Discover what PAs and EAs should look for in diary management software, from shared calendars and scheduling automation to managing multiple executives, integrations and essential features to compare before choosing a supplier. We’ve even included a handy checklist that will help you find the right tool quicker.
What is diary management software?
Diary management software helps individuals and teams organise appointments, meetings and availability in one place.
While traditional calendars such as Outlook and Google Calendar cover the basics, more advanced scheduling tools can automate meeting bookings, coordinate multiple diaries and reduce the endless back-and-forth emails.
For PAs and EAs, this means spending less time arranging meetings and more time supporting executives with higher-priority tasks.
Six essential features to look for in diary management software
1. Shared calendars and visibility
When managing an executive’s schedule, visibility is everything. Look for software that allows you to:
- Access and update calendars with the appropriate permissions.
- View colleagues’ availability before suggesting meeting times.
- Share selected calendar information without revealing confidential appointments.
- Receive notifications when meetings are changed or cancelled.
Top tip: Check whether the software offers different permission levels. You may need full editing access while other colleagues should only see availability.
2. Managing multiple executives
Supporting two or more executives? Switching between separate calendars can quickly become confusing.
Look for tools that offer:
- A combined view of multiple calendars.
- Colour-coded diaries to distinguish between executives.
- The ability to identify scheduling conflicts.
- Delegated access to create, edit and cancel appointments.
For EAs supporting senior leadership teams, the ability to coordinate several diaries without constantly switching accounts can be particularly valuable.
3. Scheduling automation
One of the biggest advantages of modern meeting scheduling tools is automation.
Instead of exchanging five emails to find a suitable meeting time, scheduling software can allow participants to book directly into approved available slots.
Useful features include:
- Automatic meeting invitations and confirmations.
- Reminders and follow-up notifications.
- Booking links with predefined availability.
- Buffer time between meetings.
- Automatic rescheduling when plans change.
However, automation shouldn’t mean losing control. Make sure you can protect important diary commitments and manually approve bookings when necessary.
For more practical advice, read PA Life’s top tips to keep your meetings on track.
4. Integration with existing workplace tools
Before investing in new software, check whether it works with the platforms your organisation already uses.
Common integrations include:
- Microsoft Outlook and Microsoft 365 – For calendar synchronisation and meeting invitations.
- Google Workspace – For shared calendars and appointment scheduling.
- Microsoft Teams and Zoom – For automatically generating virtual meeting links.
- CRM and project management platforms – For connecting appointments with client records and tasks.
A tool that integrates smoothly with your existing systems is usually more useful than one requiring additional administrative work.
Explore PA Life’s guide to five essential digital tools every modern PA should master.
5. Time zone management
Coordinating meetings between London, New York and Dubai? Time zone mistakes can cause unnecessary confusion.
Choose software that automatically converts meeting times into participants’ local time zones and accounts for daylight saving changes.
For international EAs, it’s also worth checking whether the platform can display multiple time zones simultaneously and highlight suitable meeting hours.
6. Security and confidentiality
Executive diaries often contain sensitive information, including confidential meetings, travel arrangements and personal appointments.
Before choosing software, ask suppliers about:
- Data protection and UK GDPR compliance.
- Calendar access permissions.
- Multi-factor authentication and single sign-on.
- Data storage, retention and deletion policies.
- Security controls for third-party integrations.
Your IT team should review any new platform before confidential calendar information is connected.
Popular diary management and meeting scheduling tools
Several established platforms offer useful scheduling features, although their capabilities and pricing vary.
| Tool | What it’s useful for |
|---|---|
| Microsoft Outlook | Shared calendars, delegated access and Microsoft 365 integration. |
| Google Calendar | Team calendar sharing and appointment scheduling within Google Workspace. |
| Calendly | Booking links, automated scheduling and meeting reminders. |
| Doodle | Finding suitable meeting times across groups of participants. |
| Reclaim.ai | Automatically arranging flexible tasks, habits and meetings around calendar commitments. |
Before selecting a supplier, check whether the features you need are included in your organisation’s existing subscription or require an additional paid plan.
Checklist: What should you ask before choosing software?
Before committing to a new platform, consider these questions:
- Compatibility: Does it integrate with our current calendars and communication tools?
- Accessibility: Can I manage multiple executives from one account?
- Automation: Which repetitive scheduling tasks can it handle?
- Flexibility: Can I override automated bookings and protect priority meetings?
- Security: Does it meet our organisation’s data protection requirements?
- Cost: Is pricing based on users, administrators or additional features?
- Support: Is training available, and how quickly can issues be resolved?
Where possible, request a free trial or supplier demonstration using realistic scheduling scenarios.
The best diary management software should make your job easier
No two executive diaries are the same. Some assistants need advanced automation, while others simply need better visibility across multiple calendars.
The best approach is to identify your biggest scheduling challenges before comparing suppliers. After all, technology should support your judgement, not replace it.
And when unexpected changes inevitably happen, PA Life’s advice on how to deal with schedule wreckers can help you keep even the busiest diary under control.
