One of your middle market employees is going back to school, and asks for your help. First off, don't necessarily take this as bad news. It's an opportunity for both the employee and your middle market company to grow. By going back to school, employees show ambition and a praiseworthy intention to develop skills. Yes, that person's desire might inconvenience your middle market company in the short term; there will be some rescheduling to juggle work and study. However, the key for your company is simple: Be as supportive as you can, because you'll get a long-term return with increased productivity, loyalty and retention.

When employees start going back to school, offer them incentives to add to your company.

Match Your Company's Needs to the Employee's Education

Have your human resources (HR) department work with the employee to ensure the courses they select will add relevant skills to your middle market company. These should help advance the person's career with you. In the best of all worlds, your company has already worked with the employee to identify individual and organizational skill gaps, and the worker wants to go back to school to fill those areas. Even if your employee and the company have slightly different ideas about what gaps need addressing, it's important for you to engage the person and support learning.

When employees express a desire to go back to school, arrange a meeting with their managers and your HR or training person. Discuss what future career options might be available for the employee, not just in terms of more salary, but also new roles and responsibilities. Work together and help the employee develop their course load, and then see what this additional, relevant education will do inside your company.

Should the Company Offer Financial or Tuition Assistance?

A more challenging question concerns money. Should your middle market company contribute the cost of an employee's continued education? The answer depends. If the employee and the company are not on the same page about what skill gaps the courses should close, and if the courses don't cover the skills your company needs, then it probably doesn't pay to contribute. Why invest money when there seems to be no value added to the employee's career development, and no potential return on investment for the company?

On the other hand, if you've engaged in consistent communication with the employee and that person has tailored the courses to the skill gaps you have mutually identified, then financial support is justified. In this case, you make it clear that you're investing in the employee's development, and thus expect a long-term return in exchange for financial support. As long as the employee shows good results in class, you can help pay the costs. Of course, while your larger rivals likely have full-blown tuition reimbursement budgets, you'll probably have to pursue employee financial assistance on a case-by-case basis with HR.

Your middle market company can make the investment-for-return model even clearer by asking the employee to sign a contract in which they agree to stay with you for a certain period after graduation. This ensures you'll receive a return on your investment. Check with your legal department before going this route, however.

Such a contract communicates a distinct message: We're helping you grow, and we expect you to help us grow. The vast majority of employees will be more loyal (with or without a retention contract) after you've invested in their development because there's a basic human impulse to reciprocate at work. Middle market companies are perfectly balanced here: They generally feel more like families than their larger rivals, making retention easier. They're also large enough to give the newly trained employee additional responsibilities, which will help keep good talent around.

Use Developing Skills to Benefit the Team

Be flexible enough to support the employee's education. Middle market companies have an edge here. If you need to alter the employee's schedule or rearrange some other resources, then do it. Explain that the whole team is supporting the employee's educational and developmental goals. Nothing brings teams together like being flexible and managing shared sacrifice. As the employee learns, you might give them formal opportunities to coach others, make internal presentations to the whole organization or, especially, practice their new skills at work. This kind of sharing is a win-win for all involved.

How does your company approach things when an employee requests to go back to school? What has worked well — and not so well — for you in the past? Tell us by commenting below.

Boston-based Chuck Leddy is an NCMM contributor and a freelance reporter who contributes regularly to The Boston Globe and Harvard Gazette. He also trains Fortune 500 executives in business-communication skills as an instructor for EF Education.