Discovery
Before anyone quotes anything
Count mailboxes and their actual sizes
Not how many staff you have — how many mailboxes exist, including ones belonging to people who left. The two numbers are rarely the same.
Measure the file footprint
File server, OneDrive, SharePoint, Drive, or a shared folder on someone's machine. This decides the edition more often than headcount does.
Hunt for PST and local archive files
Ask your staff directly; no admin report will show them. In an organisation that has used Outlook for years these are frequently the largest single volume of mail.
List every shared address
info@, sales@, accounts@, orders@ and the ones nobody has mentioned yet. How each is currently used decides whether it becomes a group or a licensed account, which changes the price.
Establish who controls the DNS
Not who set it up — who can log in today. The single most common cause of a delayed cutover is nobody having the registrar password.
Settle the retention requirement
How long mail must be kept and whether anyone may need to search it later. This decides the edition, so it belongs here rather than after licences are bought.
Inventory every system that sends as your domain
Accounting software, CRM, booking engine, marketing platform, helpdesk. Each will need authorising, and there is always one nobody remembers.