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Starting a new job remotely can be a challenge: Here’s how to ease the transition

Starting any new job can be stressful enough in person, but there are some additional issues with 100% remote-based work. Learn some tips on how to hit the ground running.


Image: Vasil Dimitrov, Getty Images/iStockPhoto

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Like many college students, my older son faces the challenge of beginning his first semester via virtual learning. This can potentially impact his ability to network with his peers, to absorb course content, to seek extra help, and to immerse himself in campus life.

It’s no different for employees starting new jobs via virtual connections. TechRepublic has provided an array of tips on working from home strategies such as tools, cybersecurity considerations and data protection strategies. However, beginning a new job from an exclusively remote perspective adds extra challenges in the form of mastering the learning curve and becoming immersed in company culture.

SEE: COVID-19 workplace policy (TechRepublic Premium)

I gathered some insights on the topic from two industry leaders, Mark Kinsella, VP of Engineering at Opendoor, an online real estate transaction provider, and Deb Kearney, global senior director, Human Resources at Cygilant, a Cybersecurity as a Service provider.

Scott Matteson: What are the challenges for employees with starting a new job from a remote or virtual perspective?

Mark Kinsella: Starting a new job is exciting, but can present challenges, even in normal circumstances. With COVID-19, many companies are hiring remote employees, which means a completely virtual onboarding process, without meeting teammates face-to-face—myself included. 

From my experience, onboarding in-person vs. onboarding virtually isn’t drastically different. For example, when starting a new role, it takes time to understand the history and context of many decisions, whether you’re remote or not. In a fast environment, particularly at startups, teams rely on tribal knowledge since written documentation can become quickly outdated. It also will take a few weeks or months to figure out how to best work and collaborate with your new peers. 

SEE: 20 work-from-home remote jobs with salaries over $100,000 (TechRepublic)

The biggest challenge unique to virtual onboarding is how to build personal connections. Without face-to-face time, either during meetings or hallway and coffee chats in the office, it can be difficult to connect with teammates on a personal level. 

Deb Kearney: With the current global pandemic, HR managers are tasked with having to onboard new employees virtually in order to put the health and safety of all parties first. For new employees it’s important to build a foundation for them to develop new relationships in the workplace and to establish a connection with their new employer. 

Scott Matteson: What do you recommend to alleviate those challenges?

Mark Kinsella: Make a concerted effort to spend more time with your colleagues. I recommend setting up one-on-ones with as many people as you can, even outside of your direct team and manager. Partake in any virtual social events coordinated by the company, too. For example, we recently hosted a virtual treasure hunt that made for a fun team-building exercise and an opportunity to break the ice. 

In the past, I’ve created a “how I work” manual that outlined my preferred form of communication, working hours, and management style. I shared this with my team and in return, asked each colleague the same questions. Since joining Opendoor, I’ve been documenting my learnings during the onboarding process so I can share with new teammates as a helpful starting point. 

Deb Kearney: Virtual onboarding should go beyond day one. What makes a successful virtual onboarding: 

  • Regular Check-ins: Leverage video conferencing to connect with new hires on a regular basis. For some, this may be the first time they have to telecommute so keeping them engaged is key. 

  • Integrate them into the company culture: Set up a weekly employee meeting to allow a place to communicate company news and provide a forum for employees to ask questions. This will help build virtual employee engagement during these times of uncertainty and help new employees feel part of the organization. But don’t make it all formal, host virtual weekly happy hours, new hire meetups, themed employee meetings, and game nights for example. 

As the HR manager, it’s our responsibility to make sure employees understand that even though we are not in the office together we are all part of the same team.  

Scott Matteson: What challenges are employers facing in hiring remote employees?

Mark Kinsella: During the interview processes, assessing soft skills is much harder remotely than in-person. This includes how to assess highly-important culture-add attributes in a candidate.

For tech interviews, assessing technical architecture and systems design thinking is difficult, especially as most of those conversations typically occur on a whiteboard.

Scott Matteson: What do you recommend to alleviate those challenges?

Mark Kinsella: During my interview process at Opendoor, I spoke with a multitude of employees across the company, including senior executives, peers, and people who would be in my direct org. By having numerous conversations with a wide range of employees, I was able to get a good sense of the company culture. And in turn, gave them a better sense if I would be a fit, too.

SEE: Remote working 101: Professional’s guide to the tools of the trade (ZDNet)

For architecture and design, I did an extensive “take-home” pre-work project, where I was able to sit down and write out my thoughts in detail. I shared the document ahead of time, which allowed our virtual conversation to be more targeted in the absence of physical tools. 

Scott Matteson: How does virtual work affect morale?

Mark Kinsella: Remember that we’re all adjusting to new norms, some better than others. While some employees may thrive and love virtual work, others may not. Recognize that little problems can quickly become big problems. One of our core operating principles at Opendoor is to “build openness.” And in our current climate, it’s especially important. We all need to support one another and prioritize open communication to cultivate a two-way dialogue.

I think it’s especially challenging for engineers to fully disconnect and know when to turn off work. As a technical leader, it’s my responsibility to encourage team members to take time off when needed to avoid burnout. It’s also important to recognize teammates’ work, give praise, and take the time to celebrate wins. 

SEE: Zoom vs. Microsoft Teams, Google Meet, Cisco WebEx and Skype: Choosing the right video-conferencing apps for you (TechRepublic download)

Scott Matteson: How does virtual work affect productivity?

Mark Kinsella: Virtual work can bolster productivity and increase happiness. With a remote workspace, there is more flexibility to adapt work to your preferred habits and style. 

However, on the flip side, there can be a few traps that can be easier to fall into at home: For example, as mentioned above, knowing when to turn off work. Before the pandemic, you’d depart the office, commute home, and leave work behind. Now, our homes are our offices, and the line is blurred when to “leave” work. As a result, burnout can be easier to experience. My advice? Take a break when you need it, and be sure to check in on your teammates. 

Lastly, focus on the big picture. It can be easy to lose sight of your company’s mission and focus on tactical and short-term thinking. Remember why you joined the company and what gets you excited every day. 

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