Questions to Ask Your New Manager
Questions for the first weeks with a new manager, whether you have changed jobs or your old boss has been replaced: priorities, autonomy, feedback, and where you stand.
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The questions
Each question, and why to ask it
What do you already know about my work, and what should I fill in?
Why ask it
A new manager may have inherited a description of you from someone else. This is your chance to hear it and correct it while impressions are still forming.
What are you being measured on this year?
Why ask it
Their targets become your priorities whether or not anyone says so. Asking directly saves you a quarter of guessing.
What do you want the team doing differently in six months?
Why ask it
Most new managers arrive with a change in mind. Better to hear it now than to find out when your project is the one that gets cut.
How do you like to communicate day to day?
Why ask it
Settles channel and frequency: whether to message, book time, or hold things for the weekly meeting.
How often do you want one-to-ones, and what should I bring?
Why ask it
Ask what a useful one-to-one looks like to them. Some want a status update, some only want to hear about problems.
What do you want to hear about immediately, even if it's bad?
Why ask it
The escalation threshold is the most useful thing to establish with a new boss, and the easiest to get wrong in both directions.
Where should I decide without checking, and where not?
Why ask it
Ask for an example on each side. Autonomy described in principle rarely matches autonomy in practice.
How will you judge whether I'm doing well?
Why ask it
Push for something observable. If the answer is entirely about attitude, expect an unpredictable review at the end of the year.
What does my work look like from where you sit?
Why ask it
Reveals what is visible upward and what is not. Work nobody above you can see tends to go unrewarded however good it is.
How do you prefer to give feedback, and how soon?
Why ask it
A manager who saves everything for a review cycle needs handling differently from one who tells you in the moment.
What's your read on the team so far?
Why ask it
Shows how much they have worked out and how candid they are willing to be with you. It also flags who they are already relying on.
What's the first thing you'd fix about how we work?
Why ask it
More concrete than asking about process, and the answer tells you what irritates them, which is worth knowing early.
How do you want meetings to run?
Why ask it
Agendas, notes, who speaks, whether decisions actually get made in the room. Misreading this makes a competent person look disengaged.
What do you expect around hours, responsiveness and time off?
Why ask it
Worth asking early, because these norms often change with a new manager even when the written policy does not.
How much can I push back, and how would you rather I did it?
Why ask it
Ask explicitly. The answer, and their reaction to being asked, tells you whether the invitation to disagree is real.
How do you handle disagreement inside the team?
Why ask it
Listen for whether they step in or let things run, and whether they take sides. Both patterns have consequences you can plan around.
Who else should I be building a relationship with?
Why ask it
New managers often see the wider map faster than their team does, and they will usually say so if asked.
What do you need from me that you're not getting?
Why ask it
Direct, slightly uncomfortable, and the fastest route to finding out where you actually stand.
What would you like me to be doing a year from now?
Why ask it
Turns career development into a specific conversation, and shows whether they see a path for you here at all.
What's the best way to help while you're settling in?
Why ask it
Fair to ask a manager who is new to the organization, and it puts you on the useful side of their first difficult months.
What does a good first ninety days look like to you?
Why ask it
A vague answer like "settle in and meet people" means the job has not really been defined yet, which is worth knowing on day one. A specific answer gives you a standard you both agreed to out loud.
Which parts of my job matter most right now, and which can wait until later in the year?
Why ask it
The second half is the useful half. A manager who cannot name anything as lower priority will treat every later request as urgent, and you will be the one absorbing that.
What is the team working on that I should understand before I start weighing in?
Why ask it
This surfaces history you would otherwise step on: a project someone fought hard for, a vendor already tried and dropped, a decision that is settled and not open again.
What is on the team's plate right now that is not going well?
Why ask it
Someone willing to name a struggling project in your first week will tell you the truth later. "Nothing major" usually means you will find the problem yourself in a month, without the head start.
What do you plan to leave alone for the first few months?
Why ask it
Restraint is the harder half of a handover, and naming what stays gives the team something to stand on. A manager with no answer here is likely to change several things at once and then be unable to tell which change helped.
How will you decide what this team says no to?
Why ask it
New managers are eager to be seen as helpful and often accept work the team cannot absorb. Hearing an actual test, or hearing that they have not thought about it, tells you what your next quarter looks like.
What counts as a good week for this team, in your view?
Why ask it
A week is short enough that the answer has to be concrete. Look for whether the definition rests on output, on the team not being blocked, or on nothing having gone wrong, since each produces a different kind of manager.
How do you decide who gets which project when everyone is already busy?
Why ask it
Listen for whether the answer describes a process or a personality. If work goes to whoever asks loudest or whoever they trust most, that is still an answer, and you now know how to get the projects you want.
What does the org chart not tell me about how work actually gets done here?
Why ask it
Most places have someone with informal veto power who does not appear on any diagram. Learning who that is beats discovering it by routing a decision around them by accident.
What tends to frustrate you in how people work?
Why ask it
This is the closest you will get to their unwritten rules: deadlines missed without warning, being copied on everything, meetings with no agenda. Whatever they name, some earlier report did it.
How do you handle mistakes that cost real time or money?
Why ask it
Ask for the last one they were involved in and what happened afterwards. A new manager's first response to an expensive error sets the team's willingness to report the second one.
When you disagree with a decision from above, what will we hear from you?
Why ask it
The two failure modes are relaying every decision as their own and quietly signalling that they think it is stupid. Ask what they will do when they have to carry something they argued against.
What did the person before me do well, and what would you want handled differently?
Why ask it
The praise tells you the baseline standard. The "differently" half tells you what you were actually hired to fix, which is often nowhere in the job posting.
How does good work here get noticed outside the team?
Why ask it
Recognition that never leaves the team caps how far your work can carry you. If they cannot describe any path for visibility, assume you will have to build it yourself.
Where have people on this team gone next, and what got them there?
Why ask it
Actual destinations are stronger evidence than any promise about growth paths. If nobody has moved up or out in several years, the answer is the silence.
What would you want me to tell you in six months that you would not otherwise hear?
Why ask it
This asks them to plan for their own blind spot, and to say now that they want the uncomfortable version later. Their answer gives you a reference to point back to when you need it.
What part of your job would you most like to hand off?
Why ask it
Most managers have one task they resent keeping. Offering to take it is a cheap way to become useful, and the answer shows you exactly where they feel stretched.
The first weeks with a new manager
Practical guidance for the conversation itself
Opening the relationship
Book one longer conversation
Thirty minutes set aside for how the two of you will work together gets better answers than the same questions scattered across three corridor conversations.
Bring a one-page summary of your work
A new manager is meeting a dozen people at once. One page on what you own and what is at risk makes you easy to represent upward.
Ask what they inherited
Handover notes, half-finished plans and other people's opinions of you. All three are shaping their first impressions whether they say so or not.
What the answers tell you
- Whether their targets are already fixed, or still being negotiated above them.
- Whether they describe the team as people or as roles.
- Whether they give examples when asked about autonomy, or only principles.
- How they talk about your predecessor, or their own.
- Whether they can name anything specific they want changed.
Common mistakes
Waiting to be told
New managers are overloaded for the first month. The people who ask get defined priorities; the people who wait get whatever is left over.
Relitigating the old regime
Comparing them to the previous manager, favorably or not, shuts the conversation down. Describe how things work and let them decide what to keep.
Accepting a target you haven't checked
Inherited goals are often out of date by the time a new manager repeats them. Ask what the number is based on before you agree to it.