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Ruairi
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I’d go for an easy solution and just use MS Outlook, no need for an employee management solution.

Add all 12 contractors to the People section of Outlook. Either use the notes section to list their certificates or create categories for each certificate and tick them for each contractor – you can then sort, group and filter them by these categories; handy if he wants to know at a glance who is qualified to do a job.

Then go to the Tasks and send a new Task Request to each contractor. Create one for the expiry date of each certificate (pro tip: you can set up a reoccurring schedule). They’ll get an email plus it will show up in their Task list (in Outlook and any mobile device they have that they have connected). You can also categorise these tasks so you can sort, group and filter upcoming tasks.

Your brother in law will be able to see a task list for the certificates (or whatever) and both he and the contractor will get reminders and can update the status.