Avoid calendar clashes with a new breed of scheduling apps

What’s the longest it has ever taken you to schedule a meeting? I can recall being on email chains that lasted weeks, with 60 or more replies-to-all flying around to a dozen people. As soon as everyone agrees on a time, of course, someone’s schedule changes and the whole process starts over again.

Scheduling meetings is a task that has stubbornly resisted automation in part because the tools have been poorly integrated and also because of people’s natural inclination to do everything by email. Scheduling solutions may be in for a revival, though, now that businesses are settling on a limited spectrum of office productivity tools and artificial intelligence is coming into the picture.

I’ve been using Calendly for six years and love its simplicity. I can create events of different types and durations, add custom fields for details like videoconference URLs or background information, and even accept payments. For $96 a year, it saves me several hours of scheduling back-and-forth, making it well worth the price.

Growth curve

Calendly’s word-of-mouth success has been a quiet phenomenon. The company claims more than 10 million business customers and says it manages schedules for more than nine million people. It recently closed a $350 million investment round that values the company at $3 billion, which isn’t bad for a venture that scraped by for seven years on just $550,000 of initial investment.

Plenty of others are jumping into the market. HubSpot’s Sales Hub scheduler integrates with the company’s customer relationship management system. Doodle specializes in group scheduling, Squarespace Scheduling is aimed at small businesses. YouCanBook.me supports more than 40 languages.

This appointment scheduling market may be poised for strong, steady growth. Allied Market research expects global spending to reach $546 million by 2026, growing about 13% annually. ResearchAndMarkets is even more bullish, forecasting 19% annual growth.

There are two big reasons for that, I believe. One is that integration made possible by APIs now makes it possible for software developers to connect their platforms to various other tools that we use in our increasingly digital lives. These include CRM, videoconferencing platforms, workflow management, project management, and digital payments systems. Scheduling should be a natural extension of these tools rather than something that forces us to go back to our email.

AI empowerment

The other reason is the potential of artificial intelligence to significantly improve the utility of automated scheduling. An early example of this was x.ai, a scheduler that delegates some of the routine tasks of contacting people and soliciting times to a bot. The software can figure out available times by looking at recipients’ calendars, adjust for time zone differences and even parse some email responses in natural language.

An intriguing new player is ScheduleIQ, an application being developed by startup Team Huddle. When you sign up for ScheduleIQ (which is currently in beta test), the service asks you how often you work from home, whether you think you are in too many meetings in general, and whether you prefer sessions to be bunched together or spread out across your calendar. Based on your responses, the software issues color-coded invitations that suggest whether available times are harmonious with your scheduling preferences or run the risk of overloading you. In effect, it looks out for your well-being as well as your calendar.

“No two people meet the same,” said Team Huddle CEO Rob Smith. “A CEO meets for a living. A designer or engineer most likely prefers back-to-back meetings because then they can have their afternoon free.”

ScheduleIQ can intuit some preferences by looking at individual calendars, Smith said. For example, if a person is hosting a large meeting, it tries to leave breathing room on either side so the host can depressurize. Conversely, if a meeting is recurring and attendance doesn’t appear to be mandatory, it assumes another can be scheduled immediately afterward.

Team Huddle expects to offer ScheduleIQ for free “hopefully forever,” Smith said. The company hopes to make money with a line of tools that make meetings more productive.

Giving people a say

Another interesting use of AI in scheduling comes from the industrial sector where Legion Technologies has raised $85 million to develop an intelligent workforce management platform. It uses machine learning to scour a company’s line-of-business applications to determine peaks and valleys of labor demand and recommend optimal workforce levels in places like factories and warehouses.

An interesting twist is that Legion also lets workers specify their scheduling requests and attempts to balance their requests with employer requirements. Legion says most customers see a tenfold return on investment in the first year in labor efficiency improvements and a sharp reduction in employee churn because people have a say in their schedules.

No one has yet cracked the code for making scheduling tools more interoperable so that my Calendly can coordinate with your Doodle. “Not a lot of the solutions speak to one another,” Smith acknowledged. “In the future, we don’t want to care what scheduling tool you use but we can’t force people to work with us.”

Regardless, AI-powered scheduling can relieve one of the most frustrating routines of daily business life, giving us all a little more air in our schedules.

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