Leading & Training a Remote Team: Core Principles for Success

Start with the Right Hire

The foundation of successful remote leadership begins with hiring the right person. While you can train someone on processes, software, and industry knowledge, certain traits are harder to instill.

Remote workers need to be:

✅ Self-motivated – They don’t need constant supervision to stay productive.

✅ Proactive – They take initiative rather than waiting for direction.

✅ Resourceful – They figure things out and troubleshoot problems independently.

✅ Accountable – They take ownership of tasks and deadlines.

✅ Fast learners – They adapt quickly and are eager to improve.

🚨 Important: Remote work is not for everyone. Some people struggle with focus, isolation, or lack of structure. Hiring the wrong person will drain time and resources. I’ve found that you can figure out whether you've made a good hire rather fairly quickly. Do they engage during your meetings/seem to go above and beyond? 

Daily Meetings: Consistency is Key

If you’re training someone remotely, meet every day at the start—even if it’s brief. This ensures alignment, provides an opportunity for questions, and helps you track progress.

💡 Best Practices for Remote Meetings:

• Set a consistent time each day.

• Keep meetings focused: What was accomplished? What’s next? Any roadblocks?

• Encourage questions—new hires won’t always speak up unless prompted.

• Video calls help build rapport and improve communication. I like video calls with the camera on!

  
  

IT Requirements & Equipment

Technology is the backbone of remote work. Before training starts, ensure they have what they need:

✅ Reliable computer & high-speed internet

✅ Quality headset for clear communication

✅ Access to necessary software, VPNs, or tools

✅ A comfortable workspace to minimize distractions

🔹 Pro Tip: A slow laptop or bad internet can derail productivity. Make sure they have everything in place before they begin training.

Clarity, Clarity, Clarity

When leading remotely, clarity is everything.

Ambiguity leads to frustration and wasted time.

🔹 How to Set Clear Expectations:

✔ Define the goals, deadlines, and performance metrics.

✔ Communicate how progress will be tracked.

✔ Document standard processes so they have a reference point.

✔ Use project management tools (e.g., Trello, Asana, ClickUp) to keep tasks organized.

✔ Don’t assume—verify they understand by asking them to summarize instructions.

Praise & Positive Reinforcement

People thrive when they know they’re doing well. Be generous with praise.

🔹 How to Reinforce Positive Behavior:

✔ Acknowledge their wins in team meetings.

✔ Send a quick Slack or email saying, “Great job on [specific task]!”

✔ Recognize growth: “I’ve noticed you’ve really improved in [skill]. Keep it up!”

As Dale Carnegie said in How to Win Friends and Influence People: “Be lavish in your praise.” When you highlight strengths, they will continue to develop.

Learn by Doing, Not Just Planning & Talking

🔹 Don’t wait to have it all figured out. You will never have it all figured out, and you will figure more of it how when you're actually in the thick of it.

Start training, refine your own method as you go.

🔹 Hands-on experience is the best teacher—teach yourself how to be better at remote training by doing it.

Accountability Without Micromanagement

🚨 I’m not here to babysit, and neither are you. Remote work requires trust—but trust comes with accountability.

🔹 How to Keep Them Accountable Without Micromanaging:

✔ Set clear deliverables with deadlines.

✔ Use check-ins to review progress, not to hover.

✔ Have them provide end-of-day or weekly updates.

✔ If they consistently miss deadlines, address it directly.

Pros & Cons of Remote Training

✅ Pros:

• Access to a global talent pool (hire the best, regardless of location).

• More flexibility for both trainer and trainee.

• Can be cost-effective (no office expenses).

• Promotes self-sufficiency and autonomy.

  
  

❌ Cons:

• Can be harder to build personal connections.

• Can be challenging to gauge engagement and productivity.

• Technical issues (internet outages, poor hardware) can disrupt work.

• Requires stronger communication skills than in-person training.

Remote leadership requires a balance of structure, communication, and trust. The best remote leaders set clear expectations, provide consistent training, and empower their teams to take ownership of their work.

If done right, remote training can be just as effective—if not more—than in-person development.