...Continued
The Challenge: The real headache is twofold. First, this person acknowledges the rules in our meetings but then completely ignores them in practice. Second, when I bring it up to the leaders they’re running to, I get told, "Oh, we just have a relationship" or "It’s just mentoring." Because the leaders above me are framing it as a casual friendship or mentorship, it validates the behavior and makes it feel like my role as their direct leader is being bypassed or undermined.

I need some real-world advice on:

• How to handle the leaders above me who are facilitating this by calling it "mentoring."
• What to do when someone keeps agreeing to the "rules" in person but won't actually change their actions.
• How to stop being the one "chasing" information that should have been reported to me in the first place.

Additional Information: This is an outlier situation compared to how the rest of the team operates. It’s starting to feel like there’s one set of rules for this person and another for everyone else, which makes it really difficult to keep things running smoothly.

---

Faculty Response By: Joseph V. Sakran, MD, MPH, MPA, FACS

When Mentorship Becomes an End Run: Navigating Leadership When the Chain of Command Breaks

Leadership rarely fails because of one dramatic event. More often, it erodes slowly through small exceptions that become normalized over time.

One such challenge arises when a team member consistently bypasses their direct leader to communicate with more senior leadership. At first glance, this might appear harmless. Organizations often encourage open communication and mentorship relationships across hierarchies. But when those interactions circumvent reporting structures, they can quietly destabilize how teams operate.

The above submitted Hard Cases, Strong Leades submission highlighted a scenario that illustrates this tension well.

Within a well-functioning team, one individual repeatedly went directly to leaders above their supervisor to discuss operational matters. Each time the issue was raised, the individual acknowledged the importance of the chain of command and agreed to follow established communication norms. Yet the behavior continued.

Complicating matters further, the senior leaders receiving these conversations framed them as mentorship: "We just have a relationship," or "I'm just advising them."

On the surface, that explanation seems reasonable. Mentorship is an essential part of professional growth. But in practice, the dynamic created a situation where operational discussions occurred outside the awareness of the person responsible for leading the team.

The result was predictable: confusion, duplication of effort, and a leader forced to chase information after decisions had already begun taking shape.

This situation highlights a common leadership dilemma—one that many mid-level leaders face but rarely discuss openly.

Why the Chain of Command Exists

Most organizations are structured with a chain of command not to enforce hierarchy for its own sake, but to ensure clear communication, efficient decision-making, and accountability. When employees routinely bypass their direct supervisors, it disrupts those communication pathways and can leave leaders unaware of critical issues affecting their teams.

The consequences extend beyond simple frustration.

A leader who lacks full visibility cannot effectively coordinate resources, align priorities, or support their team. Meanwhile, senior leaders may unintentionally become involved in operational issues that should be handled at lower levels of the organization, distracting them from strategic work.

Perhaps most importantly, bypassing leadership sends a powerful signal to the rest of the team: that formal structures are optional and influence matters more than process.

This signal has a ripple effect. Other team members watch and learn. Some become resentful of the special access. Others begin seeking their own senior relationships. Still others grow cynical about following any process at all. What started as one person's behavior becomes a cultural shift that can erode trust and cohesion across an entire department.

The Mentorship Shield

What makes this situation particularly challenging is the role mentorship can play in legitimizing the behavior.

Mentorship relationships are valuable and should be encouraged. They allow individuals to seek career advice, gain perspective, and expand their professional networks.

But mentorship and management serve fundamentally different functions.

Mentorship supports development. Management ensures execution.

When mentorship conversations begin to include operational decisions, resource allocation, or strategy affecting a team, they can unintentionally become an alternative chain of command.

In these cases, the issue is not the existence of mentorship, it is the absence of clear boundaries between mentoring conversations and operational leadership.

Understanding the Hidden Incentives

A common misconception is that repeated bypassing is simply a misunderstanding of organizational norms.

In reality, when someone acknowledges the rules but continues the behavior, it usually reflects deeper motivations. Direct access to senior leadership offers visibility, influence, and sometimes political protection. For some, it may stem from previous negative experiences with direct supervisors or cultural backgrounds where hierarchy operates differently. Others genuinely struggle to distinguish between "operational" and "developmental" discussions.

But here's the crucial insight: If the underlying incentives remain unchanged, the behavior is unlikely to change either—no matter how many conversations occur about "the rules."

This becomes even more complex when senior leaders themselves have incentives to maintain these direct channels. They may value unfiltered information, enjoy the mentoring role, or deliberately cultivate informal intelligence networks that bypass middle management. Sometimes what appears to be unwitting enablement is intentional circumvention.

Understanding these dynamics shifts the leadership challenge. The goal is not simply to correct an individual but to address the system that allows—and sometimes encourages—the behavior to persist.

The Organizational Paradox

Modern organizations face an inherent tension. They simultaneously promote two conflicting values: clear hierarchies for efficient execution and flat, networked relationships for innovation and engagement.

Employees receive mixed signals daily. "Follow the chain of command" coexists with "bring your ideas directly to senior leadership." "Respect reporting structures" competes with "build relationships across the organization."

The employee bypassing their manager might be responding rationally to these contradictory messages. They've learned that in many organizations, informal influence trumps formal process—and they're not wrong.

This paradox doesn't excuse the behavior, but acknowledging it helps leaders approach the situation with greater nuance.

Re-establishing Healthy Leadership Channels

Addressing this type of situation requires a combination of clarity, alignment, and structural adjustments, along with a realistic assessment of what's achievable.

First, reset the principle publicly and professionally: Mentorship is encouraged, but operational discussions must flow through reporting lines to maintain situational awareness. Frame this as essential for team effectiveness, not personal authority. This depersonalizes the conflict and shifts focus from a specific individual to the functioning of the team.

Second, align with senior leadership, but prepare for resistance. Approach senior leaders respectfully with specific examples of operational impact. Many will agree that maintaining visibility for direct leaders improves execution. However, some may resist giving up their direct channel. In these cases, propose a compromise: regular three-way check-ins that preserve the relationship while including the direct supervisor.

Third, create transparent mechanisms that make bypassing unnecessary. Implement shared meeting summaries, documented decisions, or structured reporting channels. When information flows naturally through the system, there's less incentive to work around it. Consider also whether the direct supervisor's availability or communication style might be inadvertently encouraging the bypass behavior.

Fourth, establish a graduated response framework. Start with clarifying conversations focused on organizational impact rather than personal frustration. Document these discussions. If behavior continues, involve HR to ensure consistent messaging. Be prepared to make difficult decisions if the pattern persists, especially if it's undermining team cohesion.

When Senior Leadership Won't Cooperate

The hardest scenario—and unfortunately not uncommon—is when senior leaders say they understand but continue enabling the behavior. They nod in agreement during discussions about process, then immediately return to their direct conversations.

In these situations, leaders face a stark choice: continue fighting an unwinnable battle or adapt their approach.

Adaptation might mean:

• Accepting the reality and building processes that assume these channels exist
• Documenting all decisions and communications to maintain an audit trail
• Focusing on what remains within your control, the rest of your team
• Having frank conversations with your own leadership about the situation's impact on your effectiveness

Sometimes the most professional response is to recognize when organizational culture supports the exception more than the rule—and plan accordingly.

Managing High Performers Who Bypass

The situation becomes particularly delicate when the bypassing employee is a high performer or possesses specialized knowledge. Leaders must balance addressing the behavior while retaining talent.

In these cases, consider whether the individual's need for senior visibility might be met through structured opportunities—formal presentations, strategic project involvement, or official mentorship programs. This channels their ambition constructively while preserving reporting structures.

The Broader Leadership Lesson

Situations like this reveal an important truth about leadership.

Authority rarely collapses dramatically. It erodes through small exceptions that gradually redefine the rules.

Leaders who address these exceptions early protect not only their own effectiveness but also the integrity of the organization's decision-making structure. But they must do so with eyes open to the organizational realities and mixed signals that create these situations.

Mentorship networks, informal relationships, and open communication are all vital components of healthy institutions. But they work best when they reinforce, not replace, the leadership structures responsible for execution.

The challenge, ultimately, is not choosing between mentorship and management. It is ensuring that each serves its proper role while recognizing that in modern organizations, that boundary is constantly being negotiated.

Perhaps the most valuable skill for today's leaders is not preventing these situations entirely that may be impossible given organizational paradoxes, but managing them with clarity, professionalism, and strategic thinking when they inevitably arise.

Because in the end, leadership is not about perfect structures. It's about navigating imperfect ones with wisdom and grace.