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Challenges in Creating and Finding Opportunities in Remote Work

By Kimberly Bringas, Remote HR Expert

Any opinions expressed within this blog post are those of the author and not necessarily held by Workplaceless itself.


A common misconception about remote work is it doesn’t require anything more than giving an employee remote based tools to do their work. “Here is slack, zoom and a working computer, you’re remote now.”—it’s not quite that simple. In actuality, it’s often overlooked that building a successful remote work environment requires the same level of care, attention and proactiveness as an actual office space. As the former Senior HR Manager at Olark, I worked on converting PeopleOps based programs, processes and policies using a specific remote lens. It was during this time I learned that remote and office environments have the same goal of ultimately wanting engaged and thriving employees, however remote requires different approaches. This is profoundly evident in the area of employee development.  

That’s why I was excited to join the September Networkplaceless event to discuss Challenges in Creating and Finding Opportunities in Remote Work -- highlighting this next stage of the remote worker struggles. A decade ago, the main struggle for a remote worker was simply finding a job. Now with companies struggling to retain talent, especially in larger cities, more companies are loosening the reins and creating more remote job opportunities. In our event group alone, 46% of us have worked 5+ years remotely. While the group discussion did bring out struggles of finding remote work, one overarching theme was an overall lack of awareness and structure for remote employee development. Once hired, remote workers can often get overlooked or completely forgotten when it comes to their career development. The top common themes were: 

  • Lack of - Leaders creating and fostering opportunities
  • Lack of - Relationship building opportunities
  • Lack of - Structured resources: remote work policies + remote L&D programs + hybrid hiring platforms
  • Lack of - Trust and foundational understanding about remote team members

In my break out group, the term “legacy thinking” was brought up as one of the contributing factors to the above concerns. “That’s just the way we’ve done things” is just not good enough of a reason. Whether a company’s leadership team is willing to break away from their fixed mindset and embrace a growth mindset, is a strong indicator if the company can evolve and address remote specific needs. One remote need my group all agreed on is remote settings require proactive leadership efforts. Without organic “watercooler” moments, those impromptu opportunities to run into your manager or other people in the company who can provide relationship or career building conversations are simply not there. 

I credit my former manager with modeling what a proactive and growth focused manager/employee relationship can be. What did she do and what steps can other virtual leaders replicate?

Foster conversations specific to remote development. She didn’t just say she supported me, she created specific spaces and opportunities to focus on my career development. A simple, but effective change was setting aside at least one of our recurring 1:1s during the quarter to talk big picture. The attempt was to try and align the work I was doing to my bigger career path goals. 

Create space for virtual network building. Furthermore, she encouraged me to use part of my work time to build my remote advocates network and contribute to various publications (special shoutouts to Acework, RebelandConnect, Support Driven and Remote People Operations Group). 

Stay tuned into the person along with the work. She also insisted on receiving updates during our work syncs and even helped me edit. By helping me, it had one BIG additional benefit, I developed a profound level of trust in my manager. So much so when it became clear my career ambitions no longer aligned with what Olark could provide me, she worked with me to gracefully exit. 

Pro tip: If you’re new to leading remote employees, or just need to up your game, Workplaceless has also created a program specific to remote managers, Leadplaceless, that’s worth a look.

While companies can approach remote worker development in a variety of ways, the main takeaway here is that it IS a focus. The October Networkplaceless event topic segues beautifully and will cover professional development and networking for remote Workers with guest speaker Julia Taylor Kennedy, Executive Vice President at the Center for Talent Innovation. Looking forward to connecting with fellow remote advocates as we explore and share how to leverage remote opportunities that best suits our respective career paths.

Click here to view the complete Networkplaceless - September outcomes infographic. 

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