Let me tell you a secret about executive promotions.

They don’t happen during performance reviews.

They happen in conversations you’re not in. Backchannel chats. Executive team meetings.

If this sounds familiar, read this breakdown of why you are being overlooked for VP.

Moments where someone says:

“What about Maya?”

“She’s sharp. I’d bet on her.”

That’s how people get promoted behind closed doors.

And most of your peers aren’t doing anything to influence those conversations.

But here’s the good news: you can.

And it starts with one powerful relationship—your skip-level manager.

If you learn how to impress your skip-level manager in the right way, you create the kind of sponsorship that gets your name brought up in VP promotion conversations.

Why your skip-level matters more than you think

Your manager might support your growth.

But they rarely control the budget, the org structure, or the big promotion decisions.

That’s the skip-level’s job.

They’re the ones your boss is trying to impress.

They’re the ones with influence over your future.

And if you can earn their trust? That’s when sponsorship begins.

Most people never learn how to use skip-level meetings strategically, which is why they stay stuck even when they do great work.

The problem? A lot of the time, we are so nervous that we blow our skip-level meetings.

We wing it. Ramble. Revert to status updates.

And walk out no more memorable than when we walked in.

Let’s change that.

5 Ways To Impress Your Skip-Level Manager (And Start Building Real Executive Visibility)

1. Never skip the intro.

They may be your skip, but that doesn’t mean they actually know you or the details of your work.

Not to mention, they’ve been running from meeting to meeting and probably need a second to catch up and set the right context.

Don’t launch into a project summary. Start with a short introduction.

• Introduce yourself if it’s a first meeting, using the power intro:

“Hi, I’m [Name]. I lead the [Team] team, where we’ve been focused on [business problem]. Last quarter, we [tangible result]. I’m here today to share how we’re supporting [strategic goal].”

This does three things fast:

✅ Establishes your role and credibility

✅ Highlights business impact

✅ Signals strategic alignment

• Highlight the goal of the meeting to give context

“I asked for this meeting to learn more about the business priorities of the company for Q4”

• Share your agenda if you have one

I want to cover:

1. Where we are at right now

2. Understand priorities for next quarter

3. Get your feedback on our progress

Don’t jump in without context. You’ll lose them quickly.

2. Speak to their priorities.

Skip-levels don’t care how busy you are. They care if your work moves the business forward and supports their priorities. Don’t show up and ask them what their goals are. Do your homework and come prepared to show how your work supports their priorities.

So instead of listing everything you’ve done…

Say this:

“This supports your priority around [X].

Here’s how we’re moving the needle.”

Need help finding their priorities?

• Rewatch recent town halls

• Review org-wide memos

• Ask your boss what’s top of mind for them

When you tie your work to their vision, you don’t just look proactive.

You look like executive material.

3. Share your wins—strategically.

You may think your wins are visible to your skip. After all, your manager sent a project summary email after your last win, and your skip was cc’d…

But it’s more likely they have no clue. Not because your manager doesn’t advocate for you, but because they have 7 direct reports with teams of 20+ and they can’t remember everything.

That means you have to use this opportunity to position yourself as a leader. Not by bragging, by being strategic.

Skip-levels want a clear, business-focused update. Not a bullet list of your to-dos.

Use this 4-slide quarterly brief format:

1. Business Goals — What’s the north star?

2. Wins + Blockers — What’s working? Where’s friction? (this is where you casually drop wins)

3. Decisions Needed — Any exec input you need?

4. What’s Next — What’s coming up or evolving? (showing your vision)

Why it works:

• It’s concise

• It mirrors how they think

• It positions you as a results-oriented leader

Pro tip: Use this format even if you’re not presenting slides—it shapes your story.

4. Ask smarter questions.

One of my worst experiences as a VP was when my skip-level reports asked me questions that could easily be answered by their manager (and sometimes with a Google search).

It’s disrespectful to your skip level’s time, and it undermines your executive presence.

Instead, prepare strategic questions that only your skip can answer, or questions that require their specific input and perspective.

Avoid asking about:

• Day-to-day operations

• Things your boss should cover

• Generic career advice

Instead, ask questions that show strategic curiosity:

“What’s your biggest focus area for the next 6–12 months?”

“Where do you see the most opportunity for cross-functional collaboration?”

“What capabilities will be most important as we grow?”

These aren’t just questions.

They’re a chance to show how you think—and where you want to grow.

5. Follow up—with value.

You don’t really need to thank your skip for their time. You need to show them that you listened.

That means following up with clear, strategic, and actionable updates.

Here’s a simple structure to follow:

Subject: Recap from Today’s Meeting

Thank you for the conversation today. Here’s a quick summary:

• Key insight: [e.g. Focus on cross-functional efficiency]

• Next step: [e.g. We’re exploring a new handoff process]

• Timeline: [e.g. Draft by end of next week]

That’s it. Keep it tight.

This shows you heard them, and you act on input.

Two core traits every exec looks for.

Your Next Steps

Your skip level can make or break your promotion.

One of my clients was recently up for promotion, and even though his manager was happy to support his nomination, there were budget constraints. The tie breaker came from his skip-level leader. They approved the promotion despite the budget.

Your skip-level manager could be your greatest advocate.

So the next time you get 30 minutes with them, make it count.

Be clear. Be strategic. Be worth remembering. Because when they are in the room and your name comes up, you want them to say: “She is ready.”

If you want a complete strategy for turning relationships like this into VP level promotions, watch my free masterclass where I walk you through the five elements leaders use when they decide who gets promoted and how Directors in tech become the obvious choice for VP.

Free training: How Directors In Tech Become The Obvious Choice For VP

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

Maya❤️