I've been building a scheduling tool for solopreneurs and small businesses, and along the way, I realized how many people dislike using tools like Calendly — even if they rely on them.
Here are some of the common complaints I've heard (and experienced myself):
Feels impersonal: Sending a link feels transactional, not collaborative. Especially awkward in cold outreach or with high-trust clients.
Too rigid: Most tools assume static availability or recurring blocks. Life isn’t always that predictable.
Hidden costs: Features like payment integration, group bookings, or email/SMS reminders are often behind paywalls or require multiple tools.
Overkill for simple use cases: Sometimes you just want to quickly agree on a time without creating a new "meeting type."
Poor UX on mobile: Many tools are clunky on phones, yet that’s where a lot of scheduling happens.
Curious to hear from others — do you run into these problems? What’s your biggest frustration with scheduling tools right now?
Here are some of the common complaints I've heard (and experienced myself):
Feels impersonal: Sending a link feels transactional, not collaborative. Especially awkward in cold outreach or with high-trust clients.
Too rigid: Most tools assume static availability or recurring blocks. Life isn’t always that predictable.
Hidden costs: Features like payment integration, group bookings, or email/SMS reminders are often behind paywalls or require multiple tools.
Overkill for simple use cases: Sometimes you just want to quickly agree on a time without creating a new "meeting type." Poor UX on mobile: Many tools are clunky on phones, yet that’s where a lot of scheduling happens.
Curious to hear from others — do you run into these problems? What’s your biggest frustration with scheduling tools right now?