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

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

. 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: 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.

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. 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.

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