The Strategic Audition - MAC163

You have fifteen minutes on the calendar with a vice president who oversees two hundred people. She's been friendly from the first second. She leans forward, smiles, and asks the easiest question in the world: "So, what's your team working on right now?"

And you answer it. Of course you do. The vendor migration. The new intake form. The quarter-end reconciliation. About three projects in, you notice she's nodding the way people nod at a weather report. You've just spent the most valuable fifteen minutes of your quarter taking an exam nobody asked you to take.

This is a sequel. In Skip Level 1x1 (MAC-064), I made the case for asking for a skip-level at all, since most people never request one, and I gave three goals for it: build the relationship, highlight your contributions, and learn where your leader is taking the organization. All of that still holds. What that episode didn't give you was the words. This one is the script.

The oral exam versus the strategic audition

Most people prepare for an oral exam. They assume the leader is checking whether they know their stuff (what the team is doing, what's on schedule, what's late), so they rehearse the status. But a vice president with two hundred people doesn't need your project list. Somebody already put it in a deck.

What the deck can't tell them is how you think. Can this person see past their own desk? Do they understand what I'm actually worried about? When something breaks, do they bring me a complaint or a choice? Those are the questions a senior leader is quietly answering in fifteen minutes. That isn't an exam. It's an audition, and it assesses judgment. An exam looks backward. An audition looks forward.

The standard advice doesn't get you very far here. Search for skip-level questions and you'll find long lists of perfectly reasonable ones: what do you hope our department achieves this quarter, where is the company going, what feedback do you have for me. Good questions. They're also the questions everyone else on that leader's calendar is asking this month. They get you an answer. They don't get you remembered. So instead of thirty questions, here are three moves and a way to fit them into fifteen minutes. They only work after one piece of homework.

Look up before you walk in

Your team has a scoreboard: deadlines hit, requests closed, campaigns launched, the month-end close finished on time. You know it cold, because it's the one you're measured on. Your skip-level leader has a different one, measuring outcomes, risk, and a much longer time horizon. Most people walk in knowing every number on their own scoreboard and none on the leader's, then wonder why the conversation felt polite and flat.

So before the meeting, build the Leader's Scoreboard: a three-line page with your best guess at what this leader is measured on this year. Not what they care about in general. What their boss will ask them about. Look in places you've already been: the all-hands slides, the goals your organization published at the start of the year, earnings calls or annual reports if you work somewhere public, and the requests that keep reaching your own team from that leader's office. Whatever gets asked for over and over is on the scoreboard.

One guardrail: this is homework, not espionage. You read what's been shared openly. You don't interview your manager for gossip or poll colleagues for what they've heard. If you wouldn't be comfortable saying where you read it, it doesn't go on the page.

Then translate. Rewrite each of your current projects the way the leader would describe it. A practitioner piece on speaking to senior leaders puts the principle plainly: drop the internal vocabulary and talk about the business outcomes they actually track. "The vendor migration" becomes "we're taking about four days out of the month-end close." Same work, different scoreboard. And your page will be partly wrong. That's the point. It's a guess you bring into the room to be corrected, and being corrected by a vice president in the first five minutes is about the best thing that can happen to you.

Move one: the Strategic Horizon

The first move is a question: "What's the metric leadership is watching most closely this quarter that you think our team isn't paying enough attention to?" It doesn't ask the leader to summarize strategy, which they've done at every all-hands. It asks them to name a blind spot, and specifically yours, which tells them you're willing to hear it.

With your homework done, sharpen it: "My read is that what you're watching hardest this year is the cost per order in the new region. Is that right, or is it something else?" Now you've handed them a draft to edit, and people love editing a draft. That same Learning Guild piece recommends simply asking executives which results they expect. This is that question, aimed one level past the obvious. Then stop talking and write down whatever they say, because there's a decent chance your own manager doesn't know it yet either. In Are You Asking the Right Questions? (MAC-150), we talked about how a good question can signal more than a good answer. This is that idea at the highest altitude you'll get all year.

Move two: the Tradeoff Test

The second move is how you bring up a problem. Consider a finance team where the month-end close drags because three regions submit numbers in three formats. "Our close process is broken" is true, and it's also a grievance: it hands the leader a feeling and no decision, and in a skip-level it can sound like a complaint about your manager.

The Tradeoff Test turns the same problem into a choice, in three parts: the choice the organization is currently making, what each side costs, and what you'd recommend. "Right now we're letting each region keep its own format, which saves them rework. The cost is about four days of reconciliation every month on our side. If we standardized, they'd take a one-time hit and we'd get most of those days back. I'd standardize, starting with the two largest regions." Now it's a decision about a system instead of a person, and you've shown judgment at the level above yours because you weighed somebody else's cost. It works in any function: in marketing, "We're choosing a full brand review on every asset, which costs about a week per campaign. I'd move low-risk formats to spot checks."

If that sounds familiar, it should. In Own the Problem, Bring Solutions (MAC-084), we talked about taking a problem to your manager when you already have a plan and need approval to run it. The Tradeoff Test is that habit one level up. Your manager needs to know you can own a problem. Their boss needs to see that you understand what the fix costs somebody else.

Worried about a recommendation that turns out to be wrong? A piece from Arizona State on what makes someone start to sound like an executive argues that having a perspective, even one that isn't guaranteed to be right, is what signals confidence and leadership. A leader can disagree with your recommendation. They can't do anything with your frustration. One rule: the tradeoff is never about your manager. In Your Manager Is Not Your Career Sponsor (MAC-139), we talked about how your manager is constrained by the same system you are. Describe the system. Leave the people out. A grievance asks them to feel what you feel. A tradeoff asks them to decide.

Move three: the Memory Anchor

Some weeks after your skip-level, your name will come up in a room you're not in: a talent review, a calibration meeting, a conversation about who leads the new initiative. Somebody will ask that leader, "Do you know this person?" and they'll have about one sentence to answer with.

The Memory Anchor is you writing that sentence for them, said near the end of the meeting. Something done, what changed, and what it was up against: "The short version of my year is that I took the close from nine days to five, while the regions were changing systems underneath us." No adjectives about yourself, no list, nothing a stranger would need context to repeat. If the leader could say it to a peer next month without getting it wrong, it's done.

If you heard Busy Is Not Visible (MAC-161), this may sound like the Forwardable Update. It's a cousin, not a twin. The Forwardable Update is written, goes out monthly, and travels through your manager. The Memory Anchor is spoken, once, and placed directly with the person above them. One reaches the leader secondhand. The other reaches them in your voice. You won't be in the room when they decide. Your sentence can be.

The fifteen-minute run of show

Before the meeting, send a one-line agenda ("I'd love to hear what you're watching most closely this quarter, and share a little about where our team is") and tell your manager the meeting is happening. A guide written for the leaders who run these meetings warns that a direct manager who feels blindsided puts the whole conversation off on the wrong foot. Your manager should hear it from you, before.

Then the clock. Minutes zero to two: the person, not the work. Minutes two to eight: the Strategic Horizon, the biggest block, on purpose. Minutes eight to twelve: one Tradeoff Test, the problem closest to what they just said is on their scoreboard. Minutes twelve to fifteen: the Memory Anchor, a genuine thank-you, and one small thing you'll follow up on. The leader does most of the talking, and that's deliberate; that same guide names talking too much as a common skip-level mistake, and the warning cuts both ways. If the meeting shrinks to eight minutes, keep the question and the sentence and drop the tradeoff. Before you walk in, say all three moves out loud once, to find out which one you stumble over. And within a day, send a short note tied to something they said. That's the relationship goal from MAC-064, delivered with substance instead of a thank-you card.

I can give you the shape of all three moves. What I can't give you from a microphone is your leader's scoreboard, your tradeoff, or your sentence. If you've got a skip-level coming up and want to work through yours with someone who's sat on both sides of that table, I do one-on-one coaching. Reach out through the contact form at managingacareer.com/contact, and we'll see if we're a good fit.

The action plan

Four steps: build the Leader's Scoreboard and translate three projects onto it; turn one gripe into a tradeoff; write your Memory Anchor; and book the meeting and tell your manager. The first three come with prompts, below. You know your projects far too well to see them from two hundred people away, and an assistant doesn't have that problem.

So go back to that vice president. When she asks what your team is working on, she's really asking whether you can see what she sees. Answer the question she meant. Tell her what you think she's watching, and ask whether you're right. Bring her a choice instead of a complaint. And before you leave, hand her one sentence she can use when you're not in the room. An exam asks where you've been. An audition shows where you're looking.

Get the Episode + Prompts

The full episode and show notes are at managingacareer.com/163. The prompts from the action plan are below. Copy them, and change them to fit how you actually work.

Prompt — the scoreboard.

Below are notes from all-hands meetings, my organization's published goals, and recurring requests that reach my team from [the leader's role]. Identify the three outcomes this leader is most likely measured on this year. For each one, quote the line from my material that supports it. Rules: use only what is in the material I've pasted. If an outcome is your inference rather than something stated, label it "inferred" and tell me what would confirm or rule it out. Do not include internal politics, rumors, or guesses about individuals. Then rewrite the three projects listed at the end as outcomes on that scoreboard. If a project doesn't connect to any of the three, say so plainly instead of stretching it to fit. [Paste your material here] [List three current projects here]

Prompt — the tradeoff.

Here is a problem I'd like to raise with a senior leader, written the way I'd naturally say it. Rewrite it as a tradeoff in three short parts: the choice the organization is currently making, what each option costs and who bears that cost, and my recommendation. Rules: remove every reference to a specific person, including my manager — describe the system, not the people. If my version only shows the cost on my side, ask me what the other side gains from the current approach rather than inventing an answer. Keep it under 80 words. Then give me the strongest objection a senior leader would raise to my recommendation. Do not soften it. [Paste your problem here]

Prompt — the anchor.

From the notes below, draft three candidate one-sentence summaries of my work this year that a senior leader could repeat to a peer. Each must contain one thing I did, what changed as a result, and the constraint I was working against. Rules: under 30 words each. No adjectives describing me — no "strong," "driven," "excellent," or anything like them. If my notes don't contain a result for something, stop and ask me what changed instead of supplying one. Then, for each sentence, write how a busy person might misquote it a month later, and tell me which one survives that best. [Paste your notes, brag document entries, or last quarter's updates here]

Links & References

• Research & sources — Questions to Ask Your Boss's Boss in a Skip-Level Meeting (CareerBuilder)
• Research & sources — Can You Communicate With Senior Leaders in Their Language? (The Learning Guild)
• Research & sources — 3 Ways to Start Sounding Like an Executive (Arizona State University)
• Research & sources — Skip-Level Meeting Guide: Questions, Format and Tips (Read.ai)
• Episode inspiration — Skip Level 1x1 (MAC-064), the parent episode; this one is its sequel
• Episode inspiration — Busy Is Not Visible (MAC-161)
• Related Managing A Career episodes — Skip Level 1x1 (MAC-064)
• Related Managing A Career episodes — Busy Is Not Visible (MAC-161)
• Related Managing A Career episodes — Are You Asking the Right Questions? (MAC-150)
• Related Managing A Career episodes — Your Manager Is Not Your Career Sponsor (MAC-139)
• Related Managing A Career episodes — Own the Problem, Bring Solutions (MAC-084)
• Episode page — managingacareer.com/163

TAKE THE SURVEY!

Are you looking for a career coach? If you reach out to me via the contact form, I will arrange an introductory session where we can talk about your career goals and how I can help. If we're a good fit, we can schedule regular coaching sessions.