The EntreLeadership Podcast My Employees Keep Wanting More Time Off (Bad Sign?)
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Sep 29, 2025 This discussion covers the complexities of PTO requests in small businesses, exploring when employees feel entitled to more time off. It dives into the strategic timing and value of selling a well-run business, weighing profits against market conditions. Listeners learn about confronting disengaged team members and the importance of creating a supportive work environment. There's also advice on effectively hiring key roles in a growing business, ensuring that new employees are trained and aligned with performance goals.
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Small Business PTO Growing Pains
- Denise started a pest control company from her dining room and grew it to a multi-tech team and $2.3M revenue.
- She raised PTO over 15 years and now faces employees exhausting PTO early and requesting more time off.
Set And Enforce PTO Expectations
- Set clear PTO tiers and communicate them at hiring and onboarding so expectations are fixed up front.
- Enforce the policy consistently and be prepared to terminate repeat offenders to protect operations.
Document PTO In Writing During Onboarding
- Put PTO and unpaid-time rules in the employment letter and review them verbally during onboarding.
- Make an example by enforcing the policy so new hires understand you mean it.