leave management

Ways to Improve Your Leave Management Process

Leave management can be a complicated process, even for entrepreneurs and small businesses. 

The logistical sides of leave management can confuse any sole proprietor or LLC owner. Even freelancers can find it difficult to take time for themselves. However, organization in this area isn’t impossible. Both freelancers and small business owners can detangle their leave policy plans.

Freelancers, independent contractors and sole proprietors 

Going into business for yourself is exciting, but do you ever notice how difficult it can be to separate yourself from your clients? As a new business owner, you want to show your clients you’re always available to separate yourself from the competition. But even you need a break.

While you don’t need a formal policy, you should follow your own set of rules:

  • Give your clients advanced notice, either two weeks or a month ahead, so you or your client can make arrangements. Prioritize wrapping up assignments at this time.
  • Front-load your assignments before taking time off. Ask if your clients are open to you submitting work two weeks ahead of schedule (if you’re planning a two-week vacation).
  • If you plan on taking a two-week vacation, save for a month’s vacation to supplement your income. Or, you could do a workcation, where you maintain a semi-regular workload.
  • Take a shorter break (like a long weekend), or consider a 2/8 schedule (two hours working, six hours sightseeing), so you can get back to work at a moment’s notice.

Vacations can help you avoid burnout, improve your mental health and increase your physical well-being. After your time off, you’ll likely be a more productive, efficient contractor.


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Small business owners and startups

Depending on the size of your business, you could benefit from buying an annual leave management software. A general rule of thumb is if you can’t manage your time off requests in your head (aka, you have two or more employees), then you should adopt some helpful tools.

Step 1: Ensure your leave management policy is compliant.

Even if you choose not to use a leave management software, you still need to create a policy that complies with your state laws. For example, if your employees have to file for jury duty leave, as they were selected to serve, it’s against the law to deny them this request. 

As the employer, your job is to simplify the leave process while remaining lawful. Consult the U.S. employment and labor laws handbook for more information on leave law compliance. 

Step 2: Develop a procedure that covers for absent employees.

Since your startup likely only has enough employees to remain operational, you need a procedure that fills in the gaps of an employee’s absence. While you can account for vacations or maternity/paternity leave, you won’t be prepared for sudden leaves of absence.

Life comes at us quickly, and it’s possible your employees will need to take time off for a death in the family, disability or for their physical or mental health at a moment’s notice.

As the business owner, you may need to take on their additional work or ask your other employees to share the work among themselves. Or, you could hire an on-call contractor. You could also hire a nonpermanent employee or freelancer to cover long-term absences.

Make sure to include a return policy, as you may need to offer some support as the employee is reintegrated into your business. Inform them of what’s changed during their absence. 

Step 3: Establish “no vacation” zones.

These “no vacation” zones shouldn’t apply to sudden absences for health- or family-related absences but should account for actual vacations. These zones can be implemented because you’re in a busy season or too many employees have already booked off time in that month.

It’s inadvisable to set vacation request deadlines, as it shouldn’t matter when your employees take time off as long as you can cover them. A flexible policy will produce happy employees!


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