Product Management Nightmares

Welcome and Introductions

Dean Peters | 00:00–03:00
Welcome everyone to “Product Management Nightmares: The Out of Control Episode.” I’m Dean Peters, Principal Consultant and Trainer at Productside, based in Raleigh, North Carolina. We’re going to talk about those product management moments that keep us up at night — the projects that spiral out of control, the roadmaps that get trampled, and the features that refuse to die.

Roger Snyder | 03:01–05:00
Thanks, Dean! I’m Roger Snyder, Principal Consultant and Trainer at Productside, coming to you from the Santa Cruz mountains in California. I’ll be your moderator and occasional snarky commentator. Today’s discussion is all about tackling chaos — from feature creep to AI anxiety — with humor and practical advice.

About Productside

Roger Snyder | 05:01–07:00
If you’re new to Productside, we’re an outcome-driven product partner dedicated to helping product teams transform their practices and deliver measurable impact. We work with product managers, product owners, and product leaders to improve decision-making and strategy — no cookie-cutter solutions here.

Poll #1 – What Keeps You Up at Night?

Dean Peters | 07:01–08:30
Let’s start with a quick poll. Which nightmare scenario gives you the most sleepless nights? Is it shifting roadmaps, runaway MVPs, demanding stakeholders, aging products, or AI taking over your job?

Roger Snyder | 08:31–09:00
Looks like the biggest culprit is the ever-changing roadmap — no surprise there. That’s exactly where we’ll start.

Nightmare #1 – Roadmap Roadkill

Dean Peters | 09:01–14:00
Roadmap Roadkill happens when your carefully planned strategy gets flattened by urgent fixes, executive drive-bys, and “just one more thing” requests. Before you know it, your roadmap turns into a Gantt chart zombie. The antidote? Build outcome-focused roadmaps that communicate direction and value — not just delivery dates. Roadmaps should be strategic conversations, not tactical commitments.

Roger Snyder | 14:01–16:30
Right — too many of us have turned roadmaps into release plans filled with features. We color-code them, call them “strategic,” but they’re really tactical timelines. A roadmap should answer *why* we’re doing something, not just *when*. And we need to leave room for the unexpected — bugs, customer needs, and the occasional HIPPO crash.

Nightmare #2 – The Taking of Feature 1-2-3

Dean Peters | 16:31–21:30
This one’s a hostage situation — critical features held captive by stakeholders. Maybe sales insists on adding a custom feature to close a deal, or executives push pet projects. It’s feature hostage negotiation at its worst. Instead of caving, shift the conversation to outcomes: “What problem are we solving? What value does this create?” Use techniques like “Buy-a-Feature” workshops to make trade-offs visible and collaborative.

Roger Snyder | 21:31–24:00
Exactly. I once gave each regional VP Monopoly money equal to their revenue targets. We put features on a whiteboard with “price tags.” Suddenly, negotiations became teamwork. Stakeholders realized they couldn’t buy everything — they had to prioritize what mattered most.

Nightmare #3 – The MVP from Hell

Dean Peters | 24:01–29:30
Ah, the runaway MVP — what starts as a “minimal viable product” turns into a bloated beast with endless scope creep. Or worse, it’s released once and abandoned. The fix? Define clear success metrics and remember: MVPs are for learning, not launching. I call mine “Proofs of Life.” They exist to validate hypotheses — not to be version 1.0 forever.

Roger Snyder | 29:31–32:00
I’ve seen this happen too often — companies treat MVPs as finished products. Then they wonder why adoption stalls. Be explicit: “This is phase one. Here’s what success looks like, and here’s what’s next.” That keeps momentum and funding alive.

Nightmare #4 – The Product That Wouldn’t Die

Dean Peters | 32:01–37:30
This one’s for all the product managers stuck maintaining zombie products. You inherit a legacy system that’s still generating revenue, so no one wants to kill it. But the codebase is ancient, the bugs are immortal, and the cost of maintenance keeps climbing. If you can’t kill it outright, create a migration plan — phase it out slowly, and show customers the value of moving to your new product.

Roger Snyder | 37:31–39:00
Exactly. Sunsetting takes patience. Show users how the new product delivers clear benefits. Add “delighters” — small wins that make migration worthwhile. And always bring legal and finance into the loop before you pull the plug. Surprises there can turn your sunset into another nightmare.

Nightmare #5 – The AI That Ate My Job

Dean Peters | 39:01–44:30
Here’s the scary one — the “AI Apocalypse.” Everyone’s wondering, “Will AI replace product managers?” My answer: yes, it’ll replace the *old way* of product management. The job as we know it is already changing. You’re now an AI product manager — whether you like it or not. You need to understand how AI impacts your business model, your workflows, and your decision-making.

Roger Snyder | 44:31–47:00
Exactly. AI isn’t here to replace you — it’s here to *outrun* you if you ignore it. Use it as your partner. I use AI to brainstorm, summarize data, draft personas, and pressure-test strategies. It’s like having an always-available research assistant.

Poll #2 – How Are You Using AI?

Dean Peters | 47:01–48:30
We asked the audience how they use AI today. Most say they’re experimenting — using it for ideation, analysis, and communication. A few are still skeptical. That’s okay — but start now. The bear’s chasing you, and you just need to run faster than the next PM.

How to Survive the Nightmares

Roger Snyder | 48:31–51:30
Here are your survival strategies:
1️⃣ Focus on outcomes over outputs.
2️⃣ Use transparent prioritization and communicate trade-offs.
3️⃣ Keep MVPs small and learning-focused.
4️⃣ Prune legacy products and show migration value.
5️⃣ Embrace AI as your co-pilot, not your competition.

Q&A and Closing Remarks

Dean Peters | 51:31–End
Thank you to everyone who joined our “Product Management Nightmares” session! Remember — every nightmare is just a lesson in disguise. The key is to stay curious, stay outcome-focused, and laugh when things go sideways. You’ll receive the recording and a link to our next webinar: “Problem Statements vs. Solution Speak.” Until next time, sleep well — and keep those hippos off your roadmap!