Questions to Ask Leaders
Twenty questions for employees who get time with the leaders of their own organization, at a skip-level, a town hall, or a one-to-one with someone several levels up. They focus on direction, decisions and trade-offs rather than leadership philosophy.
The questions
Open any question for the note
What is taking up most of your attention this quarter?
Why ask it
A leader's attention is a better guide to what actually matters than any published priority list. If the answer has nothing to do with the stated strategy, you have just learned which one is real.
What are we doing now that you expect us to stop doing within a year?
Why ask it
Companies announce what they are starting and go quiet about what they are ending. A specific answer gives you early warning about which projects and teams are being wound down, months before it is formally communicated.
Which goal on the plan do you think is hardest to hit?
Why ask it
Every plan has one number everybody privately doubts. Naming it tells you where the pressure will land later in the year, and a leader who says all the goals are equally achievable is either uninformed or managing you.
If we hit the plan, what does that make possible that we cannot do today?
Why ask it
Targets are easier to work toward when you know what they buy. The answer also exposes whether there is a coherent next step behind the numbers or whether the numbers are the whole strategy.
What do you know that would change how my team sets priorities?
Why ask it
Information gets lost on the way down more often than it gets hidden. This is a direct request for the context that has not filtered through yet, and it is usually the most immediately useful question you can ask.
What are you being measured on this year?
Why ask it
A leader's own scorecard explains behavior that otherwise looks arbitrary: why one project gets protected, why a metric suddenly matters in October. It also shows you where your work does and does not help them.
What do you wish people here asked you about more often?
Why ask it
Leaders usually field the same handful of questions and have thinking on subjects nobody raises. This hands them the floor and often produces the part of the conversation you could not have planned.
What decision have you made recently that you know is unpopular here?
Why ask it
Asking them to name it themselves is far more productive than complaining about it. You learn whether they know how it landed, and whether they can defend it without retreating into the language of the announcement.
What was the reasoning behind that decision that never made it into the announcement?
Why ask it
Internal communications are compressed and sanitized, so the actual argument often goes unheard. Some of what was left out will be confidential, and watching where they stop tells you how much room there is in this relationship.
Where do you think we are still guessing?
Why ask it
Strategy documents are written with more certainty than anyone feels. A leader willing to point at the unresolved parts is inviting help there, and that is usually where individual work has the most leverage.
What does good look like for someone in my role a year from now?
Why ask it
Senior leaders describe a role differently than your direct manager does, and the difference is worth knowing. Vague answers may simply mean they do not think about your level, which is itself worth finding out early.
How would you know whether my team's work is useful to you?
Why ask it
Plenty of work is well executed and invisible to the people who allocate resources. The answer tells you which outputs actually surface at their level, and often reveals that the wrong things are being reported upward.
Who else should I be talking to, and what should I ask them?
Why ask it
The second half makes this more than a networking request: it gets you a specific question, which is what makes a cold introduction work. Their choice of names also shows you who they consider load-bearing in the organization.
What would you want to hear from someone at my level that you are probably not hearing?
Why ask it
This gives them permission to ask for the unvarnished version, and it puts the burden on you rather than on them. Whatever they name is what you should bring next time, and it is usually more specific than feedback in general.
What is the trade-off you are least comfortable with right now?
Why ask it
Leadership at this level is mostly choosing what to underfund. Naming the uncomfortable one shows judgment and shows you what they know they are neglecting, which is different from what they are defending.
What would have to go wrong for us to change course?
Why ask it
A leader who has thought about this has stated conditions in advance, which is how companies avoid riding a failing plan to the end of the year. No answer at all suggests the strategy will be defended past the point of usefulness.
Which part of the company do you worry about that we never discuss?
Why ask it
The subjects absent from all-hands meetings are often more consequential than the ones on the agenda. Even a partial answer tells you where the organization has decided not to look.
When you disagree with a decision made above you, what do you do?
Why ask it
This shows whether they argue internally and then commit, or pass the disagreement downward as complaint. It also tells you what happens to your own objections when you send them up through this person.
What have you said publicly here that you would now put differently?
Why ask it
Leaders are rarely asked to revise anything on the record. Willingness to correct a prior statement, especially a reassuring one, is a strong signal about how much weight the next reassurance should carry.
What is the question you were hoping I would not ask?
Why ask it
Late in a conversation, this often produces the most candid moment in it. Some will deflect with humor, but a real answer identifies the topic they are carrying and cannot yet talk about openly.
Getting real answers from senior leaders
Practical guidance for the conversation itself
Before you get the time
Do not spend it on things you could look up
Read the last all-hands notes, the strategy deck and the recent announcements first. Time with a senior leader is worth spending on judgment and context, which are the only things not written down anywhere.
Pick three questions and one purpose
Decide in advance whether you want context, feedback, or a decision unblocked. Conversations that try to do all three usually deliver none, and the leader leaves unsure what you needed.
Tell your own manager you are meeting them
Skip-levels go wrong when they look like a route around someone. Mentioning it beforehand costs nothing and prevents the version of events where you were going behind their back.
Bring one thing they will not get elsewhere
Something you have seen firsthand, a customer reaction, a process that quietly fails at scale, makes the exchange two-way. It is also the reason they will agree to a second conversation.
Reading the answers
- Distinguish will not say from cannot say. Legal, personnel and market-sensitive limits are real, and pushing at them only wastes the goodwill you will need later.
- Note what they name first. The order in which priorities come out is usually more accurate than any ranked list they have approved.
- Watch for the shift into announcement language. When a leader starts repeating the phrasing from a company message, the informative part of the answer has ended.
- Take specific numbers, dates and names seriously, and treat everything hedged as intention rather than plan.
- If they ask you a question back, answer it properly. That is usually the moment the conversation becomes useful to both of you.
Common mistakes
Using the meeting to complain
A grievance delivered to a senior leader without a proposal reads as a request for rescue, and it tends to land on your manager afterward. Bring the problem with the two options you see.
Asking for reassurance
Questions like whether jobs are safe put leaders in a position where the only available answer is a soothing one. Ask instead what would have to happen for the plan to change, and you get something you can act on.
Repeating the question you already asked in public
If it was answered at the town hall, ask the next question instead. What you want is the part that could not be said to three hundred people at once.
Never following up
If they suggested you talk to someone or promised to find something out, close the loop within two weeks and tell them what came of it. Almost nobody does this, and it is most of the reason some people get a standing invitation.