Issue #43: Calendly now has an AI that books your meetings by email and writes your follow ups. Is the $8 upgrade worth it?

“Running shos” shouldn’t return zero results. Neither should “red waterprof trail runners under $150.”

Traditional search needs exact keywords. Gladly understands what shoppers mean, typos and all, and turns dead-end searches into products that fit what they asked for.

See how Gladly reads between the typos

Turn Dead Ends Into Sales

Launched August 19. Callie is in beta. English only. Available on the new "Plus" plans.

If you sell anything that starts with a call, you know the email tag. "How about Tuesday?" "Tuesday doesn't work, what about Thursday afternoon?" Four emails later, you still do not have a meeting. Then after the meeting you spend 15 minutes writing the follow up you promised to send.

Calendly, the scheduling tool millions of people already use, added two AI features aimed at exactly those two problems. A lot of Calendly users have no idea they exist.

Calendly released two new AI products on August 19. They come as a bundle on two new plans, called Standard Plus and Teams Plus.

Callie, the scheduling assistant.

You add [email protected] to an email thread where a meeting is being discussed. Callie checks your calendar and replies with times, usually within a minute. According to a review of Calendly's documentation, it offers up to three days of availability with up to five slots a day. It will not book outside your availability and asks for your approval before changing meeting details. The other person can reply in the same thread to reschedule.

There is also "Ask Callie," a chat inside the Calendly app. It uses your schedule, contact profiles and past meeting notes to help you prepare for a meeting or answer questions about previous ones.

Notetaker, the meeting recorder.

It joins meetings on Zoom, Google Meet and Microsoft Teams, including meetings that were not booked through Calendly. Afterward it produces a recap with a summary, key points and action items, plus a draft follow up email. You can edit the recap before sharing it, and recaps can be shared by passcode protected link.

What Calendly says is coming. The company says Callie will eventually take proactive actions on your behalf, with you in control. That is a plan, not a current feature.

The verdict: If you already pay for Calendly and run lots of one on one calls with clients or prospects, this is a clean upgrade. If you do not use Calendly today, there are cheaper note takers and schedulers, so do not switch just for this.

Take a solo financial coach in Raleigh, North Carolina, who runs about 15 discovery and client calls a week on Zoom. She already uses Calendly for booking.

Here is how she could use it. Prospects who email instead of using her link get a quick fix: she copies Callie on the thread with a line like "Looping in my scheduling assistant." Callie proposes times from her real calendar and books the call. After each call, Notetaker gives her a recap and a drafted follow up. She changes two sentences, hits send, and moves on.

This is an illustration, not a case study. The time saved depends on how often clients email instead of clicking your link.

"Does Callie work if the other person does not use Calendly?"

Yes. The other person just replies to the email thread, so they do not need an account. The limits: it works only from the one email address you log into Calendly with, it does not support shared mailboxes, Bcc does not trigger it, and it handles one on one meetings only.

The Plus plans add $8 per seat per month. You cannot buy Notetaker or Callie separately, and the $8 applies to every seat, even for team members who never use the AI. Calendly's own pricing page was confusing when I checked, since the Plus cards showed the base price while the features were listed as included. The prices above come from a review published by a competing scheduling tool, so confirm the real number on Calendly's site before you buy.

Before you pay, look at your last 20 meetings. How many were booked through a link and how many through back and forth email? If more than a third came through email threads, Callie is worth a trial. If almost everyone uses your link, you may want a standalone note taker instead.

Scheduling tools are turning into assistants. Claude Duet, ChatGPT Dots and Meta Muse can also manage your calendar, but Calendly sits inside a workflow millions of people already use.

On privacy, Calendly says it does not sell customer data or use it to train AI models. It uses large language models from OpenAI and offers no blanket opt out of the AI features.

Skip turning on Notetaker without telling the people on the call. Recording laws differ by state, and many require consent from everyone on the call. The sources I read did not cover how Notetaker announces itself or how long recordings are kept, so ask Calendly directly and read its settings before you use it with clients.

Also skip trusting the recap blindly. Reviewers note that recaps can contain errors such as misheard numbers, and that Notetaker is unlikely to beat dedicated note takers on transcription quality. If a meeting involves money or commitments, check the recap against your own notes.

Until next issue, Kris

The Layman's AI: The only AI updates your business actually needs.

Start building, $5 off

_{^{Discount of $5 applies to first month of any paid plan. You need to sign up via this webpage in order to claim the discount. The discount applies to new and returning users without an active paid plan. Terms apply.}}