When You Don’t Have The Clout (or Desire) To Order Remote Workers Back To The Office

Happy Sunday morning!

Before we dive into a new week, here’s something worth your time:

1. Feature: When You Don’t Have The Clout (or Desire) To Order Remote Workers Back To The Office. 
   (4 min read)

2. Dear TCoL: Should I Have Regular Meetings With Remote Workers? 
   (1 min read)

Take a moment to unwind today — a relaxed Sunday is the best setup for a successful week.

-TCoL

Missed our last feature article? LLC Insurance 101: A New Owner’s Guide to Essential Coverage. Read it here.

Running a small or medium-sized business (SMB) is already a challenge. Now, add remote work into the mix, and you’ve got a whole new set of problems—and opportunities.

Unlike corporate giants like Meta, X, or the U.S. Government, you can’t simply issue a return-to-office mandate and expect compliance.

The reality is, top talent is out there, and many of them have no intention of giving up remote work.

So, you either fight the tide or figure out how to make remote work... work. We chose the latter.

We dug deep, researching more than 50 remote work ideas and best practices to find the best ones for SMBs like yours. Our criteria? They had to be:

• Brilliant – Truly effective at tackling common remote work challenges like morale, communication, and productivity.

• Practical – Feasible for businesses with limited budgets and lean teams.

• Relevant – Focused on fostering voluntary cooperation, not forced compliance.

Hopefully, you will find a few of these useful. Here are the ones that made the cut:

1. Set Clear Expectations with Flexible Deadlines

Your employees value autonomy. You don’t have the resources (or frankly, the time) to micromanage. The best approach? Be crystal clear about deliverables but allow flexibility on the “how” and “when” they get done. Trust breeds accountability.

2. Use Asynchronous Communication Tools

Your team won’t always be online at the same time—and that’s okay. Tools like Slack, Loom, or Notion let employees collaborate without waiting for real-time responses, reducing unnecessary meetings and interruptions.

3. Implement ROWE (Results-Only Work Environment)

Big companies track hours. You care about results. ROWE shifts the focus from time spent working to what actually gets done. Employees deliver outcomes, not just clock-in hours.

4. Provide Free or Low-Cost Software

You don’t need expensive enterprise software. Trello for project management, Google Workspace for collaboration, and Zoom for meetings—these get the job done without breaking the bank.

5. Host Virtual Stand-Ups Once a Week

Daily check-ins feel like babysitting. Instead, hold a short weekly virtual stand-up to keep everyone aligned and engaged without wasting time.

6. Offer a Small Stipend

A modest monthly allowance for home office expenses (even $50) shows employees you value their setup. It’s a fraction of what you’d spend on office space but pays off in morale.

7. Encourage Peer Recognition

A simple shoutout in a team chat can do wonders for morale. No need for a formal (read: expensive) program—just make recognition a habit.

8. Adopt "Core Hours"

Mandating 9-to-5 across different locations doesn’t work. Instead, set a few core hours when everyone overlaps, then let employees structure the rest of their day.

Also, think about how to have your business working 24/7. Would one of your remote workers prefer a Wed-Sun schedule? Good, would that improve workflow and efficiency for the rest of the team come Monday morning?

9. Train Managers in Remote Leadership

Managing remotely isn’t the same as managing in-person. Luckily, free resources (webinars, articles, podcasts) can equip managers with the skills they need.

10. Leverage Cloud-Based File Sharing

Universal access to files is a must. Google Drive, Dropbox, or OneDrive all offer free tiers that work just fine for SMBs. With remote employees, it is best to mandate that all files must be worked on and kept in the cloud.

11. Make Social Hangouts Optional

Not everyone wants to attend virtual happy hours. Offer social events but keep them optional. Forced fun isn’t fun.

12. Use a Simple Onboarding Checklist

New hires need structure. A basic onboarding guide (a Google Doc will do) helps them get up to speed without unnecessary hand-holding.

13. Use Time-Tracking Sparingly

Tracking every minute of work signals distrust. If you must use time-tracking, do it selectively—only for roles where it truly matters.

14. Rotate Meeting Facilitators

Letting different team members run meetings keeps things fresh and encourages participation. Plus, it prevents one person from monopolizing the agenda.

15. Set Up Feedback Loops

Use free tools like Google Forms or Typeform to gather anonymous employee feedback. Insight without an expensive HR department.

16. Prioritize Video for Key Conversations

Video calls are useful—but only when necessary. Default to async communication, and reserve video for high-stakes discussions.

17. Offer Skill-Sharing Sessions

Your team already has valuable knowledge. Let them teach each other. A casual lunch-and-learn (virtual or not) costs nothing but adds value.

18. Define Communication Norms

Specify what goes in an email vs. a Slack message vs. a meeting. It prevents chaos and wasted time.

19. Gamify Milestones

Recognize progress with fun incentives—badges, leaderboards, or even small rewards. Motivation doesn’t have to be expensive.

20. Build a Knowledge Hub

A shared space (Google Docs, Notion, or Confluence) for policies, FAQs, and best practices ensures employees find answers without pinging you constantly.

What Surprised Us in Our Research?

• Employees Hate Over-Monitoring – Tracking every keystroke destroys trust. Focus on results, not surveillance.

• Low-Cost Perks Go a Long Way – SMBs can replicate corporate benefits (like stipends) at a fraction of the cost—and they work.

Our Favorite Takeaways

If we had to pick three top strategies for SMBs, we’d go with:

1. Core Hours – Flexibility with just enough structure.

2. Weekly Stand-Ups – Keeps teams connected without micromanaging.

3. Peer Recognition – Free, simple, and highly effective.

Have your own remote management hacks? We’d love to hear them. Email us at [email protected] or DM us on X [here] or LinkedIn [here].

Because at the end of the day, your SMB deserves to thrive—remote or not.

Dear TCoL: Should I Have Regular Meetings With Remote Workers?

Question: I have a remote worker and feel like I should have an in-person meeting every once in a while. Nowadays, is it even worth the effort? Thanks!

Answer: Yes, but evaluate the situation like this:

1. Performance check. Are they crushing it? Probably not necessary. Doing well? Maybe occasionally. Slipping? Yes, get in front of them.

2. Experience level. Seasoned pro? Let them be. Mid-level? A check-in now and then. Intern or fresh hire? Yes, face time matters.

3. Meeting frequency. Let your answers to #1 and #2 dictate the cadence.

4. Location logistics. Should they come to you or vice versa? Optimize for productivity—yours and theirs. Also, check if an existing company event (monthly or quarterly) makes for a natural meetup.

5. Distance factor. If they’re far, combine the meeting with something else:

   • A conference you’re already attending or a new one you might want to try

   • A business development trip

   • A personal trip where you’ll be nearby anyway

Remote doesn’t mean invisible. You pay them; you should check in as warranted. No ambushes—make meetings useful, engaging, or both.

Have an interesting business question and need a free bit of advice? Send your question to [email protected]. No confidential info, please!