How to Have a Successful Meeting with Your Boss’s Boss

Taking the time and effort to invest in upward relationships, such as those with skip-level managers, requires strategy, humility, and diligence. After all, leadership is not only about managing those below you, but also navigating the complexities above. In this article, the author offers practical tips for holding a successful skip-level meeting. 

How well do you know your manager’s manager? How much time have you spent with them without your boss present? If you’re like most of the professionals I work with, then the answer to both of these questions is probably “very little.” And yet, managing up doesn’t stop at influencing your immediate boss. It also requires that you build relationships with leaders further up your chain of command, including with your “grandmanager” or “big boss.”

One of the most effective ways to forge a connection with those above you is through a skip-level meeting. Put simply, a skip-level is a one-on-one meeting between you and your boss’s boss. It’s an opportunity to communicate directly with a higher-up who you may not have much regular access to — or interaction with. 

While you might have assumed that this practice is only for junior employees, skip-levels become more valuable the higher you rise and the further you advance in your career. As the scope of responsibilities and the impact of your actions become more expansive, having skip-levels ensures you’re not just effective in your role, but also aligned, informed, and increasingly visible. That’s because they allow you to: 

  • Gain a broader perspective. Interacting directly with your manager’s manager helps you align with the company’s broader strategic direction and pitch projects and initiatives that resonate with what’s valued at the top.
  • Build social capital. Creating a rapport with your boss’s boss lays the foundation for trust, which can prove invaluable during times of change, transitions, and uncertainty. 
  • Enhance advocacy. These meetings provide a platform to showcase accomplishments, request the resources your team’s needs, and position yourself for further growth. 

Here’s how to set up, hold, and leverage upward skip-level conversations for your own benefit — and the organization’s as a whole. 

Consider your culture. 

For many of the professionals I coach, the mere thought of interacting directly with their skip-level manager can be downright intimidating. Self-doubt creeps in and they worry about wasting a senior leader’s time or coming off as “trying too hard.” These are valid concerns. Navigating a relationship with your manager’s manager requires a delicate balance. Overstep, and you might be seen as bypassing your immediate supervisor. 

So tread carefully. Before you jump to schedule a skip-level, consider your workplace culture and how such a request would be perceived. Would it be welcomed — or seen as a threat? Some companies encourage open communication, while others may have more hierarchical structures. Reflect on past interactions and feedback from your supervisor. Have they previously encouraged you to take initiative, or have they advised a more cautious approach? This can offer insight into how they might perceive your request. 

Bring your boss in the loop. 

If you do proceed, transparency is key. Choose a private time when you and your immediate supervisor can have a candid conversation. Explain why you believe a skip-level meeting would be beneficial for you and the team as a whole. Perhaps share how it will help you make informed decisions, lessen back-and-forth, or avoid last-minute surprises that use up valuable time and resources. Emphasize that your intention is not to undermine or bypass your manager, but rather to enhance your own understanding and alignment with the organization. Your boss will appreciate understanding the motivation behind your request.

Asking your boss questions like “How would you suggest I maximize the time?” or “Are there specific topics you think would be good for me to cover?” demonstrate you respect their expertise and position the request as a collaborative effort. If your boss expresses reservations or suggests waiting for a more opportune moment, listen. They may have insights about workplace politics that you aren’t privy to.

Define your goals. 

Executives are busy and the last thing you want to do is disrespect your skip level’s time by coming unprepared. So define your objectives in advance. Clarifying expectations? List out your current understanding and ask for affirmation or correction. Seeking guidance? Outline specific challenges or opportunities you’re facing, the solution you’re leaning towards, and ask how they’ve dealt with similar situations in the past. Presenting information? Share a clear, concise summary and tailor the data to what would interest an executive, focusing on impact and results.

Prepare powerful questions. 

Regardless of what you want to get out of the conversation, your primary job is to listen. Follow the 70/30 rule: you should aim to speak 30% of the time, while allowing your boss’s boss) to speak for 70% of the time. By listening more, you avail yourself of their experiences and insights and can more easily pick up on non-obvious nuances. 

Plus, you’re forced to be concise and purposeful in your communication. Your speaking time becomes more about asking the right questions — ones that showcase your strategic thinking and derive clarity. For example: 

  • From your perspective, what do you believe are the most significant challenges our team should be addressing?
  • How do you envision our team’s role evolving given the company’s long-term strategy?
  • Based on your observations, how can I grow in my role to better support both our immediate team and the larger organization?
  • What trends or changes in the market should we should be paying attention to or learning from?
  • When you envision our company five or 10 years down the road, what are the key milestones you hope we’ve achieved?
  • Given the challenges our industry faces, what keeps you optimistic?

Build the relationship. 

Building a genuine, meaningful relationship with anyone — especially your manager’s manager — is about consistently demonstrating respect, integrity, and initiative. A little appreciation goes a long way, so always send a follow-up email after the meeting to thank your skip-level boss for their time. You might also summarize key takeaways or share how you plan to act on their guidance. 

Accountability matters. If you said you would circle back about a certain point or question, make good on your promise and show you’re reliable. Also consider asking for a quarterly meeting and get it on the calendar as soon as possible.

Taking the time and effort to invest in upward relationships, such as those with skip-level managers, requires strategy, humility, and diligence. After all, leadership is not only about managing those below you, but also navigating the complexities above. 

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