How to get AI to challenge your thinking

You don’t need an AI yes man.

Nathan Rodgers
2 min readJun 29, 2024
Image created by me in ChatGPT

I’ve noticed that AI chatbots tend to agree with whatever I tell it I want to do:

Screenshot by me from ChatGPT

And you can easily get it to tell you that what you already want to do is a good idea.

I recently asked Claude to help me work through how to respond to some family drama happening in a group chat.

Initially, it told me to respond directly to the person rather than in the group.

But I thought responding in the group was the right option (side note: it wasn’t, and luckily Claude, and reason, prevailed).

But before I changed my mind, I was able to get Claude to agree with me:

All I had to do was keep angling the conversation toward the outcome I wanted.

If you find this happening, you’re missing out on one of the benefits of using AI as a sounding board and thought partner — it can be completely objective and doesn’t care about your feelings.



Nathan Rodgers

I share how you can use digital marketing, AI, and automation to grow your business. Get free resources daily -