How to trial an AI legal assistant in Outlook

Open a routine email and ask the assistant what needs attention. Can it separate a deadline from a newsletter? Can it find the relevant thread, suggest a reply and put a draft somewhere you can inspect? Try correcting a wrong assumption. You should be able to reject the suggestion without anything being sent or filed.

Make sure the proposed installation suits your Microsoft 365 setup. Microsoft describes how administrators can manage Outlook add-ins through the Microsoft 365 admin centre. Some firms let users add approved tools themselves; others need IT to deploy an app centrally. Check this before sending a trial link to every solicitor.

For an example of what an Outlook-based assistant can prepare, explore the fictional Nova workflow sandbox. You can edit drafts and proposed tasks there without linking a client mailbox.

Give the tool three ordinary exercises. First, draft a short client update after a delay. Second, summarise a long thread without making up details. Third, flag the questions you would ask before using a clause from a supplied document. The point is not to ask the hardest legal research question you can invent. It is to learn where an assistant helps your practice and where a human still has to do the work.

Keep a small review log: what the tool prepared, whether the facts were right, how much you edited and whether it made the next step clearer. If it gives a legal citation, check the cited source yourself. If it omits a missing date or confuses two clients, note that openly. A short list of observed mistakes is more useful than a broad claim that an AI is accurate.

Use fictional information or your firm's approved process for real data. The Office of the Australian Information Commissioner recommends due diligence, attention to personal information and human oversight when organisations assess commercial AI tools. Ask each vendor where text is processed, what data is retained and who can access it.

If you use Smokeball, use a fictional test matter to see how proposed filing and time entry actions are reviewed. Do not assume an AI can pick the correct matter from an ambiguous email. Check how it handles two plausible matches, an email with no matter and an existing time entry that might cause duplication.

Smokeball's own AI Legal Toolbox integration guide explains how an authorised user connects the Outlook app and where Matters, Time, Contacts and History appear after connection. Matter filing and time recording in Nova require the Smokeball connection. A firm using a different practice management system should not assume the same integration exists.

If you do not use Smokeball, spend this part of the trial on the inbox, drafting, diary preparation and document review instead. Make sure any time saved can be observed in your own work rather than taken from a product claim.

Ask each tester one direct question: would you choose to open this tomorrow without being reminded? If the answer is yes, identify which tasks improved. If it is no, write down whether the problem was installation, trust in the output, missed context, poor wording or an awkward extra step. These are different problems and should not be hidden behind a satisfaction score.

Compare the full ongoing price, number of users, setup effort and support route. Have one person confirm the cancellation path before the trial ends. Read the vendor's product and data-handling facts, not only its homepage, and check any statement about where AI text processing happens. For AI Legal Toolbox, its public facts page distinguishes the Australian application host from US-based AI text processing.

A sensible decision is a small, supervised rollout to the people who saw value in the exercises. If the tool does not earn its place, do not keep it just because the demo looked clever. This guide is general information, not legal advice.

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