The 5 Most Difficult Employees (And How To Actually Handle Them)

Leaders constantly bump into employees who seem immune to ordinary coaching. The article distills those encounters into five recurring archetypes and shows that the difference between a stuck team and a high-performing one is recognizing the pattern and responding with a tailored playbook. By naming the problem you stop treating each flare-up as an isolated incident and start building systematic fixes. The first archetype is the veteran who lives in the company's past. Their deep institutional memory gives them credibility, but it also becomes a shield against change. The author advises leaders to acknowledge the veteran's history, then pivot the conversation to present expectations, create inclusive accountability, and link the person's legacy to new goals. Concrete language such as "Your experience can help us keep our core values while we adopt new processes" reframes resistance as an opportunity. The second archetype, the passive resister, smiles and agrees in meetings only to miss deadlines later. Their behavior is a silent erosion of trust. The piece recommends setting explicit checkpoints, documenting agreements in writing, and tying missed milestones to clear consequences. By focusing on patterns rather than isolated failures, managers can break the agree-and-avoid cycle before it becomes normalized. The third difficult employee is the high-performing technical star whose brilliance is offset by toxic interactions. The author suggests quantifying the hidden cost of their behavior, establishing behavioral expectations, and linking technical output to team health metrics. If the employee cannot meet both technical and interpersonal standards after clear feedback, the guide counsels leaders to consider a swift transition to protect the broader culture. Across all archetypes, the article equips leaders with specific questions and scripts to assess whether the employee's impact is net-positive and when it's time to move on.