Your Guide to the Best Business Calendars

Running a business isn’t for the faint of heart. From planning major launches to keeping your finances in order, entrepreneurship comes with a lot to juggle. But one tool can make it a lot more manageable: the right calendar to keep everything on track.

Before you settle on the first calendar you find online, it’s important to weigh your options and think about your unique business needs.

In this guide, you’ll learn:

• How to choose the right calendar for your business
• 5 apps that work great for businesses
• What to consider before you choose a calendar app

Ready to make your business run smoothly? Let’s get started.

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Importance of a good calendar program for business

Choosing the right calendar isn’t just about setting dates and times; it’s about creating a workflow that complements your business processes. A well-designed calendar app can help prevent missed deadlines, improve team communication, and even increase client satisfaction by simplifying scheduling.

What’s more, a good calendar program is an investment in time management. You probably know this already, but time is one of your most precious resources as a business owner! And optimizing your schedule means gaining hours that can be better spent elsewhere — whether that’s on strategic planning, nurturing client relationships, or developing new offerings. 

Every business is different, and your business calendar should reflect those nuances.

• If you’re managing a remote team or frequently on the go, a mobile app that supports real-time notifications across platforms (like Android and Apple devices) might be ideal.

• For others, an online calendar that integrates with productivity tools like Slack, Asana, or Todoist may be a priority.

Whatever your business looks like, having a proper calendar management tool is a must-have.

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Key features to look for in a business calendar program

Here at Clockwise, we think a lot about time. (It’s the reason we’ve spent years developing an AI-powered calendar assistant that builds better and more productive schedules for individuals, teams, and entire companies.) And as time-obsessed folks, we have a thing or two to say about which calendar features make for the best work calendar:

• Compatible across devices. Whether you're using a laptop, phone, or tablet, your calendar should be accessible and sync seamlessly across all platforms. This way, you can run your business from wherever you are! It’s also important to consider operating systems like iOS and Windows. 
• Works in harmony with your current tools. The secret to juggling multiple apps? Integrations. Your calendar should connect easily with the apps your business already relies on, streamlining your workflow.
• Widgets and notifications: Stay updated on your schedule with real-time notifications, widgets for at-a-glance views, and reminders for birthdays, meetings, or time-sensitive tasks. Widgets are especially handy for quick access to your calendar on mobile devices.
• Ease of use. A business calendar should be intuitive and user-friendly, saving time rather than adding complexity to your day. If you have a team, ease of use is especially important since it minimizes training time.
• Collaboration features. If you run a small business with a team, ensure that your calendar allows for shared access, managing permissions, collaborative scheduling, and time zone support for video conferencing. You might want to explore apps with an enterprise plan for scaling businesses.

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Top calendar programs for business in 2024

From AI-powered assistants to tools that integrate payments and bookings, today’s business owners have a lot of apps to scope out. We’re here to make the job easier. Below are five of the best calendar tools available in 2024:

Clockwise

Clockwise is an AI-powered calendar assistant that builds better and more productive schedules — designed to alleviate the stress of calendar management for busy professionals.

Powered by automation and AI, Clockwise rapidly calculates the best time for meetings, tasks, and deep work — all based on your preferences. No more mind reading or trying to conjure time out of nowhere. Clockwise works across individuals, teams, and entire companies, and it gets smarter and more powerful as more people use it.

Business owners will especially love Prism, a feature of Clockwise that allows users to shortcut manual complex scheduling. The intelligent calendar offers a chat + drag-and-click interface where you can interact directly with Clockwise to manage your calendar.

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Simply type your scheduling needs into the Prism chat or directly click on a calendar event to view and manage meeting options. Clockwise processes your request to propose changes and help you achieve your ideal schedule.

Here are a few things you can do with Clockwise Prism:

• Schedule, reschedule, and cancel meetings, no matter how urgent or complex
• Find time for a meeting where there’s nothing available on the calendar 
• Schedule in bulk (like clear my week, or schedule 1:1s with everyone on my team)
• Transform a to-do list into calendar task holds
• Create scheduling links or generate list of availability (an essential for external scheduling!)

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Pricing

Get started with Clockwise, including Prism, for free! The free version also automatically finds the best time for your tasks and routines, protects personal time (e.g. lunch, travel, appointments), and lets you schedule seamlessly outside your organization with unlimited Clockwise Scheduling Links. After that, paid plans start at $6.75 per user per month and include Focus Time holds, group Scheduling Links, and more.

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Google Calendar

Are you looking for a calendar app that’s effective and easy to use, look no further than Google Calendar. Don’t let its simplicity fool you, though — Google Calendar offers plenty of advanced features and customization options for you to play around with. If you’re a service provider, you can take advantage of Google Calendar’s appointment booking pages. If you have a team behind you, you can put shared calendars to good use. Whether you run a small business or a large enterprise, Google Calendar is a great option because it can adapt to your needs. Bonus: It integrates with Clockwise for AI-powered scheduling.

Pricing

Google Calendar is free for personal use. However, for more business-forward features, we suggest checking out Google Workspace’s business plans, which come with a professional Gmail address and start at $6 per user per month. 

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Microsoft Outlook

For a business calendar that’s tried and true, Microsoft Outlook is a solid choice. Outlook brings together calendar, email, and contacts — so you can manage it all in one place. Some users may find there’s a learning curve, but that’s because Outlook calendar is packed with functionality! It’s especially great if you plan on using the entire Microsoft ecosystem since it integrates seamlessly with other Microsoft apps.

Pricing

To use Outlook, sign up for a Microsoft 365 (previously Office 365) account. Anyone can get started with Microsoft Outlook for free for personal use. Microsoft 365 Business Standard plans start at $12.50 per user per month. 

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Calendly

For service-based businesses — e.g. salons, photography, and marketing — your booking system can make or break your client experience. Tools like Clockwise Scheduling Links and Calendly are fantastic options for communicating your availability with clients while also allowing them to book directly with you.

Business owners enjoy using Calendly for its 2-in-1 scheduling and payments functionality as it connects with Paypal and Stripe. It also embeds on your business’s website for straightforward appointment scheduling for your clients.

The downside is that Calendly isn’t meant to be used as a calendar, but a scheduling tool instead. You’ll still need to manage your schedule from another calendar interface such as Google Calendar or Outlook.

Pricing

Calendly offers a free version that includes a customizable booking page, unlimited one-on-one meetings, and one event type. For payments integration, team scheduling, and other advanced features, you’ll need a paid plan starting at $10 a month.

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Asana

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Google Calendar, Microsoft Outlook, and Calendly are great options to schedule meetings. But when it comes to scheduling work, we recommend Asana. Asana is a work management platform that lets you track projects, set company-wide goals, and collaborate with teammates — all from one place.

Business owners will appreciate the flexibility to switch between various project views, allowing them to visualize work in the way that best fits their needs. To use Asana as a business calendar, go to calendar view and see your deadlines and milestones organized by week or month. For complex project management, you might enjoy timeline view, which gives greater insight into how different tasks relate to and depend on one another.

Overall, Asana is a must-have for staying on top of tasks, coordinating team efforts, and keeping operations running smoothly for business owners. Pair it with a separate scheduling app for meetings/appointments (psst, it integrates with Clockwise) and you have a winning biz tech stack!

Pro tip: Use one of Asana’s 80 ready-made templates to kickstart your next project plan.

Pricing

Asana offers a free version for individuals and small teams looking to manage tasks and personal to-dos. The free plan comes with unlimited tasks and projects and lets you collaborate with up to ten team members. Paid plans with advanced features, like Asana AI and robust automation, start at $10.99 per user per month.

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How to choose the right calendar program

Picking a calendar for your business might seem like a trivial decision. However, the perfect calendar can make a real difference in your day-to-day operations. After all, time management dictates success!

There are plenty of options out there, but the key is to choose something that not only fits your needs today but can also grow with you as your business evolves. Ask yourself these questions:

1. What specific needs does my business have? Consider what “business scheduling” looks like for you. Do you run a service-based business where clients book appointments with you? Do you book time internally with team members? How about external scheduling? Think through how you plan on using your business calendar.
2. How many people will be using this calendar? If you work with a team, you’ll want a calendar app that makes it easy for everyone to stay on the same page. Look for features that allow you to share calendars, assign tasks, and manage permissions. This way, everyone knows who’s doing what, and when. It’s a real time-saver for avoiding those "who’s handling this?" moments.
3. What tools or apps do I currently rely on? Whether it’s Zoom for virtual meetings, iCal/iCloud for managing your personal life, or task management software like Asana, the right integration can make a world of difference for your workflow.
4. Do I need access across different devices? Consider whether you’ll be managing your calendar from your smartphone, tablet, desktop — or all of the above.
5. What’s my budget?  Some calendars are free, while others offer more advanced features through a subscription. Be sure to check the pricing to find what works within your budget — and remember, investing in the right tool can pay off in smoother operations down the road.

Ultimately, the best calendar program is the one that feels like a natural extension of your day-to-day tasks. It should help you get organized, not overwhelm you. And if you find something that clicks, your business (and peace of mind) will thank you.

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Tips for effective calendar management

Set aside daily and weekly reviews.

At the end of each workday, spend a little time reviewing what’s scheduled for the next day. A few minutes can help you feel better prepared the following morning. And, it’s also an opportunity to revisit your business goals and make sure your schedule is actually supporting them. With Clockwise, you can choose to receive a summary of your agenda — called a daily forecast — in Slack every morning.

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Don’t just schedule events.

A calendar becomes your business sidekick if you know how to make the most of it. Use your calendar to carve out focused time, pencil in important business dates (ahem, tax deadlines!), and make time for strategic planning.

Use widgets for quick access.

For even faster access to your calendar events, consider adding widgets to your home screen on your mobile app for iPhone or Android.

Don’t spend more time than you have to.

Real talk: How much time do you spend managing your time? From rescheduling meetings to fitting in last-minute projects, calendaring is a full-time job. Yet, we don’t all have the resources to hire our own EA. Here’s where automation and AI like Clockwise Prism come into play, handling your calendar management for you.

Sync your different calendars.

Staying on top of your schedule can be hard when your various obligations are scattered across multiple apps. By connecting your work calendar to your personal calendar, you make it so you can view all your commitments from one place.

Create a shared team calendar

One of the best ways to stay aligned as a team? Calendar sharing. Create a team calendar that houses info like team meetings, birthdays, and OOO days. Emphasize that team members can choose to share as much or as little as they want. For example, a doctor’s appointment can be labeled “Busy” in the team calendar. (Pro tip: You can create a shared calendar in seconds with Clockwise.)

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Going forward

Time is your most valuable resource — not just for your business but your personal life as well. Choose a calendar app that reflects your business’s current needs while allowing you the flexibility to grow and scale in the future.

To recap:

• Clockwise is ideal for teams looking to build better, more productive schedules with the help of AI.
• Google Calendar is a good option for calendar sharing abilities.
• Microsoft Outlook can be useful if you take the time to learn the Microsoft ecosystem.
• Calendly can serve as a handy scheduling tool (but you still need a separate calendar app).
• Asana is a great choice for project calendars and managing work.

Get started with intelligent calendaring today with Clockwise!

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