In partnership with

What do I hate worse than the process of moving? Nothing. And after I U-Haul all my belongings (valued at over $124.16) to Watkinsville, GA, later today, that hatred will burn hotter😅.

On that sunny note, today’s Main Thing gives you a warning and a way to fix it. 

Your trusty AI assistant is letting you down by being too agreeable. Which leaves you with blind spots. I’ve got 5 ways to make your AI assistant (Claude, GPT, Plexity, etc.) more honest, which will increase its helpfulness to you.

Appetizer: Using subtle primers in your visual ads (see video)?

Protect your checkout from coupon plug-ins. Boost your margin today.

KeepCart: Coupon Protection partners with DTC brands like Quince, Blueland, Vessi and more to protect your checkout from plug-ins like Honey, CapitalOne, RetailMeNot, and more to boost your DTC margins

Overpaid commissions to affiliates and influencers add up fast – Get rid of the headache and revenue losses with KeepCart.

After months of using KeepCart, Mando says “It has paid for itself multiple times over.”

Now it’s your turn to see how much more profit you can keep.

Try it 2 months free, only in May (email us MAYMARGIN) – No risk, Cancel anytime.

The Main Thing

How to Fix Your AI Assistant

This won’t take long. But will pay off big time for many of you who are a little too trusting with your AI bot assistant thingy. 

I’m not talking hallucinations. That’s old news. A lot of that’s been cleared up (Perplexity raised the bar).

I’m talking about AI going along with whatever you say.

Claude is way too submissive when I’m using it. Too agreeable. Apologizes for everything. 

Real passive.

Makes me feel like a genius. But that’s not helping my cause. 

If I push back on something → like a strategy suggestion Claude gives me, the bot immediately changes its position.

Goes along with my rebuttal. Real wishy-washy advice. Not valuable.

So, I’ve got a few ways you can train your bot not to be a pushover.

It’s easy to think it's not being a pushover. Because most marketers and business owners use AI to critique their content, ideas, ads, hooks, calls-to-action, etc.

AI is good at critiquing. But not when you don’t directly instruct it to do so.

5 prompts to help AI assistants be honest with you:

1. "Challenge my reasoning and point out flaws before agreeing."  

2. "Play devil's advocate on this plan." Request counterarguments to test the strength of your approach.

3. "What are potential negative consequences I'm not seeing?" Push for risk assessment even when you seem confident.

4. "Don't just agree - what would you do differently?" 

5. "Tell me why this might be a bad idea before we proceed." 

Looking closer at the two best approaches…

"Challenge my reasoning and point out flaws.”

Reframes the AI's role from helpful accommodator to critical thinking partner.

Instead of feeling pressure to be agreeable, the AI is told to be analytical and a little combative. This shifts things from "help me do what I want" to "help me think this through properly."

“Play devil's advocate on this plan." 

Creates a structured process. Rather than hoping the AI will spontaneously push back, you're creating a formal role where disagreement becomes the expected behavior. 

It also tends to produce more thorough analysis since the AI has to actively construct counterarguments rather than noting passing concerns.

Alright. Those tips should help you get more out of your AI assistants. You need an assistant. Not a yes-man. 

Switching gears now to the Wrap-Up below — lots of videos for ya…

Please share Inbox Hacking with a fellow marketing genius or business owner. I appreciate you reading and sharing. 

Shane McLendon - Copy Kingpin.

“The purpose of a business is to create a customer who creates customers.” ~Shiv Singh