A Mom to my Business Family

As women, we often run our businesses like we run our families: like moms. We’re not just the Chief Executive Officer—we’re also the Chief Emotional Officer.

Greenfield Services was a business I co-founded with my husband, but it was my idea. The culture had my stamp all over it. We were family-focused, employing many moms who were returning to work or needed flexibility for things like a sick child at home. We even had a paid-time-off bank for exactly those situations.

With that mindset, I became the business mom.

When one employee’s marriage was falling apart, I was there for her. I lent money to a few who were struggling to make ends meet. When one woman’s daughter was battling addiction, I offered flextime and support. I was proud of our compassionate, family-first culture. Our business made space for love.

But leading with love has a downside. Sometimes, love blinded me to reality.

I didn’t want to believe someone on our team was stealing from the chocolate bar box in the kitchen—but they were. I was stunned when a former employee sued us for wrongful dismissal... even though he had quit. And when I confronted a supervisor about a romantic relationship with another staff member, I was crushed to learn she’d been lying to my face.

This over-compassionate streak extended to clients too. Jim—an American direct marketing guy—once accounted for 60% of our revenue. He treated me like his personal therapist, unloading everything from his daughter’s boyfriend drama to complaints about his clients. I didn’t push back, afraid I’d lose the business.

Then there were the big corporations that took 90+ days to pay us. But hey, at least they weren’t as emotionally exhausting as Jim, so I let it slide.

Looking back, mixing love and business bit me in the butt more than once.

Am I sorry I led the way I did? Not anymore. I burned out, learned my lessons, and eventually sold the business. I've had time to reflect. If I were in the same position today, here’s what I’d do differently—and what I’d still stand by.

Compassion with Boundaries: Leading with Heart and Boundaries

With Employees:

• Set emotional boundaries early. Don’t play therapist. Offer empathy, but refer employees to trained professionals when personal issues arise. Compassion doesn’t mean taking on their emotional weight.
• Put policies in writing. Clear contracts and employee handbooks set expectations and protect everyone. Documented boundaries are your best defense against drama, confusion, or litigation.
• Create a feedback loop. Regular check-ins (not just performance reviews) help address small issues before they become big ones. Use them to reinforce shared values and accountability.

With Clients:

• Define the relationship. Be clear about what you’re offering—and what you’re not. You’re a service provider, not a therapist, mediator, or life coach.
• Stick to payment terms. Add penalties or incentives if needed. Kindness doesn’t mean waiting 90 days to get paid.
• Know when to walk away. If a client consistently disrespects your boundaries or drains your energy, it’s time to move on. You can’t afford to carry toxic relationships—financially or emotionally.

As a woman entrepreneur, I’ll always believe in love and compassion as guiding principles. But that doesn’t mean I’m willing to be a doormat. Keeping people accountable—whether it’s employees, clients, or partners—is just as important as being kind.

The same goes for raising kids, managing a family, or running a business: love without respect and boundaries isn’t sustainable. And it sure as hell isn’t leadership.

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