Why Your Trial Users Aren't Converting
You know the pattern: someone signs up, logs in once or twice, maybe clicks around, then ghosts. A week later they're gone. A month later you've forgotten their name.
Most founders assume they need more features or better marketing. Wrong. Your conversion problem falls into one of three categories, and once you identify which one, you can actually fix it.
The Three Conversion Killers
1. Value Gap: They Expected Something Different
A value gap happens when what users expect doesn't match what they experience.
Common signs:
- Users say your product is "too expensive" (translation: they don't see the value)
- High signup rates but low activation
- People sign up then never complete setup
- Exit surveys mention "not what I was looking for"
Why this happens: Your marketing promises one thing, your product delivers another. Maybe your homepage talks about "increasing productivity" but your onboarding focuses on features. Maybe you target "busy founders" but your setup takes 2 hours.
How to diagnose it: Talk to users who didn't convert. Ask:
- What outcome were you hoping for when you signed up?
- What didn't match your expectations?
- Why wasn't this the right solution?
If they struggle to articulate what value they expected, your messaging is probably vague. If they clearly expected something you don't deliver, you have a positioning problem.
2. Friction: It's Too Hard to Get Value
Friction is anything that slows users down before they experience your core value. Every extra click, confusing screen, or required field is friction.
Common signs:
- Users start setup but don't finish
- High drop-off at specific steps in your flow
- Support tickets asking "how do I..."
- Time to first value takes days instead of minutes
Why this happens: You're making users work too hard before they see results. They have to connect integrations, import data, configure settings, invite team members—all before they experience why your product matters.
How to diagnose it: Watch real users go through your onboarding. Use tools like FullStory or Hotjar, or just hop on Zoom calls with new signups. Watch where they get stuck, confused, or give up.
Better yet: try signing up for your own product with fresh eyes. If you find yourself thinking "this is annoying," your users definitely think so too.
The fix preview: We'll cover this in detail in article 4, but the short version: remove every step that doesn't directly lead to your activation event. Be ruthless.
3. Free Tier: You're Giving Away Too Much
If your free tier delivers all the value users need, why would they ever pay?
Common signs:
- High activation rates but low conversion
- Users stick around on free plans forever
- Free users rarely hit feature limits
- When you ask why they didn't upgrade: "the free plan works fine"
Why this happens: You're scared of seeming cheap or limiting users, so you give away your best features for free. Or your free trial is 30+ days and users forget about you before it ends.
How to diagnose it: Look at your free user behavior:
- What percentage hit their usage limits?
- What features do paid users use that free users don't?
- How long does it take free users to need paid features?
If free users aren't bumping into limitations, you're giving away too much. If your trial is longer than 14 days, you're probably losing urgency.
The balance: Your free tier should let users experience your core value, but not deliver all the value they need long-term. Think of it as a sample, not a free lunch.
Which Problem Do You Have?
Most products have one primary conversion killer:
You have a value gap if: Users sign up but never activate, or they tell you it's "not what they expected"
You have a friction problem if: Users start your onboarding but don't finish, or it takes days to reach your aha moment
You have a free tier problem if: Users activate and use your product regularly, but never upgrade
Pro tip: You might have more than one. Fix the biggest one first.
What's Next
Now that you know what's killing your conversion, you need a framework to fix it. That's what the next article covers: the systematic approach to shortening time-to-value and improving conversion.