I Asked ChatGPT to Roast Me

A ChatGPT roast asks the AI to use everything it knows about you to poke fun at your contradictions. It is good for a laugh. It is also, occasionally, an uncomfortably accurate mirror, naming the blind spots you spend your working life helping other people see.

A client showed me how to get roasted by ChatGPT last week. You feed it everything it knows about you and ask it to, well, roast you. Naturally, I treated this as a development opportunity.

It was accurate in a way that had me roaring out loud and cringing at the same time, at the truths it spat out at me. Exaggerated ones, obviously.

It noted that I spend my days helping founders see they are the bottleneck in their business, then drive home thinking “oh, interesting insight to share with Client X” without noticing the giant flashing sign above my own head, about said insight.

The machine catalogued my contradictions with forensic glee

I coach executives to let their people fail and learn, while remaining personally convinced that every email, every project and every minor crisis within a hundred kilometres still requires my intervention.

I help leaders see the bigger picture, then lose a multi-day battle to a Philips VoiceTracer that has somehow become my most formidable strategic opponent. Whilst the CEOs are focused and the leadership teams aligned, I cannot work out why my voice recorder holds a thirteen-hour recording of absolutely nothing.

Do not get it started on how I treat it as an instruction manual for the minutiae of global travel: how to turn on the heat pump, the microwave, the TV in every new hotel room. How rude. Surely that is not just a me thing.

It noted that whilst most people go on holiday and buy a fridge magnet, I come back with a new framework, which I find almost as exciting as seeing elephants roaming in Botswana.

Then it found the one that actually landed

“You tell clients freedom through focus. Your life appears to be freedom through saying yes to seventeen interesting opportunities which devour your freedom.”

Reader, the machine had a point.

It is not just my point. Organisational psychologist Tasha Eurich, writing in Harvard Business Review, found that while around ninety-five per cent of us believe we are self-aware, only ten to fifteen per cent actually are. Worse, the gap widens with seniority. The more experienced and powerful we become, the less accurately we tend to see ourselves. The cure she points to is not more introspection. It is honest feedback from what she calls loving critics. On this occasion, mine just happened to be a large language model in a motel car park.

The seventeen-opportunities line stung because the research backs it too. A survey of 1,800 executives reported in HBR found that chasing too many priorities is one of the most common and most corrosive habits in leadership. Saying yes feels like ambition. Often it is just a slow leak in your own business growth strategy.

So, I did the only sensible thing

I sat in that car park, somewhere between amused and exposed, and started turning the roast into a lesson. Possibly a framework. Maybe a workshop. At the very least, a blog post. Oh, the irony.

I told a client about all this the next day. She laughed. “I do not need ChatGPT to roast me, you do that every time we connect.” Then she added that she would not change a thing. The roasting, or, as I prefer to call it, light-hearted banter with important lessons, propels her toward her version of success.

Which is the whole point, really. The value was never in the roast being clever. It was in having someone, or something, hold up the mirror at the exact angle you have been avoiding. We are all brilliant at spotting the flashing sign above everyone else’s head. The skill is letting someone point at the one above your own without getting defensive about it.

So, now you want to try it yourself, do you not? Go on, get roasted. What uncomfortable truths are sitting there for you and your coach to work through?