AI Insiders Community for Exclusive Tips & Resources → Request to Join our Private Community
- Ask us about the IMPACT Framework course—a strategic way to communicate effectively with the AI → Email Howard & Howard Holdings, Inc.
- Ask us about the Small Business Transformation Model (SBTM)—a simple, step-by-step framework designed forbusiness owners → Email Howard & Howard Holdings, Inc.
- Have a question or an AI success story? DM us on LinkedIn or Facebook!
---
Music Credit: “I Am with You” by Dream Cave; EpidemicSound via iStock.com
Sound Effects: https://pixabay.com/sound-effects/