Smarter Scheduling: A Review of Digital Scheduling Assistants

| June 17, 2019

Smarter Scheduling: A Review of Digital Scheduling AssistantsIn a business world where personal connection is essential, scheduling can often become a game of email ping-pong. Imagine that you meet Janet at a networking event. She says, “Hey, we should get coffee sometime.” You get her business card, but there’s no time to talk. So, you email her to follow up.

You: Hi, Janet. It was nice to meet you. How about grabbing coffee on Tuesday at 3?

Janet emails back: Sounds good, but I can’t do Tuesday at 3. How about Friday at 10?

You: Sorry, I’m out of town then. How about Wednesday at 4?

And on it goes. This method takes too many emails and too much time. So, what is a smarter way to schedule business meetings?

Choose a Digital Scheduling Assistant

Here are three software options, with my perspective on each.


Monthly cost: $6.50+, based on the version

Calendar integration: “Two-way integration with the most popular calendaring systems”

My Mobile Experience: Not great

I used TimeTrade for many years but have become frustrated by its lack of flexibility and features. It limits my time slots in such a way that if I make myself available from 1–2pm and 2–3pm, my clients can’t book a 1-hour meeting from 1:30–2:30pm. Also, if a client cancels a meeting, the deprecated appointment still ties up my availability, so future appointments cannot be scheduled at that newly available time. I also don’t have the option to include questions to the person scheduling with me, such as giving him/her the option of suggesting a location for our meeting. In the end, I found TimeTrade to be too expensive, inflexible, and not easy enough to use.


Monthly cost: $0–$15, based on the version and billing frequency

Calendar integration:

  • Google Calendar
  • Office 365
  • Outlook
  • iCloud

My Mobile Experience: Good

I am now using Calendly instead of TimeTrade, and quickly liked it better. I have the flexibility to tailor my meeting duration and to set a gap time between appointment slots. This is helpful when I need to allow for travel time or breaks between meetings. I can also mark myself free or busy, in case I have another all-day event listed on my calendar. For example, I might have a conference listed as an all-day event, but I can still make myself available for appointments during that day. However, for Apple users, the free/busy mark needs to be done through iOS and cannot be done through the MacOS Mail application. I recommend Calendly because it’s cost-effective, flexible, and easy to use. 

Monthly cost: $8–$24, based on the version

Calendar integration

  • Google Calendar
  • Office 365

My Mobile Experience: Good

A colleague of mine uses and really enjoys it, so I decided to check it out. is an artificial intelligence system, providing AI scheduling assistants (named Andrew and Amy) and a calendar page. I can provide preset time slots for clients to choose from, set breather time between meetings, and mark myself unavailable on certain dates. The distinct difference with is that it presents itself as if you have a virtual secretary. The AI assistant emails the client on your behalf to schedule the meeting. If you’re already hiring someone to help you with scheduling, then why not save yourself some overhead and try a virtual assistant? offers good flexibility and customization at an affordable price.

Take a Shot at It

The technology exists to save you from the hassle of back-and-forth emails. You will not be wasting you time to start a free trial of one of these options. Next time you want to meet with a prospect or client, do it the smarter way.

Category: Technology

About the Author ()

Email | Website | Ken Kinard, MM, CPCC, PCC Ken’s goal is to be the most creative guy you know. He is the founder and chief creative officer at Accent Interactive, a creative agency in Baltimore. As a certified coach, he is passionate about helping people find their calling and unleash their career potential. He helps business teams become more innovative through interactive workshops known as Creativity Labs.