Leave Management for Startups: When to Ditch the Spreadsheet

The Startup Leave Management Journey

Stage 1: The Founding Team (1-5 people)

At this stage, leave management is barely a thing. Everyone knows everyone. If you're taking time off, you mention it in the daily standup or Slack channel.

What works: Nothing formal. Just communication.
What breaks: Nothing yet.

Stage 2: The First Hires (5-15 people)

Now you need something written down. The spreadsheet appears. It probably has columns for name, start date, end date, type of leave, and maybe who approved it.

What works: A simple spreadsheet, owned by someone.
What breaks: The spreadsheet gets out of sync with reality. Nobody's quite sure how many days they have left.

Stage 3: Growing Pains (15-30 people)

The spreadsheet is now a monster. It has multiple tabs (one per year, maybe one per department). Formulas are breaking. You've hired someone into a People/HR role and they're spending hours each week maintaining it.

What works: A proper system of some kind.
What breaks: The spreadsheet, constantly.

Stage 4: Scaling (30+ people)

You can't function without proper leave management. Payroll needs accurate data. Managers need to plan capacity. The spreadsheet died months ago but its corpse haunts you.

Signs You've Outgrown the Spreadsheet

Check if any of these sound familiar:

You've had to fix formula errors more than once this quarter
Multiple people have edit access and it's getting messy
Nobody trusts the leave balances shown
"Who's off next week?" requires checking multiple places
The person who built the spreadsheet left and nobody understands it
New starters don't understand how to use it

If you checked 3 or more, it's time to move on.

What Startups Actually Need (Not Enterprise Features)

Here's the trap: you Google "leave management software" and find enterprise HR systems designed for 500+ employees. They have features you'll never use and pricing that doesn't make sense for a 20-person startup.

What you actually need:

Must have:

Simple request and approval workflow
Leave balance tracking
Team calendar view
Works on mobile

Nice to have:

Slack/Teams integration
Calendar sync (Google/Outlook)
Basic reporting
API access

Don't need (yet):

Complex org hierarchy management
Multiple approval levels
Enterprise SSO
Dedicated account manager

Comparing Options for Startups

Approach	Cost	Best For
Google Sheet	Free	Under 10 people
Notion/Airtable	Free-£20/mo	10-20 people
Dedicated leave tool	£1-3/user/mo	15+ people
Full HR suite	£5-15/user/mo	50+ people

The Dedicated Leave Tool Sweet Spot

For most startups between 15-100 people, a focused leave management tool hits the sweet spot:

Cheap enough that the ROI is obvious
Simple enough that everyone can use it without training
Powerful enough to handle your actual needs
Focused enough to do one thing well

Making the Switch

When you're ready to move from spreadsheet to system, here's how to do it smoothly:

1

Export Your Current Data

Pull all current leave balances and any approved future leave from your spreadsheet.
2

Choose Your Tool

Pick something with a free trial that integrates with your messaging app.
3

Set Up in Parallel

Run the new system alongside the spreadsheet for 2-4 weeks.
4

Kill the Spreadsheet

Pick a date. Announce it. Archive the spreadsheet. Make the new system the single source of truth.

Why OrOut Works for Startups

We built OrOut specifically for teams who think HR software is too complicated and spreadsheets are too messy.

5-minute setup: Connect Slack or Teams, invite your team, done
No training needed: People just type "I need Friday off" and it works
No portal to remember: Everything happens in Slack or Teams
Transparent pricing: £1.20/user/month, everything included
Grows with you: Works for 5 people or 500

Frequently Asked Questions

When should a startup get leave management software?

Most teams hit the pain point around 15-20 people. Before that, a spreadsheet works. After that, you're spending more time maintaining the spreadsheet than it would cost to just buy a tool.

How much should a startup spend on leave management?

At £1-3 per user per month, leave management software is one of the cheapest tools you'll buy. For a 20-person team, that's £20-60/month. Compare that to the cost of someone spending 2-3 hours a week managing spreadsheets.

Should we build our own leave system?

No. Unless you're in the business of building HR software, this is a solved problem. Buy something for £1/user/month and focus on your actual product.