How do you know if your free tier is too generous without killing top-of-funnel growth?

In the beginning, offering a generous free plan felt like the smartest way to build word-of-mouth momentum. It worked for getting signups, but over time, our active user base grew while paid conversions completely flatlined.

The hardest realization was that our power users were happily running their entire daily workflow on the free plan without ever hitting a wall. Every time we considered tightening the limits, we worried about triggering backlash or tanking organic sharing.

For founders who have adjusted their pricing tiers post-launch: where did you draw the line between free utility and paid urgency?