I was recently talking with a nonprofit CEO who was venting about one of the trickiest aspects of modern management: remote workers.

“I can’t see what they’re doing,” she said. “I don’t know if they’re actually working or just folding laundry between Slack messages and sending emails from the wine department at Costco.”

Her frustration isn’t unique. And oddly enough, it reminded me of a conversation I had with my dad years ago when I was struggling through a long-distance relationship.

As it turns out, Dad’s advice on dating from a distance doubles as a pretty solid guide for managing remote employees.

Take Communication to 11
“Distance doesn’t kill relationships,” Dad said. “Crappy communication does.”

The same goes for managing remote workers. You can’t rely on casual hallway updates or quick desk drop-ins. With remote staff, communication has to be deliberate and frequent—regular check-ins, video calls, and project updates are essential. When in doubt, err on the side of overcommunicating.

Align Expectations
“Is it okay to stay out at the bars until closing time without calling? You better get on the same page with that stuff now before the you-know-what hits the fan.”

Remote employees need clear expectations just like partners in a long-distance relationship. And the best time to discuss these expectations is before employment begins.

Two of the most obvious expectations are often overlooked in pre-employment discussions:

  • Remote employees must have a quiet, private home office with a door that allows for continuous work without interruptions and distractions. Coffee shops, open/shared rooms, and the like are inadequate.
  • Personal obligations (including childcare, errands, pottery classes, and pilates) must be handled outside of work hours unless explicitly okayed by the supervisor.

If expectations are not being met, immediately schedule a meeting with your employee to address the issues.

Create a Schedule
“Hope is not a strategy. Put your visits on the damn calendar.”

In a relationship, planned visits help you stay connected. In management, office hours can do the same.

Set regular business hours and make your virtual employee stick to them. No exceptions. This provides structure and keeps employees focused. And it also allows for teamwork! Employees cannot connect with each other if one’s day begins at 9 am while the other’s day commences at 9 pm.

Responsiveness Matters
“If he has a habit of not picking up the phone when you call, he’s probably cheating on you.”

Okay, maybe a little dramatic, but Dad was onto something.

Responsiveness is a signal of engagement. Let me say that again for anyone who was distracted. Responsiveness is a signal of engagement.

If your employee frequently ghosts Slack, dodges check-ins, or takes 24 hours to reply to a simple email, something’s off. Address it directly and early.

Commitment: Trust but Verify
“He’d be a moron to cheat on you, honey. But there are a lot of morons out there.”

Even in relationships built on trust, some level of accountability is just smart. The same logic applies to managing remote employees.

Remote workers should have clear benchmarks for success and scheduled deliverables. Set up a system that makes it clear if your employee is meeting expectations. Data points and deadlines are critical.

Because here’s what I’ve learned the hard way: even seemingly “nice” people will game the system if they can (and if their moral compass allows it). A little structure can go a long way in preventing you from being blindsided six months into the relationship.

Find the Right Person
“Ultimately, if he’s the right guy for you, the distance doesn’t matter.”

Remote work isn’t for everyone. Some people thrive in flexible environments and manage their time like pros. Others struggle without direct supervision or in-person interaction.

When hiring for remote roles, look for people with the discipline, maturity, communication skills, and self-direction to succeed from a distance. The right person makes all the difference.

Final Thought
You won’t meet a bigger advocate for virtual work than me. I’ve been doing it for 16 years, and I can attest to the fact that it has dramatically improved my productivity and allowed me to continue to work in the liberty movement while living in the Lowcountry.

But I’ve also seen virtual work go off the rails—especially when expectations aren’t clear, communication is weak, or commitment is half-baked. And like any long-distance relationship, it takes intentional effort and the right employee to make it work.

And don’t forget: following Dad’s advice will keep you out of trouble. Story of my life!