Opening
You're preparing for a skip-level meeting with your director. You talk about current projects and answer their questions. The conversation is pleasant but generic. They nod, thank you, and move on. Six months later, a high-visibility project needs an owner—they don't think of you.
Now imagine this: You share three specific outcomes from your work, connected to their strategic priorities. You mention 40% faster deployment cycles and $200K in cost savings. They ask follow-up questions and note your approach to cross-team alignment. Two weeks later, you're invited to lead a strategic initiative that puts you on the promotion track.
The difference? You turned a check-in into a strategic conversation that opened doors.
Marshall Goldsmith's work with executives showed that promotions go to people visible at higher levels, not just those doing good work quietly. Skip-level meetings are visibility opportunities. AI helps you prepare conversations that position you for growth, not just report status.
Skip-levels have always been visibility opportunities, but most people treat them as status updates. AI helps you transform project details into strategic narratives that land with senior leaders and position you for bigger opportunities.
The Principle
Skip-level meetings are career accelerators disguised as casual check-ins. Senior leaders use them to identify who thinks strategically, who drives impact, and who's ready for bigger responsibilities.
The challenge isn't getting the meeting—it's making it memorable. Most people share what they're working on. High performers share what they've achieved and how it connects to what leadership cares about.
The magic happens when you translate your work into their language. You're not just shipping features—you're reducing time-to-market. You're not fixing bugs—you're improving customer satisfaction scores. You're not mentoring teammates—you're building bench strength.
When senior leaders see you thinking at their level, doors open. Not because you're playing politics, but because you're demonstrating readiness for the next level.
The Prompt
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Why It Works
Senior leaders are constantly scanning for people who are ready for more responsibility. Skip-levels are their research method.
They're not just evaluating your current work—they're assessing your thinking level. Can you see beyond your immediate tasks? Do you understand business priorities? Can you articulate impact in ways that matter to the organization?
When you speak their language and connect your work to strategic outcomes, you're not just reporting—you're demonstrating that you already think like someone at the next level. That's what opens doors to high-visibility projects, stretch assignments, and promotion conversations.
The best part? You're not inventing impact. You're learning to recognize and articulate the strategic value that's already in your work.
Try This
Do this right now:
1. List your last 3 months of work—projects shipped, problems solved, improvements made (spend 5 minutes brain-dumping everything)
2. Run it through the prompt and identify which 3 outcomes have the strongest numbers and clearest connection to business priorities
3. Practice saying those 3 outcomes out loud in under 60 seconds—conversational tone, not rehearsed (record yourself if it helps)
Takes 15 minutes. You'll have a strategic narrative ready for your next skip-level, and you'll start seeing your own work through a leadership lens that accelerates every future conversation.
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