Your managers are overwhelmed and it’s quietly draining your talent pipeline, productivity, and retention. When career conversations break down, internal mobility stalls, employee disengagement rises, and top talent walks out the door.

The truth is, most managers aren’t equipped to be career coaches. They lack the tools, visibility, and bandwidth to guide employees down the best personalized development paths. And that’s okay. Because solving this challenge doesn’t mean asking managers to do more. It means rethinking how organizations support strategic career growth at scale.

It’s not that your managers don’t care. The managerial role has evolved, and the expectations have outpaced the support they’re given. For HR and L&D leaders looking to build a future-ready workforce, this article explores how to support workforce development without overburdening your managers.

Why education benefits are your best retention strategy

While HR leaders are faced with the challenge of finding and retaining talent in an environment of shifting company needs, creating an internal pipeline is becoming more difficult in the wake of the “boreout” phenomenon. More employees are bored at work and this means lower productivity and higher turnover rates. 

Companies can overcome this growing disengagement by implementing strategies that enable career development and close the skills gap for young talent. Education benefit programs that solve this career development challenge are impactful, too. Companies that invest in visible career pathways see a 70% boost in retention, translating to millions saved in turnover costs. Their employees are also 2.3 times more engaged in their work.

Unfortunately, managers don’t have the time or expertise to manage consistent, scalable career plans. While there is demand for better career development, companies often rely too much on managers who often already feel overwhelmed. An EdAssist survey revealed that while 75% of managers want their team to access training opportunities, less than half say they have available resources to support their direct reports. 

How to help managers rethink career development

Employees who want more of a challenge at work need structure and follow-up to maximize their potential within the organization. Here are five challenges and solutions that organizational leaders can implement to make career development easier and strengthen the talent pipeline within the organization.

Focus on skills gaps, not poor performance

Challenge: It’s hard for managers to reengage employees by focusing solely on performance reviews.

Solution: A more effective approach is to focus on missing skill sets rather than mistakes made on the job. That’s not a stretch to believe: according to a LinkedIn study, job skill sets have changed 25% since 2015, and that number is expected to jump to 50% by 2027. Navigating this approach and employee upskilling needs is a tough task for most managers without support. They’re not trained to diagnose gaps in the workforce, so consider how HR or L&D can provide a clear framework for these conversations.

Here are a few ideas to take action:

• Offering simple verbiage shifts, like focusing on skills to build instead of problem areas, is an easy way for managers to encourage their direct reports.
• Consider offering tax-free tuition assistance, either direct pay or reimbursement, so employees can pursue education to help bridge those skill gaps. Access to degree or non-degree programs, like certifications, can also significantly improve financial wellness for empolyees.
• You can also help managers connect underperforming employees with clear next steps that make them more engaged at work, like training modules. EdAssist offers a resource for learners called Level Up Studio that can serve as a great entry point for employees (and managers) who don’t yet have a clear development plan in place. Employees can watch videos and listen to podcasts on topics related to career, finance, and education.

Incorporate career conversations outside of the review process

Challenge: Managers often feel blindsided when top talent quit for better opportunities when they never had a conversation about career goals. Don’t wait for annual or semiannual reviews to check in with direct reports about educational and growth opportunities.

Solution: To avoid losing top talent to outside opportunities, organizations need to embed career development into everyday culture, not just performance cycles. Normalize career conversations year-round. Encourage ongoing conversations that focus on development rather than performance and compensation.

Here are a few ideas to take action:

• Scheduling check-ins throughout the year helps make skill building a priority, for both the employee and the business.
• Share specific questions that managers can ask about career goals so they can incorporate development opportunities into regular check-ins, not just during annual reviews.
• But it doesn't need to fall entirely upon your managers’ shoulders. For better results, bring in professional help with expert coaching. These experts help employees find professional direction in the context of their company as well as their personal lives.                                                                         

EdAssist coaches have experience guiding workers through career, academic, and financial concerns. Outside support is a much more realistic approach to talent development because you have coaches who can respond to employee objections and create personalized solutions that help turn their professional development dreams into reality.

Train managers to refer, not advise

Challenge: EdAssist’s survey shows that 58% of workers want to learn new skills but don’t know where to start. That’s great news for HR professionals who want to build an internal pipeline of quality candidates for the future. But it also means that you may need better communication to help managers navigate these questions.

Solution: Your managers don’t need to be a one-stop shop of information for their direct reports, but they do need to know where to point their team. They can learn about the company’s upskilling priorities over the long-term, as well as the education programs available.

Here are a few ideas to take action:

• Put together a Career Resource Toolkit for managers that equips them with a simple easy-to-use reference guide. This may even look like a create a centralized resource hub to make available resources easy to find in one place, for both managers and employees.
• Hold manager information sessions and share one-pagers or FAQs about available programs. Managers do not need to be experts, but they should be informed.
• Make career development and continuous learning a regular part of culture and leadership. Encourage the celebration of promotions and learning milestones.

To bridge the gap between employee curiosity and program engagement, HR and L&D should empower managers to act as connectors. For example, do managers know you offer education benefits and how to refer employees to get started with tuition assistance or student loan support?

Design career pathways unique to your company

Challenge: Not every company has the same needs, so workforce development will differ based on industry and changing priorities. Resources can’t be limited to traditional four-year degree programs that may not actually fit the needs of your workforce. Stackable, skills-based learning opportunities are becoming increasingly popular among both employers and workers.

Solution: Stackable learning opportunities are a great starting point to an even more strategic development plan that managers can share with employees: internal career pathways. Career pathways are mapped series that outline the exact steps and training employees can take to advance into different roles within the company.

Here are a few ideas to take action:

• Take a look at your critical or hard-to-fill roles. Whether it’s to fill frontline needs or strategic succession planning, identifying these roles and where the gaps are is a great first step.
• Establish clear steps on how to move forward for those roles. Clear upskilling or reskilling steps not only benefits the employees who want to enroll in the program, it also simplifies the process for managers. They get an achievable roadmap to point their workers in the right direction and track progress over time.
• Companies can tailor opportunities to fill skill gaps in young talent, while employees can take individual courses or certificate programs that can be completed quickly and applied on the job.

Taking the time to customize pathways instead of using off-the-shelf frameworks make a huge difference in employees being able to visualize how to get from point A to point B (or even C, D, and beyond) by staying with the same company.

If you don’t want to start from scratch, consider bringing in a partner like EdAssist to help you design career pathways that make sense for your organization.

Regularly share opportunities organization-wide

Challenge: Once you have education benefits like career pathways in place, you need to let employees know about them. Many organizations have incredible education benefits programs but employees (and managers) aren’t aware of them. This limits the impact that these programs were designed to achieve. 

Solution: Manager education and outsourced coaching both help scale access to the development and training programs at your company, but it’s not useful if it’s not utilized. While information may be shared with new employees during onboarding, those employees are not likely to take advantage at that time.

Here are a few ideas to take action:

• Treat your education benefit programs like a product launch. Share details in all-hands or share on the internal sites so employees can access this information on their own when they’re ready.
• Share communications regularly through internal marketing to share available opportunities with all employees - not just for new hires or at program launch.
• If you have an education benefits partner like EdAssist, ask about what customer marketing support they provide. In addition to helping map out career pathways, EdAssist also helps with internal marketing to make this program easy for both managers and HR!

Creating internal visibility prevents employees from feeling like they need to look outside the organization for new opportunities. This also widens the talent pool by hiring for skills and retaining employees with education benefits, like tuition assistance and student loan support.

Broken career conversations need a scalable fix

Good managers are rare and career coaches are even rarer. Expecting every manager to be both is a big ask, and it’s not a scalable talent strategy.

Even if career conversations are broken, leading organizations are finding success by creating clear career development pathways and bringing in a partner like EdAssist for coaching and tuition assistance. Especially when complemented by other education benefit programs, student loan support, these strategies not only combat employee disengagement but also protects managers from burnout by removing the pressure to be career experts.

The reality is that many managers don’t have the time or training to execute consistent, scalable development programs. But employees who crave growth need structure, visibility, and actionable next steps to thrive.

Stop losing top talent. Start building a future-ready workforce today and download EdAssist’s Playbook for Building Future-Ready Talent to design career pathways that retain, engage, and upskill. Ready to take the next step?