I’ve wanted to write about skip-level meetings for a while now. Let’s starting with a definition. A skip-level meeting is a one-on-one interaction between a senior leader and an employee who is two or more levels below them in the organizational hierarchy. Throughout my leadership career, these conversations have been more than just a management technique – they’ve been a cornerstone of my leadership philosophy.
My passion is also rooted in my personal experience as an employee. I’ve never missed an opportunity to meet one on one with my boss’s boss and with other senior leaders. These connections had a profound positive impact on my career trajectory. However, it took time for me to fully grasp how to leverage these meetings to their full potential.
My motivation for writing this article is simple: I want to encourage more leaders and their team members to embrace skip-level meetings as a strategic tool for organizational growth and individual development.
For executives, skip-level meetings are windows into the organization’s true operational landscape. They provide unfiltered insights that traditional reporting structures often obscure. A senior leader might discover innovative solutions percolating at lower levels, identify emerging talent with transformative potential, or understand the real challenges facing frontline teams. These conversations break down hierarchical barriers, allowing leaders to sense the organization’s cultural pulse and demonstrate their genuine commitment to understanding their people.
From an employee’s perspective, these meetings represent a rare opportunity to step beyond the constraints of their immediate management structure. They are chances to showcase skills, share innovative ideas, and make a direct impression on decision-makers. Many professionals struggle with the “visibility problem” – feeling their exceptional work goes unnoticed. Skip-level meetings offer a direct channel to leadership, potentially changing career trajectories.
The most successful of these meetings are characterized by genuine curiosity and mutual respect. Executives who approach these conversations with authentic interest create safe spaces for honest dialogue. Employees who come prepared with thoughtful insights, strategic questions, and a clear understanding of how their work connects to broader organizational goals can transform these meetings from routine check-ins to meaningful career moments.
Preparation is key for both parties. Executives should review the employee’s background, understand their recent contributions, and create an environment of open dialogue. Employees should research the organization’s and the executive’s strategic priorities, reflect on their unique perspectives, and be ready to share not just achievements, but potential solutions to existing challenges.
The magic of skip-level meetings lies in their ability to humanize these interactions. They remind both leaders and team members that behind titles and reporting structures are individuals with unique insights, aspirations, and potential. These conversations can spark mentorship opportunities, reveal hidden talents, and create alignment between individual ambitions and organizational objectives.
However, the true power of these meetings is not in a single interaction but in creating a culture of continuous, transparent communication. When skip-level meetings become a normalized practice, they signal an organization’s commitment to meritocracy, individual growth, and collaborative success.
While the benefits of skip-level meetings are clear, it’s crucial to implement them thoughtfully to avoid unintended consequences. One potential pitfall is the risk of making an employee’s direct manager feel excluded or bypassed. Transparency is key – employees should inform their managers about upcoming skip-level conversations, and executives should encourage this openness. The focus should be on supplementing, not replacing, the regular management chain.
Moreover, the content of these meetings should generally avoid discussions that undermine the authority or effectiveness of the direct manager. Instead, they should concentrate on broader organizational insights, career development, and high-level strategic discussions. By framing skip-level meetings as a complement to regular management interactions rather than a replacement, organizations can maintain strong relationships at all levels while still reaping the benefits of cross-hierarchical communication.
This approach isn’t just a theoretical concept for me. Over years of leading teams and participating in skip-level meetings as an executive and a team member, I’ve witnessed remarkable transformations – employees who gained confidence, leaders who gained unprecedented insights, and organizations that became more agile and connected through these deliberate conversations.
My hope is that by sharing these insights, more leaders will recognize the value of stepping outside traditional communication channels, and more employees will proactively seek and fully leverage these opportunities. Skip-level meetings are more than a management technique; they’re a philosophy of leadership that values transparency, individual potential, and organizational learning. Whether you’re a senior executive or an ambitious employee, embracing this practice can open doors to growth and success.
