How To Win Over Your Skip-Level Boss

As an ambitious high-achiever, you already know that getting the support of your skip-level boss (the manager who oversees your direct manager) can be a total game-changer when it comes to leveling up in your career. Those VPs and C-suite leaders hold a ton of influence over the big decisions - promotions, high-visibility projects, stretch assignments, you name it.

But let's be real - actually winning over your skip-level boss isn't always easy. It's not like you can just waltz into their office and be like, "Hey, I deserve that promotion, okay?" More often than not, they're buried in meetings, putting out fires, and trying to keep the whole operation running. How the heck are you supposed to get on their radar?

Well, my fellow go-getter, I've got your back. Here are some proven strategies to help you cultivate that crucial skip-level support:

Understand Their Priorities (and Speak Their Language)

The first step is to get inside the head of your skip-level boss. What are their top priorities and pain points right now? How are they being evaluated and compensated? Aligning your contributions to directly support their goals is key.

You’ll need to do some stalking. This involves researching their past projects, public statements, and the strategic goals they are known to champion. You can also get your HR partner involved and ask for their support in setting up a “skip level check-in” meeting.

Set up a 1-on-1 meeting and come prepared with smart questions. Ask about their vision for the team and organization, the challenges they're facing, and the initiatives they're working on. Then, look for ways you can step up and make their life easier. When they see you as a valuable partner who "gets" what matters most, they'll be much more likely to go to bat for you.

Example: If a skip-level leader is focused on expanding the company’s market reach, showcase how your project contributes to this goal by increasing reach (marketing), expanding contracts into new territories (sales), or localizing the product experience (product).

Get Creative with Quick Touchpoints (When 1-on-1s Aren't Possible)

I know, I know - trying to actually schedule 1-on-1 time with a busy skip-level exec can feel like trying to book a meeting with the President. But it's worth being persistent, even if that means getting a little creative. Look for opportunities to briefly connect before or after meetings you both attend, swing by their office for a quick update or see if you can snag a few minutes during a larger team gathering.

The key is to make the most of these brief interactions - come prepared with a clear, concise update or request and make it easy for them to provide input or guidance. Over time, these quick check-ins can help build rapport and keep you top-of-mind.

Build Relationships Across the Organization

In addition to buttering up your skip, it's crucial to build genuine relationships with your manager's peers - the other leaders who report to the same boss. Get to know them, understand their work, and find opportunities to collaborate or lend a hand.

The more positive interactions and "face time" you can create with this broader circle, the more they'll start seeing you as a team player who adds value beyond your role. That recognition and goodwill will absolutely translate up to your skip-level boss.

Example: Attend cross-departmental meetings or social events to understand other teams' challenges and goals. And get close to your skip’s team members to learn what they need and how you can collaborate with them. They may not have the influence your skip has, but they have her ear.

Make Your Wins Visible (Don't Be Shy!)

Finally, make darn sure your skip-level boss is aware of your major accomplishments and contributions. focus on communicating the impact of your work rather than just the tasks you've completed. Highlight how your projects contribute to the company’s strategic goals, improve efficiency, or drive revenue. This approach positions you as a strategic thinker contributing to the organization's success.

Work closely with your direct manager to ensure your work is being properly communicated up the chain. Offer to provide highlights or summaries for their staff meetings. The more they see your fingerprints on important initiatives, the more they'll recognize your leadership potential.

Your next steps

I get it; courting that skip-level support takes time, energy, and intentionality. But it's crucial if you want to take that next big leap in your career. By aligning your work, building strategic relationships, and actively managing your visibility, you can position yourself as an invaluable asset that your skip-level boss will be eager to champion.

It’s also a great insurance policy if things don’t go well with your boss or they leave or change roles.

I believe in you, and I’m rooting for you.

Maya ❤️