Managing Time Off When Your Team is Under 20 People

Managing PTO for a small team is weird. You're probably not big enough to have HR, but you're past the point where everyone just figures it out. Half your company being out sick hits different when half your company is 3 people.

This guide covers the real challenges of PTO management for teams under 20, and practical solutions that actually work at this scale.

The Unique Challenges of Small Team PTO

Everyone Is Critical

In a 500-person company, one person being out barely registers. In a 10-person company, one absence is 10% of your workforce. When that person is your only backend developer or your only salesperson, things get complicated fast.

There's No HR Department

You're the founder, the manager, AND the HR department. You don't have time to create elaborate policies or manage complex systems. You need something that works without babysitting.

Relationships Are Personal

Saying "no" to a PTO request feels different when you eat lunch with that person every day. The line between professional policy and personal favor gets blurry.

Coverage Math Is Brutal

If you need 2 people to answer customer support and you have 3 support people, only 1 can be off at any time. The coverage math at small scale leaves almost no margin.

The Minimum Viable PTO Policy

For teams under 20, you don't need a 20-page handbook. You need answers to five questions:

1. How much time off does everyone get?

Keep it simple. Most small teams do one of:

• Fixed amount: Everyone gets 15 days
• Tenure-based: 10 days for year 1, 15 days for years 2-3, 20 days for 4+
• Unlimited: (More on this below)

Our recommendation for teams under 20: Fixed amount. Tenure-based systems add complexity that isn't worth it until you have more employees to track.

2. How do people request time off?

Options, from least to most structured:

• Just tell me: Works for 3-4 people, breaks fast
• Slack/email request: Better, but easy to lose track
• Shared calendar: Visual, but no approval workflow
• PTO software: Best for 5+ people

Don't overthink it early on, but don't wait too long to add structure. The sweet spot for moving to software is usually 5-8 employees.

3. How far in advance should requests be made?

Simple framework:

• Same day: Sick leave only
• 1 week: 1-2 day requests
• 2 weeks: 3-5 day requests
• 1 month: 1+ week requests

These aren't hard rules - emergencies happen. But setting expectations helps with planning.

4. What happens when two people want the same time off?

Common approaches:

• First come, first served: Fair and simple
• Seniority wins: Rewards tenure, can breed resentment
• Manager discretion: Flexible but inconsistent
• Alternating priority: If Sarah got Thanksgiving last year, Mike gets priority this year

For small teams, first-come-first-served with manager discretion for special cases works best.

5. What are the blackout periods?

Be explicit about times when PTO is restricted:

• Product launches
• Busy seasons
• Company events
• Year-end close (if relevant)

Even if you're flexible, knowing the constraints helps people plan.

The Coverage Problem

The math of small team coverage is unforgiving:

Strategies for Managing Coverage

Cross-train aggressively In a small team, everyone should be able to do basic functions of at least one other role. Not expert-level, but enough to keep things moving.

Identify true single points of failure Who, if they're out, stops something critical? For those people, have a backup plan documented.

Stagger vacation approvals When approving time off, always check who else is out. A visual calendar makes this much easier.

Plan for sick days PTO requests you can plan around. Sick days you can't. Always assume 1-2 people might be unexpectedly out.

Reduce customer-facing commitments during light weeks If 3 of 8 people are on vacation, don't schedule major customer calls that week.

The "Unlimited PTO" Question

Small teams love to consider unlimited PTO. It sounds modern, attracts talent, and removes tracking hassle. But is it right for your team?

When Unlimited PTO Works

• Strong culture of accountability
• Outcome-focused work (results matter, not hours)
• Leadership models healthy time off
• Team doesn't need permission to feel okay taking vacation

When Unlimited PTO Fails

• People take less time off (fear of judgment)
• Workhorses feel resentful of those who take more
• No benchmark creates anxiety ("is 15 days too much?")
• Hard to say "no" to any specific request

Our Take for Small Teams

Unless you have a strong, established culture, start with a generous fixed amount (15-20 days). You can always move to unlimited later. Going the other direction is awkward.

If you do unlimited, set minimums: "We expect everyone to take at least 15 days off per year."

Handling Tricky Situations

"Can I take 3 weeks for my honeymoon?"

Big life events deserve accommodation. Say yes if at all possible. These moments build loyalty.

Suggestions:

• Ask for extra advance notice (3+ months)
• Plan coverage explicitly
• Consider unpaid time if they're short on PTO

"I need tomorrow off - my kid is sick."

This is what sick leave is for, even if it's someone else who's sick. Don't make parents feel guilty.

For small teams without separate sick leave, have a generous policy for family care. People remember how you treat them in tough moments.

"Everyone wants the same week off."

December holidays and summer months create conflicts. Options:

• Rotate priority yearly: Sarah got Christmas off last year, Mike gets it this year
• Split coverage: Sarah takes Dec 23-26, Mike takes Dec 27-Jan 1
• Limited PTO, unlimited WFH: Not full vacation, but work from anywhere
• Close the company: If most people want off, maybe just close

"Someone never takes PTO"

This is a problem. Burnout hurts the team, and hoarded PTO creates liability.

Approach it as concern, not criticism: "I noticed you haven't taken time off in 6 months. Everything okay? I want to make sure you're taking care of yourself."

Consider use-it-or-lose-it policies with generous carryover caps.

"A key person is out during a crisis"

It happens. Handle it gracefully:

1. Don't guilt them. They're on approved vacation.
2. Ask, don't demand. "We have an emergency. Any chance you could take a call?"
3. Make it optional. If they can't help, figure it out.
4. Comp them. If they work during vacation, give that time back.

Tools for Small Team PTO Management

Under 5 People

A shared Google Calendar with PTO events might be enough. Color-code by person, add events for approved time off.

Pros: Free, visual, everyone already has access Cons: No approval workflow, easy to overlook conflicts

5-15 People

This is the sweet spot for dedicated PTO software. You need:

• Simple request/approval workflow
• Team calendar view
• Balance tracking
• Mobile access

You don't need:

• Complex integrations
• Advanced analytics
• Payroll connections

15-20+ People

At this size, you probably need software, and you might benefit from features like:

• Manager-level views (each manager sees their team)
• Department-based calendars
• Basic reporting
• Integration with your HRIS (if you have one)

Building a Healthy Time Off Culture

Tools and policies matter, but culture matters more. At small scale, you set the culture.

Lead by Example

If you never take vacation, your team won't either. Take your PTO visibly. Send a "I'm offline next week" message. Come back rested and talk about what you did.

Celebrate Time Off

When someone returns from vacation, ask about it. Make time off something to share, not hide.

Don't Reward Martyrdom

The person who never takes vacation isn't a hero - they're a risk. Don't praise overwork; praise sustainable performance.

Make Requests Easy

If requesting PTO feels like asking for a favor, people won't do it. Make the process simple and normalize it.

Key Takeaways

• Small team PTO is different. Coverage math is brutal and everyone is critical.
• Keep policies simple. Five questions answered beats a 20-page handbook.
• Coverage requires planning. Cross-train, identify single points of failure, stagger approvals.
• Culture trumps policy. Lead by example and make time off normal.
• Use tools appropriate to size. Shared calendar under 5, software at 5+.

Ready to Simplify Your PTO?

Symple Team was built for teams exactly your size. Simple enough that you don't need HR to manage it, powerful enough to handle real team needs.

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