Mid-Year L&D Checkpoint: 7 Questions Every Learning Leader Should Ask

Posted on 06/02/26 By Lorman Team

As we reach the midpoint of the year, learning and development (L&D) leaders have an opportunity to evaluate the effectiveness of their training programs, workforce development initiatives, and employee learning strategies.

By June, most organizations have already invested significant time and resources into employee training, leadership development, compliance education, and skills development programs. Before planning for the second half of the year, it is important to assess what is working, identify gaps, and ensure learning initiatives remain aligned with business goals.

This mid-year review is especially important as organizations continue to face evolving skill requirements, declining employee engagement, and increasing pressure to demonstrate the business impact of learning and development programs.

According to Gallup's latest State of the Global Workplace research, employee engagement fell to 20% globally in 2025, the lowest level recorded since 2020. The report also found that manager engagement continues to decrease, creating additional challenges for employee development, leadership effectiveness, and workforce performance.

For HR and L&D leaders, these trends highlight the importance of evaluating learning strategies before entering the second half of the year.

The following seven questions can help assess the effectiveness of your learning and development strategy and identify opportunities to improve employee engagement, training adoption, and business outcomes.

1. Are Our Learning Programs Aligned With Business Goals?

One of the most important indicators of a successful learning and development strategy is how well it supports organizational priorities. Training programs should support the outcomes that matter most to the business. As priorities evolve throughout the year, learning initiatives should evolve as well.

Consider whether your current employee training programs are helping address key organizational objectives such as:

• Employee retention and engagement
• Leadership and manager development
• Productivity and performance improvement
• Compliance and risk management
• Workforce development and skills readiness

When learning programs are disconnected from business goals, participation often declines and executive support can become more difficult to maintain.

Organizations that align learning initiatives with measurable business outcomes are better positioned to demonstrate the value of their training investments. As part of your mid-year review, consider how success is being measured. Are learning programs contributing to improvements in retention, employee engagement, leadership effectiveness, productivity, or compliance performance? The more clearly learning outcomes connect to business objectives, the easier it becomes to justify investments, maintain executive buy-in, and identify opportunities for continuous improvement.

For additional guidance, explore our article on creating an effective employee training program.

2. Are Employees Engaging With Training Programs?

Training participation is important, but completion rates alone do not tell the full story. A more meaningful measure of success is whether employees are actively engaging with learning opportunities and applying new knowledge and skills on the job. This may be reflected through manager observations, employee feedback, increased participation in development activities, or visible changes in performance and workplace behaviors.

Low engagement may indicate that:

• Training content feels disconnected from employees' daily responsibilities 
• Learning experiences require too much time 
• Employees do not understand the purpose or value of the training 
• Managers are not reinforcing learning objectives 

Reviewing participation data alongside employee feedback, manager input, and evidence of skill application can help uncover barriers to engagement and identify opportunities for improvement.

Organizations that achieve higher learning engagement often focus on delivering relevant, accessible, and practical training that supports employees in their current roles while preparing them for future growth.

3. Are Managers Reinforcing Employee Learning?

Manager support plays a critical role in learning adoption and training effectiveness.

According to LinkedIn Workplace Learning research, 56% of employees say they would spend more time learning if their manager directed them to complete a course to improve their skills.

Despite this influence, many organizations focus heavily on training content while overlooking the role managers play in reinforcing learning.

Ask the following questions:

• Are managers discussing development goals during one-on-one meetings?
• Are they encouraging employees to apply newly acquired skills?
• Do they understand how learning contributes to team performance and business success?

When managers actively support employee development, learning becomes more relevant and employees are more likely to apply what they learn. Organizations looking to improve learning outcomes should consider investing in manager training and leadership development alongside employee learning initiatives.

4. Are We Developing Skills Employees Want to Build?

Career development remains one of the strongest drivers of employee engagement, retention, and job satisfaction. In fact, LinkedIn Workplace Learning research found that 94% of employees would stay longer at a company that invests in their career development.

As part of your mid-year L&D review, evaluate whether employees can clearly connect learning opportunities to their professional growth.

Consider whether your training programs are aligned with:

• Career advancement
• Internal mobility opportunities
• Leadership development pathways
• Professional skill development
• Future workforce needs

When employees understand how learning contributes to their long-term success, they are more likely to engage with training and take ownership of their development.

For additional insights, read our guide on developing career paths for employees.

5. Are We Addressing Skill Gaps?

Skills gaps continue to be a major concern for organizations across industries. Technological advancements, changing workforce expectations, regulatory updates, and evolving business priorities can quickly create new training needs. A mid-year review provides an ideal opportunity to reassess workforce capabilities and identify gaps that may already be affecting performance, productivity, or employee confidence.

Questions to consider include:

• Which skill gaps are having the greatest impact on performance today?
• Are managers equipped to lead in a changing workplace?
• Do employees have access to training that supports business objectives?
• Are there critical knowledge gaps that could impact performance or productivity?

Conducting regular skills assessments helps ensure learning investments remain aligned with organizational needs.

Our article on performing a skills gap analysis provides a practical framework for evaluating workforce capabilities and identifying development priorities.

6. Is Learning Accessible Within the Flow of Work?

One of the most common barriers to employee learning is lack of time. Employees often recognize the value of professional development but struggle to fit training into already demanding schedules. Modern learning and development programs are most effective when they make learning accessible without significantly disrupting productivity.

Strategies may include:

• Short, focused learning modules
• On-demand training access
• Personalized learning recommendations
• Role-based learning paths
• Opportunities to discuss and apply learning during team meetings

The goal is to integrate learning into the employee experience rather than treating it as a separate activity. Organizations that make learning easier to access often see stronger participation, higher engagement, and better knowledge retention.

7. Are We Preparing for the Skills and Leaders We Will Need Tomorrow?

While it is important to address today's skill gaps, learning leaders must also prepare for future workforce needs. A strong learning strategy should not only solve current challenges but also build capability for the future.

As part of your mid-year review, consider questions such as:

• Are we developing future leaders before leadership vacancies occur? 
• Do employees have opportunities to build skills that support long-term organizational goals? 
• How will emerging technologies, including AI, impact workforce development needs? 
• Are we creating clear development pathways for high-potential employees? 

Future readiness is not limited to technical skills. It also includes leadership, communication, change management, problem-solving, and other capabilities that help organizations adapt to change.

Organizations that invest in future-focused development are often better positioned to navigate workforce transitions, support internal mobility, and build stronger leadership pipelines.

For additional insights, explore our guide on developing career paths for employees.

Looking Ahead: Planning for a Stronger Second Half of the Year

A mid-year learning and development review is more than a reporting exercise. It is an opportunity to strengthen your strategy, improve employee learning outcomes, and ensure training investments support organizational goals.

The most effective organizations continuously evaluate their learning programs, gather employee feedback, identify emerging needs, and adapt their approach as business priorities evolve.

By asking these seven questions, HR leaders, training managers, and learning and development professionals can better assess the effectiveness of their current programs and make informed decisions for the remainder of the year.

Whether your focus is employee engagement, leadership development, compliance training, workforce development, or closing critical skills gaps, a thoughtful mid-year checkpoint can help ensure your learning strategy delivers meaningful results.

If you are evaluating your learning and development strategy for the second half of the year, Lorman can help. Our enterprise training solution provides flexible, role-specific learning designed to support employee development, compliance, leadership growth, workforce readiness, and organizational performance at scale. Schedule a demo to learn more.