Running an office prize drawing

Workplace drawings are supposed to be a small morale boost. A few clear rules keep them from becoming a source of complaints.

Office prize drawings show up at holiday parties, quarterly all-hands, safety milestones, wellness challenges and the last day before a long weekend. They are low stakes, but they happen in front of colleagues who will compare notes, so fairness and transparency matter more than you might expect. This guide covers how to plan one, run it in person or on a video call, and handle the awkward cases.

A workplace drawing should usually be free to enter. Once employees pay for chances, you may be running a raffle that is regulated where you are, and your company may have its own policy against it. See raffle legal basics and check with HR before charging anything.

Set the purpose and eligibility

Start with what the drawing rewards. “Everyone at the holiday party” is different from “everyone who completed the security training by Friday.” Write the eligibility rule in one sentence and share it before the drawing:

• Who is eligible: all employees, a specific department, contractors, interns?
• How entries are earned: one per person, or one per completed activity?
• Does the person need to be present, or on the call, to win?
• Can one person win more than one prize?
• Are the organizers and the people who bought the prizes eligible? (Many teams exclude the organizer to avoid awkwardness; others include everyone. Decide and say so.)

Be careful that eligibility rules do not unintentionally exclude people on leave, part-time staff or remote employees. If the drawing is for “everyone who attends the party,” consider how people working shifts or in other time zones feel about it, and offer a remote way to be included if possible.

Building the entry list

Pull the list from a source everyone recognizes: the party RSVP form, the training completion report, the team roster. Paste it into a spreadsheet first and clean it up: one name per row, consistent spelling, no stray email signatures. If people earned multiple entries, either repeat their name once per entry or keep a count column and expand it before drawing.

When you paste the list into The Hat Draw, check the name count it shows against your spreadsheet. If each person should have exactly one chance, turn on “Remove duplicates,” which ignores capitalization, so “Sam Lee” and “sam lee” count as the same person. If people earned extra entries, leave it off so each repeated line counts as a chance.

Choosing prizes

Common office prizes include gift cards, an extra paid day off, a good parking spot for a month, lunch with a leader, company swag, or a donation to a charity of the winner’s choice. A few considerations:

• Taxes. In many countries, including the US, gifts and prizes from an employer can be taxable compensation, and gift cards are often treated like cash. Ask payroll or HR how prizes should be handled.
• Equal appeal. If you have several prizes, rank them and draw for the top one last, or let winners choose in drawn order.
• Remote-friendly. Prefer prizes you can deliver digitally or ship easily, so remote winners are not stuck with a cake in a different city.

Running the drawing live

In a room, put the drawing on the main screen. Show the entry count, explain the rules in one sentence, and draw. For several ranked prizes, “Build suspense: reveal last place first” turns the drawing into a countdown: The Hat Draw reveals the last place first and works up to first place, one name at a time, with the list always shown in order from first to last.

On a video call, share your screen with the browser window, not the whole desktop, so private notifications do not appear. Say each winner’s name out loud, because some people will be listening without watching. Pause for a reaction; that is the fun part.

Have one other person watch the drawing and confirm the results. For larger or more valuable prizes, note the time of the drawing and who was present.

Announcing and recording winners

After the draw, use “Copy names” to paste the results into chat or an email, or “Copy results link” to share a page showing only the drawing title and the winners. The link does not include the full list of entrants, which is a nice privacy touch when the list came from an internal report. Print the winner sheet if you need a paper record for payroll or finance.

Follow up privately with each winner about delivery. Some people do not enjoy public attention; a short direct message is enough.

Handling awkward cases

• The winner is absent. Follow your stated rule. If you said attendees only, draw again. If presence was not required, contact them later.
• The boss wins the top prize. It happens. If leaders are eligible, they are eligible. Some leaders choose to pass the prize back for a redraw, and that is their call, not the organizer’s.
• The same person wins twice. If each person should win only once, use “Remove duplicates” and draw all winners from the same list in one session. Winners leave the hat as they are drawn, so they cannot be picked again in that session.
• Someone was left off the list. If you discover it before the drawing, add them. If after, be honest about it and consider a separate small prize rather than redoing the whole drawing.
• Accusations of favoritism. This is why you share the eligibility rule in advance, show the count on screen and have a witness. Being able to explain the process calmly is the best answer.

Privacy at work

Employee lists are personal data. Avoid pasting extra details such as email addresses, employee IDs or home locations into any drawing tool; names or first-name-and-last-initial are enough. The Hat Draw keeps the list in your browser and does not upload it, but it may save a draft on that device so a page refresh does not lose your list. On a shared computer, press Start over after the drawing to clear it.

A simple office drawing checklist

1. Confirm with HR that the drawing and prizes are fine, and that entry is free.
2. Write the eligibility rule and the prize list; share them in advance.
3. Export and clean the entry list; check the count.
4. Decide on duplicates, present-to-win, and multiple wins.
5. Draw live with a witness; read names out loud.
6. Copy or print the results; message winners privately.
7. Clear the list from the computer if it is shared.

Done well, an office drawing takes ten minutes and gives people something to talk about besides the agenda. Done carelessly, it becomes a thread in the anonymous feedback survey. The difference is mostly writing things down before you start.

More: all guides · how the draw works

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Last updated 10 October 2026.