Should You Build a Relationship With Your Boss’s Boss?

Most employees focus on building a strong relationship with their direct manager. That makes sense. Your manager assigns your work, evaluates your performance, and often has significant influence over your next promotion.

But another relationship can also have an important impact on your career: the skip-level relationship.

A skip-level relationship is a professional relationship with someone above your direct manager—your manager’s boss, a department head, a divisional leader, or another senior executive.

Handled correctly, these relationships can be extremely valuable. Handled poorly, they can create unnecessary problems.

Why Skip-Level Relationships Matter

Senior leaders often have a broader view of the organization than your immediate manager. They know where the business is heading, which departments are growing, what skills are becoming important, and where future opportunities may exist.

Getting appropriate exposure to these leaders can also increase your visibility.

If a VP knows you as “the assistant designer who helped turn around that important program” rather than simply recognizing your name on an organizational chart, that can matter when promotions, reorganizations, or new opportunities are being discussed.

Skip-level relationships can also provide valuable career perspective. A senior leader may see strengths or potential career paths that aren’t obvious from your current position.

And in fashion, where people frequently move between companies while remaining within the same market segment, those relationships can continue paying dividends long after either of you leaves the company.

But There Are Risks

The biggest mistake is making your manager feel that you are going around them.

Regularly taking problems directly to your manager’s boss, complaining about your manager, seeking approval from senior leadership, or appearing to cultivate executives purely for personal advancement can quickly create tension.

Your skip-level relationship should never become an alternate reporting structure.

There is also a fine line between visibility and self-promotion. Senior leaders usually appreciate employees who are knowledgeable, curious, and engaged. They are less likely to appreciate someone who constantly looks for opportunities to advertise their accomplishments.

Build the Relationship Naturally

You don’t need to manufacture reasons to speak with senior leadership.

Take advantage of legitimate opportunities: cross-functional meetings, presentations, company events, project reviews, mentoring programs, or occasional skip-level meetings.

When those opportunities arise:

• Ask thoughtful questions about the business.
• Be prepared to discuss your work concisely.
• Give credit to your manager and teammates.
• Show interest beyond your immediate responsibilities.
• Avoid gossip and complaints.
• Don’t ask for favors every time you interact.

Most importantly, continue building a strong relationship with your direct manager.

The best skip-level relationships don’t undermine your manager. They complement that relationship.

Your goal isn’t to bypass the organizational chart. It’s to gradually build a broader professional network inside your company.

Done well, that increased visibility can lead to mentorship, stronger internal advocates, and opportunities you might otherwise never hear about.

Build upward—but don’t step on anyone on the way.