How to Upskill Your Team

How to Upskill Your Team


5 Ways to Upskill Your Remote Team 

 2020 was a year of transformative change with the landscape of in-demand jobs taking a massive shift toward digitalization. As office doors shuttered, remote work, distributed workforces, and hybrid work has become the new normal. Companies had to refocus their initiatives on future-proofing their business strategy. 

According to Rusen from Microsoft, it is expected that within the next five years, “the global workforce can absorb around 149 million new technology-oriented jobs.” As digital transsformation touches every corner of the global workforce, Microsoft is launching a global skills initiative using data and technology to help 25 million people acquire digital skills needed.  


As Transcends is a remote-first team that values continuous learning, we know upskilling is crucial to future-proofing your team. As calendars fill up with client meetings and high priority work, it can seem difficult to find any time left for skill development. Here are 5 ways to upskill effectively in busy workplaces. 



Build a culture of mentoring 

Mentoring is an effective way of upskilling, and is especially beneficial for new employees. Even if an employee has basic understanding of the role and previous experience in the industry, there will still be a knowledge gap on how to apply that knowledge in their workplace.  

At Transcends, we use a “buddy system” for all new hires. A more senior team member is paired up with a new hire to help make their transition to the team comfortable and fun. 


Even as a remote team, you can build a culture of mentoring. Our CEO is a part of several virtual mentorship groups including The Executive Committeethe International Associate of Microsoft Partners (IAMCP), and WEConnect. We hold high standards for collaboration and do so through weekly marketing team strategy sessions and learning sessions, where employees mentor each other in areas of expertise. Not only does this help deepen relationships and create a positive working environment, but it is also crucial to integrating the different segments of your team. 




Set goals  


At Transcends, one of our values is Digital Freedom. We embrace innovation and flexible working conditions that enable us to have a diverse team and clients that transcend geographical boundaries.  

As a remote-first team, we know working in a purely digital environment can bring unique challenges such as lack of structure and cross-communication. But, this doesn’t deter us from setting & pursuing our monthly, quarterly and yearly goals. Remote work forces us to be on our A game when it comes to communicating our company and/or personal goals. Here are some of our favourite goal-setting processes:  


  • Objectives & Key Results (OKRs) for quarterly goal setting  
  • Twice monthly townhall-style meeting where we discuss company objectives & direction  
  • Monthly values-sessions 

Allocate training time  


In his book “Outliers”, Malcolm Gladwell wrote that it takes 10,000 hours to really master a skill. Deliberate practice is key to strengthening skills day after day. Our growth mindset leads us to embrace new challenges, develop our craft, and learn from failure. The best way to make upskilling effective, is to make it part of an employees work hours. At Transcends, we allocate a time during the workday for team members to engage in learning new skills. It is important to use time-blocking in your calendar to ensure it remains prioritized. The training time could take a whole workday or some hours in a specific workday and could include webinars and video conferences. 




Emphasize on personal development plans (PDP) 


As a team manager, you have an idea of what your employees should learn. But do you know what your employees want to learn? Upskilling team members is not as simple as it seems, and a team member might have a more accurate view of steps to take to get the best results out of their work.  


Let employees lead their skill development. The Transcends team has one on one meetings with our CEO to discuss personal development plans. Not only does this empower employees, but also ensures the skills are relevant to the workplace and having a PDP can help hold employees accountable to the plan.  




Take advantage of online training content 


Never before has so much resource been available for upskilling online – and lots of it is for free.  

Some of our favorites include: 


When it comes to digital marketing, Transcends Marketing has extensive experience in supporting our partners. You can read more about our services or contact us directly for a quick chat by clicking below. 


Interested in joining our team? Transcends Marketing Ltd. Is hiring! Head to our Careers page to see our latest openings.



#upskillingemployees #upskill #training #alwaysbelearning 






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