12 Mistakes to Avoid When Hiring and Onboarding Remote Teams

A massive realignment of the modern workforce is currently underway. Across industries, companies are ditching traditional approaches to hiring in favor of building remote teams.

In addition to hiring employees across the globe, organizations are increasingly leveraging freelancers within their wider workforces. This “hybrid” approach produces nimbler remote teams, with precise skill sets drawn from a global talent pool.

However, with all the possibilities that remote hiring offers, it can also bring challenges.

Whether you’re engaging independent professionals or looking for someone to join your team full time, here’s what to avoid when hiring and onboarding remote teams:

1. Not searching far enough
2. Not conducting an interview
3. Not aligning on expectations
4. Not preparing employees
5. Not discussing communication etiquette
6. Not creating training processes
7. Not discussing performance
8. Not helping employees adjust
9. Not having the right communication tools
10. Not securing your company network
11. Not taking regular surveys
12. Not evolving your hiring practices

1. Not searching for candidates outside of your locale

One of the biggest benefits of remote work is the freedom it gives you. Remote work erases geographic borders and significantly expands your talent pool. Expanding your search radius enables you to:

• Find the best person for a job—not just the best person in your vicinity
• Increase the diversity of your hires
• Secure the ideal talent within budget
• Fill needs faster
  

Such as when Digicel, a telecom provider in 32 countries, launched a global rebrand. To tailor assets to local audiences, Digicel engaged independent creatives within each region.

Finding talent outside of your locale provides operational flexibility so that you can nimbly overcome business obstacles, as these companies did:

• The marketing team at CompuVision, an IT support company, couldn’t increase productivity by adding headcount. So they engaged independent professionals in specific time zones to create a production cycle that never sleeps. The result: They realized 3x the output at a 70% savings.
• The engineering team at Zendesk, a customer support software company, found certain skills and bodies of knowledge concentrated in specific regional markets. Persuading people to come to Zendesk in San Francisco resulted in a fraction of the talent they needed. So now they go where the talent is by building engineering teams from Copenhagen to Singapore. The result: Zendesk quickly seizes on software trends and maintains a pipeline of in-demand talent.

2. Not conducting an interview

When shifting to remote hiring, many managers skip key steps they normally take for in-person hires. But you’ve probably seen how hiring the wrong onsite person can affect everything from a team’s productivity to an entire organization’s culture. Imagine hiring the wrong person with the added complication that they work remotely.

That’s why vetting is at least as important when hiring remote workers as onsite workers. One strategy is to conduct video interviews. Seeing someone on screen yields a number of useful insights about a prospective hire, including intangible qualities that can’t be fully conveyed in writing or in a resume.

During the interview, be sure to ask questions that provide insights about how they may perform as part of a remote team. Take note of the following areas, which a video call can reveal quite clearly:

• Synchronous communication skills: Even if much of the work revolves around written updates, they may need to communicate effectively in meetings.
• Enthusiasm for the opportunity: Do they seem genuinely interested in the work you’re discussing and motivated to get the job? If they’re lukewarm about the opportunity, it may reflect in their quality of work.‍
• Technical concerns: Do they seem comfortable using the video conferencing tool? It may signal their inability to use the cloud-based collaboration tools that the team relies on daily. ‍
• Personality and culture fit: Do they seem likely to fit in with your team and collaborate well? Working remotely may increase the risk of communication issues with teams and disengagement. Having someone who fits in well from the beginning may lessen those challenges.

3. Not aligning on expectations

Setting expectations for remote employees differs slightly from independent professionals. Expectations for independent professionals are usually established in a project post. You do this by providing details about the work to be done and include must-haves such as:

• Project milestones
• Quality expectations
• Deadlines
  

Then, before the selected independent professional begins work, try to discuss expectations in more detail. Share relevant project documents. Give examples of what “good work” looks like. And confirm deadlines and deliverables.

Establish expectations for remote employees throughout the hiring process. To avoid misunderstandings and unqualified candidates, start with a detailed job description that clearly states requirements upfront. For example, you may mention:

• If they must split their time between remote and the office, or work remotely 100% of the time.
• Who can apply for the job, such as people in certain regions or time zones.
• Working hours. Are they flexible, or does the candidate have to be at their desk from 9-to-5 in a specific time zone?
• How experienced they must be at collaborating with remote teams.

4. Not preparing employees for remote work

Independent professionals are business owners; they have the tools required to jump into a project and start producing right away. However, some employees may be new to remote work, so they’re not as prepared.

You can set employees up for success by ensuring they have a comfortable workspace and access to collaboration and communication tools. To that end, consider providing employees a budget for:

• Office equipment: Especially if your business requires specialized equipment or software, offer employees a stipend. Even basics like a monitor, Wi-Fi router, and noise-canceling headphones can yield a return on your investment.
• Coworking spaces: Sometimes, employees may be more productive outside of their home or neighborhood coffeehouse. Also, if remote employees meet other team members, vendors, or clients in person, they’ll appreciate having a professional space for conducting business.
• Internet connection: Perhaps subsidize part or all of a person’s monthly subscription so their internet connection is speedy and reliable enough to meet work needs.

5. Not discussing communication etiquette

Not long ago, people thought working remotely meant hardly working. The pandemic busted that myth, and studies have proved remote employees work longer days than their cubicle counterparts.

Remote employees tend to work longer hours because work is visually, emotionally, and physically intertwined with their personal life. Be it a laptop on the kitchen table or an office that’s just a few steps away.

This blurring of work and personal life makes it too easy to check emails while sitting on the couch at night, or to update a spreadsheet after dinner. The problem is that there’s no mental or emotional buffer between work and personal life, so people working from home never wind down. This leads to exhaustion, burnout, and higher turnover.

You can avoid this during onboarding by clarifying expectations for accessibility and responsiveness. For example, you could set:

• What hours emails and instant messages should be responded to
• When it’s best to call
• When texting is permitted, if at all
  

Remember to address the issue of time zones. Don’t make people feel they have to answer messages when it’s morning for you but after hours for them.

Be sure to walk your talk. You could encourage employees to power down by 6 pm, but if they regularly receive emails from you at 10 pm, they may feel pressured to work late too.

6. Not creating training processes

When an employee starts off, they must learn new processes, tools, details about their job, and the company’s culture. It’s a lot to digest.

But remote employees may have a harder time during onboarding because they can’t walk up to someone and ask questions.

You can get them up to speed faster by including training as part of their remote onboarding process. Training can be done in two ways:

• Synchronous: This could be one-on-one training where an experienced employee teaches the new hire how to use a collaboration tool. It may also be a group live-webinar or in-person class led by an instructor.
• Asynchronous: Under this model, training is usually self-guided and enables remote workers  to learn at their own pace, such as in most e-learning courses.
  

Having a centralized document hub, where employees can access guides, organization charts, and other information relevant to their role, is also helpful. Having this at their fingertips enables them to answer their own questions, so they can remain productive rather than wait for answers. And team members can remain focused on their work.

7. Not discussing how remote work could impact performance

Today, enough people have experienced remote work to dispel the stereotype that it’s all visions of bunny slippers and lazy afternoons in front of the TV.

Many employees work remotely because the flexibility enables them to work and juggle caregiving responsibilities. Some work remotely because a medical or physical disability prevents them from going to an onsite job. Others find remote work is less emotionally and mentally stressful.

An Upwork study showing why professionals quit their jobs to freelance echoes these reasons.

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These findings are a reminder that an employee’s personal life doesn’t stop once they log into work. The stress that comes with being human is inextricably interwoven into their workday.

When you remain open and empathetic to such discussions, you can better support employees, and understand when they may need to take things easy. Zoë Harte, Chief People Officer at Upwork, explains how this may look:

“For example, if you know a team member’s brother-in-law is gay, and there’s an increase in anti-gay violence, you can check in by asking, ‘I know there’s a lot going on—are you okay? How’s your family?’”

“And if a team member confides they’re a bit unfocused because their father is in the hospital, you could reduce some of their stress by telling their colleagues, ‘Hey, Zoe is dealing with a family emergency. Can you give her some space by pushing out some deadlines? Handling some of the work yourself? Minimizing meeting requests for the next couple of weeks?’”

Discover more about the link between empathy and performance in Harte’s article: How Empathetic Leadership Leads to Higher Business Outcomes

8. Not helping newly remote employees adjust

You may have noticed from the tips already mentioned that managing remote teams is as much about technology and operations as it is leadership. Here are ways to help remote employees adjust, and more quickly acclimate to your team.

Pair them with a buddy

Too often, onboarding goes something like this: Dump as much information as possible in a short amount of time, then leave the new hire to figure it all out as they’re simultaneously learning and doing their job.

This can be so overwhelming that new employees feel frustrated and alone at a time when they most need support.

One effective resolution creates an intentional, digital form of the personal interactions that occur naturally in offices. Upwork, for example, pairs a seasoned team member (a buddy) with each new hire. This buddy system provides new hires with a dedicated, friendly, go-to person for their first 90 days.

If you’re considering a buddy program, you may want to establish clear guidelines that keep the program constructive. You may want to lay out what a buddy should do, like answer questions and establish a regular cadence for checking in with a new hire. And what they shouldn’t do, such as discuss salaries and reviews.

Offer time management tips

New employees are in learning mode and tend to say yes to everything. This can lead to long days and counterproductive habits.

It’s not their fault, as it takes time to understand the nuances of their job, like which meetings to accept and how to prioritize tasks. You could set them up in the beginning by:

• Having their buddy offer tips for managing their time more efficiently
• Including time-management training as part of their onboarding
• Providing resources for them to review on their own, such as this article of 18 time management strategies, and these practical tips for working from home

Not setting productivity time

In a day filled with bouncing between meetings, calls, and emails, losing track of time is all too easy. A conscientious employee can be so busy reacting to other people’s demands that they leave themselves with little time to produce—unless they work longer hours, and that’s not a sustainable or healthy solution.

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To avoid a tail-wagging-the-dog scenario, consider helping new hires block space in their schedule for production. That’s time for settling into work that requires deep and sustained focus. No emails, instant messages, or interruptions of any kind are allowed during this sacred time.

Better yet, why not time-block teamwide? For example, a team could block 9 am to 12 pm every Monday and Wednesday as production time, which may not only make it easier for everyone to avoid interruptions, but may also increase overall team productivity.

You’ll find more details in this guide to time blocking from Todoist.

9. Not having the right communication tools

Having the right communication tools are as critical to remote work as a reliable internet connection. The right tools depend on your team’s needs, and it’s best to include a combination of synchronous and asynchronous communication channels. Synchronous communication takes place in real time, like a video call. Asynchronous doesn’t require immediate response, like email.

Provide multiple tools to avoid tech burnout (e.g., Zoom fatigue), reduce miscommunication, and maintain productivity. The chart below offers some suggestions.

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10. Not having your company network secured

Ensure the processes are in place to keep data secure when working with independent professionals and employees. These two resources may help you establish a strong foundation:

• Securely Working with Remote Freelancers
  

Since data security is so critical for business continuity, it shouldn’t be delayed. If you’re short on in-house resources, get help by engaging independent cybersecurity professionals through work marketplaces such as Upwork.

Here are just a few of the quality specialists you can contract:

• Vulnerability assessment professionals to identify potential holes and close them off
• Firewall protection specialists to keep unwanted visitors and malicious software out of your network
• Penetration testers to stay ahead of problems each time you open new locations, update software, and make infrastructure changes
  

If you’re short on time, select one of the set-priced projects on Upwork to get started right away. Browse the cybersecurity projects you can start today.

11. Not taking regular surveys

Avoiding remote hiring mistakes is an iterative process. There are so many details and nuances to learn that few, if any, get it right the first time. Regularly surveying new hires and the team for feedback is helpful.

You may get more insightful and actionable feedback by creating separate surveys that address the unique issues for independent professionals and employees.

Know that you don’t have to spend a lot of time or money creating surveys. Many tools are free, like Google Forms and SurveyMonkey, Here are a few ways to get more out of your surveys:

1. Keep it anonymous so that respondents feel safe sharing candidly. At the beginning of your survey, include some type of reassurance like, All responses are anonymous.
2. Set a survey goal to keep questions focused. Make it specific. Avoid saying, I want to know if they like the remote onboarding process. Instead, aim for something like, I want to understand why they’re not completing the online training timely.
3. Mix open- and closed-ended questions to avoid survey fatigue and gather qualitative and quantitative data. For example, an open-ended question may be, How could we help you become productive sooner? Closed-ended questions can include ratings and multiple choice questions like, How long did it take you to manage your day using time-blocking?
4. Use simple, clear words and short sentences. Avoid asking, Was the training not good? Instead, consider, How would you rate the training overall?
5. To avoid bias, pay attention to how you phrase things. For example, try not to create negative impressions, like this, What problems do you have with our communication practices? Instead, frame questions in a neutral manner, like, What are your thoughts about our communication practices?

12. Not being able to evolve your remote hiring practices

Workforce trends shift and change over time, so it makes sense that your remote hiring practices should evolve as well. Life is changing so quickly that what today’s remote workers expect from an organization may not look the same a year, or even just a few months, from now. How you find and qualify talent may look different as talent shortages persist and new skills emerge. And how you work with remote talent may transform as new business goals surface and business conditions shift. So, keep a pulse on workforce trends and remain open to change.

Start hiring remote talent today

If you’re new to hiring remote talent, you can mitigate your risks by contracting independent professionals through Upwork. You may want to start with a smaller project to get a feel for how the platform works, and to identify areas in your hiring and onboarding processes that may need beefing up.

For example, you could contract a human resources specialist to review your hiring and onboarding processes. As remote workers themselves, they may provide ideas that could lessen your workload and improve the overall hiring experience for employees and independent talent.

If you want to get started without posting a job and reviewing proposals, you could choose a prepackaged, set-price project from Project Catalog™ where you can see what’s possible and browse projects offered by experts in their field.