Questions to Ask Your Boss
Questions for a one-to-one with the person you report to, about the working relationship rather than your next promotion: what good work looks like to them, which decisions are yours, how they want to hear bad news, what they are being measured on, and the feedback they have not got round to giving you.
The questions
Open any question for the note
What does a good week from me look like to you?
Why ask it
Managers rarely say this unprompted, and the answer is usually narrower than expected: two things finished, one problem raised early, no surprises. It replaces a vague sense of being behind with a standard you can actually meet.
Of everything on my plate, which two things matter most this month?
Why ask it
Forcing a choice of two exposes where your picture of the work differs from theirs. If they will not choose, that is the answer: propose an order yourself and get it confirmed in writing.
What can I decide on my own, and what do you want to hear about first?
Why ask it
Unclear decision rights cause more friction than actual disagreement. Name three real examples, a refund, a date change, a reply to a client, and the boundary becomes usable instead of theoretical.
How do you like to get updates: written, in our one-to-one, or only when something's off?
Why ask it
You are judged partly on how easy you are to manage, and a mismatch here reads either as poor communication or as concealment. Some managers want a Friday summary, others consider that noise and want a call the moment something slips.
When you're under pressure, what do you want me to stop doing?
Why ask it
This tells you what is genuinely optional. Under pressure managers reprioritise silently and then feel let down, so agreeing the drop list in advance protects both of you.
What's worrying you about this team at the moment?
Why ask it
Their anxiety will drive their behaviour for the next quarter. Work that touches it gets attention and cover; work that does not, however good, competes for neither.
What are you being measured on this year?
Why ask it
Your manager has targets of their own, and your work either serves them or it does not. This single question explains more of their otherwise baffling decisions than any theory about their personality.
Is anyone above you unhappy about something in my area?
Why ask it
Asked plainly rather than as gossip, this surfaces the political weather around your work. If criticism exists, you would far rather meet it now than read a version of it in a review.
What do I do that makes your job harder?
Why ask it
Almost nobody asks, and most managers have an answer ready: late handovers, decisions requested in corridors, work that arrives needing reformatting. It is usually cheap to fix and buys a lot of goodwill.
Is there feedback you've been sitting on because there hasn't been a good moment?
Why ask it
Awkward feedback tends to get saved for review season, by which point it has been said to other people first. This gives permission to raise it now, while you can still act on it.
When I get something wrong, how do you want to hear about it?
Why ask it
Agree the route before you need it. A manager who wants to know immediately, even half-formed, is telling you that hiding the problem is the real offence, which is useful information before your first serious mistake.
What's the last piece of my work you read closely?
Why ask it
This tests whether your output is actually seen. If the honest answer is nothing for months, you are either trusted or invisible, and those need opposite responses, so ask which it is.
What does the rest of the company think this team is for?
Why ask it
Reputation can only be managed once you know what it is. The answer often reveals that other departments think you are slower or narrower than you believe, which is fixable once someone says it out loud.
Which of my meetings could I drop without anyone minding?
Why ask it
Managers usually know which meetings are ceremonial but will not volunteer permission to skip them. Asking recovers hours and signals that you are thinking about your own cost to the organisation.
How much of my time should go to the long project versus the daily requests?
Why ask it
Long work always loses to urgent work unless somebody states a ratio. Even a rough number gives you something to point at when the incoming queue starts eating the project.
If two people give me conflicting priorities, how do you want me to handle it?
Why ask it
This happens to everyone and mishandling it makes you look either obstructive or overcommitted. You need to know whether they want to arbitrate personally or expect you to negotiate and then tell them.
What's changing in the next six months that I don't know about yet?
Why ask it
Reorganisations, budget decisions, departures and system changes are known one layer up before they are announced. Even a hedged answer stops you starting work that is about to be cancelled.
What do you wish someone had told you when you were doing my job?
Why ask it
This invites comment on the job rather than on you, which is easier to answer honestly. What comes back is usually local knowledge about a person, a process or a trap that appears in no handover document.
In the week before a big deadline, what's the most useful thing I can do for you?
Why ask it
Anticipating the crunch is one of the few things that genuinely distinguishes people at work. The answer gives you a specific, repeatable way to be valuable exactly when their attention is scarcest.
Is there anything you need from me that you haven't asked for because you assumed I'd say no?
Why ask it
Managers censor requests they expect to be refused: travel, a weekend, an unglamorous project, a role nobody wants. Hearing the list lets you choose one deliberately instead of being volunteered for it later.
Working Well With the Person You Report To
Practical guidance for the conversation itself
Making one-to-ones worth having
Send an agenda the day before
Three bullets: a decision you need, a risk you are flagging, a question. Managers arrive at back-to-back meetings with no context, and whoever supplies the context sets the subject.
Lead with the thing you least want to say
Slippage, a mistake, a disagreement. Said in the first two minutes it is a status update; said at the end, or discovered later, it becomes a credibility problem. Bring a proposed fix alongside it.
Keep one running document
A shared note of decisions, commitments and dates, updated after each meeting. It removes arguments about what was agreed and quietly becomes the record you draw on at review time.
When either of you is new
Worth establishing in the first month
- What they consider urgent, and what they consider late
- Which decisions they want to see before you act
- How they prefer to be contacted out of hours, and whether that is ever expected
- Who they trust for information about your area
- What their own manager cares about
Worth telling them about yourself
- How you like feedback: immediately, or written first, or in a scheduled conversation
- The commitments outside work that are fixed for you
- What you are trying to get better at this year
- The kind of work you would put your hand up for
What damages the relationship
Bringing problems with no options
A problem with two possible responses attached is a conversation. A problem with nothing attached transfers the work upward, and managers remember which people do which.
Using the one-to-one to complain about colleagues
One account of somebody else's behaviour is information; a weekly pattern of it makes you the difficulty. Raise the specific incident and what you want done, then stop.
Silent disagreement
Agreeing in the room and then not doing it is the fastest way to lose trust. Say the objection once, plainly, and if the decision stands, commit to it or say clearly that you cannot.
Only talking when you need something
If every conversation is a request, the relationship becomes transactional and requests get weighed more suspiciously. Report an outcome occasionally with nothing attached to it.