Stop deciding by opinion. Ten questions per desk, five minutes each, and the right Outlook chooses itself - with the answers written down for the day someone asks why.
Every other page in this set goes deep on one difference - PST, add-ins, offline, rules, privacy. This page is the method that combines them: a per desk checklist you run with the actual user, scoring the features their work truly touches. Any single hard blocker keeps that desk on classic. No blockers means the new app is a safe, even pleasant, move. Run it before a pilot, keep the sheet, and your office's Outlook decision becomes documentation instead of debate.
Example score panel - one hard blocker outweighs every soft preference.
Sit with the desk's actual user, not their manager. Ask the ten questions about last month's real work, not imagined work. Questions one to five are blockers: PST archives in weekly use, COM add-ins or VBA macros, client only rules, hours of offline work weekly, or regulated non Microsoft mail under contract. Any yes keeps the desk on classic today. Questions six to ten are preferences: love of the cleaner interface, multi account Microsoft life, Copilot interest, pain with huge OST files, desire for identical look on Mac and Windows. Preferences only count when the blocker list is empty.
One: do you open a PST archive in a normal week - for search, filing or replying? Two: does any button in your Outlook come from an add-in, or does any macro run in your day? Three: do any rules move mail to local folders, run scripts or print on arrival? These three protect the classic-only machinery. Offices are often surprised here: a desk described as just email turns out to file every invoice into a year PST by rule. That discovery, made by checklist in October, is the one that prevents the December filing gap.
Four: in a normal week, do you work mail for more than an hour with no or bad internet? Five: is shared mailbox or delegate calendar work your main job? Six: do you send OFT templates or rely on Quick Parts daily? Seven: is your mailbox self hosted or covered by a client contract about data processing? A yes on four, six or seven is a blocker today. A yes on five is not an automatic blocker - the new app handles much shared work - but it earns that desk a longer pilot with their shared tasks as the test script.
Eight: do you suffer classic's real pains - corrupt OST files, slow search on old hardware, profile trouble? Nine: do you live in several Microsoft accounts and want one clean app for all of them? Ten: do you want the new features - Copilot assistance, modern scheduling, the same interface everywhere? These are the new app's genuine strengths, and for a desk with zero blockers they make switching a positive, not a compromise. Record the preference answers too, because they identify your happiest pilot users - always pilot with volunteers whose sheets are all clear and whose preferences lean new.
Each sheet ends with three lines: the decision, the date, and the review trigger. Decisions change legitimately - when full PST support lands, when a vendor ships a web add-in, when a contract is renegotiated. Note which blocker, if removed, would flip this desk. Then the quarterly review is mechanical: check the triggers, retest what changed on copies, flip the desks whose blockers cleared. This is how a cautious office still moves forward - by evidence per desk, instead of by announcement per vendor.
See both Outlook apps side by side in the full video - every difference shown on a real PC, step by step.
Watch Full VideoAbout five to ten minutes with the user, including opening the Rules list and Add-ins page together. A whole office usually fits in one or two days of short sessions.
It stays on classic today, with the blocker written as its review trigger. When that feature officially arrives or the tool changes, retest and decide again.
Uniformity is tidy but not required. Per desk decisions with written sheets are supportable and honest; mixed offices are normal during a staged migration.