Exceptional Leadership: Practical Advice for First Time and Emerging Managers · Mathew Hamilton

#41 When Employees Bypass the Chain of Command

July 6, 2025·20 min·1 clip

Matt Hamilton opens with a plain workplace question about employees who bypass their immediate supervisor and bring concerns to a higher manager. He treats the issue as one that needs nuance. An employee may have a legitimate reason for working around the chain of command. An employee may also be trying to get around a supervisor for bad reasons. The host encourages listeners not to assume motive before doing the work. He starts by saying the concern should be taken seriously. He then recommends checking whether the supervisor is actually acting properly. That means speaking with the employee directly. It also means talking with other employees who may have seen the same pattern or felt the same issue. He wants leaders to ask what people are saying, how they are saying it, and whether the environment feels unfair to them. After that, the supervisor should be spoken to directly as well. Hamilton stresses the value of hearing how the supervisor communicates and how that communication is being received. Once the facts are clearer, the leader can decide whether the supervisor is operating with integrity. If the supervisor is operating well, the episode turns toward the possibility that the employee is trying to undercut them. Hamilton then describes that as a wider engagement issue, not just a single complaint. In that case, leadership needs to present a united front. He uses a simple family-style analogy to make the point that one manager should not be allowed to go to a second manager for a different answer. The organization has to show that leadership is aligned. He recommends getting the relevant people into the same room and discussing the issue openly. He also advises that the senior manager should not dominate that conversation. Instead, the immediate supervisor should lead it so the reporting line stays intact. The episode closes with a reminder to balance compassion with critical thinking. Hamilton suggests that leaders should try to help people operate well and make the best possible decisions, while still being firm about the chain of command and leadership alignment.

As heard by us

A practical look at skipped supervisors and the balance between fairness and authority.

Matt Hamilton looks at a workplace problem that can test a leader's judgment: an employee going around a direct supervisor with a complaint or gripe. The episode stays practical.

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Why you'd press play

You need a calm way to handle someone who skipped their boss.

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