Gülcan YaylaA few years ago, I spoke with the HR director of a financial services company. They had automated their customer service processes — 12 out of a 40-person team could no longer do their jobs the way they used to. Job descriptions had changed, competency requirements had changed.
"What are you going to do with these 12 people?" I asked.
"We don't want to lay them off," she said. "But we don't know what to do either."
Hearing this question has become something I'm used to. Automation, AI tools, and rapidly changing job descriptions — many companies are choosing to invest in their own people rather than resorting to layoffs. But there's a huge gap between the decision to "invest" and the plan for "how."
Upskilling and reskilling bridge exactly that gap. In this article, we'll walk through how to build a program from scratch, step by step.
The Difference Between Upskilling and Reskilling
The terms upskilling and reskilling are often used together, but they are actually two distinct strategies:
Upskilling: The employee continues in the same or a similar role, but the skills required for that role deepen or expand. For example: teaching a sales representative to use AI tools in the sales process, or equipping an accountant with data analysis skills.
Reskilling: The employee transitions to an entirely different role. Their former position has either been eliminated or changed significantly — a new career path is opening up. For example: transforming a data entry specialist into a customer success manager, or turning a call center representative into an AI tool trainer.
Both are valuable, and both require different resources and time investment. Before designing your program, clarify which one takes priority.
Why Now?
According to the World Economic Forum, by 2030, half of the global workforce will need to acquire new skills. This figure may seem abstract, but it's already playing out concretely: in the finance and retail sectors, AI automation is advancing rapidly, and employee profiles in these industries are changing fast.
Rather than trying to solve this through external hiring, a "grow from within" strategy is becoming the preferred approach for organizational sustainability.
Preparing an employee for a new role through reskilling costs nearly 60% less than hiring externally (when you factor in both the recruitment process and the onboarding period).
How to Build an Upskilling and Reskilling Program: 7 Steps
Step 1: Needs Analysis — Who, What, Why?
Before building the program, we need to answer these questions: Which roles are at risk or changing? Which new competencies are a strategic priority? And who is most likely to adapt to these competencies quickly?
Needs analysis operates on two layers:
Organizational layer: Where is the company headed strategically over the next 2-3 years? Which processes will be automated? Which new departments, products, or markets are on the horizon? The answers to these questions reveal which skills will become critical.
Individual layer: Each employee's current competencies and learning capacity. Employee competency assessments are the primary data source for building this layer.
Combining both layers produces the answer to "who needs to learn what."
Step 2: Define Target Role Profiles
This is especially critical for reskilling: there must be a clear profile of the role you want to transition employees into. If you're saying "customer success specialist," what competencies does success in that role require, and at what minimum level?
Build this profile from three sources: people who are already successful in that role (internal benchmarks or external references), industry standards, and job listing analysis (to see what the market is looking for in that role).
Step 3: Select Participants and Build Ownership
A common mistake: forcing participation in a reskilling program with "we have to send these people." This both reduces learning efficiency and creates resentment.
A better approach: voluntary pre-selection. The question "The company needs people in role X and we're evaluating you for this journey — are you interested?" brings a very different energy. The person feels chosen, not forced.
But volunteering alone can't be the only criterion — learning capacity, the distance between current competencies and the new role, and career motivation should also be evaluated. A mini preliminary assessment clarifies this process.
Step 4: Design the Learning Path
Every program should include these three elements:
Knowledge acquisition: Theoretical foundation, conceptual framework. Classroom training, online modules, reading materials. This is typically the easiest part to design but the least effective on its own.
Application: Trying what's been learned in real or simulated work contexts. Case studies, project assignments, job shadowing. The brain only builds the bridge between knowledge and competency through hands-on practice.
Coaching and feedback: Regular mentorship, progress reviews, manager support. If participants feel alone, the dropout rate increases dramatically mid-program.
Balancing these three elements is critical. Most programs spend too much time on the first element and neglect the second and third.
Step 5: Set a Time Frame
Upskilling can typically be managed with 1-3 month programs — a new competency layer is being added to an existing role.
Reskilling takes longer: 3-6 months is a realistic framework, and for some roles it can extend to 12 months. If employees are expected to continue their current work during this period, program design must be carefully considered — when learning load clashes with workload, both suffer.
Best practice allocates 20-30% of working time to learning. Less than that: insufficient depth. More than that: workflow disruption.
Step 6: Measure Progress
Measure progress throughout the program — not just at the end, but at intermediate checkpoints. You can do this in three ways:
Knowledge tests: Brief assessments after each module is completed. These show whether concepts have been understood.
Project evaluation: A real work output — a report, analysis, or presentation. Can they translate learning into practice?
Manager observation: Is behavioral change reflected in the work environment? This is the latest signal to emerge but the most valuable.
Have an early intervention mechanism for participants who aren't meeting targets. Identifying "this employee isn't progressing" mid-program is far better than declaring "the program failed" at the end.
Step 7: Job Transition and Follow-Up
The final step of a reskilling program is the most critical: what happens to the learner next?
The transition plan to the new role must be clear — not "we'll figure it out after the program ends." On what date, in which position, under which manager, with what responsibilities do they start? Providing this clarity from the beginning keeps participants motivated and builds trust in the company.
A 90-day follow-up after the program matters as well. Are they succeeding in the new role? What additional support do they need? What did the program teach well, and what did it leave out? This feedback makes each subsequent cohort significantly better.
Reskilling in Practice: A Real-World Example
Let me return to the financial services company's 12-person customer service team. We spoke again six months later. What had they done?
They had enrolled 8 people in a reskilling program. Target roles: customer relationship specialist and digital tool trainer. The program lasted 4 months — 2 days per week for learning, 3 days continuing in their existing role. Seven of the participants who completed the program had started working in their new roles.
"Instead of hiring 7 people externally, we developed them internally," the director said. "They already know our company culture, they know our customers. The adaptation period was very short."
One person entered the program but dropped out midway — they decided they wanted a different direction. That's also an outcome, not a failure.
Common Mistakes
Only providing training, not building a program: "We did a 3-day course, reskilling is complete." No. Training is one part of the program, not the whole thing.
Moving forward without manager buy-in: The program was built by HR, but the employee's manager isn't involved. The employee can't find time for on-the-job learning because their manager keeps them occupied with old tasks every day.
Leaving the career path undefined: "Finish the program, then we'll see." This kills employee motivation. The destination needs to be clear.
Focusing only on technical skills: Especially in role transitions, technical competency isn't enough. Communication, relationship management, self-management — these skills need to be included in the curriculum.
Final Thoughts
The decision to invest in upskilling and reskilling is one of the biggest trust signals a company can send to its employees. It says: "We're not letting you go — we're growing with you."
But for that message to be real, the program needs to be real. Not a well-intentioned PowerPoint — a program with clear goals, structured content, measurable outcomes, and real career results.
Building this isn't easy. But it's possible — and it gets a little better every time.
Sources: PwC - Reskilling: A Business Case for Financial Services Organisations, World Economic Forum Future of Jobs Report 2025