We Tried to Invite Someone on Calendly and It Took Way Too Long

We use Calendly a lot at Pyango. It's one of those tools that does its core job well — someone clicks a link, picks a time, done. But the moment you try to do anything beyond the basic flow, it starts fighting you.

Georgi and Roya sat down to walk through the specific pain points they've run into, and filmed the whole thing for our Build in Public series:

Here's what came up.

The invite flow is unnecessarily complicated

The thing that kicked off this whole conversation: trying to invite a new host to an event. It should be one of the simplest actions in the product — you want someone else to be available on a calendar link. Click invite, type their email, done.

Instead, the current flow takes you through multiple screens, and it's not always clear what each step is actually doing. Georgi and Roya both agreed the fix is straightforward: a single, visible invite button that does what you'd expect it to do. No extra navigation, no hunting through settings menus. Just "invite host" right where you need it.

This isn't a niche complaint. If you're running a team where multiple people take meetings — which is basically every agency and every startup with a sales function — you're hitting this flow regularly. Every unnecessary click adds up.

Hidden fees are a trust problem

This one came from Roya, and it's less about UX design and more about how Calendly communicates pricing.

When you add a new person to your account, there can be extra charges. That's fine — SaaS companies charge per seat, everyone understands the model. The problem is when those charges aren't made clear at the point where you're actually adding someone. You go through the invite process, and the cost implication either shows up late, shows up vaguely, or doesn't show up at all until the invoice.

That's a trust issue. Nobody likes opening a bill and seeing a charge they didn't expect. If there's a cost associated with an action, it should be visible before you confirm that action. Not after. Not buried in a pricing page you'd have to go find separately. Right there, in the flow, before you click the button.

It's a small thing to fix and it would eliminate a recurring source of frustration.

Group creation and event type summaries need work

Roya walked through her experience trying to create groups and manage event type summaries. The short version: it's clunky.

Creating a group should be intuitive — select people, name the group, save. But the interface makes it harder than it needs to be. Steps that should be obvious require clicking around to figure out, and the event type summary doesn't give you a clear at-a-glance view of what you've set up.

When you're managing multiple event types across a team, you need to be able to see quickly what's configured and for whom. The current summary view doesn't do that well. You end up clicking into each event type individually to check settings, which defeats the purpose of having a summary in the first place.

The bigger picture

None of these issues are deal-breakers. Calendly still does its core job. But they're the kind of friction that builds up over time, especially for teams that rely on the tool daily.

What's interesting from a product perspective is that these are all solvable problems. An invite button in an obvious place. Fee transparency in the invite flow. A cleaner group creation process. A summary view that actually summarizes. None of this requires rethinking the product — it's refinement of flows that already exist.

And that's kind of the point we keep coming back to in our Build in Public work: the difference between a good product and a great one usually isn't some revolutionary feature. It's getting the small stuff right so that people stop thinking about the tool and just use it.

Roast my Product Episode 6: Calendly

Latest blogs