How to Run a 14-Day Scheduling Software Trial (Day-by-Day Checklist)
30 October 2026 · The Rosterly team · 4 min read
To get a real answer from a scheduling software free trial, test it on your own roster with your own staff, not a demo account. Use the first two days for setup, days three to nine to run a real week with swaps, leave and clock-ins, and days ten to fourteen to check the hours export, the cost and what your team thought. Most 14-day trials are wasted by starting late.
Most scheduling apps offer a free trial. When we checked on 17 October 2026, When I Work offered 14 days with every feature and no card, 7shifts a 14-day trial of its Pro plan, and Deputy free trials on its main plans. Rosterly's is 14 days with every feature, no card. Fourteen days is enough to decide, but only if you plan it.
Before day one: decide what you're testing
Write down three things before you sign up:
1.
The problems you want solved. For example: swaps in the group chat, retyping hours for payroll, nobody knowing who can close.
2.
Your must-haves. Anything that rules a tool out, such as award interpretation, POS integration or native apps.
3.
Your trial team. Two or three staff willing to try it: ideally one confident, one hesitant and one who works odd shifts.
Have your current roster and last pay period's hours handy for comparison. If you're still on a spreadsheet, our staff roster template guide shows what a clean roster should contain.
Days 1–2: set up
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Add your business and first location. Check opening hours, time zone and currency.
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Add skills. These are the jobs only some people can do: open, close, barista, keyholder, alcohol service.
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Add people. Tag each person's skills. Invite your trial team.
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Rebuild one normal week. Don't rebuild an unusual one. Note how long it takes.
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Copy it forward. See how much of next week builds itself.
Check: could a second manager do this without you?
Days 3–5: publish and use it
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Publish next week to the trial team only, or to everyone if you're confident.
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Ask the trial team to open it on their phones. Watch how they find their shifts. Note any confusion.
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Clock in and out for real shifts. Include a break.
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Make one change to a published shift and check the person is told.
Check: did anyone need help? Did anything need installing?
Days 6–9: stress-test the hard parts
This is where tools differ most:
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Swap: ask a trial staff member to request cover from a colleague. See who's checked and what happens while it waits for approval.
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Release: have someone ask to give up a shift. Can qualified people claim it?
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Leave: request leave for a day you've rostered them. Does the roster flag it?
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Skills: try to assign someone without a required skill. Are you warned or blocked?
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Mistakes: forget a clock-out on purpose, then correct it. Is a reason recorded?
Check: was every request visible in one place, and did the roster stay correct throughout?
Start your trial on a real week
Rosterly's trial includes every feature for 14 days, no card needed. Rebuild your week today and run this checklist.
Approve a week of hours. Compare against what you'd have paid from the old system.
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Export for payroll. Send the export to your payroll provider or bookkeeper and ask whether they can use it as is.
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Price your real headcount. Work out the monthly cost now and at your size in a year, including any minimums or add-ons.
Days 13–14: decide
Ask your trial team three questions:
1.
Was it easier than what we do now?
2.
What annoyed you?
3.
Would you be happy if everyone used it?
Then score the tool against the problems and must-haves you wrote down on day one. If it solved two or more of your problems and failed no must-haves, it's a yes.
Red flags during a trial
Some problems only show up once real staff are involved. Treat these as warning signs:
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Staff need help to find their own shifts. If it's confusing on day three, it will still be confusing in month three.
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Requests disappear. A swap or leave request that a manager can't find in one place will end up back in the group chat.
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The roster and hours disagree. If an approved swap isn't reflected when the person clocks in, payroll will suffer.
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Corrections leave no trace. Every changed time should carry a reason.
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The export needs reworking. If your bookkeeper has to reformat it every pay run, the time saving disappears.
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You can't get an answer. Note how quickly support replies during the trial; it won't get faster after you pay.
Running two trials at once
Comparing two tools side by side is tempting, but it doubles the setup and confuses staff. A better approach: