How AI Turned Job Applications Into a Joke

Sorry to break it to you… but the most honest cover letter you’ve ever written is probably also the most unemployable one.In this episode, I talk about my long, painful relationship with cover letters—and how AI quietly ruined (and exposed) the whole hiring game. I walk you through my journey of watching recruiters, candidates, and algorithms outsmart each other in the modern job application circus. From AI-written cover letters to recruiters using AI to read them, this is what hiring looks like now—and why sincerity is suddenly back in fashion.I share three very questionable strategies for writing a cover letter in the age of AI, ethics, and resume keyword obsession. If you’re navigating job search, hiring, or recruitment in 2025, this episode might help—or get you blacklisted. Either way, you’ll never look at a cover letter the same way again.IN THIS EPISODE00:00 | Why cover letters exist — and why you hate them  01:22 | How AI quietly broke the cover letter game  02:26 | Trick #1: The fastest way to stand out instantly  03:03 | Trick #2: Using AI without getting caught  03:34 | Trick #3: Radical honesty recruiters don’t expect  04:19 | Extra tricks recruiters secretly fall for  Sponsor: Coromandel ProductionsAt Coromandel Productions, we aim to showcase human interest & heart-warming stories from all walks of life. We do this through short films, documentaries, sports television, corporate films, feature based content & promotional videos. Instagram: instagram.com/coromandel_productions YouTube: www.youtube.com/@coromandelproductions518 Vimeo: vimeo.com/coromandelproductions Website: coromandel-productions.com Rahul PhondkeRahul Phondke has been a prolific writer of humour columns since his childhood days which ended sometime last year. People are still wondering how this happened. He turned to writing humour at an early age in an effort to find some meaning to the angst of life, which he found almost immediately after his first two cans of beer. Based in Singapore, he is extremely sought after by the locals ...unfortunately most of whom happen to be the police. He is an active member on Facebook and can be easily reached...unless he happens to owe you moneyConnect with Rahul at  https://www.linkedin.com/in/rahul |phondke |522a17Paddy RangappaPaddy Rangappa has worked in marketing for more than twenty six years. After over a decade in Procter & Gamble in India, Indonesia, and Singapore, he became vice president, brand development for McDonald’s in Asia Pacific, Middle East, and Africa (APMEA) and developed strategies to significantly grow breakfast, beverages, and desserts, especially the McCafé brand, across APMEA. He has also taught Integrated Marketing Communications (IMC) to senior undergraduates and MBA students at the Singapore Management University (SMU). He is the author of Been There Bungled That and Spark.Connect with Paddy at https://www.linkedin.com/in/paddyrangappa/About the ShowThe Jest Business is a podcast that pokes fun at the wild world of corporate speak and boardroom absurdities. It’s where business meets banter—with a healthy dose of self-deprecating humour. From buzzwords to bloopers, we decode jargon, laugh at leadership, and challenge the serious side of success.