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8 of the biggest remote work challenges (+ tips to overcome them)

Illustration of a person with their laptop looking overwhelmed

It’s no secret that more companies are taking remote work seriously. About 25% of professional jobs in North America will be remote by the end of 2022, and remote opportunities will continue to increase through 2023. According to Statista, 80% of employees claim they'd recommend working remotely to a friend.

It’s not hard to see why, either. Remote work’s benefits are well documented — improved operating costs, access to better employees, profitability. But it’s not all smooth sailing. Remote work also poses a host of challenges that’ll cost you key talent and business battles if you're not careful.

In this post, we break down the most common remote work challenges — and provide tips on how to overcome them. These include:

  • Recruiting and hiring

  • Career development

  • Documentation and processes

  • Onboarding

  • Socializing and team-building

  • Too many Slack alerts

  • Too many video meetings

  • Work-life balance

Let's review!

Remote work challenge #1: Recruiting and hiring 🎣

One major perk of remote working is it gives you acces s to global talent because you're not limited by location (though time zones may be a consideration!). As Elie Y. Katz, president and CEO of National Retail Solutions, succinctly put it in his Forbes article:

“Talent knows no nationality.”

But this convenience comes with its own set of challenges and questions, namely a) fighting off competitors who hire globally, b) finding the best-fit employee for your team, and c) sorting through more applications than ever before. Here's how to be more strategic about remote hiring:

  • Be super clear on what you need (and align your team around this). This might sound trivial but if you’re not clear on what role you need to fill, you’ll never find the person you need. For instance, if you’re looking to hire someone for your content team, ask yourself if who you need is a long-form content writer, an editor who can manage production, or a conversion-focused copywriter.

  • Use the right channels or partner with a remote-friendly recruiter to attract applicants. There are different ways to get your job posting in front of the right set of applicants. The obvious choice is LinkedIn — if you’re going this route, be sure to use the right filters or keywords (i.e work from home, virtual, remote), and specify if your job is remote to your country, or remote global.

  • Use job boards designed specifically for remote jobs. Some of these include FlexJobs, Working Nomads, We Work Remotely. Online communities, like Slack groups where your applicants hang out, can also prove useful.

  • Record a short video about your company’s remote culture. This humanizes your brand. With a recorded video, you’re able to show off the best parts of your company and show candidates how they'd fit within your organization — here's an example video from Otka.

Remote work challenge #2: Career development 🌱

Visibility. Networking opportunities. Mentorship.

These are some of the unnamed perks that come with a physical office – perks that are crucial to the development of a young employee and may be lost in a remote setting.

As Corrine Purtill writes in the New York Times, “Remote work is often favoured by established employees who know their manager and are established in their role… For those just starting, working in isolation can make fitting into an organization – and eventually progressing up it ranks – more difficult.”

Here's how to pay more attention to learning and development in your company:

  • Build career development conversions into your regular one-on-one schedule. What this does is clearly define expectations regarding each employee’s role and development. Set quarterly goals or OKRs to guide your team members and schedule regular one-on-one career development meetings as part of your assessment framework.

  • Start an internal mentoring program. Pair more junior employees with senior ones who volunteer as mentors. Provide an environment for them to connect on Slack and over video, as well as a formal feedback loop. This will recreate some aspects of a physical setting.

  • Provide online learning resources. Provide your employees with the budget and time to acquire new skills or get certifications using platforms like Pluralsight, Skillshare, and Udemy.

Remote work challenge #3: Documentation 🗄️

If you manage team members across different countries and multiple time zones, one problem that immediately rears its head is dealing with the async nature of your relationship with each of them. You miss out on in-person conversations and context sharing.

If your team doesn’t make up for this with a strong documentation foundation, you could unnecessarily compartmentalize needed information. Maybe a team member missed out on a video meeting and didn’t hear an important announcement. Or maybe they're spending time trying to figure out a process that's already been documented (but is hard to find).

Here's how to build a strong documentation culture for your remote team:

  • Decide on a single point of truth for your documentation. A useful documentation framework is one that is trusted by every team member. At Vowel, we use Notion for all our documentation — so even if someone creates a Google Doc somewhere else, it’s always linked back to Notion.

  • Make it transparent. What use is documentation if it can’t be accessed by those who need it? Help your team members make better decisions by sharing and giving them access to the information they need to work effectively.

  • Take better meeting notes and record your meetings. Meeting notes, transcripts, and recordings allow team members to easily reference decisions made during your meeting, even if they weren't there! If you use a tool like Vowel for team meetings, all your meeting notes will be stored in a single location (along with the transcript and recording), where they can easily be accessed at anytime. You can also make folders with saved videos for all-hands, onboarding, team meetings, projects, and more.

Folder of recorded meetings in Vowel

A folder of recorded meetings in Vowel :)

Remote work challenge #4: Onboarding 🤝

Remote onboarding is tricky. How do you onboard new hires when it could be months before they meet other team members? Working in isolation can make fitting in difficult. If not dealt with, your employees will wonder if they made the right decision to join your team.

Here’s how to make onboarding and team culture better:

  • Focus on "preboarding." Preboarding is the time between an employee accepting your job offer and their first day. Don’t wait until day one to engage your new hires. You can invite them to a virtual Friday Happy Hour or team social in preparation for their first Monday as an employee.

  • Set new employees up with mentors or “onboarding buddies” A workplace buddy can quickly demystify organizational culture and processes for a new employee. And it gives them someone to regularly check in with who's not their manager.

  • Create a 30-60-90 day plan for new employees. This plan is your new hire’s guide through your onboarding process. It helps your employees check of essential items as they familiarize themselves with your policies, team, and goals. Use a mix of documents to read, product tours, or recorded meetings (like the latest all hands meetings!) to keep things interesting.

Folder of Vowel's recorded all hands meetings

Remote challenge #5: Team-building 🏐

Once upon a time, you could swivel your chair to engage your colleague in a conversation. Or take part in a friendly argument with a team member on your way to lunch.

These scenarios are a critical part of a team-building environment. How do you recreate them if you don’t see your team members everyday? Here are a few tips:

  • Create a virtual watercooler channel for non-work related activities. Create specific channels on Slack or your preferred software for team communication. (Examples at Vowel include #random-pets, #random-pastime, #random-music, and #parents).

  • Hold regular all hands meeting. Rather than have crucial company information spread from person to person (or department to department), all hands meetings ensure everyone receive information at the same time and in the same context. This ensures transparency and clarity within your team.

  • Arrange occasional in-person meetups. Bringing everyone together in-person still remains undefeated. It might be a hassle to plan and budget. But you’d reap the benefits when everyone gets back to work rejuvenated. It doesn’t always have to be an exotic location, either. Your company’s headquarters or a company event is a great place to get everyone together.

Remote challenge #6: Too many Slack alerts 😖

On June 27, 2018, when Slack went down for a few hours, RescueTime (a time tracking and time management tool) discovered its users spent more time on productive work than during the same time a week before when Slack was live.

The importance of Slack in workplace communication can’t be overemphasized. But its ease of use has also become its biggest problem. Here are tips you can give your team members to help them reduce Slack distractions.

  • Make it okay not to respond right away unless urgent. Encourage team members to engage in conservations as they have time. For instance, Mode allows employees to read and respond to messages within 24 hours (if appropriate). This takes away the pressure of having to deal with unimportant notifications immediately.

  • Encourage team members to prioritize sharing complete thoughts. Rather than share a stream of messages that convey a single point, team members should collect their thoughts and send one clear message. This protects their colleagues’ workflow.

Remote challenge #7: Too many video meetings 🙄

In a similar vein to Slack messages, video meetings can quickly become an annoying momentum killer to your employees (which is why a whole bunch of Zoom memes like this exist).

Zoom meme productive day

Video meetings are easy to set up. And unlike in-person meetings, you don’t have to worry about boundary restrictions. But just because it’s easy to set up doesn’t mean managers should invade other employees’ work hours.

If a meeting could be an email, then it should be an email. And if you need to have a meeting, here’s how to make sure it's productive:

  • Always have a meeting agenda. This tells every attendee when they should attend and what they should expect from the meeting. Vowel makes this task a breeze. You can connect with Google Calendar to create and distribute agendas for upcoming meetings. And you don’t have to create one from scratch, either. We have easy-to-use templates in Vowel, or this template library you can use for inspiration.

Vowel meeting agenda
  • Be clear on next steps and deliverables. This will help each team member leave your meetings with a sense of purpose. You can automate this process in Vowel by turning your notes into a sharable summary of decisions, next steps, and action items.

  • Schedule fewer meetings. If your team members say they have too many meetings, listen! Then make steps to batch meetings on specific days or limit your meeting duration to improve meeting culture.

Remote challenge #8: Work-life balance ⚖️

According to Buffer’s 2022 State of Remote Work report, flexibility is remote work’s main benefit. But the inability to unplug from work remains one of its disadvantages. And it’s easy to see why. How do you take a break when you work from the same place you sleep?

Here’s how to inspire your remote team members to have a balanced work/life relationship:

  • Encourage your employees to use their annual leave. Working from the comforts of a home doesn’t equal a holiday. Encourage your employees to take time off — if you offer "unlimited vacation," this could even mean implementing a "minimum vacation" requirement.

  • Review their workload periodically. Uses one-on-one meetings to make sure no one is struggling in silence.

  • Offer work-from-home perks. The free lunch at the office is of no use in a remote setting. Replace it with a perk that’ll appeal to your remote team members, like lunch vouchers, remote setup stipends, or subscriptions to a fitness app of their choice.

  • Make it okay to miss meetings. If your team meetings fall outside an employee’s working hours, don’t force them to stay up late to attend. Instead, send a recording and make note of any action items that fall to them. You can also send them certain parts of the meeting to get them up to speed (this is easy to do in Vowel!).

Share meeting recordings with others in Vowel

Choose the right SaaS tools to make remote work better

Building an efficient distributed team requires the right set of remote collaboration tools.

The best set of tools shouldn’t just help you with key operations (like video conferencing & note-taking, communication, project management, and internal documentation); they should also play well together. The remote work tech stack at Vowel looks like this:

  • Messaging: Slack

  • Internal wiki: Notion

  • Writing: Grammarly

  • Video meetings: Vowel

  • Other docs: Google Docs

  • Scheduling: Calendly

  • Design: Figma

  • Whiteboarding: Miro or Figjam

  • Engineering: Jira

  • Bug documentation/async communications: Loom

It’s no easy task managing a remote team at a time when more companies are beginning to realize that remote work is here to stay.

Each of the above challenges will stand in your way of making remote work work for you and your team. But the tips provided in this article will make it easier to overcome these challenges, and ultimately improve productivity and happiness.

P.S. Want to have more productive meetings with your remote team? Try Vowel for free. With Vowel, you have video conferencing, live meeting transcription, instant recordings, and collaborative agendas + notes – all in one place.