AI Over 50: How to Talk to AI

Hosted by Brett Bouchard

Thu, Jul 23, 2026

4:00 PM UTC (45 minutes)

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AI Over 50 - Level 1: Set Up AI to Work for You
Brett Bouchard
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What you'll learn

Lead AI through a conversation, not a one line query

Give it direction and keep the back-and-forth going, instead of taking the first reply to a quick question.

Talk to your AI by voice

Speak for thirty seconds instead of typing, and give it far more context to work with. A true game changer!

Stop settling for the first answer

Keep leading and pushing back, so the second or third answer is the one you actually wanted.

Why this topic matters

Most people fire one line questions at AI and take whatever comes back. The fix is not a clever prompt, it's leading a real conversation: set your ground rules once, talk to it by voice and push past the first reply. For those of us over 50, this is where decades of steering people and meetings pay off. You already know how to lead a capable new colleague. Do that with AI and the answers change.

You'll learn from

Brett Bouchard

Ex-Google Director, 20+ yrs in tech, Founder of AI Over 50

I spent more than 20 years in tech, including time at Google and multiple startups. When AI started changing everything, I began using it to augment my own solo practice, and I learned it the way a skeptic does, by testing it on real work. Along the way, one thing was missing: hardly any of the AI advice out there is focused on experienced professionals who have spent decades building real judgment.


That gap is why I started AI Over 50, and I'm on a mission to help experienced folks thrive in this new AI era. There is a real need for those of us between 50 and 65 to put AI to work, skeptically, practically, on our own terms, with no hype and without the overwhelm. My job is to make it genuinely useful, peer to peer, without the jargon.


Everything I teach comes back to three beliefs I have developed working with these tools:


Be the skeptic who uses AI. Stay wary of the technology and get proficient enough to question it firsthand. The person who uses AI and still asks the hard questions is who we should all be right now.


Bet on your foundation. Learn the fundamentals that do not change with every new model release, and look past the noise to the systems underneath.


Your experience is the edge. Decades of work and change gave you judgment, pattern recognition, and the instinct to push back. That is the one thing AI cannot supply on its own, and it is exactly what makes it work well.


If you have been curious about AI but unsure where to start, you are in the right place. Let's put your experience to work.

Previously at Google, Ancestry, AOL

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