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How to Upskill Employees: an L&D Manager’s Guide

In a recent LinkedIn survey, 59 percent of learning and development (L&D) managers listed upskilling as a top priority, up 15 percent from the same survey in 2020. 

Companies that prioritize upskilling employees are more competitive in a constantly-changing work environment. As a result, they have fewer skills gaps, their employees are more agile, and they retain top talent. 

Organizations are treating upskilling as an investment, not just another expense. So make sure you’re prioritizing it and empowering your team members to reach their full potential. 

Why is it important to upskill your team?

There are a few reasons why it’s essential to upskill your team. When all your employees have the skills they need for their jobs, they’re more efficient and effective. 

Upskilling reduces the skills gap 

Upskilling fills in skills gaps—the gap between the skills your employees need and those they have. Upskilling equips your team with the necessary competencies to do their jobs effectively.

Skills gaps can result in unfinished or delayed projects and the need for costly contract workers. In a CareerBuilder survey, more than half of employers said they’ve seen a negative impact on their business due to extended job vacancies they can’t fill. Employers listed specific impacts such as productivity loss, lower quality work, and an inability to grow the business. 

Upskilling helps your teams remain agile

Agile teams have the necessary qualifications to help their companies stay competitive. They can complete tasks quickly and easily. Plus, you have more employees who can complete a particular task. Agile teams are less likely to cause project delays because more people can handle them.

For example, if you need more people to be able to complete a specific task, like coding, you can train your current employees. Training employees gives them new skills and reduces the need to hire new team members. You’ll also have more people to perform a specific task when someone is out sick or on leave.

Upskilling helps your company attract and retain employees

Your company is more attractive to a wider net of employees when you offer opportunities for them to upskill and grow professionally. In LinkedIn’s 2022 Workplace Learning Report, 94 percent of workers said they would stay at a company longer if they invested in helping them learn. 

Companies that don’t prioritize continuous learning risk losing valuable employees to other companies that offer professional advancement opportunities.

How to upskill employees

Perform a skills assessment

The first step is to conduct an assessment or skills gap analysis to understand where the most significant knowledge gaps lie. 

A skills assessment should include:

  • Employee self-assessments and team assessments. Ask employees to evaluate their own skill set and the skill set of the whole team. Ask them specific questions like, “What skills do you feel you or the team are missing to do your job effectively?” 
  • Evaluations of their work. Evaluate your employees’ past tasks and projects to assess their skill level. Ask yourself, “What qualifications would make their work stronger?”
  • Simulations or test scenarios to determine their competency. Practice solving problems using simulations or real-life business scenarios. Evaluate the skills team members use to work toward a resolution. If there are skills they need but aren’t equipped with, having them work through a real-life example can bring them to light. 

After the assessment, you can plan and implement training for specific skills. 

So how do you actually upskill your team members? 

Once the assessment is complete, document the aptitudes each individual and team needs to improve. Then make a plan for implementing upskilling opportunities. 

Make sure you consider how your employees want to learn. For example, in one Salesforce survey, three-quarters of employees said they prefer to learn on the job and in small moments throughout the day.

Here are three ways to upskill your employees:

Use a Learning management system (LMS) to create customized training

An LMS is a tool that lets you create personalized training modules for your employees based on the skills they need for their roles. An LMS enables you to develop courses that focus on precisely what your employees need to know for their job to help them improve their performance. 

For example, presentation skills are necessary for successful sales teams. With a learning management platform like WorkRamp, you can create courses designed to improve presentation skills. In addition, you can use the resources and knowledge you already have and add visuals, videos, examples, and additional reading material to enhance each course. 

Plus, it’s convenient for employees because they can sign up for courses and work through them at their own pace, as it fits into their schedule. Read our guide for more information on how to find the best LMS for your company.

Host peer-to-peer skill-share sessions

Take advantage of the skills your team already possesses. Set up peer-to-peer training or skill-share sessions so employees can share their skills with other employees. You can do this virtually or in person. 

Peer-to-peer learning helps promote more autonomy. According to ADP, peer-to-peer learning in the workplace enables employees to take greater ownership of their professional development.” It can also increase employee collaboration and communication and lead to more innovation. 

To recruit employees to host skill shares, create a form where people can volunteer or nominate an employee to host an event. Then, share the form where all your employees can see it, like through email or Slack. 

Implement job shadowing programs

Job shadowing can give your employees hands-on experience. You can match workers who need to develop certain skills with more experienced employees. For example, if you have a marketing employee who needs to enhance their social media marketing skills, you can connect them with a team member who is well-versed in social media marketing. 

As you implement this program, look for potential candidates. Find top performers whose skill sets align with company and employee goals. 

What are examples of upskilling in the workforce?

Many companies can attribute part of their success to their focus on upskilling. Sprout Social is an excellent example.

In a recent webinar, Lydia O’Malley, Learning and Development Manager at Sprout Social, talked about their approach to attracting and retaining top talent. Their strategy includes a robust learning and development program. 

Sprout Social uses WorkRamp as its primary L&D platform. They use their L&D programs to upskill their employees and leadership teams to set themselves apart as a top employer. 

“I’m very passionate about ensuring that there are learning and development opportunities for literally everyone in our company because you never know who your shining stars will be if you’re not actively working to develop everyone.”


-Lydia O’Malley, Learning and Development Manager, Sprout Social

How to upskill managers

Upskill your managers to provide better support for your teams and keep them engaged and happy. Upskill them in soft skills like leadership and conflict resolution and hard skills related to their job. 

Accessible education opportunities 

Find learning and development opportunities and share them with your managers, like formal education or seminars and events. Offer to cover the costs, too! 

Formal education, like degrees or certificates, is an effective way for managers to upskill. The curriculum for these programs is designed to teach them everything they need to know about a specific skill or trade. Industry-related events like seminars and summits can help your managers hone their skills, too. 

Upskill managers with a learning management platform

Your managers can benefit from WorkRamp’s All-in-One Learning Platform just as much as your other employees. With a learning management platform, you can personalize courses for the skills your managers need to obtain. Personalized courses are the most effective way to educate them on what they need to know. You’d be hard-pressed to find external courses specific to your company with your goals and values. With a learning management platform, you can create customized courses with insights based on how you operate as a company. 

Your managers probably won’t take the same courses as other employees, but you can house all the materials—for teams and managers—in one place. 

Upskill your employees to create an unstoppable team

Upskilling can help your team stay prepared for a changing future. It keeps them flexible in an unpredictable environment by equipping them with the skills they need to be successful.

Want to learn more about how WorkRamp can help you optimize your learning and development program to upskill your team members? Contact us to schedule a free demo. 


Maile Timon

Maile Timon is WorkRamp’s Content Strategist. She has more than 11 years of experience in content marketing and SEO and has written for several publications and industries, including B2B, marketing, lifestyle, health, and more. When she’s not writing or developing content strategies, she enjoys hiking and spending time with her family.

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