From Top Performer to First-Time Manager: The Hard Lesson of Leadership

Early in my career, I worked at Sears. It was my first real job, and like most new hires, I started at the bottom in Menswear, folding shirts and helping customers. I worked my way up to Sporting Goods, then Lawn & Garden, where the products were bigger, the commissions were better, and the stakes were higher. I excelled. I was always near the top in total sales and consistently sold the add-on products that the company cared about like credit cards, maintenance plans, and warranties.

I was reliable, eager, and vocal about my desire to grow with the company. So when a supervisor position opened up, I got the promotion. I had earned it, right?

What I didn’t realize was that I had just stepped into a role I was completely unprepared for.

Thrown Into Management Without a Playbook

One day, I was a top salesman. The next, I was responsible for managing my former coworkers. Most were in their early to mid-twenties, just like me. Some were older salespeople who had been at Sears since the 60s and 70s when selling at Sears was a career, not just a retail job.

I was handed a list of sales goals and expectations. That was it. No training. No guidance. No real transition plan.

I did the only thing I knew how to do. I managed the way I wanted to be managed. Direct, no-nonsense, results-focused. It…went…horribly.

• Some people pushed back immediately, making it clear they weren’t about to take direction from a former peer.
• Others ignored me entirely, doing their jobs the way they always had, treating my new title as meaningless.
• I burned bridges quickly, delivering feedback the way I preferred to receive it. I was direct and blunt which didn’t sit well with everyone.
• When I tried to course-correct, I overcompensated in the other direction, hesitating to enforce standards, which only led to more frustration.

What followed was years of trial and error, avoidable conflicts, and a slow realization that knowing how to do a job well does not mean knowing how to lead others doing that job.

Looking back, I would do almost everything differently.

The Problem with How We Promote First-Line Managers

This isn’t just a retail problem. It is everywhere in manufacturing and distribution.

Top performers get promoted into leadership because they are skilled, reliable, and successful. But being great at a job doesn’t mean you’ll be great at managing people who do that job.

Too many new frontline supervisors are put in charge of a team with no leadership training, no coaching, and no roadmap for success.

Without support, these new leaders struggle. Their teams struggle too. Some will figure it out through trial and error. Others will burn out. Some will take their best skills and leave for a company that will invest in their growth.

The cost of poor leadership development is high:

• Increased turnover. Employees leave because they don’t feel valued, supported, or heard.
• Lower productivity. Confusion, disengagement, and poor morale lead to inefficiency.
• More operational mistakes. Lack of clear leadership results in miscommunication and preventable errors.
• Missed growth opportunities. Poorly trained leaders often fail to recognize or develop talent within their teams.

These are fixable problems, but only if companies are intentional about preparing first-line managers for success.

The Key to Successful First-Line Leadership

The solution is simple: train your frontline supervisors. Give them the tools they need to lead before throwing them into the fire.

1. Supervisor Bootcamps for Immediate Impact

For companies with existing first-line managers who never received proper leadership training, a focused leadership bootcamp can help them catch up quickly and positively impact their teams right away.

A supervisor bootcamp covers:

• How to transition from peer to leader without damaging relationships
• How to set expectations clearly and enforce them fairly
• How to handle conflict before it escalates
• How to motivate employees without micromanaging
• How to deliver feedback that people actually listen to

Instead of waiting for years of trial and error, these programs fast-track leadership development so companies can see immediate improvements in engagement, retention, and productivity.

2. Ongoing Leadership Development for Long-Term Success

The best leaders are not made in a day. Even after an initial training program, ongoing leadership development is essential.

• Structured training programs. Leadership courses covering everything from emotional intelligence to problem-solving.
• Peer mentorship programs. Connecting new supervisors with seasoned leaders for real-world guidance.
• Coaching and feedback loops. Providing continuous support to help leaders adjust and grow in their roles.

3. Building Leadership Culture from the Top Down

Leadership training isn’t just about frontline managers. It has to be embedded in the company culture.

• Executives and senior managers must reinforce leadership expectations.
• HR and workforce management teams must support supervisor development.
• Recognition and rewards should encourage strong leadership behaviors.

When leadership development is intentional and prioritized, companies don’t just promote employees, they develop leaders.

Landrum Workforce Management: Leadership Development That Works

At Landrum Workforce Management, we work with companies to build high-impact leadership training for frontline managers.

• Supervisor Bootcamps. A focused, intensive training to help existing first-line leaders quickly catch up and improve team performance.
• Ongoing Leadership Development. Structured programs designed to develop new and future leaders at all levels.
• Custom Workforce Solutions. Leadership training that aligns with your organization’s specific challenges and culture.

Great frontline leadership is not just about improving metrics. It is about building a strong, engaged workforce that drives long-term success.

What Was Your First Management Experience Like?

Were you trained before taking on a leadership role, or did you have to figure it out the hard way? What advice would you give to a new supervisor today? Drop your thoughts in the comments.