We gave a prospect a 60-day free trial. They churned and told us we were "too accommodating."

A few months ago, we were in talks with a mid-sized company for a $500/month contract. Their team was swamped, so they asked if we could extend our standard 14-day trial to 30 days. Wanting to close the deal, I said yes.

A month later, they still hadn't onboarded their team, and asked for another 30 days. I agreed again because the deal was "so close."

By the time the 60-day trial ended, we had spent over 15 hours in support calls helping them set up, built two custom CSV imports for them, and basically acted as their dedicated onboarding team—for free.

When the trial finally expired, the VP told me they decided not to move forward. His reasoning was baffling: "Because you kept extending the trial, it felt like there was no urgency to actually roll it out to the team. We just kept putting it on the back burner."

I was furious. I spent 60 days giving them white-glove service, and because I didn't enforce a deadline, I accidentally made our product feel disposable. They never felt the "pain" of losing access, so they never prioritized adopting it.

I realized that by trying to be accommodating, I removed the urgency to buy. I basically trained them to keep kicking the can down the road.

For B2B founders: How do you handle prospects who ask for massive trial extensions?

Do you charge for the extension, offer a paid pilot instead, or just have a strict "no extensions" policy? I need to figure out how to enforce boundaries without losing the dea