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Why Your Organization Needs an Upskilling Strategy — and How to Create an Effective One

Deanna deBara
Freelance Content Writer
Table of contents
June 6, 2022

In today’s environment, attracting and retaining top talent is more important than ever. And to successfully achieve this, you need to show workers that as an organization, you’re invested in their professional growth. One of the best ways to demonstrate to your employees you’re invested in their growth — and support your organization’s growth at the same time — is through upskilling.

The right upskilling strategy can be a gamechanger in terms of both helping your employees grow and continually fostering the skills you need within your organization to take it to the next level. Below, we’ll examine what upskilling is, why it’s important, and how you can build an effective upskilling strategy that supports both your organization and its people.

What Is Upskilling?

“Upskilling [also sometimes called reskilling] is a strategy whereby a business invests in continuous training for existing employees to support them in their personal and professional growth within the organization,” explained Monica Parker, founder of HATCH, a People analytics and change management consultancy that specializes in the future of work.

Any sort of learning and development (L&D) initiatives, training, or professional learning opportunities a company offers its employees with the intent to support their professional growth — whether that’s a day-long workshop on more effective communication, a training on a new industry software, or individualized development plans — fall under the upskilling umbrella.

“When an employer facilitates an employee gaining the new skills and knowledge needed to advance to the next level in their career, that's upskilling,” added Whitney Omosefe, an organizational culture and learning and development consultant with a focus on diversity, equity, and inclusion (DEI).  

Why Upskilling Is Important — and Why Your Organization Needs an Upskilling Strategy

Upskilling offers a huge variety of benefits, both to the organization and its employees alike. “Upskilling supports recruitment, retention, engagement, satisfaction, well-being, and, of course, benefits the bottom line,” Parker said.

Let’s start with the organizational benefits: According to a 2020 report from PwC, CEOs of companies with defined upskilling programs credited the program with both improving productivity (30% of respondents) and creating a stronger company culture and improving employee engagement (41%). These top executives of companies with upskilling programs also reported improved talent acquisition and retention (28%).

Top talent cares about learning and growing...that is, after all, how they became top talent,” Omosefe noted. “So in order to attract and retain top talent, you have to make it clear that yours is an organization where skills and knowledge will always be growing.”

Not only does having a solid upskilling strategy help organizations attract and keep top talent, but those improvements to talent acquisition and retention can also have a direct impact on a company’s bottom line. “Between losing a member of staff, recruiting for that role, and onboarding and training for the position, that process can cost as much as a full year’s salary for that role,” Parker pointed out. By using upskilling to promote from within and keep employees with the company, an organization can save on those costs and then reinvest in other areas of their business.

By continually investing in your employees’ growth and helping them develop new skills, you’re also laying the foundation for innovation, success, and growth for your organization. “Upskilling is an investment that ensures long-term growth,” Omosefe said.

Upskilling offers significant advantages for organizations, but it’s also a major win for employees. “From the perspective of an employee, it's enticing to join a team where you'll be engaged in your work because you know you're growing,” said Omosefe. “It's a simple choice to stick around when you know that not only will there be opportunities for advancement, but also that your organization is actually going to support you mastering the skills needed to move forward.”

4 Expert Tips for Effective Upskilling

An effective upskilling strategy is a must if you want your team — and your organization — to thrive. Here’s what experts recommend.

1. Identify what your company needs…

Having your employees learn new skills just for the sake of learning them isn’t the most effective approach to upskilling. If you want your upskilling strategy to benefit your organization, you need to figure out what skills gaps exist within your business, and then build an upskilling strategy around those gaps.

“Like all good learning strategies, an effective upskilling strategy is planned backward,” said Omosefe. “Start with the end in mind; determine where you want to be in terms of employee skill and capability — and then identify the gaps between where you want to be and where you are currently.”

For instance, if one of your company’s goals is to get into the Web 3.0 space, you might consider investing in training your engineering team on blockchain technology. Or perhaps your long-term goal is to improve company culture. In this scenario, you might roll out an L&D initiative to help your HR team build the skills necessary to bring your desired organizational culture to fruition, whether that’s through trainings on DEI or nonviolent communication in the workplace, or different tools and software to improve employee experience. In order to get the maximum benefit from upskilling, you need to determine what kind of skills your organization actually needs — and then use those needs to drive your strategy.

2. …and what your employees want.

Identifying what your organization needs is an important part of building a successful upskilling strategy. But arguably even more important is identifying what your employees want

In order for upskilling to be effective, managers need to schedule one-on-ones with their employees to discuss their career goals and how they’d like to grow. From there, managers can identify what skills each direct report needs to learn, improve, or develop in order to take the next step in their careers. Then, the pair can work together to create an individual development plan to help the employee achieve their goals.

For example, say you’re a director of marketing and you’re meeting with one of your junior marketing assistants to discuss their career trajectory. Once you know where they want to go in their career, you can work to create a development plan that takes them from where they are to where they want to be (like from marketing assistant to marketing manager, for example). Next, you can use a competency matrix to identify what skills they need to develop (e.g., People management, copywriting, or marketing analytics) before they can transition into their next desired role. Then build your upskilling approach around developing those skills.

Involving your employees in your upskilling strategy not only ensures that they’re getting to develop skills that are in line with their career goals, but it can also give employees a sense of ownership in the process, which can make them more likely to follow through on developing the skills they need to advance.

“Engage the employees to the fullest extent so they see themselves in the initiative,” Parker advised.

3. Don’t forget about soft skills.

Often when organizations think about upskilling, they think about it in terms of hard skills — helping their employees develop the specific knowledge, abilities, or technical know-how needed to grow and progress in their careers. And while developing hard skills is important, when it comes to upskilling, soft skills are just as essential.

Investing in developing your workforce’s soft skills (e.g., flexibility, adaptability, leadership, collaboration, or communication) can help employees become more well-rounded team members, which will not only help them grow in their careers, but can also have a positive impact on company culture and the overall workplace environment.

Plus, investing in soft skills pays off: Research by Assistant Professor in Applied Economics at MIT Sloan School of Management Namrata Kala, in collaboration with her colleagues at University of Michigan and Boston College, found that a year-long workplace training program in a factory setting in India that focused on soft skills delivered a whopping 250% return on investment — and that was just within eight months of the program’s completion.

Upskilling soft skills (like training your managers to help develop their listening skills) is just as important as upskilling hard skills (such as investing in software training), so make sure you’re balancing the two for the best results.

4. Sell the benefits of upskilling.

Upskilling doesn’t just benefit the organization; it also directly benefits employees. But developing new skills takes time and energy. So if you want your upskilling strategy to succeed, you need to generate buy-in from your employees.

Whenever you roll out a new upskilling initiative, make sure you’re communicating to your employees how that initiative will support their professional growth. Sell them on the benefits of learning and developing these new skills and how it will set them up to take the next steps in their careers, both in terms of career or title progression and compensation increases.

If you’re not sure how to position your upskilling strategy, loop in the communications experts at your organization to help build the case. “Consider bringing in your internal communications team to ensure that upskilling opportunities…are presented in a compelling manner,” Omosefe recommended.



If you want to attract and retain top talent and foster growth and innovation within your organization, you need an effective upskilling strategy. These expert tips and best practices will help your organization build a strategy that supports your employees’ professional growth — and helps your organization thrive in the process.

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