Blog

Risks in Upskilling Initiatives: What to Watch Out For and How to Mitigate Them

Written by TalentJam | Aug 25, '25

Upskilling is a strategic investment in an organisation’s workforce, aimed at closing skill gaps, enhancing employee capabilities, and preparing teams for future demands. However, implementing upskilling initiatives comes with its own set of challenges and risks. If not managed effectively, these risks can diminish the return on investment (ROI) and lead to disengagement or resource wastage.

By aligning programs with business needs, fostering a culture of continuous learning, ensuring equal access, and providing strong managerial support, organisations can mitigate these risks and ensure successful outcomes for both employees and the business.

In this article, we outline the common risks associated with upskilling programs and suggest some common strategies to mitigate them.

Misalignment with Business Needs

Risk: Upskilling efforts that do not align with current or future business needs can result in employees developing skills that are not relevant, leading to wasted time and resources.

How to Mitigate:

  • Conduct a Skills Gap Analysis: Before launching an upskilling initiative, perform a skills gap analysis to identify the critical skills needed to support business objectives.
  • Set Clear Learning Objectives: Define the outcomes of each training program in relation to business goals. For example, if the goal is digital transformation, focus on upskilling in data analytics, cloud computing, and digital literacy.
  • Involve Key Stakeholders: Ensure that leaders, managers, and department heads are involved in the planning process to provide input on the strategic skill priorities for their teams.

Resistance to Change

Risk: Employees may resist upskilling initiatives due to fear of change, lack of interest, or concern that the new skills might not be relevant to their roles. This resistance can lead to low engagement and participation rates.

How to Mitigate:

  • Promote a Growth Mindset: Foster a culture that values continuous learning and frames upskilling as an opportunity for personal and professional growth.
  • Communicate the Benefits Clearly: Clearly articulate how upskilling will benefit employees’ career development, increase job security, and enhance their employability.
  • Offer Support and Incentives: Provide support through mentoring and coaching, and offer incentives like career progression opportunities, bonuses, or public recognition for those who actively participate.

Insufficient Resources or Budget

Risk: Upskilling programs can be resource-intensive, requiring investment in training platforms, course materials, and time away from regular duties. Insufficient funding or resources can result in incomplete or ineffective programs.

How to Mitigate:

  • Prioritise High-Impact Skills: Focus on developing critical skills that offer the highest return on investment (ROI). For example, prioritise leadership skills if succession planning is a key objective.
  • Leverage Cost-Effective Solutions: Use scalable digital learning platforms like Coursera, Udemy for Business, or LinkedIn Learning that offer high-quality content at a fraction of the cost of traditional training.
  • Set a Realistic Budget: Include all costs in your budget, from learning materials and software to employee time off for training. Ensure senior leadership supports the budget allocation.

Employee Burnout and Overload

Risk: Employees may feel overwhelmed if they are expected to upskill while maintaining their regular workload. This can lead to burnout, disengagement, and even attrition.

How to Mitigate:

  • Integrate Learning into the Workflow: Use on-the-job training, microlearning, and blended learning approaches that fit into the daily work routine.
  • Adjust Workloads: Ensure that employees have the bandwidth to focus on learning by adjusting their current work responsibilities or allowing flexible time for training.
  • Encourage Work-Life Balance: Promote a balanced approach by offering learning resources that can be accessed at the employee’s convenience, including during quieter periods.

Uneven Access to Upskilling Opportunities

Risk: Some employees may not have equal access to upskilling opportunities due to location, lack of resources, or managerial bias, which can lead to disparities in skills development across teams.

How to Mitigate:

  • Create an Inclusive Learning Environment: Provide digital learning options that are accessible to all employees, including remote workers, part-time staff, and those with different learning needs.
  • Track Participation by Demographics: Use analytics to monitor participation rates across different groups to identify and address any gaps in access or support.
  • Offer Multiple Learning Formats: Cater to different learning styles and preferences by providing a mix of online, in-person, and self-paced training options.

Limited Immediate ROI

Risk: Upskilling is a long-term investment, and organisations may not see immediate benefits. This can create frustration or scepticism about the value of the initiative.

How to Mitigate:

  • Set Short- and Long-Term Metrics: Track progress through short-term indicators like course completion rates and certification attainment, as well as long-term metrics like internal mobility, retention, and productivity.
  • Communicate ROI Expectations Clearly: Set realistic expectations with leadership about the time frame for seeing a return on upskilling investments. Emphasise long-term benefits, such as reduced recruitment costs and improved innovation.
  • Showcase Early Wins: Highlight quick wins and small successes, such as improved efficiency in a particular process or project success due to new skills, to build momentum and support.

Knowledge and Skill Decay

Risk: If newly acquired skills aren’t applied regularly, employees may lose proficiency, especially in rapidly evolving technical fields.

How to Mitigate:

  • Provide Continuous Learning Opportunities: Offer follow-up courses, regular refresher sessions, and access to ongoing learning resources.
  • Encourage Real-World Application: Assign projects, tasks, or responsibilities that allow employees to apply their new skills immediately and frequently.
  • Create Learning Communities: Set up peer-learning groups, mentorship programs, and internal knowledge-sharing platforms to reinforce new skills.

Lack of Managerial Support

Risk: Without active managerial support, employees may not prioritise upskilling, and the programs may not align well with team goals.

How to Mitigate:

  • Train Managers to Support Upskilling: Provide managers with the tools and knowledge to support their teams’ development, including setting realistic goals, providing feedback, and integrating learning into team activities.
  • Involve Managers in Goal Setting: Ensure managers are part of the development planning process to create alignment between individual upskilling and team objectives.
  • Recognise and Reward Supportive Managers: Publicly acknowledge and reward managers who actively support upskilling efforts within their teams.

Failure to Personalise Upskilling Programs

Risk: Generic or one-size-fits-all pathways may fail to cater to diverse employee goals and career aspirations, reducing their relevance and appeal.

How to Mitigate:

  • Use Data to Personalise Learning Paths: Leverage skills assessments and employee feedback to create customised learning paths that align with each employee’s personal career goals and organisational needs.
  • Offer Learning Options: Provide diverse learning options such as microlearning, instructor-led training, or experiential learning to cater to individual learning preferences.
  • Offer Multiple Pathways: Develop a variety of pathways, including technical, managerial, specialist, and cross-functional tracks, to cater to different career aspirations.
  • Encourage Flexibility: Allow employees to switch between pathways or modify their plans based on changing interests or goals.

Over-emphasis on Technical Skills

Risk: Focusing solely on technical skills can result in a lack of soft skills, such as leadership, communication, and critical thinking, which are essential for holistic employee development.

How to Mitigate:

  • Balance Hard and Soft Skills Training: Include soft skills training as part of the upskilling curriculum to ensure employees are well-rounded.
  • Conduct Regular Soft Skills Assessments: Evaluate interpersonal and leadership skills as rigorously as technical skills, using 360-degree feedback and peer reviews.
  • Promote Interdepartmental Learning: Encourage cross-functional learning experiences that require both hard and soft skills, such as leading cross-departmental projects.

Skills Gap and Training Bottlenecks

Risk: Employees may face difficulties progressing through career pathways due to insufficient training resources or a lack of mentorship and support.

How to Mitigate:

  • Invest in Learning and Development (L&D): Align L&D programs with career pathway requirements. Ensure that there are enough resources to support employees at all levels, from foundational training to advanced skills development.
  • Create a Mentor Network: Establish mentorship programs where experienced employees can guide others through complex skill-building activities.
  • Utilise Digital Learning Platforms: Offer digital learning platforms that provide on-demand training, making it easier for employees to access learning resources when needed.

Poor Communication of Pathways

Risk: Employees may not understand how the available pathways work, and what steps are needed to progress, even if they are well-designed.

How to Mitigate:

  • Develop a Clear Communication Plan: Create a structured communication strategy that explains how career pathways work, the benefits they offer, and how employees can get started.
  • Use Multiple Channels: Leverage multiple communication channels such as internal newsletters, intranet posts, workshops, and manager one-on-ones to disseminate information.
  • Provide Visual Aids and Guides: Use visual aids like career maps, pathway flowcharts, and step-by-step guides to make the pathway process more accessible and easier to understand.
  • Explicitly Link Pathways to Personal Development Plans (PDPs): The employee’s PDP should explicitly reference the development pathway(s) they are on, showing what actions and targets or goals will lead to which development track. This offers the employee agency to progress toward their professional development and career goals.

Difficulty in Measuring Progress

Risk: Without the right metrics and tools, tracking progress through career pathways can be difficult, making it challenging to evaluate success and make improvements.

How to Mitigate:

  • Use Digital Talent Management Tools: Implement software solutions like talent management systems or learning management systems that can track employee progress, skill acquisition, and performance.
  • Establish Clear Metrics and Milestones: Define what success looks like for each stage of the pathway, including skills mastered, performance goals met, and certifications achieved.
  • Regularly Review Data: Use analytics and reports to monitor employee progress and pathway effectiveness and make data-driven adjustments as needed.

Overcomplication of Pathways

Risk: Career pathways that are too complex or have too many steps can confuse employees and managers, leading to low engagement and difficulty in tracking progress.

How to Mitigate:

  • Simplify Pathways: Focus on the most critical milestones and skills for each pathway and remove unnecessary layers that add complexity.
  • Create Visual Roadmaps: Use simple visual roadmaps that outline the main stages, key skills, and required steps for progression.
  • Automate Tracking and Communication: Leverage technology to streamline tracking and automate updates, so employees and managers always know what is next.

Bias in Career Progression

Risk: Unconscious biases can affect who gets opportunities for growth and who progresses through career pathways, creating inequality and reducing overall effectiveness.

How to Mitigate:

  • Implement Standardised Assessments: Use consistent, objective criteria for evaluating progress and readiness for advancement.
  • Use Bias Mitigation Techniques: Train managers and leaders on recognising and mitigating unconscious bias in talent development and promotions.
  • Track Diversity Metrics: Regularly review pathway participation and progression rates by gender, ethnicity, and other demographics to identify and address any disparities.

Unrealistic Expectations

Risk: If career pathways are presented as fast tracks to promotion or major salary increases, employees may become frustrated when progress takes longer than expected.

How to Mitigate:

  • Set Realistic Expectations: Clearly communicate the expected timeline for progression and reinforce that development often includes lateral moves or skill-building rather than immediate promotions.
  • Emphasise Continuous Growth: Position career pathways as part of a broader journey of continuous professional development, not just a ladder to climb.
  • Provide Regular Feedback: Keep employees informed of their progress, acknowledge small wins, and help them see how they are moving forward, even if major milestones take time.