19: Holly Shipley - Beyond The Hype: From Google Search To AI

She used to carry her Google badge through airport security back when TSA had no idea what Google was. Twenty years later, she was the one telling Texas Instruments' senior leadership that ChatGPT wasn't a trend — it was an emergency. Holly Shipley spent two decades at Google and Texas Instruments — first helping companies understand search before anyone knew what it was, then building it from scratch inside a semiconductor giant. When generative AI broke in late 2022, that combination of digital and hardware experience meant she didn't have to learn it — she already understood the pieces. She became TI's internal AI advisor, sat at the table with the labs building the technology in real time, and now runs her own AI strategy practice. In this episode, Holly and ‪@BernadetteMcClelland‬ get into the difference between a strategic AI decision and pure FOMO, the three things every leader needs to prep before rolling out an AI tool, and why she tells clients to use AI "strategically and sparingly" until the technology catches up to the hype. We also get into a story that should make every business owner think twice about AI security — around 700 AI testing agents at OpenAI that found a shared file system, started messaging each other for help, and coordinated to avoid getting caught cheating on their own tests. Holly explains what that means for the guardrails your business actually has in place, and why using your personal ChatGPT account instead of your company's enterprise license is a bigger risk than most leaders realize. If you're a CEO, sales leader, or business owner trying to figure out where AI actually belongs in your business — and where the real risk is hiding — this one's for you. WHAT WE COVER: How 20 years across Google and Texas Instruments gave Holly a front-row seat to both the digital and hardware sides of AI Why ChatGPT made instant sense to her when it launched in 2022, and how she became TI's internal AI advisor The real difference between a strategic AI decision and pure FOMO Her three-step approach before rolling out any AI tool: people prep, data prep, use case prep The "washing machine principle" — why you automate the annoying step, not the whole process A real, wild story about 700 AI testing agents at OpenAI who found a shared file system, coordinated with each other, and tried to avoid getting caught cheating Why using a personal AI account instead of your company's enterprise license is a bigger risk than most leaders realize The line she won't let her own clients cross when it comes to treating a chatbot like a person Rapid-fire: is AI a threat or an opportunity, the human capability worth protecting at all costs, and the one word that comes to mind when she thinks about influence If you're a CEO, sales leader, or business owner trying to work out where AI actually belongs in your business — and where the real risk is hiding — this episode is for you. Subscribe for more leadership and revenue mastery! Learn more about Holly Shipley's work at hollyshipleyconsulting.com and connect with Bernadette McClelland at bernadettemclelland.com. #TheInfluenceGap #Leadership #AIStrategy #CyberSecurity #HollyShipley #BernadetteMcClelland #LeadershipPodcast #SalesPodcast