Hey everyone! New format this week, the one I’ve been wanting to try for a while.
About once a month, I'll sit down with a founder or growth expert and ask them three things: what frustrates them the most about user behavior, what mistakes teams keep making trying to fix it, and which products actually did a great job and converted them personally.
Pretty cool, huh? I know you don’t care about the textbook. You want to know what actually happens in those bloody growth trenches.
And the first issue is with Lisa Heiss — a UX designer and PLG expert. We've collaborated on projects at ProductLed and bonded over a pretty similar approach to growth.
She didn't give me polished answers, thank God, it’s pretty spicy.
Btw, don’t ignore this 👇
The user behavior that kills our lovely funnel
I asked Lisa what drives her crazy about users right now. She went straight for it:
The attention span. How bad we've gotten at paying attention to anything longer than two seconds. If I'm trying to market a product to you and you can't even read three bullet points, it gets very hard."
And the landscape around this has shifted fast. Users aren't stuck with you anymore (bummer, I know). They find another tool by tomorrow. They build their own over the weekend (or they think they can and that’s enough).
"If I can't solve it with your tool, either I build my own or I figure out another tool. There's not much dependency on what you do."
So you've got users who won't read your copy, won't sit through your onboarding, won't give you more than a few seconds, and they have zero reason to try harder because the next alternative is one search away.
Now look at what most teams do about it.
How teams make it worse
Mistake one: explain harder.
Teams see users skipping their flows and think the problem is comprehension. So they add more. More onboarding steps. More tooltips. More checklists. Lisa fights this approach like hell:
"Show how the product drives and changes behavior. That is your explanation. If you can do that with fewer screens, that's the thing we care about."
Your explanation should be the product working, not words about the product working.
I never adopted Notion (almost a crime for a person in SaaS). Never paid for it. I keep forgetting it exists, it never built itself into how I already work. My husband downloaded it once. Back then, they had this typed-in checklist on the main page as their onboarding. He didn't even register it as an onboarding. He saw text sitting there and moved on. Had no idea he was supposed to do anything with it.
For every clever onboarding, there's a person who just wants things very clear, very simple, and right next to where they are. Clever that doesn't land is invisible. Invisible loses users before they've done a single thing.
Mistake two: trap them.
Some products skip the explanation entirely and go straight to making it impossible to leave. Lisa has a real grudge against Adobe (who doesn’t?):
"I was tricked into what started as 20 bucks a month. It renewed for 60, and it turned out to be an annual contract I was paying monthly, tied in without knowing it. I will do anything to not use Photoshop. Any AI product that does the same job, I'll use it just because of that."
I had my own. A transcription tool, I needed one file done, signed up for what looked like a weekly trial, tried to cancel. No button. Nothing. I dug through their knowledge base, found a hidden email address, and sent a pretty aggressive message threatening a fraud claim with my bank (I know, very dramatic). The product did its job fine. But I will never open it again.
No one loves an abuser. We leave abusers. It's 2026, for God's sake.
"People aren't obligated to stay with you. So these techniques just mean you end up with no loyal customer base. Nobody loves you for doing that."
Mistake three: stop at the aha moment.
This is the one nobody wants to hear. I asked Lisa what she used to believe about growth that she's completely changed her mind on. She went straight for the sacred cow:
"I'm not saying the aha moment doesn't matter, but that is not it. If you stop there, it's as good as having a good first date. You won't make him your boyfriend because you had a good first date."
I've had a chicken-and-egg problem with this for a long time. Does performing this action make users motivated? Or are the users who perform it already more interested, and that's why they do it? If you bully everyone into one activation event, what happens to users who would've found value a different way? Would you even see the same correlation between that event and long-term upgrades if it's the only option you give people?
The part almost nobody designs for is what comes after. The daily loop. The thing that brings someone back on Tuesday without a reminder. Lisa said it directly:
"Building a habit is incredibly hard. Very few designers are educated about it. Very few companies think about it in enough detail to actually make the product sticky."
How many good habits do any of us even have? I quit my diet this week because a friend brought wine, and I was like, well, farewell. That's how easily a habit you actually want breaks. Now imagine building one around your SaaS product, in a market where users have a hundred alternatives and zero reason to be loyal.
How to earn an upgrade from a professional
I asked Lisa which products she started using for free and ended up happily paying for. Three came up. They all did the same thing, but each in a different way.
Magic Patterns — an AI design/prototyping tool that I love love love.
Lisa was skeptical, tried it free, got into a creative flow, and ran out of credits. The upgrade prompt didn't slam a gate. It pitched what she'd gain:
"The way you were asked to upgrade didn't feel intrusive. They were marketing benefits instead of taking something away, you'll get double the speed, you'll deliver your work faster. It felt like a soft switch. You could come back the next day with free credits. Nobody was pressuring you."
I know that feeling from Lovable. You're building something, you're in the middle of it, credits run out, and you just aren't done. The upgrade doesn't feel like a wall. It feels like continuing. But I pushed Lisa, because I've hit that "not done" moment with plenty of products and didn't upgrade most of them. Same interruption, completely different reaction. The difference is whether the product earned enough momentum before it asked. Whether you already experienced enough value that paying feels like a continuation, not a transaction.
CleanMyMac — laptop cleaning software, the kind of product Lisa would normally never buy. But before it mentioned money, it ran a full diagnosis of her machine:
"You felt like they were giving you something real, this is how your laptop looks right now, here's what's working versus what's not. I wasn't learning about the product. It was showing me how it can help. It just felt effortless."
The diagnosis was the onboarding. Value first. Payment second. No explanation needed because the product already proved itself.
Granola — a note-taking app that took the same principle even further. It read her calendar, detected a meeting, and just started working. No setup, no bot joining the call, nothing to configure. Every step she would've had to take was already handled.
Three products. One pattern. None of them tried to teach Lisa how they work. They all fit into the way she already works:
"Our job is not to educate the users. Our job is to match the way they already think right now."
And transparency counts just as much. If users know exactly what they'll get, if that gap between "I don't know what will happen" and "I know exactly what I'm paying for" is as short as possible, trust builds fast.
One piece of advice for every growth team
I asked Lisa for the one thing she'd want every founder and growth team to hear right now. She said the fear in the market, am I being replaced, is my product even relevant tomorrow, is paralyzing people who should be moving:
"The shift isn't as black and white as the market makes it out to be. You're not an old SaaS that can't renew, and you're not a new AI product just hoping to survive. There's a very valid middle path: you have the distribution, you have a problem worth solving. Go innovate on that. Even if it's small pieces, even if the AI is for certain challenges only."
She's right. I see this with teams I work with: they're so overwhelmed by the idea of rebuilding everything that they rebuild nothing. Meanwhile small, targeted improvements could already be making their product stickier.
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🎉 Woow, you finished the issue, that’s awesome!
Hi, I’m Anastasia Kudrow, and I write Ghosted.
I also help SaaS teams get more upgrades by using psychology instead of cheap tricks. Because hype aside, people will be buying your product for many more years, AI or not AI.
