EP 53A Claude Interviews me: Teach Your AI To Push Back Until Your Real Voice Shows Up

March 26
17 mins

Episode Description

You can’t stand out online with the same polished lines everyone else uses. Claude turns the tables and interviews me about what actually happens when you try to “sound more human” with AI and why most people fail on the first try: they serve the boardroom version of themselves. We unpack the cliché laundering problem, where AI doesn’t fix generic messaging it can amplify it unless you explicitly train it to challenge your answers, call out platitudes, and push for what the customer would care about.

From there, we move into the hard part of storytelling for LinkedIn and personal branding. The issue usually isn’t that people have no stories, it’s that they don’t know which moments are interesting to someone else. We talk through practical ways to surface better material: paying attention to moments with tension, keeping quick notes, using AI to interview you until the specifics show up, and shaping the story around the audience’s perspective rather than your timeline.

We also pressure-test my frameworks like the 3x5 method for commenting and AAE (acknowledge, add value, extend). Structure helps people start, but if you follow it like a script, you’ll sound robotic, and sameness kills attention. That’s where the Von Restorff effect comes in: the different thing gets remembered, and often the “different thing” is emotion. We close with the simplest takeaway that almost nobody does: have the same real conversation in comments that you’d have face to face.

If you want your content to carry your voice, not just your tips, listen now, then subscribe, share this with a colleague who posts safe, and leave a review telling me what you’re going to change first.

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