Questions to Ask Your Leader
Questions for a one-on-one with the person you report to, covering what they actually want from you, how your work is judged when you are not in the room, what you can decide alone, and what promotion would require. For employees who want direct answers rather than encouragement.
The questions
Open any question for the note
What does a good quarter look like for you, and where does my work fit into it?
Why ask it
Managers are measured on a handful of things, and your work either helps with those or sits to one side. Asking about their quarter rather than your goals gets you the honest ranking, and sometimes reveals that your biggest project barely registers.
If you had to name the two things you most want from me, what would they be?
Why ask it
Capping it at two forces a choice, which a general question about expectations never does. If they cannot narrow it down, that is useful information: it usually means priorities are being set above them and passed through unfiltered.
What am I doing that you would like me to keep doing?
Why ask it
Easier to answer than a request for criticism, and it protects you from quietly dropping the thing they value most. Vague praise here often means they do not have visibility into your work, which is a separate problem worth solving.
Where am I falling short of what you expected when I took this role?
Why ask it
The wording gives them a specific comparison to answer, which is much harder to deflect than asking how you are doing. Nothing comes to mind is worth gently testing again in a month, because unspoken disappointment tends to surface first in a review.
How is my work judged when I am not in the room?
Why ask it
Much of your reputation is formed in meetings you do not attend, based on a summary someone else gives. Their answer tells you whether your results travel on their own or depend entirely on your manager relaying them.
What is the last thing you heard about me from someone else?
Why ask it
Direct, slightly bold, and often the most useful question here. Feedback that arrived second-hand is usually never passed on, and it is the kind that shapes decisions about you.
If you had to drop one of my projects, which would it be?
Why ask it
A safe way to find out what your manager considers low value without accusing anyone of wasting your time. If the answer is the project you are most invested in, better to hear it now than after another quarter of effort.
What are you being measured on this year?
Why ask it
Their targets explain most of their behaviour, including the requests that seem arbitrary. It also shows you where your effort will be noticed by the people who evaluate them.
What do you know about where the team is heading that I probably do not?
Why ask it
Invites them to share context rather than secrets, and gives them room to say what they can. A long pause followed by nothing much is worth noticing, particularly during a reorganisation.
What decisions can I make on my own, and which ones do you want to see first?
Why ask it
Most friction between a manager and a good employee comes from a mismatch here rather than from performance. Ask for examples at the boundary, because the clear cases were never the problem.
How do you prefer to hear bad news, and how early?
Why ask it
Some managers want a heads-up on a risk the day it appears, others treat that as noise and want it once you have a plan. Getting this wrong is one of the fastest ways to be seen as either alarmist or evasive.
What is the fastest way to lose your trust?
Why ask it
Blunt, and it produces something specific: missed deadlines announced late, surprises in front of their own boss, going around them. Whatever they name is the thing to be careful about all year.
Between our one-on-ones, when is it fine to interrupt you?
Why ask it
Answers the practical question of whether to sit on something for six days. It also tells you how they think about their own availability, which is a fair predictor of how supported you will feel.
What would need to be true for me to be promoted, and who else decides?
Why ask it
The second half matters more than the first. If the decision involves a committee, a budget cycle, or a peer manager, then your manager's enthusiasm alone will not do it, and you need to know whose view counts.
Is there a gap that would hold me back even if my results were good?
Why ask it
This is where the real blockers live: writing, running a meeting, handling conflict, visibility with a particular group. Strong results with a persistent gap is a very common reason people stall without being told why.
Who in the organisation should know my work and currently does not?
Why ask it
It converts a vague ambition into a short list of names, and it invites your manager to make introductions rather than just endorse you. If they cannot name anyone, ask who they think will be consulted at the next round of decisions.
What part of your job would you hand off if you could?
Why ask it
Often the most direct route to work that grows your scope, and it asks them for something they actually want. Be prepared for the answer to be genuinely unglamorous, which does not make it a bad trade.
What is the team doing out of habit that no longer makes sense?
Why ask it
Gives them permission to criticise their own process, which most managers find easier than criticising a person. Whatever they name is something you could propose changing with their backing already in place.
What do people ask you for that you cannot give them?
Why ask it
Reveals the constraints they are working inside: headcount, budget, a decision made two levels up. It also stops you from spending months pushing on something they were never able to grant.
What is a mistake you made at my stage that you would rather I skipped?
Why ask it
Ends on a question they will enjoy answering, and the specifics tend to be more useful than general career advice. If the answer is polished and abstract, ask what it actually cost them.
Using these in a one-on-one
Practical guidance for the conversation itself
How to ask
Send the question ahead for the hard ones
Questions about promotion, gaps, and what they have heard about you get thin answers on the spot and considered ones with a day's notice. A single line in the meeting invite is enough.
One or two per meeting, not a list
A one-on-one that turns into a questionnaire puts your manager on the back foot and uses up the time you need for actual work. Pick the one you most want answered and leave space for the follow-up.
Write down the answer and bring it back
Repeating what they said last month, in their words, is the single most effective thing you can do with this list. It shows the conversation had consequences, which makes the next answer more candid.
Separate the feedback conversation from the promotion conversation
Asking where you fall short and what promotion requires in the same half hour invites a diplomatic non-answer to both. Different meetings, ideally different weeks.
Ask for an example, once
Feedback without a specific instance is not actionable, so ask for one. Asking twice reads as arguing, so take what you get and come back to it later.
What goes wrong
Asking the blunt ones in front of other people
What is the fastest way to lose your trust and where am I falling short both require privacy. In a team setting they put your manager in a position where the safe answer is a compliment.
Treating an answer as a commitment
A manager describing what promotion usually requires is not promising you one. Ask separately what they are willing to advocate for and by when, so you are not relying on your own interpretation.
Only asking about yourself
A one-on-one made up entirely of questions about your career reads as extraction. The questions about their quarter, their constraints, and what they would hand off change the balance and usually produce better answers to the rest.
Asking and then doing nothing
The second round of honest answers depends on visible movement on the first. If you cannot act on it, say why, rather than letting it look ignored.