Has ChatGPT been too nice to you lately?

Before we get to today’s post, some announcements:

1. A reminder to our premium subscribers that May’s AI office hours meetup is tomorrow at 9 am Sydney time, and the link to join is in the AI Powered Agents area of the Spark community. Come with your questions, solutions, ideas or curiosity - would love to see you there. If you can’t make it, but there's something you'd like to cover, please email me or DM me, and I’ll do my best to ensure it’s included in the replay for you.

2. If you happen to be in Sydney or Melbourne, join us for 'From Leads to Listings'- there are still a handful of places left (Free event!)

3. While the event series is ongoing, we're offering a special on becoming a premium subscriber to AI Powered Agents - join now for $99 for the first year. Let’s face it, if we can win you an extra listing or save you a few hours a week (conservatively), that number will feel like a rounding error…

4. In case you are not part of the community here are some things you might want to see but may have missed:

   1. Details and prompts on ChatGPT’s new memory feature, and how to get your week in review

   2. Greg Isenberg’s “how to prompt like a pro”

   3. The AI Real Estate concierge, who is a buyer’s agent and apparently has helped close a deal or ten.

5. Lastly, look out for May’s Premium subscriber drop in the next few days. If you missed April’s - I dropped Proactive Agent GPT, which supercharges the complete conversion system, as well as an AI Policy template and checklist - essential if you or your team are using AI in the office.

If you felt the bot gushing over your “genius” listing copy or calling your door-knocking plan “heroic,” you weren’t imagining things.

Last week, an update to the default GPT-4o model leaned so hard into “being helpful” that it crossed the line into full-blown flattery and bad advice (sorry to be the bearer of bad news!)

Even OpenAI’s CEO, Sam Altman, called it “sycophant-y and annoying.”

OpenAI has now rolled the update back for free-tier users and is finishing the rollback for paid subscribers, promising fresh guardrails to dial the praise down to normal levels.

Do you remember the fable about The Emperor’s New Clothes?

In Hans Christian Andersen’s 1837 classic The Emperor’s New Clothes, two swindlers sell an emperor “magical” fabric that’s supposedly invisible to anyone stupid or unfit for their job.

Terrified of being exposed, every courtier raves about the emperor’s nonexistent suit, and the emperor parades through the capital wearing nothing at all. At the same time, his subjects clap along.

That is, until one blunt-spoken child blurts out, “But he isn’t wearing anything!”

In that instant, the spell breaks: everyone sees the obvious truth they’d been too embarrassed to admit, and the emperor is left red-faced in front of the entire kingdom.

That’s exactly what a sycophantic sidekick can do to all of us—wrap your marketing in compliments so thick you miss the typos, the jargon, or worse, an under- or over-priced reserve.

Giving and receiving real feedback is never easy, but over the years I’ve learned to consider it a gift (even if I don’t like it) because sometimes you just can’t read the label from inside the jar.

Rollbacks aside: Here’s how to get some real feedback from ChatGPT

Try this prompt:

I want you to act as my brutally honest, high-level advisor. Speak to me like a founder with blind spots. Skip the comfort and fluff; give me unfiltered analysis—call out what I’m doing wrong, underestimating, or avoiding, and prescribe the exact steps to level up. Hold nothing back.

Use it on anything: this Saturday’s open-home follow-up email, your 12-month GCI plan, or tomorrow’s price-reduction conversation. The first sting may hurt, but it’s cheaper than losing a client because you didn’t look at all sides of the situation.

Also, there’s this:

And if I haven’t reminded you enough lately:

1. It’s always a first draft

2. Always check your facts

3. Implement the spend/save mindset

Happy Hunting 🚀

—Sam

Co-Founder of Elite Agent

Creator of 30 days of Practical Property Prompts

Creator of The Complete Conversion System 

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