Upskilling, Reskilling & Succession Planning for HR Leaders
Last Updated on January 9, 2026 / HR Strategy
Finding the right talent has never been more challenging. Many organizations report that candidates are missing the technical, experiential, or interpersonal proficiencies necessary to succeed. Often, the skilled talent we seek is right under our noses. They are our coworkers who have long stood by the organization waiting for their chance to shine. Recognizing this potential is the first step. Aligning succession planning with targeted upskilling and reskilling efforts is how organizations build a resilient, future-ready workforce.
Why Upskilling and Reskilling Are Critical
3 major trends are reshaping workforce strategy
- Talent scarcity – Organizations struggle to find candidates with the right experience and skills.
- Changing nature of work – Automation and AI are projected to transform a significant portion of U.S. jobs over the next five years, requiring new capabilities.
- Workforce demographic shifts – Younger generations and increasing diversity bring different baseline skills and development needs.
Together, these trends reinforce the need to develop existing talent. Upskilling and reskilling programs allow organizations to adapt quickly and maintain a competitive edge.
The Difference Between Upskilling and Reskilling
Knowing the difference enables HR leaders to deploy the right strategy:
Upskilling
Enhancing the skills an employee already uses, allowing them to perform their current role more effectively. Examples include advanced Excel training for analysts or leadership coaching for frontline managers.
Reskilling
Training employees for new roles or responsibilities, such as moving a support specialist into project coordination or preparing an operations associate for a leadership position.
Both approaches are complementary and should be part of a broader talent strategy.
A Six-Step Approach to Building Skills
Successful upskilling and reskilling programs follow a structured process:
- Determine future skills needs – Use strategic planning and stakeholder input to identify critical skills over the next 1–5 years.
- Conduct a skills gap analysis – Compare existing capabilities against desired skills at organizational, operational, and individual levels.
- Prioritize the gaps – Focus first on skills that will have the greatest impact on performance, risk mitigation, and growth.
- Design a learning plan – Choose methods that match the skill and employee level, such as mentoring, workshops, microlearning, or stretch assignments.
- Implement the plan – Roll out the program with milestones, accountability, and resources.
- Evaluate and iterate – Measure outcomes, gather feedback, and refine the program to improve effectiveness.
Three Levels of Skills Assessment
When planning development, consider these three levels:
- Organizational level – Identify capabilities the company needs to achieve strategic objectives.
- Operational/departmental level – Determine the skills required for specific units or processes, using process maps to understand step-by-step requirements.
- Individual level – Assess what employees currently possess and what they will need to succeed in future roles using performance reviews, career path planning, and competency assessments.
Linking Skills Development to Succession Planning
Upskilling and reskilling are most effective when tied to succession planning. This ensures you have a pipeline ready for critical roles. Key considerations include:
- Timeline planning – Map ramp-up windows for critical positions, noting short-term versus long-term readiness.
- Readiness tiers – Identify employees who are “ready now,” “ready with development,” or “longer-term prospects.”
- Resource allocation – Decide where to accelerate development through coaching, assignments, or targeted training.
This alignment allows HR leaders to forecast promotions, allocate resources efficiently, and maintain operational continuity.
Practical Methods to Close Skills Gaps
- Mentoring and coaching – Particularly effective for leadership and interpersonal skills.
- Stretch assignments and rotational programs – Offer hands-on learning experiences in new roles or tasks.
- Targeted workshops and microlearning – Short, role-specific training modules for scalable development.
- Manager training – Equip leaders to provide effective feedback, coach employees, and support change initiatives.
- Blended approaches – Combine digital learning with in-person practice and follow-up for maximum retention.
Prioritization and Measuring Success
Hone in on skills that deliver the greatest impact. Two guiding questions can help:
- Which skills will produce the most significant performance improvements?
- Which foundational skills do all employees need to elevate the organization to the next level?
Measure program effectiveness through:
- Time-to-fill critical roles internally
- Internal mobility rates
- Ramp-up time to full productivity
- Training completion and competency assessments
- Retention of high-potential employees
- Operational performance metrics linked to the skills
Realistic Timelines
- Quick wins – Frontline upskilling through workshops or microlearning: 3–6 months
- Mid-range impact – Manager development and rotational exposure: 6–12 months
- Long-term results – Executive leadership development and deep reskilling: 1–3 years
Document timelines within your succession plan so stakeholders understand expected outcomes and resource requirements.
Next Steps for HR Leaders
- Identify top 3 roles that must be secured over the next 12–24 months.
- Conduct a focused skills gap analysis for one critical role.
- Launch a pilot development plan using mentoring, stretch assignments, and targeted workshops.
- Track outcomes and refine the approach before scaling across the organization.
Looking for guidance on designing an upskilling and succession plan?
Clark Schaefer Strategic HR helps businesses build targeted, measurable programs that link skills development directly to succession planning. Contact us to discuss a pilot program tailored to your organization’s critical roles.
Written by: Terry Wilson
