How to upskill your employees: A 6-step strategy

Learning how to upskill employees effectively is one of the most essential leadership capabilities in resilient organizations. Through systematically upskilling your employees, you are both preparing the business to fill available gaps as well as creating pathways for internal growth that reduce costly external hiring and employee turnover. You can achieve this through a deliberate focus on two key strategies:

Upskilling: Teaching a person in your team advanced skills to help them excel in their current role.

Reskilling: Training a person in a new set of skills to prepare them for a different role within the organization.

In the words of Mikell Parsch, CEO of global IT training company New Horizons Computer Learning Centers: “Companies are having to change what they do and how they do it. The double change — pace of technology and pace of business evolution — is making workplace skills training essential." The rapid adoption of new technologies, such as AI, is accelerating the need for organizations to build robust and up-to-date upskilling programs.

Here’s how leading organizations upskill employees at scale. Benesch, a premier civil engineering and professional services firm, exemplifies this approach. Facing fierce competition for skilled AEC (Architecture, Engineering, and Construction) professionals, Benesch recognized that traditional hiring wasn't enough.

As their talent development leader explains, "Everyone's hiring, and we have to stand out. Our people are our greatest asset, and we invest in them through our learning and development initiatives. We take into consideration what they want to do with their careers and help them get to that point." The company implemented a comprehensive skills mapping initiative to provide a detailed understanding of competencies within the organization, helping identify gaps and upskilling opportunities for development while aligning training programs with both company needs and individual career aspirations.

How to build the business case for upskilling employees

Building a future-ready workforce is now business-critical. The World Economic Forum's Future of Jobs Report 2025 projects that nearly six in ten workers will require significant training by 2030 to meet evolving business needs. For the people in your business, this is more than just job security. It’s also about opportunity, growth, and having a meaningful role in your organization's future.

Organizations often underestimate people’s appetite for development. As Cornerstone's workforce development experts have noted, "58% of the workforce needs new skills to successfully do their jobs today, and 70% of workers indicate they would switch jobs if offered opportunities to learn new skills." This reveals that the challenge isn't willingness on the part of employees, but rather the organizational capacity to deliver relevant, personalized learning experiences that align with both individual aspirations and business needs.

The good news is that when it comes to upskilling your employees, your workforce is ready and willing. A recent found that 77% of employees are eager to learn new skills or completely retrain. The organizations that bridge the gap between this ambition and real opportunity will be the ones that are best prepared for the future of work.

How to get manager buy-in when you upskill employees

Managers' buy-in is a critical success factor when upskilling employees. One of the most effective ways to gain their support is by providing clear, data-backed insights that show how targeted learning investments directly impact team performance and employee engagement. To secure buy-in:

• Present a skills gap analysis to show where capability shortfalls impact performance.

• Link learning investments directly to productivity, engagement, and hiring metrics.

• Cite evidence: 87% of organizations expect to face skill gaps within five years (McKinsey).

• Emphasize that upskilling fills roles faster and more affordably than external hires.

• Provide role-based learning paths aligned with real-time team needs.

• Collect feedback from managers and existing employees regularly to refine upskilling strategies and keep skills profiles current.

• SHRM data reinforces the business case for upskilling employees: organizations that invest in learning and development see stronger retention and improved hiring efficiency, both of which are critical for managers under pressure to deliver results.

Pair these insights with accessible, role-based learning paths that align to real-time business needs, and managers will not only buy into the upskilling and reskilling initiative, but they’ll become its champions within the business.

A 6-step framework for effective upskilling and reskilling

Here’s how to upskill employees using this structured, data-driven framework with a strategic approach that connects the learning process directly to business outcomes. This framework is designed to address reskilling or upskilling needs across the entire organization, ensuring all departments benefit from workforce development. By implementing the framework, organizations can improve performance at both the individual and organizational levels.

Step 1: Start with a skills gap assessment

You can’t solve a problem that you don’t understand. Before you can build skills, you first need to identify your most critical gaps. A comprehensive skills gap assessment will help you identify skills you have in your business versus the skills you need to achieve organizational goals. This data-driven foundation ensures your investments are targeted at the areas that will have the greatest business impact.

For example, a retail company plans a major strategic shift to e-commerce. A skills gap assessment reveals that while they have strong in-store sales skills, they have a critical organizational gap between "digital marketing analytics" and "supply chain logistics." This allows them to focus their Learning and Development budget on these two specific areas to support the new business goals.

In summary:

• Audit current roles, functions, and capabilities across current employee base.

• Use surveys, performance data, or AI tools to assess proficiency in technical and soft skills.

• Identify high-impact gaps tied to business goals.

Step 2: Build personalized, role-based learning paths

Generic, one-size-fits-all training doesn’t work. To drive engagement, learning must be relevant to the individual employee. By leveraging the data from your skills assessment, you can create personalized learning paths that guide people toward proficiency in their current role (upskilling) or prepare them for a different one (reskilling). A modern learning platform can automate the delivery of these paths, suggesting content that aligns with an employee's career goals and the organization's needs.

Here’s how to reskill employees for internal mobility: For example, to transition a high-performing "Customer Support Rep" to a "Salesforce Administrator" role, their personalized learning path might include:

Month 1: Foundational e-learning modules on CRM basics.

Month 2: A project-based course on building custom reports.

Month 3: Mentorship with a senior admin and a final capstone project that demonstrates their expanded skill set.

Connecting upskilling and reskilling to career mobility

Effective upskilling and reskilling programs don't build skills in isolation, but rather, they create clear pathways to career advancement within the organization. By linking skills development directly to internal mobility opportunities, organizations can demonstrate tangible career progression while filling critical roles from within.

A powerful learning platform can map skills data to available career opportunities, showing employees exactly which competencies they need to develop for their next role. This transparency transforms upskilling from an abstract development activity into a concrete career strategy, while simultaneously securing employee buy-in.

As an example, let’s take a marketing coordinator interested in moving into data analytics might follow a structured 6-month learning path:

Months 1-2: Complete foundational courses in Excel and SQL basics
Months 3-4: Develop proficiency in data visualization tools like Tableau and take more advanced programming languages like Python and R.
Months 5-6: Apply skills through cross-departmental projects while being mentored by a senior analyst

The business impact is substantial. According to Gartner, employee willingness to go above and beyond at work is 27% higher, and employee intent to stay is 33% higher at organizations with a more vibrant internal labor market. The same research also shows that employee turnover due to a lack of future career opportunities costs an organization $49 million per year.

But many organizations struggle with upskilling implementation. A May 2024 Gartner survey of 3,375 employees found that one in three employees feel they could have a bigger impact on another role in their organization, while only 6% of respondents say that their organization is excellent at enabling internal mobility.

The key is making career pathways visible and achievable. When employees can see how their learning investments translate directly into advancement opportunities, engagement with upskilling programs increases dramatically while reducing the costs and risks associated with external hiring for critical roles.

Step 3: Deliver learning in the flow of work

For learning to be effective, it must be accessible. The most successful reskilling and upskilling programs deliver training directly within the flow of work. This means moving beyond formal, off-site workshops and embracing methods like:

Microlearning: Short, bite-sized content consumption that addresses a specific skill-need and supports continuous skill development.

Project-based learning: Applying new skills to real-world business challenges.

Social learning: Creating channels for employees to learn from and teach one another, fostering professional development across teams.

For example, a sales team member about to make a prospecting call accesses a two-minute microlearning video on "Handling Common Objections" directly within their CRM, allowing them to apply the new skill moments later.

Step 4: Foster a culture of continuous learning

Upskilling and reskilling are not one-off exercises; they are ongoing business functions. Success requires fostering a culture where continuous learning is valued, encouraged, and rewarded, ideally through integrated performance management systems.

This approach to uncovering how to upskill employees is validated by global business leaders; the WEF report found that 85% of organizations identify upskilling the current workforce as their most common workforce strategy. When leaders champion development and provide time and resources, people internalize growth as a core part of their job.

The following are tactics that will work:

• Dedicate regular time for self-directed learning (“Development Fridays”).

• Encourage leaders to model learning and celebrate progress.

• Integrate learning achievements into performance reviews as best practice.

For example, a company implements "Development Fridays," where employees are encouraged to dedicate two hours to their learning paths, and managers are prompted to recognize and share learning achievements in weekly team meetings to celebrate progress and boost employee satisfaction.

Mentorship and coaching programs

While structured learning paths provide the framework for skill development, mentorship and coaching relationships accelerate knowledge transfer and provide the human connection that makes learning stick. Effective mentorship programs pair experienced employees with those developing new competencies, creating valuable knowledge transfer while strengthening organizational culture.

Mentorship programs excel at addressing the practical application gaps that formal training often misses. While a course might teach project management theory, a mentor can share real-world insights about navigating organizational dynamics, handling difficult stakeholders, and avoiding common pitfalls that only come with experience.

The business case for mentorship is compelling. Four in five organizations that offer formal mentorship programs find them effective in addressing talent shortages, according to Fortune. Many HR executives (54%) rank coaching and mentoring as the top area for skills improvement among people managers, while McKinsey research found that the top reason employees cited for quitting previous jobs was a lack of career development and advancement (41 percent).

Modern mentorship programs extend beyond traditional one-on-one relationships to include:

• Reverse mentoring: Younger employees sharing digital and technological expertise with senior staff

• Group mentoring: Cross-functional teams learning together through shared challenges

• Micro-mentoring: Brief, focused interactions addressing specific skill development needs

• Peer coaching circles: Employees at similar levels supporting each other's growth

For instance, a technology company might implement a structured mentorship program where senior developers guide junior team members through complex coding challenges while simultaneously being reverse-mentored on emerging technologies and modern development practices. This bidirectional knowledge transfer ensures that both technical expertise and industry innovation flow throughout the organization.

Successful mentorship programs require structure and support. Clear objectives, regular check-ins, and defined outcomes ensure that both mentors and mentees gain value from the relationship while contributing to broader organizational learning goals.

Step 5: Measure the ROI of your internal learning programs

To secure ongoing executive buy-in for employee upskilling strategy, you must be able to measure and report on the return on your investment. Track metrics that connect directly to business value, such as:

Time-to-fill for key roles: (e.g., reducing the average time to fill a senior engineering role from 90 days to 30 days by hiring internally).

Internal mobility rate: (e.g., achieving a 25% increase in the internal fill rate for critical leadership roles).

Employee retention: (e.g., seeing a 15-point higher retention rate for training program participants vs. non-participants).

Skills proficiency: Tracking the measurable improvement in key skills across teams and the organization.

For example: By tracking these metrics, an organization might report to leadership that its reskilling program successfully filled 20 critical tech roles internally over the last year, saving an estimated $500,000 in recruitment fees and reducing the average time-to-productivity by 45%.

The compelling business case upskilling investment.

When measured correctly, investing in upskilling employees can pay worthwhile dividends. As Ryan Eudy from Cornerstone notes, "For every dollar invested in training, companies received $4.53 in return, that's a 353% ROI.". He adds that according to a report by True Focus Media, companies utilizing e-learning tools have the potential to boost productivity by 50%. “For every $1 the company spends, it's estimated they can receive $30 worth of productivity." Conversely, nearly 25% of employees leave their jobs because of inadequate training and development opportunities.

Learning programs must include leadership

Leaders play a crucial role in modeling how to upskill employees and support their team’s growth. Future-ready companies invest in building the skills of their leaders just as deliberately as they do in technical training. As business complexity grows, so does the need for adaptive, emotionally intelligent, and digitally fluent leaders.

Effective employee upskilling includes leadership capability building. Focus on the following:

• Adaptive decision-making in fast-changing environments

• Coaching and emotional intelligence

• Hybrid and remote team management

• Data and AI fluency for performance insights

Modern learning platforms can deliver curated leadership academies that identify high-potential talent early and provide clear internal career growth pathways. This both strengthens the succession of pipelines and reinforces a culture where learning and leadership go together.

Step 6: Scaling learning in a global context

For multinational enterprises, delivering equitable and effective upskilling requires regional nuance. A global strategy must go beyond translation; it needs to ensure content is culturally adapted to local norms, values, and learning preferences.

In regions where bandwidth is constrained or device access is limited, downloadable or offline learning formats can ensure accessibility. Compliance also matters; programs must align with local labor laws, professional requirements, and cultural expectations.

AI-powered learning platforms can help tailor delivery while preserving consistency. By adapting learning pathways to regional contexts while maintaining a unified learning framework, global organizations can empower employees everywhere to grow.

To summarize:

• Adapt content culturally, not just linguistically.

• Provide offline access in low-bandwidth regions.

• Ensure compliance with local labor laws and credentials.

• Use AI-powered localization to balance consistency and flexibility.

By tailoring delivery while maintaining a unified framework, global enterprises achieve equitable learning experiences.

The role of AI and technology

AI now helps organizations understand how to upskill employees at scale, mapping current and desired skills to learning content automatically.

As we’ve noted before, "AI revolutionizes training programs by identifying skill gaps at scale and creating personalized learning paths. Based on job titles, current competencies, and required skills, AI generates customized course recommendations that accelerate upskilling initiatives while ensuring relevance to each employee's role and aspirations." This technology enables organizations to move beyond one-size-fits-all training to truly individualized development experiences.

Chief People Officer at Cornerstone, Carina Cortez, adds that “The gold standard for learning and development is a one-to-one approach that meets employees where they are in their career journey. AI enables organizations to scale this personalization, making Learning and Development programs more relevant, timely, and meaningful. With AI, managers and HR teams can better support their team members by enabling their long-term growth. When done right, this builds trust, increases engagement, and improves performance."

Modern AI learning tools redefine how to upskill employees at scale. They can:

• Map and analyze organizational skills automatically.

• Create personalized learning paths aligned with job roles.

• Generate real-time learning recommendations.

• Provide dashboards that measure progress and business impact.

Even traditional institutions are embracing modern upskilling approaches with measurable results. Penn State University transformed from a manual, DOS-based training system to a comprehensive learning platform that revolutionized talent development.

The impact was immediate and quantifiable. As their implementation leader noted, "Look what we can do now. We're getting our employees better products, better service even through our department." The transformation went beyond compliance tracking to supporting growth and development, contributing significantly to employee retention and engagement. The comprehensive capabilities allowed Penn State to foster a culture of continuous learning and professional growth, with employees gaining access to broader development opportunities that aligned personal growth with the university's mission.

This level of insight helps HR leaders understand how to upskill employees while providing real-time data to optimize strategies and resource allocation. Learning becomes continuous and contextual, agile enough to adapt to shifting priorities and powerful enough to close gaps before they become business risks.

With AI, learning is no longer reactive. It’s responsive, scalable, and tightly aligned with both personal aspirations and enterprise outcomes.

Frequently asked questions

What is the main difference between upskilling and reskilling?

Upskilling focuses on enhancing an employee's existing skills to make them better at their current job. Reskilling focuses on teaching an employee a new set of skills to prepare them for a different job within the organization.

How does upskilling benefit employees directly?

It increases their value and effectiveness in their current role, often leading to better performance and career advancement. More importantly, it demonstrates that their employer is invested in their growth, which, as the PwC survey shows, is something employees actively want.

How do we get manager buy-in for these programs?

Manager buy-in is critical. The key is to provide them with data. Show them the current skills gaps on their teams and how targeted upskilling programs can directly address those gaps, leading to improved team performance and a reduction in the need for difficult external hiring.