Questions to Ask a Senior Leader
Questions for the twenty minutes you get with an executive, in a skip-level, a coffee or after a town hall. They cover what the leadership team is actually deciding, what information reaches them, how budget and promotion really work, and what they want people to stop doing.
The questions
Open any question for the note
What is taking up most of your attention this quarter?
Why ask it
Opens with something they can answer without preparation, and the answer is often not what the company communications emphasise. The gap between the two is the most useful thing you will learn in the meeting.
What are we saying no to this year?
Why ask it
Any leader can list priorities. Naming what was rejected shows there was a real trade-off, and it gives you something concrete to check your own team's work against. Vagueness here usually means everything is still officially a priority.
Which recent decision do you think was misunderstood internally?
Why ask it
Invites them to explain reasoning that never made it into the announcement, which is usually where the actual constraint lives. It also tells you where they know communication failed, and whether they intend to fix it.
How would you know if the strategy was not working?
Why ask it
Look for a specific indicator and a date. Leaders who can name the signal they are watching have a plan that can be falsified, and leaders who describe only success conditions are likely to keep going long past the point of doubt.
What kind of news reaches you late, or not at all?
Why ask it
Senior people are usually aware they are the last to hear certain things, and they will often name the category: quality problems, attrition risk, a customer quietly leaving. It is also an invitation to be the person who tells them earlier.
Which part of the plan depends on something outside our control?
Why ask it
A regulator, a supplier, a single large customer, a hiring market. Knowing the external dependency tells you which internal goals are likely to move, and it stops you reading a change of course as indecision.
What do you wish teams brought to you earlier?
Why ask it
Practical and immediately usable, because it tells you what to escalate rather than absorb. Note whether they want problems or proposals, since bringing the wrong one is how people learn to stop bringing anything.
What is the first number you look at each week?
Why ask it
Whatever they name is what the organisation optimises for, whether or not it is in the strategy deck. If it is not a number your team affects, that is worth understanding before your next planning cycle.
Where do you think we are slower than we should be?
Why ask it
Leaders usually have a candidate: approvals, hiring, decisions returning to the same committee. Ask what they have tried already, because the answer tells you whether the bottleneck is a process nobody owns or one they cannot get past.
How does budget actually get decided, and when should a team be asking?
Why ask it
The calendar is the part people miss. Requests that arrive after the allocation is set are refused for timing reasons that look like judgement, and one clear answer here can be worth a year of frustration.
What did the last reorganisation fix, and what did it not?
Why ask it
Honest answers acknowledge that structures trade one set of problems for another. Someone who describes only improvements either was not close to it or is not willing to discuss the cost, and both are useful to know.
What sort of work gets someone promoted here, and what gets overlooked?
Why ask it
The second half is the real question. In most organisations maintenance, cleanup and preventing problems are undervalued next to launching things, and hearing a leader admit that tells you how to position your own work.
How do you decide to reverse a decision you have already announced?
Why ask it
Reveals how they weigh consistency against being right. A leader with a threshold and an example has changed course before, and that makes it safer for people below them to raise evidence that something is not working.
What do you want people to stop doing?
Why ask it
Asked less often than what to start, and more actionable. A report nobody reads, a meeting that outlived its purpose, a habit of copying them on everything. Expect at least one thing you personally do.
What feedback do you get most often, and what have you done about it?
Why ask it
The second half separates leaders who collect feedback from leaders who act on it. A specific change, even a small one, is a better signal than any statement about being open to input.
Roughly how does a normal week break down for you?
Why ask it
The proportion spent on external meetings, internal reviews and actual decisions surprises most people. It also explains response times, and it usually makes clear why a short written summary reaches them and a long document does not.
If you were three levels down with my view of things, what would you be pushing for?
Why ask it
Turns the conversation from information to advice without asking them to solve your problems. The answer often names an issue they cannot raise themselves for political reasons.
What risk to the company do we not talk about enough?
Why ask it
Ask this once the conversation has warmed up. Answers tend to be structural, a dependence on one customer, ageing infrastructure, a skill nobody is replacing, and it is the closest you will get to their private worry.
What keeps you here?
Why ask it
A fair question to a leader who asks it of others. Listen for whether the answer is about the work or the position, and note that a senior person who has to think hard about it may be closer to leaving than the organisation assumes.
If we talk again in a year, what would tell you the year went well?
Why ask it
A better closing question than asking about the vision, because it forces a small number of testable outcomes. Write them down, and bring them back next time, which is what turns a one-off meeting into a relationship.
Making twenty minutes with an executive count
Practical guidance for the conversation itself
Before the meeting
Send one line about why you asked
I would like your view on where our team's work fits with the shift in priorities gets a prepared answer. A request for a chat gets small talk and a check of their watch.
Choose three questions and accept you will ask two
These conversations run short and get interrupted. Rank them, lead with the one that would change what you do next week, and leave the interesting-but-optional ones at the bottom.
Tell your own manager you are meeting them
Skip-levels read badly when they are discovered afterwards. A sentence beforehand removes the ambiguity and often gets you a useful briefing on what the leader cares about.
Bring one thing they will not already know
A pattern from customer conversations, a recurring failure, something that took your team three weeks and should have taken three days. Senior people remember whoever gave them information they could not get elsewhere.
What the answers tell you
- Cannot name anything the company said no to: priorities have not really been chosen.
- No stated signal for the strategy failing: expect the current course to continue regardless of evidence.
- Weekly number that has nothing to do with the published strategy: believe the number.
- Reorganisation described with no costs: they were not close to it, or will not discuss it.
- No answer on what gets overlooked: promotion here is less legible than the framework suggests.
- Feedback received but nothing changed as a result: treat their openness as decorative.
How these meetings get wasted
Using it to complain about your manager
It will be relayed, usually within a day. If there is a real problem, take it through the proper route. If there is not, do not spend the meeting on it.
Asking questions answered in the last all-hands
It signals you did not attend or did not listen. Ask about the reasoning behind what was announced instead, which is the part that never gets said on stage.
Pitching for twenty minutes
If you want something, say it in two sentences and ask what would make it easier to approve. Long pitches get a polite yes and no follow-up.
Leaving with nothing written down
Send three lines the same day: what you heard, what you will do, what you will come back with. That note is the reason a second meeting happens.