How does it connect to Outlook?
Ask any vendor whether their system integrates with Outlook and the answer will be yes. It is the wrong question. The right one is how it integrates, because there are three very different answers.
1. A COM or VSTO add-in
Software installed on every computer that plugs into Outlook. Often mature and capable, but it runs only in classic Outlook for Windows, needs installing and updating on every machine, does not work on a Mac, and is not supported in the new Outlook for Windows, which Microsoft is moving customers towards. Classic Outlook is expected to be supported until at least 2029; a practice management system is usually a ten-year decision.
2. A Microsoft web add-in
Runs in classic Outlook, new Outlook, Outlook on the web and Outlook for Mac. Deployed centrally from Microsoft 365, so there is nothing to install and new starters have it the moment they sign in.
3. A server-side integration
The system connects to Microsoft 365 in the background, filing email by rules and synchronising calendars whatever device people use. Powerful, which is why the permissions it needs deserve careful thought (see What did you just give it permission to do?). Many good systems combine this with a web add-in.
Why it matters
If your fee earners manage their work from Outlook, and corporate and commercial teams usually do, this one detail decides whether the system works on a Mac and on the web, whether new starters need software installing, and whether you hit a wall when Outlook changes.
What to ask, and what to see
- Which technology does your Outlook integration use?
- Show it working in the new Outlook and in Outlook on the web.
- Show it on a Mac, if you have or might have Mac users.
- If any part still depends on a COM add-in, what is your plan and timetable?
Technical notes: small decisions, big consequences
Start with the overview: The details that decide the project
Accounts and finance
- Core accounting is still the gold standard
- One-way or two-way sync? Connecting your legal system to Xero
- Units or minutes? How time is recorded
- Your matter and nominal structure
- Making Tax Digital: the firm and its clients
Workflow, data and documents
- Workflow: deep, basic or none?
- Client onboarding and matter inception: portal, e-signature and ID checks working as one
- Custom data: what you rely on, and how you move it
- Precedents, merge codes and macros: your document bank in a new system
Your types of work
- Legal aid: your records, not just the Legal Aid Agency’s
- Litigation: Precedent H starts with time recording
- Family: Form E and financial disclosure
- Private client: where does the tax software fit?
Security and access
- Roles or individuals? How user permissions are set up
- Why manage security twice? Linking application security to Microsoft Entra
- How granular is the security inside the system?
- Who can see what in reporting?
- Shared platform, your data: separation, restore and erasure
- When the supplier is the target: where your data lives, who can reach it, and your real risk
Microsoft 365
- How does it connect to Outlook? (you are here)
- What did you just give it permission to do?
- What happens behind the scenes? Background integrations with Microsoft 365
- OneDrive is not a document management system
- Microsoft 365 is not a backup
Data and decisions
Where does your firm stand?
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