You Promoted Your Star Employee. Now They’re Struggling. Don’t Panic—Read This

Almost nothing can cut an entrepreneur deeper than misjudging the aptitude of a long-time employee. It’s an almost unbelievable and unbearable situation: giving a strong team member a shot at management only to learn the individual isn’t up to performing on the next level. Such a circumstance surely prompts a business owner to question their own instincts. Aside from the shock is what to do to resolve the problem.

Navigating the Promotion Pitfall: What Small Business Owners Can Do When a Star Employee Struggles in a New Role

Promoting a top-performing employee is one of the most rewarding decisions a small business owner can make. It recognizes hard work, boosts morale, and fills key positions internally. However, what happens when that promotion doesn’t pan out?

The employee, once a standout in their previous role, now falters under the demands of greater responsibility—a classic case of the Peter Principle in action. For small businesses, where every team member counts, this scenario can disrupt operations and strain relationships. The good news? There are proactive, compassionate strategies to address it without losing valuable talent.

1. Assess the Situation Objectively

Before taking action, step back and assess the situation. Is the issue skill-based (e.g., lacking managerial experience) or something else, like burnout or mismatched expectations? Schedule a candid, private conversation with the employee to discuss their challenges. Utilize tools such as performance reviews or 360-degree feedback from peers to gather valuable insights. In a small business, this personal touch can reveal if the promotion was premature or if external factors are at play. Remember, admitting a misstep early prevents bigger problems down the line.

2. Invest in Training and Support

Often, the employee just needs a bridge to success. Offer targeted training, such as leadership workshops, online courses, or mentorship from you or an external coach. Pair them with a seasoned colleague for shadowing, or implement a performance improvement plan (PIP) with clear, measurable goals and timelines—say, 30-60 days. This approach shows commitment to their growth and can turn things around. For cash-strapped small businesses, free resources like SCORE mentoring or LinkedIn Learning can be game-changers.

3. Consider a Graceful Demotion or Lateral Move

If training doesn’t yield results, demotion might be necessary, but frame it as a “role realignment” to preserve dignity. Explain how returning to their strengths benefits the company and them—perhaps with a title like “senior specialist” to maintain status. Alternatively, explore lateral moves to roles that leverage their skills without the added pressure. In small teams, this flexibility can help maintain high morale and retain institutional knowledge. Always document discussions to protect against potential legal issues, and consider offering incentives, such as a bonus, to ease the transition.

4. Foster a Culture of Open Communication and Learning

Prevent future pitfalls by building a promotion process that includes trial periods or assessments. Encourage employees to voice concerns about readiness for advancement. As a small business owner, lead by example: Share stories of your own career hiccups to normalize setbacks. This creates a resilient team where promotions are seen as opportunities, not traps.

Ultimately, handling a failed promotion thoughtfully can ultimately strengthen your business. It demonstrates empathy, fairness, and strategic thinking—qualities that attract and retain top talent. By viewing it as a learning experience, you’ll not only salvage a great employee but also refine your leadership for long-term success.

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