Working With Family: The Good, the Bad, and Firing Grandma

Let’s be honest — running a small business in a rural community often means your first hires are people you already know.

Your cousin runs the cash register. Your old high school bestie helps with marketing. Grandma bakes the muffins. And at first… it feels kind of cozy.

Until the day you have to have “the talk.”
Yes. The talk.
The one where you realize you might have to fire Grandma.

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Don’t Hire Someone You Can’t Fire

It’s a simple rule that nobody likes to follow: don’t hire someone you can’t fire.

When you bring in family or close friends, you’re not just managing an employee — you’re juggling Thanksgiving dinner, Sunday potlucks, and a whole family grapevine that talks faster than email.

Firing “Stranger John” is awkward.
Firing Grandma? That becomes the story of the decade.

“Remember when you fired your own grandmother?” becomes a permanent piece of local legend.

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The Risk of Mixing Business With Family

When you hire family or friends, it’s easy to blur lines:

• They expect special treatment (“But we’re family!”).
• They might expect free or discounted work (“I’ll owe you one”).
• You hesitate to enforce rules, give feedback, or, worst-case, fire someone.
  

Even the best intentions can lead to resentment, confusion, and missed goals — and that can hurt your business.

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Solutions: Treat Everyone Like Employees, Not Dinner Guests

Here’s how to protect your business and your relationships:

Set Clear Roles and Expectations

• Everyone needs defined responsibilities.
• Make sure they know what success looks like and how it’s measured.
  

Everyone on Payroll

• Pay family members the same as any other employee for the same work.
• Keep payroll regular and documented — no exceptions.
• Payroll should be on the books; no cash under the table.
• Workman’s comp applies to everyone, family included — no exceptions.
  

Written Agreements

• Even a simple email outlining hours, duties, and pay counts.
• Consider an employee handbook and regular safety meetings.
• Written agreements protect both sides and avoid awkward “But I thought we agreed…” conversations.
  

Feedback and Accountability

• Treat family like any other employee — give constructive feedback, set goals, and hold them accountable.
• Avoid favoritism; consistency is key.
  

Know When to Say No

• Don’t hire someone just because you’re related or have a shared history.
• You are not “special.” If someone got fired before for drinking on the job, it could happen to your family hire too — plan accordingly.
• If you can’t enforce rules, it’s okay to keep them out of the business.
  

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Bottom Line

Working with family and friends can be wonderful — warm, familiar, and full of laughter.

But it can also be a shortcut to drama if you don’t set clear expectations. The “bestie discount” or “Grandma’s special shift” might seem harmless at first, but over time, those small things can turn into big problems. Take the precaution that will keep everyone at the Thanksgiving table.