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👋 Hey friends,

A few weeks ago I started a new round of customer calls. I had a theory going in. New HubSpot reporting users who were struggling were probably new to CRMs entirely, or coming from simple point solutions that couldn’t do much. They just needed guidance on the basics.

By the third call I was getting a feeling.

By the fourth I was sure.

I was completely wrong.

The customers hitting the hardest walls weren’t beginners. They were coming from complex, enterprise-grade tools. Not because those tools are better, a lot of them didn’t even like what they were leaving. But they were fluent in them. They knew the data model, understood how everything connected, and had spent years building muscle memory around how reporting worked.

And then they moved to HubSpot, which works differently.

It’s like switching from manual to automatic. That should be seamless, right? It’s still a car. But your hand keeps reaching for a gear shift that isn’t there, and suddenly a car you’re supposed to find easier feels completely foreign. They weren’t struggling because HubSpot is hard (not saying some aspects aren’t). They were struggling because they had to unlearn something first.

I went into these calls thinking I’d hear about missing features or confusing UI. What I actually heard was people trying to rebuild their old data model inside HubSpot. Using workarounds to recreate something familiar instead of learning how HubSpot’s model actually works.

That’s not a user failure. That’s a product problem. If getting started with reporting feels hard regardless of where you’re coming from whether you’re importing data, migrating manually, or starting from absolute scratch that’s something we need to fix. Which is exactly why the design sprint I’ve been in all week matters more now than it did before I made those calls.

I went looking for one type of struggling user and found a completely different one. That’s only possible if you’re actually talking to people instead of assuming you already know what they’ll say.

Here’s what I’m doing differently going forward:

None of this is complicated. But it does require you to question how you’ve been defining your user segments. Behavioral data tells you what people are doing. It doesn’t tell you what they expected before they got there, and that gap is where the real friction lives. This is why you have to actually call people.

Data will show you the what. It will never show you the why.

The best customer insights don’t come from the users who love your product. They come from the ones trying to make it work in a way you never anticipated. Still processing everything from this week’s sprint, more on that soon.

See you next Friday,
Stef

P.S. If you’re in a CS or support role right now, this is exactly the kind of discovery work that makes you a stronger PM candidate. You’re already doing it, you’re just not calling it research yet. If you want to talk through how to translate that experience into product, I’m mentoring on ADPList. Book a free session with me right here.