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The Good, The Bad, and The Ugly of Appointment Scheduling Software

James Roloff
James Roloff
4 min read
The Good, The Bad, and The Ugly of Appointment Scheduling Software

We’ve all been there. You are trying to schedule a meeting with someone. Your upcoming week is busy, and you know the other person likely has a busy schedule as well.

Do you:

  1. Send them an email proposing a few times next week? Know you’ll need to block and hold those times as you wait for the inevitable 2-3 email volleys back and forth to confirm.
  2. Send them an email asking what times work for them (trying to let them propose the best times for them)? Again, know you’ll have a few back and forth emails and ongoing calendar blocks.
  3. Give them a call, hash it out over the phone? But also awkwardly not discuss the matter at hand in the process.
  4. Send them a Calendly link, and let them automatically reserve a spot on your calendar that works best for both of you?

New to the business development technology stack is “appointment scheduling software” tools like Calendly, Doodle, and their CRM embedded ilk.

They try to tackle one of the major problems that plague human-to-human interactions - scheduling. Going back and forth via email to try to find a time between two or more busy people can be frustrating. But these software providers offer a promising solution.

What Is Appointment Scheduling Software?

Appointment scheduling software is a platform that allows you to share access to your calendar through a simple web interface. You can share links that let other people (prospects, customers, vendors, etc.) view your open availability and automatically schedule a meeting.

These tools automatically sync with major calendar platforms like Outlook, Google, and iCloud, meaning your availability automatically updates and ensures that customers don’t accidentally book over existing appointments. You can also set custom availability windows and rules to ensure that your day isn’t overwhelmed with external meeting requests.

But like any tool, these appointment scheduling software platforms have their pros and cons. Here are the good, the bad, and the ugly.

The Good

First, let’s start with the good. With their rapid adoption, they have to be doing something right.

Efficient - Appointment scheduling software is incredibly efficient. It allows for faster collaboration, and drastically cuts down on the back and forth of emails. Your client can pick the time that works best for them, but also is open to you.

User Friendly - These tools provide a great user experience as well. Being able to visually pick a day and time, and see availability is far more effective than having to manually share (via email text, or voice) what possible meeting times could work.

Integrations - And of course since these tools are digital, they offer plenty of integrations. You can connect appointments to CRMs, marketing automation platforms, and video conferencing tools. Any automation of data entry is a win!

The Bad

But it’s not all sunshine and rainbows… There are some drawbacks to using these tools. Here are a few I’ve noticed.

Perception - By far the biggest problem with scheduling applications is their perception issue. Some people get mildly offended when you send a link asking them to schedule the meeting on your calendar. Which, given the wrong context, can seem self-centered. Be sure to send the link to your schedule in a friendly way, and always give the option for your recipient to reply the old-fashioned way with days/times that work best for them.

Inflexible - Like all software, these scheduling platforms are operated based on logic and rules. While normally this is a good thing, it makes them a little inflexible. There are some times, like when scheduling an urgent meeting with an important person, that you would be more creative with your schedule. But with these tools, your weekly check-in meetings, or recurring reminder meetings show you as “busy”, and disallow scheduling.

The Ugly

Then there is the straight-up ugly side to appointment scheduling software. When used poorly, these tools can be a force of evil!

Tacky Lead Gen - We’ve all seen that salesperson that just sprays and prays LinkedIn messages or cold emails with their scheduling link. Instead of providing something of value, they use their Calendly link as a bad attempt at lead generation.

Setup Incorrectly - Availability that isn’t accurate. Locations of meetings that are wrong. Email notifications that are never received. When these tools are set up incorrectly, you are opening the door to a very frustrating experience for all involved. I’ve had to re-schedule multiple meetings with people who use appointment scheduling software because they had a scheduling conflict with the time I selected… Ugly stuff!

Should I use appointment scheduling software?

Yes, I do think these tools are great, and personally use Calendly for my business. As a minimalist by nature, I like that I can drastically cut down on the number of emails for myself and my clients.

The key is really to be thoughtful in your approach to integrating these tools into your workflow. Below are some tips I’ve found to be helpful:

  1. Ensure your availability is accurate. - Go through every setting in the configuration of the availability to ensure that your availability is accurate. I’d recommend being more restrictive at first, to avoid accidentally allowing scheduling over a time that you need to have your focus somewhere else.
  2. Keep your calendar current. - Be diligent about blocking off your calendar for any appointments. Internal meetings, external meetings, kid's events, etc., are all items that need to be on your calendar to prevent a meeting from being scheduled.
  3. Create custom meeting options. - Configure different meeting types, such as 30-minute calls, 60-minute in-person meetings, video calls, etc., that allow for more robust scheduling options.
  4. Ask politely. - Always offer the old-fashioned back and forth option to schedule. Never force anybody to use your Calendly link, and/or assume that it is something they are comfortable with.
  5. Only use for planned meetings. - Don’t send your meeting link to cold contacts as a way to generate leads. Not only is this tacky, but it also could lead to a bloated calendar with many no-shows.