One-on-One Meeting Scheduling Tools

In a world filled with too many meetings, if there’s one type of meeting we all should strive to keep on our calendars, it’s one-on-ones. When conducted regularly and with a robust meeting agenda, one-on-one meetings can transform and strengthen work relationships, opening a space for honest conversations, career planning, task prioritization, and guidance. 

The tricky part about scheduling one-on-ones is that managers with many direct reports carry the weight of navigating calendars and conflicting schedules. Scheduling one-on-ones (and sticking to the allotted time slot) can be time-consuming and administratively daunting.

The good news? You don’t have to go it alone. Meeting scheduling tools can help streamline the process of scheduling one-on-ones so you can focus more on the contents of the meeting and less on finding a time that works. 

In this post, you’ll learn the benefits of one-on-one meeting scheduling tools and find a roundup of several scheduling tools to try. We picked tools with different features and functionality so you can find one to meet your needs and budget. Let’s get started!

The benefits of one-on-one meeting scheduling tools

One-on-one meeting scheduling tools help ensure you don’t let your one-on-ones fall off the calendar or double-book over them. While regularly scheduled one-on-ones require a lot of time, they are worth the investment. Effective one-on-one meetings build mutual trust and understanding, prioritize tasks effectively, and keep communication lines open. 

Meeting scheduling tools eliminate some of the administrative work and time that managers and their direct reports put into coordinating schedules so that they can better spend that time preparing for the meeting itself. Automating scheduling helps avoid miscommunications, all while ensuring this sacred time is set aside. 

One-on-one meeting schedulers to try

Many appointment scheduling tools can help streamline your one-to-one meeting planning. We searched for a handful of the top options so you can dig in and start automating your one-on-one meetings in no time. Below are some of the best options listed in alphabetical order.

But first, an important note: We included pricing information for your consideration. All costs are up-to-date as of November 2022.

1. Clockwise 

Overview: Clockwise is an intelligent scheduling assistant that helps people take control of their workday and manage their schedules effectively. With Clockwise, users can optimize their calendars with blocks of uninterrupted work time (we call it Focus Time), automatic meeting rescheduling through flexible meetings, and protect time for necessities like lunch and travel time. And you can forecast team bandwidth and capacity with up-to-date analytics. Clockwise integrates with Slack and Asana for ease of use across tools.

Features: Since Clockwise connects with your Google Calendar, it identifies your one-on-one meetings and allows you to manage them easily. Key features include:

• Our one-on-one dashboard shows you all of your 1:1s at a glance 
• The ability to individually select which of your one-on-ones you want to make flexible (Pro-tip: the flexible meetings setting addresses double-bookings automatically, so you don’t have to manually reschedule or skip your one-on-one) 
• Intelligent timezone detection
• Ultra-smart optimization that takes into account meeting time and Focus Time, so you and your direct reports still have protected, uninterrupted work time 

Pricing: At Clockwise, we offer various pricing options to meet your needs, ranging from free to Enterprise. Our popular Pro plan is $6.75 per user per month, billed annually, and includes unlimited schedule assists (when Clockwise schedules or reschedules intelligently on behalf of a user). We also offer a Business plan for $11.50 per user per month, billed annually. 

‍

2. DaySchedule

Overview: DaySchedule offers a web-based 1:1 meeting scheduler that makes scheduling meetings with teammates (and external customers and clients) easy. With DaySchedule, you can set up a 1:1 page and specify which conferencing software you will use. You can also set which days you want to meet. To book your one-on-one, all you have to do is share your link with your direct reports so they can choose a time that works for them based on the criteria you set for your availability. DaySchedule integrates with Google Meet, Microsoft Teams, Zoom, Goto Meeting, Cisco Webex, Join Me, Google Calendar, Office 365, and more. 

Features: Some of DaySchedule’s noteworthy features include:

• A personalized scheduling page for people to easily view your real-time availability
• Synchronized availability with Google and Microsoft Calendar syncs 
• Custom rating and feedback request emails to get ratings following a meeting
• Customizable design functionality so you can highlight your brand on your online scheduling page
• Public roadmap for you to suggest features directly to the DaySchedule team for enhancements

Pricing: DaySchedule offers three pricing plans to meet varying needs. The Basic plan is free forever and includes the 1:1 event type, one scheduling page, and unlimited events and bookings. The Pro plan costs $5 per user per month billed annually and includes multiple event types (including 1:1s), unlimited scheduling pages, unlimited events and bookings, API access, and more. The Enterprise plan costs $8 per user per month billed annually and offers even more functionality, metrics and reporting, and more.

Image source: DaySchedule

‍

3. Doodle 

Overview: Doodle is an easy-to-use scheduling tool that eliminates back-and-forth meeting coordination. Instead of using calendars and looking for open blocks for meetings, users control who they want to meet with by sharing an invite or their Booking Page. After you send your link, the recipient can choose the meeting time that works best for them, and Doodle automatically sends a calendar invitation. Doodle integrates with tools like Zoom, Microsoft Teams, Outlook, Google Meet, Zapier, and more.

Features: Doodle is known for three distinct features, including:

• A custom Booking Page that displays up-to-date availability based on your meeting preferences
• Group polling functionality to streamline juggling team meetings
• Seamless 1:1 scheduling that allows your direct report to determine a time that works best for them to meet

Pricing: Doodle offers pricing plans ranging from free to Enterprise, depending on your needs. The Pro plan costs $6.95 per user per month paid annually and includes unlimited 1:1s. The Team plan costs $.8.95 per user per month paid annually and includes unlimited 1:1s in addition to an admin console, roles and permissions, activity reports, and the ability to book on behalf of others.

‍

Image source: Doodle

4. YouCanBook.Me (YCBM)

Overview: YouCanBook.Me connects to your Google or Outlook calendar to check your availability and add events to your calendar. Then, you create a booking page to share with your team members via your booking page link. YCBM accounts for timezone differences and offers times to meet when all parties are available. Once someone schedules a meeting using the booking page link, a new event appears on the connected calendar. YCBM integrates with Google Calendar, Zoom, Google Meet, Microsoft Teams, Outlook, and more.

Features: Some of the key features of YCBM include the following:

• Control over when you want to schedule meetings through  weekly scheduling availability 
• Fixed meeting durations and padding in between meetings (so your one-on-ones never run over, and you have time to capture notes before your next meeting) 
• Automatic timezone detections 
• Customizable notifications and automated follow-up emails
• Personalized booking link capabilities to elevate your brand

Pricing: There’s a free and paid version of YouCanBook.Me, but you would need the paid version to take advantage of most of the features listed above. The paid plan runs at $9 per calendar per month, billed annually. 

‍

Image source: YouCanBook.Me 

‍

Going forward

Now that you’re a one-to-one meeting scheduling pro check out these resources to help you improve the structure of your one-on-one meetings:

• How to Use Asana Meeting Agenda & Notes for Follow-Up
• How to ace hybrid Zoom meetings
• 3 Ways to Use MS Scheduler to Simplify Scheduling
• Streamline your meeting schedule and find focus