Ctrl+Alt+PM

Welcome and Intros

Kenny Kranseler | 00:00–04:30
Hi everyone, welcome to Productside’s latest webinar: “Ctrl+Alt+PM: Reboot Your Product Management Career for the AI Era.” I’m Kenny Kranseler, one of the trainers here at Productside, and I’m thrilled to have you with us.

As always, we’ve got people joining from all over the world. I see friends from San Francisco, London, Austin, and Singapore—welcome! We’ll give folks another minute to settle in. While we do, tell us in the chat where you’re tuning in from and maybe one word that describes how you feel about AI right now. Excited? Nervous? Curious?

We’ve got an awesome topic today—rethinking how product managers can thrive, not just survive, in the AI era. Joining us is Ryan Cantwell, Principal Product Coach and AI Strategist here at Productside. Ryan’s spent the last year helping PMs and product orgs reboot their operating systems to leverage AI, not fear it. Ryan, so glad to have you.

Ryan Cantwell | 04:30–05:00
Thanks, Kenny. Hey everyone—it’s great to see such a big crowd today. This one’s going to be fun, a little unconventional, and hopefully a bit of a wake-up call.

About Productside and Interactive Format

Kenny Kranseler | 05:00–08:20
If you’re new to Productside, we’re an outcome-driven product partner. That means we help product teams connect what they build to business results. Through training, advisory, and resources, we help PMs and leaders level up their strategic skills.

Quick logistics before we dive in—yes, today’s session is being recorded, and we’ll share the replay and slides after. Drop questions in the Q&A tab anytime, and we’ll hit them live at the end. And please do chat throughout—it makes these sessions way more engaging.

Introducing Ryan Cantwell and the Webinar Theme

Ryan Cantwell | 08:20–10:30
Thanks, Kenny. Today’s theme is “Ctrl+Alt+PM”—a metaphor for rebooting how we think about product management. Just like your computer, PMs have an operating system—our habits, processes, and mindsets. But the truth is, a lot of us are still running an outdated OS built for a pre-AI world.

AI isn’t just changing tools—it’s changing what it means to be valuable as a PM. So today, we’ll talk about how to hit Control, Alt, and PM—how to stop what’s broken, rethink what matters, and reboot how you create impact.

Legacy Mode Detected: The PM Operating System Problem

Ryan Cantwell | 10:30–13:00
Let’s start with a hard truth—most product managers are operating in “Legacy Mode.” We’re overloaded with meetings, Jira tickets, and busywork, while our strategic muscles atrophy.

We’ve confused activity for impact. The tools changed, but our operating systems didn’t. It’s like trying to run Windows 95 on a 2025 MacBook—it technically works, but painfully slow and out of sync with reality.

Poll #1 – What’s Your PM OS Doing Right Now?

Kenny Kranseler | 13:00–14:30
Let’s have some fun. First poll of the day: what’s your PM OS doing right now? Options are:
A) Running smooth.
B) Constantly updating.
C) Frozen and needs a reboot.
D) Still buffering from 2020.

Ryan Cantwell | 14:30–16:30
(Laughs) Oh, looks like most of you picked “needs a reboot.” Love the honesty. Don’t worry—you’re in the right place. We’re going to fix that today.

Why Product Management Feels Broken

Ryan Cantwell | 16:30–20:00
Here’s why so many PMs feel stuck. We’re overloaded with tactical requests, feature pressure, and misaligned stakeholders. We end up acting like project managers or backlog babysitters instead of product leaders.

The world changed faster than our playbooks did—and we’re still trying to lead like it’s 2015. AI is exposing that gap faster than ever.

Reboot vs. Replacement: What’s Changing in PM

Ryan Cantwell | 20:00–24:30
Here’s the key difference: AI isn’t replacing PMs—it’s replacing *how* PMs work. The new PM isn’t the “creator” of every document or wireframe—they’re the *curator* of insight and *conductor* of systems.

In the same way automation changed manufacturing, AI is changing mental work. The PM who thrives in the AI era is the one who embraces orchestration, not ownership of every artifact.

AI Is Not the Enemy—It’s the Upgrade

Ryan Cantwell | 24:30–28:00
Let me be clear—AI is not coming for your job. The person who knows how to use AI effectively is. You’re not competing with AI, you’re competing with the PM who knows how to use it better than you.

Think of AI as your new intern who never sleeps, never forgets, and is weirdly good at PowerPoint. You just need to learn how to give it the right prompts.

Story of Two Product Managers

Ryan Cantwell | 28:00–32:30
Let me tell you a quick story. Two PMs—Sarah and Alex—get the same task: improve onboarding conversion. Sarah opens a spreadsheet and starts pulling numbers manually. Alex asks ChatGPT to summarize user feedback, then builds hypotheses in minutes. Same goal, totally different velocity.

Guess which PM spends the afternoon aligning stakeholders instead of wrangling data? That’s the AI advantage.

Control, Alt, PM: The Reboot Framework

Ryan Cantwell | 32:30–38:30
Here’s the core framework: **Control, Alt, PM.**

**Control:** Stop doing what AI can automate—status reports, release notes, and copy drafts.
**Alt:** Rethink your value—your job isn’t producing deliverables, it’s producing decisions.
**PM:** Reclaim your power as a problem solver—your superpower is connecting the dots that AI can’t.

If you remember nothing else from today, remember that PMs win by focusing on the *why*, not the *what*.

From Output to Outcome: Where PMs Win in the AI Era

Ryan Cantwell | 38:30–42:30
The biggest shift is moving from output to outcome. Your team doesn’t need another roadmap—they need clarity. In the AI era, PMs who can define, measure, and communicate outcomes become indispensable.

AI can write your PRD. It can’t align your VP of Sales. That’s still your job.

The New PM Operating System: Three Core Skills

Ryan Cantwell | 42:30–47:30
So, what does the new PM OS look like? It’s built on three core skills: discovery, storytelling, and strategic influence. Those are timeless—but now, AI accelerates each one. The PMs who master those amplifications are the ones who stay ahead.

Case Study: Priya and the Stakeholder Request

Ryan Cantwell | 47:30–52:00
Here’s a story about Priya, a PM at a fintech startup. Her VP messages, “We need a dashboard for enterprise users.” Instead of saying yes, she opens ChatGPT and asks, “Help me turn this into a problem statement.” In seconds, she gets three possible reframes.

She picks the best one, validates it with data, and comes back with a proposal that solves the real issue. That’s leverage. That’s AI in action.

Poll #2 – What Should AI Help You With First?

Kenny Kranseler | 52:00–55:00
Alright, time for our second poll: where do you most want AI’s help? Your options are: documentation, data analysis, communication, or ideation. Go ahead and vote.

Ryan Cantwell | 54:00–55:00
I’m guessing “documentation” will win by a landslide. (Laughs) Let’s see… yep, 60%. Totally fair.

Live Demo #1 – Turning Stakeholder Noise into Narrative

Ryan Cantwell | 55:00–01:04:00
Let’s do a live demo. I’ll take a messy stakeholder request—something like “we need better engagement”—and show you how to turn that into a concise, actionable problem statement.

Using ChatGPT, we can extract assumptions, generate hypotheses, and even outline a user story—all in minutes. It’s not about replacing thinking—it’s about speeding up framing.

Live Demo #2 – Using AI as a Strategy Coach

Ryan Cantwell | 01:04:00–01:12:00
Now let’s try something different. We’ll feed an idea—“launch referral program”—into AI and ask it to act as a product strategy coach. Watch how it pushes back with questions like, “What’s the goal? Who’s the user? What metric defines success?”

That’s how you move from feature factory to outcome factory.

Live Demo #3 – Building Stories That Motivate

Ryan Cantwell | 01:12:00–01:21:00
Final demo—let’s use AI for storytelling. I’ll ask ChatGPT to help rewrite a boring status update into a motivational narrative that highlights customer impact and team wins. This is where AI shines—it gives you language that inspires, not just informs.

Reinstalling Your PM Operating System

Ryan Cantwell | 01:21:00–01:25:30
To wrap it all up, think of your reboot like this: uninstall busywork, update your tools, and reinstall creativity. AI doesn’t change what PMs do—it changes how fast and how clearly we do it.

Upcoming Training and Offers

Kenny Kranseler | 01:25:30–01:31:30
We’ve got a few resources for you. Productside’s new AI for PMs certification course starts next month, plus we’re hosting a live Metabase workshop and a series on outcome roadmapping. Check your follow-up email for discounts and details.

Q&A: Security, Career Growth, and AI Skills

Ryan Cantwell | 01:31:30–01:37:30
Great questions coming in! On data security—use internal AI tools whenever possible. For career growth—start documenting how you use AI in your workflow. Those examples will differentiate you fast in interviews.

Closing and Thank You

Kenny Kranseler | 01:37:30–01:39:00
That’s it for today! Huge thanks to Ryan and to all of you for joining us. Keep an eye out for the replay and resource links. Until next time, keep iterating—and maybe hit Ctrl+Alt+PM on your mindset this week!