Questions to Ask Your VP
Twenty questions for a skip-level one-to-one, a new VP's listening tour, or the ten minutes you get after a leadership review. Written for people who sit one or two levels below a vice president and want to spend the time on things only a VP can actually answer.
20 questions · each with the reason to ask it · conversation guide
The questions
Open any question to see why it works
- 01
What's taking up most of your attention this quarter?
Why ask it
An easy opener that tells you where their calendar and political capital are going, which is often not the initiative they talk about publicly. If the answer is a project nobody on your team mentions, you have learned where decisions are being made.
- 02
What are you being measured on this year?
Why ask it
VPs have two or three numbers attached to their own review, and everything they push tends to trace back to them. Once you know the numbers, you can describe your own work in terms they can repeat upward without translating it.
- 03
Of everything my team has in flight, which part matters most to you?
Why ask it
You will often hear a different ranking than your manager gave you, and the gap itself is worth knowing. A VP who cannot name any of your work is telling you something about visibility rather than quality.
- 04
Is there anything we're working on that you would quietly drop?
Why ask it
Senior people rarely volunteer this, because cancelling work is awkward, but they will usually answer it when asked directly. It is one of the few questions that can hand back weeks of your team's capacity.
- 05
What do you hear about my team from people outside it?
Why ask it
This is information you cannot get anywhere else: how your group looks from other departments. Expect a reputation you half recognize, and pay attention to whether the complaints are about output, responsiveness or communication.
- 06
When our work comes up with your own boss, what do they ask about?
Why ask it
It reveals the questions your work has to survive two levels up, which are usually blunter than the ones asked in your team. Answering those questions in advance is most of what people mean by being strategic.
- 07
Which of the numbers we report do you actually look at, and which do you skip?
Why ask it
Most reporting packs contain metrics nobody has read for a year. A candid answer lets you retire some of them, and it tells you which single number your team is being judged on when nobody is in the room.
- 08
What would you like to know about our work that the reporting doesn't tell you?
Why ask it
This turns you into the person who fixes a gap they already feel. The answer is often qualitative, such as whether customers are actually using a feature, which no dashboard was set up to show.
- 09
What has already been decided that people are still debating?
Why ask it
Teams routinely burn weeks arguing about something settled at a level they cannot see. Asking this is the fastest way to stop that, and a VP who says nothing has been decided has told you the debate is still worth having.
- 10
What has changed in the plan since it was announced, and what hasn't been communicated yet?
Why ask it
Plans drift, and the gap between the stated plan and the current one is where wasted work lives. Note that you are asking what has changed, not for confidential detail, which makes it a fair question to answer.
- 11
What constraints are you working under that we probably can't see?
Why ask it
Headcount freezes, a contract that renews in November, a commitment made to another department. Hearing them explains decisions that look arbitrary from below, and it stops your team writing proposals that were never possible.
- 12
If your budget were cut by ten percent, what would you protect first?
Why ask it
A hypothetical that forces a real ranking, because it makes them choose rather than list. What they protect is what they believe in; what they name last is where your own work is most exposed.
- 13
How do you want to hear bad news, and how early?
Why ask it
Some leaders want the flag the moment a date looks shaky, others want a diagnosis and an option attached. Getting this wrong is the most common reason a competent person loses a senior person's confidence, and it takes one question to avoid.
- 14
What should someone at my level bring straight to you, and what should stay with my manager?
Why ask it
It sets the boundary explicitly instead of leaving you to guess, and it protects your manager from being surprised. A VP who says bring me anything is being friendly rather than useful, so follow up by asking for an example.
- 15
What's the most common mistake people make when they bring you something?
Why ask it
Answers tend to be concrete and immediately usable: no recommendation attached, too much background, a decision requested without options, or a surprise in front of an audience. It costs nothing to ask and changes how your next update lands.
- 16
What's a piece of work at my level you thought was excellent recently, and what made it stand out?
Why ask it
Far more useful than asking what they value, because it forces a real example. Listen for whether the praise is about the thinking, the delivery or the communication, since that tells you what actually gets noticed here.
- 17
What does someone have to demonstrate to reach the next level in your organization?
Why ask it
VPs usually sit on the promotion decisions and hear the objections raised, so their version differs from the published ladder. A strong answer names behaviors and scope; a weak one recites the competency framework, which means the real bar is elsewhere.
- 18
Who in the company should I know that I probably don't?
Why ask it
A cheap request that is easy for them to grant, and the names tell you where they think the useful work sits. Ask whether they would introduce you, since a one-line note from a VP opens a door that a cold message will not.
- 19
What did you believe about this business a year ago that you no longer believe?
Why ask it
The one question here that invites reflection rather than information, and it usually gets a real answer because it flatters no one. It also shows you whether this is someone who updates their view or defends last year's position.
- 20
What's one thing you'd like me to do differently?
Why ask it
Ask it last, and then stop talking. Most people get a soft answer the first time and something real on the second occasion, once the VP believes you will not argue. If you push back on the answer, you will not be given another.
Using Time with a VP Well
Practical guidance for the conversation itself
Before the Meeting
Before the Meeting
Do not ask what your manager could answer
Anything about your own workload, tooling or team process is a waste of a rare slot and reads as though you have not tried the normal channel. Save the time for the VP's vantage point: what they hear from other departments, what has already been decided, what they are under pressure to deliver.
Bring three questions, not ten
A half hour booking usually becomes twenty minutes, and one question with two follow-ups goes deeper than six asked in sequence. Pick the three that only this person can answer and let the rest go.
Tell your manager first
If you plan to raise anything about your team's work, mention it to your manager beforehand. Skip-levels turn into problems almost entirely when a manager hears about the conversation second-hand, and the cost lands on you, not the VP.
Give context in two sentences
A VP may not know what your team ships or where your project stands. Open with a short, factual framing, then ask. Without it, half the meeting goes on catching them up and you get generic answers.
Write down what you heard, and act on one thing
Send a short note the same day confirming what you took away and what you will do next. Then actually do the one thing. That single follow-through is what turns a pleasant meeting into a working relationship.
Two Ways to Run It
Two Ways to Run It
A twenty-five minute skip-level
- 1Two sentences on what your team does and what you own within it.
- 2One question about their priorities, and listen for what they mention that you had not heard about.
- 3One question about how your team is seen from outside, then let them talk without defending anything.
- 4One question that is useful to them: what they are missing from the reporting, or what they would drop.
- 5Close by asking for one thing to do differently, then confirm the takeaway in writing afterwards.
If you are raising a real problem
- 1State the problem in one sentence, in terms of impact rather than blame.
- 2Say what you have already tried and what it cost.
- 3Offer two options with a recommendation, and be clear which one you would pick.
- 4Say exactly what you need from them: a decision, cover, a name, or nothing at all.
- 5Agree a date to check back, so the issue does not quietly expire after the meeting.
What Not to Do
What Not to Do
- Using the slot to complain about your manager. Whatever the merits, the VP will hear it as a management problem to be handed back down, and it will be.
- Asking questions you have obviously copied from a list. Broad questions about culture, values and innovation get equally broad answers, and everyone can tell.
- Pitching yourself for the whole meeting. Senior people remember who asked good questions, not who talked longest about their own work.
- Asking for confidential information. Reorganization and headcount details put them in an awkward position and end the candor for the rest of the conversation.
- Nodding along when you do not understand an answer. Ask what they mean by a term, since half of senior shorthand is internal jargon nobody has defined out loud.
- Never following up. A meeting with no follow-through is the reason a second one is not offered.