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What Makes a Good Scheduling Assistant?

by Paul

Do you know how many people use digital scheduling apps to organize their appointments, meetings, and personal errands?

Over 500 million.

And why wouldn’t they?

You can schedule a meeting in a matter of seconds without uttering the dreaded phrase, “What time works best for you?” And the fears of overbooking your schedule or forgetting about a conference call no longer keep you up at night.

But no two of these web apps are the same.

Some integrate seamlessly with your favorite apps, like Outlook or Slack. And others—like Google Calendar—are better for digital invites to a child’s birthday party.

So what makes a good scheduling assistant?

A Low Cost (or Even Free!)

There are certain things you should splurge on as a freelancer, like a Nikon D7500 if you’re a photographer or a 100Mbps internet connection if you’re a web designer.

A scheduling tool should be among your smallest monthly business expenses.

So, even though unlimited meetings for $100/month sounds like a “steal,” the free version might be better if you’re still dabbling in the 1099 world.

Set your monthly cap at $50/month, unless you need a high-end enterprise solution (in which case you could pay hundreds of dollars per month).

And if you’re a scheduling fiend with dozens of appointments a month, you can always test drive free trials and see which meshes best with your visions.

Group Scheduling Abilities

Group scheduling apps

It’s challenging enough to find mutual open time slots between yourself and one other person.

Getting a group together teeters on the edge of rocket science!

So, if you need to bring a bunch of team members together in one Zoom call, you need a scheduling assistant with a group scheduling feature.

Here’s how it works:

All invitees select their “favorites” of the suggested times.

The app does its magic, finding an open slot that squeezes into everyone’s schedule nicely with as little overlap as possible.

Say, “Goodbye,” to those endless email chains!

See also: The Best Apps for Independent Contractors

In-App Chat Features

The entire purpose of using a scheduling app is convenience.

Your app should allow you to communicate with your clients and collaborators about your new meetings.

All invitees should see that Ron can’t attend or that Leslie has to make a last-minute venue change to a conference room with more chairs.

When it comes to chat features, simpler is always better. A good scheduling app can prevent you from having to search through your email account to find all your correspondence with a client.

A User-Friendly Design

The back-and-forth “Does this time work well for you?” conversations will give you the most nagging headaches of your life.

An overly-complicated scheduling assistant is a close second.

The best meeting scheduling tools make it simple to:

  • Name the event: “Brunch in the Cafeteria”
  • Choose a relevant URL: brunch-in-the-cafeteria-12-20
  • Decide on a time: 11:00 a.m.
  • Clarify who’s invited: Chase, Ryan, Whitney, Todd, and Heather

The same concept applies if it’s your clients selecting the time slot.

In the ideal world, a client would access the scheduling link on your Facebook page or website, find an opening within their free time, and add the event to their calendar.

Timely Reminder Notifications

Meeting reminder notifications

Ask anyone what day they’re leaving for their upcoming Disney cruise, and they’ll respond without having to think.

But they’ll forget about that business meeting 20 minutes after agreeing to it.

No offense to you, of course.

To make sure you don’t accidentally flake on your first meeting with a new client, choose a scheduling app with reliable reminder notifications (i.e., SMS or email).

You should be able to configure these schedule reminders:

  • As soon as an attendee RSVPs
  • A week before the meeting
  • A day before the meeting
  • Even 15 minutes before the scheduled start time

The goal is to keep your upcoming sessions top-of-mind without overbooking and tarnishing your reputation as a business owner.

Related: The Best Time Organization Hacks for Freelancers

Operating System Compatibilities

About 10% of people use Macs, 90% rely on the ever-trusty Windows, 52% are loyal iOS fans, and 47% break ranks by opting for an Android.

Everyone deserves an equal say in upcoming meeting times.

Without a doubt, the best scheduling assistants have cross-platform compatibility that attendees can access via all devices (i.e., smartphones, tablets, and laptops).

If a potential client gets an error message, they might assume your link doesn’t work and turn to another professional in your industry who’s easier to reach!

Ample Third-Party Integrations

The average person has 35 apps on their smartphone.

But as a business owner, there may be only a handful of apps that keep your business’s operations running smoothly day-to-day.

These might include:

  • Slack
  • Microsoft Outlook
  • Google Calendar
  • Quickbooks
  • Wix
  • Zapier
  • Salesforce
  • PayPal
  • Zoom
  • WebEx

… or any number of other programs.

Some top-notch scheduling assistants integrate fully with the third-party apps that you’re already using!

So, you might be able to pair your invite with a link to your Zoom meeting or accept payments via PayPal directly through your app.

Be careful about integrations, though, as they can get kind of complicated. Complex apps with lots of integration options are great for SMB companies with an IT department. But if you’re a solopreneur, a simpler product might be a better solution for you.

Automatic Calendar Syncing

It makes no sense to allow your meeting attendees to vote on a meeting time if they have to remember to enter each event into their digital calendars afterward.

In other words, automation is a necessity.

Try to choose an app that’ll automatically add an RSVP’d meeting to a client’s Google Calendar (or similar app) to keep you penned in until then.

Time Zone Considerations

There are only three types of people who think about time zones daily:

  • Truck drivers
  • Those in the airline business
  • Virtual business owners

Keeping an open schedule gives your clients all the time in the world (literally) to book a meeting with you on their time.

But when 7 a.m. EST is 4 a.m. PST, your scheduling assistant could very well set you up for a surprise early morning video call.

That’s why it’s important to find a scheduling tool that factors in time zones.

The “perfect” app will allow you to set your “available times” within your workday and translate them into other time zones for clients across the country.

Never ask about time zones again!

A Focus on Your Industry

By now, you already have a good idea of who your ideal client is. Yet, your industry can prove to be an even bigger deal-breaker when choosing a scheduling app.

For example, some meeting management tools are better for freelancers. Others factor in the needs of the medical community, and some are strictly for business.

But we have to be honest:

There’s no single “best” meeting scheduler.

The best one is the tool that does everything you need it to, takes a little extra pressure off your shoulders, and doesn’t break the bank!

A Great Reputation: The 5 Best Scheduling Assistants

Best scheduling assistants

There’s not enough time in a week to give every scheduling assistant a try.

And let’s be honest:

Experimenting with dozens of apps a week isn’t very exciting.

So, if you want to cut right to the chase, here are five of the best scheduling tools worth messing around with or outright adding to your virtual toolkit:


Best meeting calendar

Bloom isn’t a scheduling assistant by trade, but when you combine all of its features as a CRM, this tool will unquestionably give you the most bang for your buck.

And if you’re curious as to the why, here are three critical reasons:

Lead Capture Forms

There’s not enough time in the day to email or call every warm lead while still booking regular appointments. So, share your Bloom lead capture form via Facebook or your website to collect essential client information before they book a session.

Manage Your Workflow in One Place

Why are you bouncing between PayPal, Freshbooks, WordPress, and Slack when you can streamline each of their functions via Bloom? Send unlimited invoices, create a portfolio, track client contact in-app, and manage projects in one place!

Email Marketing Campaigns

Bloom’s appointment booking feature won’t matter if you can’t generate enough interest to schedule a session. With this CRM, you can plan biweekly or monthly email campaigns to stay top-of-mind and keep clients always wanting more.

Learn more about Bloom and try it free for 14 days!


If you’re looking for nothing more than a reliable scheduling assistant, Calendly will fill those shoes with little trouble.

Just take a look at the key features that “wow” business owners, and you’ll see why:

Advanced Calendar Syncing

You can compare your open slots to up to six calendars to avoid overbooking. So, if you use Outlook for paid appointments and Google Calendar for your personal schedule, you’ll never have to worry about overlaps or awkward scheduling again.

Don’t Overwhelm Yourself

Hopping from one meeting to the next or crushing through five sessions a day will take a toll on your sanity eventually. Calendly allows you to add a buffer time for a mental break between meetings and put a cap on the number of appointments a day.

Spread the Love Elsewhere

If you’re lucky enough to have a team to share the workload with, scheduling client meetings is a breeze. The Round Robin feature in Calendly distributes meetings between your reps, and clients can even choose their salesperson of choice.

Acuity Scheduling

Acuity Scheduling might be a better choice if you work in the medical community or healthcare industry (i.e., masseuse, personal trainer, etc.).

Here are the top three reasons people can’t get enough of this app:

Fast-Track the Administrative Tasks

Client intake meetings only take away from your one-on-one paid sessions, but the information you gather from them is essential. With Acuity, you can send a client intake form to new clients to ensure they’re a good fit for your business ahead of time.

Automatic Calendar Updates

There’s no sense in relying on a scheduling app when you have to key in all scheduled events manually. Thankfully, Acuity will update your calendar in real-time so you can shift your focus to the tasks that generate income.

Customize Your Scheduling Tool

Branding is everything in the business world—from your email signature to high-end business cards. Customizing your scheduling links with your logo, colors, and images will add a touch of professionalism and more memorable digital collateral.


Doodle is a stellar scheduling tool if you’re in an industry where group meetings are the norm and having everyone together makes a world of difference.

Check out the top three features that make Doodle a superb choice:

Privacy Comes First

The problem with many scheduling tools is that they put your personal calendar on full display (yes, everything). Doodle will reveal nothing more than your free time slots to keep your private life, well, private.

Group Meetings Are Easy

As a meeting organizer, all you have to do is select a handful of time slots that fit your schedule. Send out the link to all invitees, and they can choose the most convenient times for them (there’s even an “if need be” situation as a last resort).

Book Different Calendars

Do you prefer to block off your mornings for lead gen, mid-day for conference calls, and afternoons for one-on-one sessions? If so, Doodle allows you to create multiple calendars to ensure clients only book calls during your preferred time of day.

Square Appointments

Square Appointments is a scheduling tool that can also help you juggle the inner workings of running a small business, like paying employees and tracking inventory.

If you’re asking, “Why Square Appointments?” this is why:

Create Customer Profiles and Stay In Contact

Once you turn a hot lead into a paying customer, you want to keep them within arm’s reach. With Square, you can create a customer profile, remember to send out a birthday discount code, and kick-off email campaigns to stay in touch automatically.

Putting the Ball in a Client’s Court

Square doesn’t only allow clients to choose their preferred meeting time. This tool also helps you protect the value of your time by allowing you to charge cancellation fees.

Just Make Life … Easy

We know you’re tired of jumping between your website, accounting app, timecard app, and back again. Fortunately, Square enables you to create a booking site, integrate with Wix and Quickbooks, and manage employee wages all in one place.

Check out our full reviews of HoneyBook and Dubsado, too!


As of now, scheduling meetings is the most tedious and stressful part of running a business or freelancing.

It’s time to leave that mindset in the past for good.

Whether you prefer the invoicing and portfolio features of Bloom or the automatic calendar syncing of Doodle, one thing’s for sure:

All businesses need a scheduling assistant of some sort.

So, take a few free trials for a spin, get feedback from your current clients, and return to the less stressful “early days” of your business!

Sending out meeting requests should no longer sacrifice your valuable time.

Or your sanity, for that matter.

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