Why do Skip-Level Meetings matter?

They prevent senior leaders from becoming disconnected from day-to-day operations, promote openness, help identify rising stars, and foster organizational trust by discussing values in a friendly environment.

The Value of Skip-Level Meetings: Building Trust Across the Hierarchy

russellsmichalak
Apr 29
6 min read

Hierarchies exist for good reasons. They clarify accountability, define lines of authority, and help organizations operate efficiently. Regular one-on-one meetings with direct reports are foundational to effective management, allowing leaders to stay aligned with their immediate team, track progress on priorities, and invest in professional development. None of that changes when we introduce skip-level meetings into the mix. But skip-level meetings offer something that conventional reporting structures cannot: a direct, unfiltered line of communication between senior leaders and employees one or more levels removed from them in the organizational chart.

I believe skip-level meetings are among the most underused tools in a leader's repertoire. Done well, they reinforce and deepen the kind of trust that makes organizations genuinely healthy places to work.

What Is a Skip-Level Meeting?

The concept is straightforward. A skip-level meeting is a conversation between a senior leader and an employee who does not report directly to that leader, bypassing the intervening level of management. The middle manager is not present. If, in my role as library director, I sit down with a staff member who reports to one of my direct reports, that is a skip-level meeting. My direct report has been "skipped over" for the purposes of that conversation.

The purpose of skip-level meetings is to gather feedback that will ultimately help guide decision-making and to connect senior managers with front-line employees to improve transparency. They are not meant to replicate or replace regular supervision. They are meant to complement it by creating a channel for organizational information, perspectives, and concerns that might otherwise never reach senior leadership.

Without their direct supervisors present in a skip-level meeting, workers can feel more open about expressing how things are going. That candor is the point. It is not about circumventing management; it is about ensuring that leaders can hear from the people doing the work, in their own words.

Why Skip-Level Meetings Matter

The benefits flow in multiple directions. For senior leaders, skip-level meetings stop them from becoming disconnected from day-to-day operations. They can speak with greater knowledge about how things are going for their organization and its people, and then shape their strategies accordingly. There is a real danger, especially in large or complex organizations, that senior leadership becomes insulated from operational realities. Skip-level meetings are a structural corrective to that insularity.

For employees, the benefits are equally significant. These meetings promote openness within the organization. Employees feel more informed about company decisions and future plans, which fosters trust and reduces uncertainty. When a staff member who rarely interacts with senior leadership has the opportunity to ask questions, share observations, and feel genuinely heard, it changes their relationship to the institution in meaningful ways.

Skip-level meetings also help leaders identify rising stars among their staff and gather feedback on the managers they supervise, including insights into their own leadership. They are, in other words, a mechanism for leadership development at every level of the organization.

There is also an important cultural dimension. By discussing organizational values in a friendly, open environment, leaders help employees see their workplace as ethical, honest, and trustworthy. That perception does not emerge from policy statements or mission documents. It emerges from lived experience, including being invited to speak honestly with someone in a position of authority.

How Skip-Level Meetings Can Be Structured

Skip-level meetings work best when they are normalized, regular, and intentional rather than reactive or ad hoc. A quarterly, biannual, or annual schedule balances accessibility and practicality, ensuring feedback remains current without overwhelming employees. The cadence will depend on organizational size and complexity, but predictability matters. When employees know these conversations happen routinely, the meetings feel less like a special event (or worse, a warning sign) and more like an ordinary part of organizational life.

The meetings themselves should be conversational, not interrogative. Leaders should clearly state the purpose at the start: this is not a performance review; it is a chance to listen and learn. Leaders should listen more than they talk, take notes, and thank employees for their honesty. Questions should focus on processes, communication, and opportunities for improvement rather than on personalities or interpersonal dynamics.

Consistency, transparency, and follow-through are crucial to realizing the ongoing benefits of skip-level meetings. The single fastest way to undermine trust in this process is to solicit feedback and then do nothing with it. Employees notice when their words disappear into a leadership vacuum. Following up, even simply to acknowledge what was heard and explain what will or will not change, closes the loop and demonstrates that the conversation was genuine.

Protecting Trust with Mid-Level Managers

This is perhaps the most delicate dimension of skip-level meetings, and it deserves careful attention. When these meetings are handled poorly, they can damage the very trust they are meant to build, particularly the trust that mid-level managers have in senior leadership.

When managers feel they are being sidestepped and excluded, many will become protective. That is never useful in organizations. A manager who feels surveilled rather than supported will become guarded, and that guardedness will affect their entire team.

The antidote is transparency. Skip-level meetings should never be a secret. Senior leaders should communicate clearly to their direct reports (the mid-level managers) that these meetings are happening, why they are happening, and what will and will not be shared afterward. Avoid undermining their manager's authority by overruling their decisions or undercutting their management. Skip-levels should not be a secret, and leaders should not fail to follow up after making a commitment or identifying a next step.

If you are a manager and your senior leader is conducting skip-level meetings with your team, your job is to normalize them and to protect trust. Framing is everything: this is about support, not surveillance. When introducing the idea to your team, frame it as a way for leadership to understand the work better and hear directly from the people doing it.

Senior leaders, for their part, must resist the temptation to use skip-level feedback punitively. Problems arise when these conversations intentionally undermine managers, fail to maintain employee confidentiality, or use feedback punitively rather than constructively. The goal is not to catch anyone doing something wrong. It is to develop a richer, more accurate picture of organizational health. When that distinction is clear, mid-level managers are far more likely to welcome skip-level meetings as a resource rather than experience them as a threat.

Senior leaders also need to think carefully about what they share after a skip-level meeting, and with whom. Confidentiality is not simply a courtesy; it is a prerequisite for honest conversation. If employees believe that what they say will be reported back to their direct supervisors verbatim, they will not speak candidly. Protecting that candor is a leadership responsibility.

The Connection to Organizational Trust

The research on organizational trust makes clear that it is not simply a nice-to-have quality; it is structural. Organizational trust is promoted when leaders demonstrate trustworthiness by being open, competent, and compassionate, and by organizational mechanisms such as open-door policies and information sharing.

An open-door policy, in the abstract, is a good intention. Skip-level meetings give it concrete form. They demonstrate, through action rather than statement, that senior leaders are genuinely accessible and genuinely interested in what employees have to say. Skip-level meetings are not just a procedural exercise; they are a catalyst for trust, psychological safety, and a culture where great ideas have a real chance to shape the future.

There is also an equity dimension worth naming. Not every employee has the social capital, the confidence, or the proximity to power that makes approaching senior leadership feel natural or safe. Proactively creating structured opportunities for those conversations, rather than relying entirely on informal access, signals that the organization values every voice, not just the loudest or most visible ones.

Closing Thoughts

Skip-level meetings are not a substitute for strong relationships between employees and their direct supervisors. Those relationships remain the backbone of daily organizational life. But skip-level meetings are a meaningful complement to them, serving the entire organization by creating transparency, deepening trust, and giving senior leaders the ground-level perspective they need to lead wisely.

They do require intention, consistency, and care. They require that senior leaders go in as listeners rather than declarers. They require that mid-level managers be treated as partners in the process rather than obstacles around it. And they require follow-through, because a conversation without consequence teaches people that their words did not really matter.

When all of that is in place, skip-level meetings become one of the most powerful signals a leader can send: that people at every level of this organization are worth knowing, worth hearing, and worth the leader's time.