In 2018, Snapchat shipped a major redesign. The logic was sound. Stories from friends were getting buried next to Stories from celebrities and brands. Discovery was a mess. They separated the two sides: left for people you know, right for media and publishers. Within weeks, a petition to revert it hit 1.2 million signatures. Kylie Jenner tweeted that she didn’t use Snapchat anymore and the stock dropped 6% in a day. Daily active user growth stalled for the first time. Snapchat’s CEO Evan Spiegel doubled down publicly. He said the confusion was the point. That it would take time. That the right call isn’t always the comfortable one. He wasn’t entirely wrong about the reasoning. He was wrong about the cost. ——————————————— Here’s your case challenge this week: You’re the PM on this project the week after launch. The data is ugly. Leadership is split. Half the team thinks you just need to hold the line and let users adjust. Half thinks you ship a rollback immediately. What do you do? Option A: Hold. The redesign solves a real structural problem. User backlash at this scale is almost always loudest in week one. You give it 60 days and measure retention, not noise. Option B: Partial rollback. You revert the friend/media separation but keep the UX improvements underneath. Give users back the familiar structure while preserving the real gains. Option C: Full rollback, full reset. The scale of the reaction tells you something fundamental broke. You go back to what worked, study what users actually do, and redesign from their behaviour up instead of from principles down.

This one's for anyone who's ever been on a customer call and thought "I could've fixed this if I'd been the PM." You're the PM for a B2B SaaS platform. Think Gainsight or ChurnZero, a customer success tool used by enterprise CS teams. Your product has been growing steadily. But last quarter, one segment started showing warning signs: mid-market accounts (50–200 seats) had NPS drop from 42 to 31. Support tickets are actually down. No one is complaining. Three accounts flagged "reevaluating" in their renewal conversations. Your CSMs say the accounts seem "checked out." Usage data confirms it. Daily Active Users (DAU) in this segment dropped 18% over the last 60 days. You have capacity for ONE initiative this quarter. Here's what's on the table: A) Proactive Engagement Trigger Build a product-led alert system: when a key user goes inactive for 7 consecutive days, automatically flag the account for CSM outreach and surface a targeted in-app re-engagement prompt. Bet: these accounts are disengaging quietly, not loudly, an early touchpoint before the renewal conversation changes the outcome. B) Discovery Sprint Pause roadmap work for 3 weeks. Run 8 discovery calls, 4 with healthy accounts in this segment, 4 with at-risk ones. Map what "value" actually means to them vs. what you built for. Bet: you don't actually know why this segment churns, and optimizing without that data means you'll fix the wrong thing. C) Feature Fast-Track Two features this segment has requested repeatedly have been deprioritized for 6 months. Accelerate both. Bet: the churn signal is a product gap, not a relationship problem, shipping what they asked for proves you're listening and buys the renewals. Here's what I want to see in your answer: • Which option do you pick, and why? • What's the one assumption your entire decision rests on? • What would you measure in the first 30 days to know if it's working? Drop your answer below. I'll reply to every single one with real feedback. Want to go deeper on answering case study questions like this one?

This one trips up PMs who are good at discovery, because the problem isn’t knowing what to build. It’s knowing when to say no to what users are asking for. You’re a PM at a B2B project management tool. Think Monday.com or Asana, but smaller. ~2,000 paying teams, mostly SMB. You’ve been running a quarterly feedback survey for 6 months. You finally have enough data to act on it. The top requested feature, by a wide margin, is a native time-tracking module. 47% of respondents mentioned it. Your power users want it. Your CSM team wants it. Even your CEO is asking about it. But when you dig into the data, something doesn’t add up. Your highest-retention cohort, teams that have been with you 18+ months and expanded seats, almost never mentioned time tracking. They’re asking for better task dependencies and cross-project visibility. And your 90-day churn rate is highest among teams that came in specifically for project management, not time tracking. You have one quarter of focused eng capacity. HERE’S WHAT’S ON THE TABLE A) Build What They’re Asking For Scope a solid time-tracking module. Use it to reduce churn, win back churned accounts, and create a new acquisition angle. Bet: volume of requests is the strongest signal you have. 47% is not noise. If you don’t build it, they’ll find a tool that does. B) Build What Your Best Customers Actually Need Deprioritize time tracking. Focus the quarter on task dependencies and cross-project visibility, the features your healthiest, highest-LTV cohort is asking for. Bet: retention signal from your best customers outweighs acquisition signal from at-risk ones. Build for who you want more of. C) Validate Before You Commit Pause both. Run 10 discovery calls split between churned users and your best retained cohort. Build only once you know whether “time tracking” means the same thing to both groups. Bet: the survey data is directional, not decisive. You don’t know enough yet to spend a full quarter on either path.

This scenario trips up even senior candidates because it sounds like a product problem but it's really a prioritization problem. You're the PM for a mid-market B2B analytics platform. Think Mixpanel or Amplitude. Your product is growing, your enterprise pipeline is strong, and your eng team is finally hitting their stride. Then three things land on your desk at the same time. 1️⃣ A power user posts a scathing thread on X about a 3-year-old missing feature. It goes semi-viral in your niche. 200 reposts, mostly from your ICP. 2️⃣ Your sales team forwards you 6 lost deals from the past month where the same feature gap came up in the sales call. 3️⃣ And your biggest enterprise customer, 30% of ARR, submits a formal feature request through their CSM, marked urgent. They're all asking for different things. But your roadmap is locked for the quarter. And your VP of Product wants to know how you're responding, by end of day. You have one eng sprint of discretionary capacity. HERE'S WHAT'S ON THE TABLE A) Patch and Ship Scope the smallest version of the most-requested missing feature that would satisfy the enterprise customer and close future deals, build it this sprint, ship it fast, and use it as a sales asset. Bet: revenue risk is the most urgent signal here. A fast, imperfect answer beats a perfect answer in 3 months . B) Listen First, Then Build Before committing the sprint, run rapid discovery calls with the 6 churned prospects and the enterprise customer to align on what "the feature" actually needs to do. Bet: what sales heard and what customers actually need are different, and building the wrong thing fast is worse than a short delay to get it right. C) Protect the Roadmap Communicate clearly to all three stakeholders why the roadmap stays locked, offer a public commitment to a future release date, and use the sprint on what was already planned. Bet: reactive product decisions compound over time. One loud moment shouldn't derail a strategy built on broader data.

This one shows up in interviews more than almost any other scenario and most candidates fumble it. You're the PM for a B2B SaaS project management tool. Think Asana or Monday.com. Your product has a free tier and a paid tier, and growth has been solid. Then the data lands on your desk: free-to-paid conversion dropped 22% over the last 60 days. Support tickets are flat. NPS hasn't moved. Users aren't complaining. They're just not converting. The funnel looks healthy on the surface. But something changed. And your VP of Product wants a plan. My team had capacity for ONE initiative. Here's what was on the table: A) Paywall Repositioning Move the paywall trigger earlier in the user journey, surfacing the upgrade prompt at the moment of highest intent - like when a user tries to invite their third team member or set up an automation. Bet: users aren't converting because they reach the limit at the wrong moment, not because they don't see value. B) Activation Audit Run a full audit of what free users do (and don't do) in their first 14 days, then redesign the onboarding flow to drive them toward the "aha moment" faster - the action most correlated with paid conversion. Bet: users are churning before they've felt the product's core value, so no paywall optimization will fix it. C) Conversion Nurture Campaign Build a targeted in-app + email sequence for free users who are active but haven't converted after 30 days - personalized by use case, with a time-limited incentive to upgrade. Bet: the intent is there, but users need a nudge and a reason to act now. Here's what I want to see in your answer: - Which option do you pick, and why? - What's the one assumption your entire decision rests on? - What would you measure in the first 30 days to know if it's working? Drop your answer below. I'll reply to every single one with real feedback.