The Flip: Break Leadership Out of AI Feature Factory Mode
randy silver
Makes you the PM leadership listens to.
Go from off-script to in control — in a single session.
Every product leader knows the moment. Your exec wants AI. They want it now. They're not sure what it should do, but they're certain it should ship next week. And somewhere between knowing what the right conversation looks like and actually having it, something gets lost.
This isn't a knowledge problem. It's a confidence problem - and confidence comes from having the right tools and knowing how to use them under pressure.
Here's what most people don't see: the exec pushing hardest for AI is often the most frightened person in the room. They want something - anything! - that looks like action. Understanding that changes everything about how you respond.
This workshop puts you into that conversation on purpose. You'll practice both sides, get the reps in a room where it's safe to fail, and leave ready to change the dynamic in your next exec review.
Use this consistently, and the way leadership sees you changes - not because you asked for a seat at the table, but because you'll have proved that you already belong there.
What you’ll learn
Master the conversations that define your career — and become the product leader who shapes AI strategy instead of just executing it.
AI feature demands often come from fear — of competitors, of being exposed, of being left behind.
Understanding what's driving the pressure changes how you read the room and how you respond.
You'll stop reacting to the surface request and start addressing what's actually going on.
These diagnostic questions shift the focus from capability — can we do this? — to strategy — should we?
They make your exec feel heard while redirecting the conversation to what actually matters.
You'll use them in the room, in real time, without a script.
Pushing back on a poorly-formed AI demand doesn't have to damage your credibility. Done right, it builds it.
The worst outcome isn't a bad meeting — it's a bad commitment you then have to deliver on.
Learn directly from randy
randy silver
Coach & Consultant / The Product Experience podcast
Who this course is for
People who've been in the room when an AI demand went sideways and didn't have a way to control the conversation
Leaders ready to show up differently — not just survive the next meeting
Product Managers -Senior, Head, Group, VP, Director, or CPO - who have felt like they're 'off-script' when responding to AI requests
What's included
Live sessions
Learn directly from randy silver in a real-time, interactive format.
Lifetime access
Go back to course content and recordings whenever you need to.
Community of peers
Stay accountable and share insights with like-minded professionals.
Certificate of completion
Share your new skills with your employer or on LinkedIn.
Maven Guarantee
Your purchase is backed by the Maven Guarantee.
Course syllabus
Week 1
Jun
8
June cohort
Schedule
Live sessions
3 hrs
Mon, Jun 8
3:00 PM—5:30 PM (UTC)
Async content
1 hr
Watch the Lightning Lesson before the session
Testimonials
- Randy is an excellent coach - he is extremely knowledgeable about product and strategy, a very good listener, and very good at guiding people through complex problem solving. I would highly recommend him.
Antonio Gould
Executive Director @ Teach Your Monster - Whilst Randy's coaching style is supportive, his sessions can also be demanding as he is able to challenge you to unpick obstacles and think about things in different ways. Randy often digs deeper at these moments, which we focus on until something becomes unlocked in my mind.
Frederick Coulton
Head of Product & UX @ CultureAI - It’s difficult to have someone in my firm who can ask me the tough questions, with no agenda. Randy just delivers every time without fail. On the rare occasion when he doesn't have an eye opening insight, he helps me phrase, formulate, visualize and make solid the haze of thoughts, ideas and problems I have in my head.
Abdo Wahba
VP Product, Accord Partners
Frequently asked questions
$300
USD