As remote work becomes more common, managing a remote support team has its perks—like flexibility and access to a global talent pool—but it also comes with its own set of challenges. If you're feeling the pinch when it comes to onboarding, training, and keeping everyone connected, don't worry. You're not alone, and there are simple ways to handle these challenges like a pro. As I have consulted with many companies that struggle making the switch, these are the topics that we cover and discuss.

Let’s look at some common concerns executives and managers have about remote teams and how you can solve them without too much hassle.

1. Onboarding Remote Employees

Concern: Onboarding new remote hires can feel a bit detached, and it’s tough to get them settled in.

Solution: Try a hybrid onboarding model like JetBlue. New hires spend 1-3 months in the office, soaking up the culture, getting trained hands-on, and giving you a chance to see how they fit in. Once they’ve hit all their milestones, they can transition to fully remote or a hybrid/part-time office schedule.

For fully remote onboarding, you can still make things personal. Use tools like video chats, interactive training, and check-ins with a buddy to help them feel more at ease. It’s all about making them feel welcome, even from afar.

2. Training Remote Teams

Concern: How do you make sure remote employees get the proper training when you can’t physically be there?

Solution: Training doesn’t have to be complicated. Mix it up with recorded videos, live workshops, and fun quizzes to keep things engaging. If you're doing a hybrid setup, in-office training for the first couple of months can give your new hires a solid foundation before they go remote.

Even after they've transitioned, keep the learning going with regular updates, refresher courses, and online training platforms that they can access anytime. I always have my new hires go through training, then get into the day-to-day work, and then about 2-4 weeks after they've been live, talking to customers, I ask them to go through training again because they retain so much more the second time once they have an understanding of what their daily work and interactions are like.

3. Getting to Know New Hires & Assessing Fit

Concern: It’s hard to get to know a new hire when they’re not physically in the office, and you need to figure out if they’re a good fit.

Solution: A trial period with frequent check-ins can give you both the chance to feel each other out. JetBlue’s model works great here too—having new hires spend some time in the office before going remote gives you time to evaluate if they fit the company culture and learn quickly.

For fully remote teams, you can schedule weekly video calls, team-building exercises, and involve them in small group projects. Get feedback from other team members to see how well they’re fitting in with the crew. Doing a trial period regardless of if they are remote or hybrid or in-house is always a great idea to prevent a difficult firing situation and set up expectations.

4. Tracking Productivity

Concern: How do you keep track of remote workers’ productivity when you can’t see what they’re doing?

Solution: Focus on setting expectations, and tracking results, not screen time. Use project management tools like Asana or Monday to track progress and deadlines. Set clear goals and let them know what’s expected, then trust them to get it done. I have a great productivity spreadsheet that really helps keep track of things, you can reach out to me for more information.

Regular check-ins are important, but don’t go overboard—your employees will appreciate the freedom to manage their time and get the work done their way. Make sure they know when they reach those goals and celebrate those wins. Keep communication open and have transparency so they know where they stand.

5. Making Remote Employees Feel Part of the Team

Concern: Remote employees can sometimes feel disconnected from the company culture or their colleagues.

Solution: Bringing people together is key! For hybrid teams, that in-office time is golden for giving new hires a taste of the company vibe. They get to experience the culture firsthand and build those personal relationships before they go remote.

For fully remote teams, create opportunities for casual interactions. Set up virtual coffee breaks, casual Slack channels, or even a fun Zoom trivia night. And if you can swing it, organize in-person meetups a couple of times a year to really bring the team together.

The Hybrid Model: A Happy Medium

Companies like JetBlue have nailed the hybrid approach, offering employees the best of both worlds. They start off with an in-office trial period to get trained and experience the company culture, and then once they’ve hit key milestones, they transition to working from home. It’s a perfect mix of flexibility and in-person connection.

With a hybrid model, you get the perks of remote work while still building strong, personal relationships with your team. And even if you're fully remote, you can create a fun, connected culture with the right tools and a little creativity.

In the end, remote teams can be incredibly productive and engaged if you’re willing to put in a bit of effort to smooth out the challenges. From onboarding to building culture, it’s all about finding what works best for your team—and with a few tweaks, you’ll have a remote team that’s thriving. I'm a pro at this, so reach out if you'd like to discuss anything, I'm here to help!