Problems with scheduling apps like Calendly

Posted by chetansorted on Friday May 09, 2025 @01:11AM
from the self-post dept.

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?

Re:Problems with scheduling apps like Calendly by gamificationpan on Friday May 09, 2025 @02:11AM (#43934231)

I have the same feeling.

[ Parent | on HN ]

Re:Problems with scheduling apps like Calendly by tanelpoder on Friday May 09, 2025 @02:39AM (#43934359)

Yup same here. Perhaps a better experience would be to first just reach out with a "normal human being" email and later on either side of the conversation can just CC: [email protected] address to the email reply.

Downside: now this (external) service knows what you're talking about

Upside: now this (external) service knows what you're talking about - and can create a meaningful name & description for your meeting request (and you'd have some searchable history etc)