How well do you know your manager’s manager? Have you had opportunities to connect with them independently? For many professionals I work with, the answer to these questions is often “not much.” Securing a successful skip-level meeting provides a valuable opportunity to build relationships with senior leadership while gaining insight into your organization’s priorities.
No matter what stage you’re at in your career, as your responsibilities grow, skip-level meetings with senior leadership can provide valuable insights into company strategy and create opportunities to highlight your contributions.
These strategic conversations allow you to:
- Gain Perspective: Direct interaction with higher management helps align your work with company priorities.
- Build Trust: Establishing rapport with senior leaders creates a foundation of trust, particularly valuable during periods of change.
- Advance Your Position: Use skip-level meetings to showcase achievements, advocate for team resources, and position yourself for growth opportunities.
How to Initiate a Skip-Level Meeting
Understanding Workplace Culture
Before requesting a skip-level meeting, take time to assess your organization’s culture. Many professionals worry about appearing overeager or taking up a senior leader’s valuable time. These concerns are valid – after all, navigating relationships with higher-ups requires careful consideration.
Consider your company’s approach to communication and hierarchy. Some organizations encourage open dialogue and employee initiative, while others maintain more structured communication channels. Think about previous interactions and feedback from your immediate supervisor. Have they supported independence and proactive behavior, or do they prefer more traditional approaches? Understanding this context helps ensure you maintain positive relationships and respect organizational norms.
Communicate with Your Direct Supervisor
When planning a skip-level meeting, transparency is key. Find an appropriate time to discuss your intentions with your immediate supervisor. Explain clearly how this meeting could benefit both you and the team. Emphasize how it can enhance decision-making, minimize miscommunication, and help prevent unexpected challenges.
Make it evident that your goal isn’t to bypass their authority but rather to strengthen alignment with organizational objectives. Consider asking for their input: “What topics would be most valuable to discuss?” or “How can I maximize this opportunity?” This approach demonstrates respect for their experience and position.
If your supervisor expresses concerns, listen carefully. They may have insights into timing or organizational dynamics that you haven’t considered.
Defining Clear Objectives for Your Skip-Level Meeting
Preparation is crucial for making skip-level meetings productive. Here’s how to define your objectives effectively:
- Clarify Expectations: List your current understanding of goals and projects. Seek confirmation or guidance to ensure you’re aligned with senior leadership’s vision.
- Request Input: Outline specific opportunities or challenges you’ve identified. Share potential solutions and ask about their experience handling similar situations.
- Share Updates: Prepare a concise overview of your work. Focus on what matters to senior leadership – impact, results, and strategic implications. Include key metrics and outcomes that demonstrate value.
By establishing clear objectives and focusing on leadership priorities, you demonstrate professionalism and respect for everyone’s time, making your skip-level meetings more valuable for all involved.
Ask Strategic Questions
Preparing thoughtful questions for your skip-level meeting is essential for fostering meaningful dialogue and gathering valuable insights. Consider these examples that demonstrate strategic thinking and seek clarity:
- What are the most critical challenges you believe our team should prioritize?
- How do you envision our team’s evolution aligning with the company’s long-term direction?
- From your perspective, what growth opportunities would help me better support both our immediate team and the broader organization?
- Which market trends or industry shifts should we be monitoring and learning from?
- Looking ahead five to ten years, what key achievements do you hope to see for our company?
- In the face of industry challenges, what drives your optimism?
During your skip-level meeting, prioritize active listening. Apply the 70/30 principle: limit your speaking to 30% of the time, allowing your senior leader to share their perspective for 70%. This approach demonstrates respect for their experience while enabling you to capture important insights and subtle context you might otherwise miss.
By focusing on concise, purposeful questions that connect to broader organizational goals, you create opportunities for productive conversations that benefit both your professional development and the company’s success.
Nurture the Connection
Following your skip-level meeting, send a thoughtful follow-up email expressing gratitude. Thank your senior leader for sharing their time and insights, highlight key discussion points, and detail your plans to implement their guidance. This demonstrates that you value their perspective and intend to act on their recommendations.
Follow-through matters. When you commit to addressing specific items or questions, ensure prompt action. This behavior establishes your reliability and strengthens professional trust.
Consider proposing regular skip-level meetings, such as quarterly check-ins, to maintain the connection. This approach reflects your dedication to ongoing alignment and communication within the organization.
Building relationships with senior leadership requires strategic thinking, humility, and consistency. When you demonstrate genuine commitment to learning and growth, you contribute to both your professional development and your organization’s success.
Remember: effective leadership isn’t solely about managing downward. It’s equally important to cultivate strong relationships with those in senior positions. Regular skip-level meetings provide an excellent foundation for building these crucial connections.
