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The Customer Calls That Changed My Roadmap This Week

And the simple questions that unlock what really matters.

Author

Stefanie Brown
September 05, 2025

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👋 Hey friend,

This week at INBOUND has been chaos in the best way. My calendar’s been packed with customer calls, demo sessions, and random requests from the team.

My UX lead last minute gave me a prototype and said “go test this with real people.” My manager handed me some new AI tool to break. And I’ve been hopping on calls with customers everywhere, hearing how they actually use reporting day-to-day.

Here’s what I keep thinking about: Last year, I stressed about asking the “right” questions. Turns out the boring ones work best. “Wait, walk me through what you were trying to do there” has given me way more insights than any fancy research framework.

The energy that comes back to the team is the real win. Every weird quote I drop in Slack, every “oh wait, that’s interesting” moment, it gets everyone excited about what we’re building next.

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What I’m Stealing From This Week

Even if you weren’t here, here’s what’s clicking for me:

  • Stop trying to sound smart. Customers don’t care if you know all the buzzwords. They just want someone who’s actually listening.

  • Quotes hit different than charts. When I tell the team “this customer said our feature basically saved their life,” that lands way harder than showing adoption numbers.

  • Small moments change everything. Not the big keynote insights. It’s the throwaway comment that makes you rethink your whole roadmap. Like when someone casually mentioned they use our tool for something we never intended.

💡Try This: Don’t overthink your questions. Ask the obvious thing and see where it goes.

Customer Insights That Keep Hitting Me

Some patterns from this week that probably sound familiar (and what I’m doing about them):

Power users are drowning. The customers who love your product most are also the ones struggling with it most. One admin told me “I have so much data now, I can’t find anything.”

 → What to try: Ask power users “What would you delete?” instead of “What would you add?” Their answers reveal what’s actually essential.

They’ve built workarounds you’d never imagine. Found out customers are exporting our reports to Excel just to add their own notes. We spent months building in-app annotations that nobody uses.

 → What to try: When you see a workaround, ask “What does this give you that our product doesn’t?” Sometimes they’ve solved a problem you didn’t know existed.

“Training” means different things. When customers say they need training, they don’t mean tutorials. They mean “help me figure out which of these 47 features I actually need.”

→ What to try: Replace “How do I use this?” documentation with “When should I use this?” examples. Show scenarios, not steps. 

The handoff moment is brutal. Every growing company has that moment where the person who set everything up leaves. Suddenly nobody knows why things were built that way or how to change them.

→ What to try: Ask during user interviews: “If you had to explain your setup to a new hire, what would you tell them?” This reveals which parts of your product are actually intuitive.

Two Questions I’m Using on Every Call Now

“What would you get rid of?” (instead of “what do you wish we built?”) This flips the conversation from feature requests to real priorities. When that admin said “I’d delete half these reports,” it told me more about information architecture than any user flow diagram could.

“How’s that working for you?” (when they mention workarounds) Don’t assume their hack needs fixing. Sometimes their janky solution reveals a completely different problem than you thought you were solving. I learned this when I spent months building a feature to replace something customers were doing in Excel, only to find out they preferred their Excel method.

Both questions work because they make customers think differently about their own problems. Try one this week and see what happens.

See you next Friday!

– Stef

💬 What’s the weirdest thing a customer has told you lately? Seriously, I collect these stories.

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