15 Essential Tips to Support New and Junior Employees in Remote Work


Through trial and error, I learned some hard lessons in supporting new and junior employees while building my first company, Naked Apartments, in 2009. It was also my first time taking the plunge with managing an all-remote company, along with my fellow co-founders. Turns out, many of the lessons we learned can and should be applied to any work environment. They’re just that more critical to adopt when your employee is working from home, isolated from other team members.

alt text


👋 Make new team members feel welcome on their first day

There is absolutely nothing worse than starting a new job and being ignored for the first week or two, having to introduce yourself to other employees in the company who you stumble upon. As you might imagine, it’s 10x worse in a remote environment.

We found it helpful to introduce them in two ways on their first day.

  1. Introduce them formally over email or slack

    Before their first day, ask them a series of questions that gives the team an understanding of their background, personal interests, and what makes them excited to work at your company. Share the results with the team on the employee’s first day.

    Don’t forget to mention their title and where they’ll be making an impact to the organization in the coming months.

  2. Schedule a group video chat for a more personal and informal introduction

    Our weekly team call was every Monday, so it was a perfect time to introduce a new team member.

📦 Send them company swag

It’s simple as it sounds. Swag is a big deal to remote employees. The money is absolutely worth it and will make remote employees feel connected to the team and company.

I found that you get the highest satisfaction if you can get it sent out in the first week or two of them joining the company. Make it part of your onboarding checklist so you don’t forget.

🤷 Don’t expect socializing to happen organically

In a remote environment, a new employee doesn’t have the same opportunities to socialize as someone in the office. For example, meeting others in the hallways, lunchrooms, and social events.

As part of the onboarding process, it’s your role as a manager to schedule introduction video calls for their new employee to meet people around the company.

Junior employees might be hesitant to reach out too. So treat them the same as new employees. Help them socialize.

🔦 Provide team members with a great documented onboarding process

In a remote environment, the onboarding materials should be documented as much as possible. This investment is absolutely worth it, especially as you scale the organization.

Benefits of a good onboarding process:

  • They’ll appreciate the initial support
  • It will help them ramp up and be productive in their role quickly
  • Offloads responsibility from other employees to help get an employee up and running
  • Sets the bar of quality and expectations on day one around documentation
  • When they find something missing during the process, they can contribute and add value to the organization early on

This is something you and your team should agonize over. It’s really that important. There are always ways to improve the experience, so keep making it better with each new team member that goes through it.

💪 Pair them with a senior team member

Let’s face it, your onboarding will never be comprehensive. Pairing your new employee with someone in the same role will give them an opportunity to ask deeper technical and project related questions that aren’t covered by onboarding documentation.

Additionally, during the interview process, it’s not likely that you’ve uncovered some skill gaps for this new employee. Since you don’t hire solely based on skills alone, this shouldn’t be a problem! But, let’s make sure those gaps get filled.

If you didn’t make those gaps clear during the interview process, make sure it’s known in their first week. You, as their manager, should work with them on a written plan, which will be handed off to the senior pairing with them.

For junior employees, this pairing is especially important to help them become a productive team member without a lot of stress and anxiety.

☑️ Check-in daily for an initial period of time

Think back to your first few weeks at a new job. They’re exciting and also overwhelming. It’s even more difficult when you’re alone at home trying to figure it all out.

Another team member and yourself should check-in daily with the employee for the first few weeks or until there are clear signs that the employee is settled in.

Let me be clear though, “Checking in” doesn’t mean having a formal meeting, making the employee list out everything they’re working on. Instead, it should be a slack message or something very informal that gives the employee an opportunity to share they’re having difficulties with something and need help. A simple, “hey, how are you doing today?” is fine. Don’t be overbearing.

📹 Use video as much as possible

First and foremost, it helps you build a personal connection with the employee. Nothing beats meeting in person, but video is the best alternative we have in remote work.

Additionally, it’s very difficult to understand a person’s frame of mind by just listening and certainly impossible over slack. With half of human communication being body language, seeing your employee over video will help to uncover any issues they might be otherwise hesitant to share.

So, if you sense there is something off, don’t hesitate to ask the employee if they’re alright. If there is, offer up your support.

☎️ Weekly team bonding video call

One of my favorite parts about working at Naked Apartments was having a Monday video call to share our weekend adventures and do “show and tell”.

It’s important to schedule a weekly meeting for small talk and fun, giving people time to connect on a personal level. Work related team meetings (like stand ups) and 1-1s with a manager don’t count.

😂 Setup “water cooler” chat rooms

Your team should be encouraged to have fun talking about things that are not work related. Simulating the “water cooler” is important for morale and creating human connections.

Create #random (or similar) slack channels purely for banter. Use emojis and memes freely (work appropriate of course) to help create that human connection. Encourage these new employees to join and nudge them into conversations if they don’t do it on their own.

🧠 Include them in brainstorming discussions right away

Too often, new or inexperienced employees are left out of brainstorming sessions because of their lack of institutional knowledge. The fear is that they will slow down the team, asking basic questions.

It’s a silly fear, since you’d be missing out on something way more important. A fresh perspective. Invite them in. Let them share their thoughts and they’ll learn something along the way too. You’ll be surprised at what happens, I know I was.

🏝 Encourage them to take breaks and end their day at a reasonable time

Burnout is a big problem in remote work, especially for new and junior employees who are trying to impress their teammates and manager through sheer brute force. As their manager, you need to keep a very close eye on this.

It’s also a good idea to encourage new hires to schedule a vacation in their first 6 months. It sets a good precedence about your values as a company and encourages taking breaks.

During the summer months, you might want to give employees Fridays off (i.e. Summer Fridays) to enjoy the beautiful weather. This forces employees to take time off and recharge. This was especially important for us at Naked Apartments, since the prior months were usually the busiest time of the year for our company.

📅 Set expectations around availability and scheduling

  • What time do people tend to work here?
  • What does flexible hours mean to this company?
  • If someone sends me a slack message when I’m done for the day, do I need to respond?
  • How about emailing during off hours?

When you’ve got an all-remote company, there is usually someone working at all hours of the day, because of timezone differences. Setting expectations is important so people can understand when they need to be available, allowing them to fully enjoy their personal time.

In addition, you may want to define overlap time to allow for synchronous discussions (like team meetings). That overlap time should work best for the majority of the team. 2 - 4 hours of overlap worked well for us at Naked Apartments.

📋 Start them on small projects and then ramp up

I get it, you’ve got some big initiatives you want to crank out. Avoid the temptation. Don’t throw a new or junior employee into the deep end. It’s overwhelming starting a job by itself, so don’t make it harder.

Instead, use this opportunity to:

  • Build up confidence with some small wins
  • Get them accustomed to team processes and workflows
  • Provide them time to fill in those skill gaps and learn the institutional knowledge needed to be productive
  • This is a great time for a manager to continue to learn an employee’s strengths and weaknesses

😢 Don’t forget to include them

I think this is especially important for companies that have a mixture of remote and office employees. I experienced the pain my team went through vividly when they were left out of events after the acquisition of Naked Apartments by Zillow. Trust me, no one intentionally left them out, but I’m sure it felt that way to them.

Whether it’s an all-hands meeting or an office happy hour, make sure to include them and make them feel accommodated as best you can.

For in-office happy hours for example, schedule a virtual happy hour to share a drink together and celebrate wins. They might miss the physical event, but they’ll appreciate the social interactions.

🤝 Conduct weekly 1-1s

Give enough time

First off, your 1-1s should be longer for these new and junior employees compared to senior team members, since they need more support. I found that an hour a week is usually long enough.

Keep the same schedule

  • 1-1s never should be cancelled by you.
  • If they cancel frequently with you, dig in to make sure they aren’t having problems

See how they’re doing personally

Make sure to ask good questions to help dig into how they’re adjusting to working from home and their new role in the company.

Develop your employee

Make good use of the time you have with them to discuss a development plan to help them in their career goals and increase their performance. No matter if they’re alone at home or in an office, they’ll love that they’re learning and on a great path.