Question

We recently promoted one of our top-performing employees into a supervisor role. The person was amazing at the old job, but now they’re having trouble managing their team, especially since they’re supervising people who used to be their coworkers. I don’t want to lose them, but things aren’t going smoothly. What can I do?

Answer

This is one of the most common challenges we hear from employers. A top performer gets promoted, and suddenly, the person who used to be your strongest employee is struggling to lead.

What went wrong and how can you help?

This situation happens far more often than many realize. We often assume that someone who is technically strong will naturally make a great leader. But a technical skillset and a leadership skillset are two very different things.

Now add another layer: this new supervisor is managing former peers — maybe even friends. That shift can cause tension, confusion, and discomfort for everyone involved. Without the right preparation and support, even your best performer can quickly become discouraged or ineffective. You risk losing not just a supervisor, but a great employee.

Step One: Set Clear Expectations

Before promoting someone, take time to talk through what the new role really involves. Supervising others is a significant change from being an individual contributor, and not everyone wants that responsibility.

Ask your employee if they’re truly interested in growing into a leadership position — and if they are, outline how you’ll help them prepare.

Step Two: Provide the Right Training

The next step is training and development. A newly promoted supervisor needs tools, guidance, and support to succeed. Offering both internal and external training helps them build confidence, communicate effectively, and understand their new responsibilities.

Formal leadership training can help new supervisors learn to:

• Communicate effectively with their team
• Handle conflict constructively
• Manage performance issues
• Set healthy boundaries with former peers
• Make fair, legally sound decisions

Investing in this kind of training not only helps the employee succeed — it also protects your organization. Untrained supervisors can make mistakes that lead to morale problems, turnover, or even legal issues.

Why Training Matters More Than Ever

Leadership development isn’t just good practice, it’s what employees expect.

According to the 2025 SHRM Employee Benefits Survey, 65% of employers say professional and career development benefits are “very important” or “extremely important.” And a 2025 Deloitte survey found that for Gen Z and Millennials, learning and development rank among the top three reasons they choose to stay with their employer.

When companies invest in leadership development, they’re not just helping one employee, they’re strengthening engagement and loyalty across the entire workforce.

If your organization is ready to take that step, AIM HR Solutions offers more than 70 training classes, including supervisory and leadership programs. You can explore our 2026 Training Catalog to find the right fit.

What If There’s No Budget for Training?

You might be surprised at how many affordable options exist — especially in Massachusetts.

Through the Workforce Training Fund Program, employers can apply for grants to offset training costs:

• Express Grant – For companies with 100 or fewer employees that pay into the Massachusetts Unemployment Insurance Fund.
• General Grant – For larger employers that also pay into the Massachusetts Unemployment Insurance Fund.

Applying for a grant may sound daunting, but it doesn’t have to be. AIM HR Solutions members can connect with our grant expert, Rachel Gillis, who can guide you through the process and help determine the best option. Learn more about Workforce Training Grants.

The Bottom Line

Promoting a high-performing employee into a leadership role can be a win but only if they get the support and training needed to succeed.

Clear communication, thoughtful preparation, and access to leadership development programs can make all the difference between a struggling supervisor and a confident, effective leader who grows with your company.

Have a question?
Contact the AIM HR Solutions Helpline at 800-470-6277 or email helpline@aimnet.org.  If you have questions about training opportunities contact the team at AIM HR Solutions at www.AIMHRSolutions.com.