Questions to Ask a New Boss
Questions for early one-to-ones with a manager you have just started working for, covering what they will judge you on, how they want to hear bad news, decision rights, the pressure they are under, and the habits that annoy them. Written for anyone starting a new job or inheriting a new manager.
The questions
Open any question for the note
What would you like me to focus on in my first month?
Why ask it
Gives them an easy, concrete opening and gives you something to be measured against. A manager who cannot name anything specific is telling you the role is undefined, which is worth knowing in week one rather than month six.
Three months from now, what would make you say this was going well?
Why ask it
Forces the answer into observable outcomes rather than adjectives like proactive or reliable. Whatever they name here is what your first review will actually be about, whether or not it appears in the job description.
What does your week look like, and when is the worst time to bring you something?
Why ask it
Practical and rarely asked. Knowing which days are consumed by their own reporting cycle saves you from raising an important decision at the moment they have the least capacity for it.
How do you want to hear about problems: straight away, or in our one-to-one?
Why ask it
The single most useful thing to establish, because the mismatch causes most early friction. Some managers want a message the moment something slips; others treat that as panic, and you cannot guess which.
What kind of update do you find useful, and how often?
Why ask it
Ask for an example of a good one from someone else. Managers differ enormously in appetite for detail, and the ones who say keep it brief often mean weekly rather than never.
What can I decide on my own, and what should come to you first?
Why ask it
Explicit decision rights prevent both the overstep and the bottleneck. If the boundary is fuzzy, ask about a specific decision you expect to face this month rather than in general.
What are you being measured on this year?
Why ask it
Their targets are the reason some of your work gets attention and some does not. Understanding the pressure above them explains behaviour that otherwise looks arbitrary, and it lets you offer help that actually counts.
What is the team known for, and what is it known for getting wrong?
Why ask it
The second half is where the information is. A manager willing to name the team's reputation problem is inviting you to help fix it, and one who insists there isn't one may not hear criticism at all.
Who outside the team do I most need a good relationship with?
Why ask it
Names and reasons, not an org chart. This surfaces the people whose cooperation you will need and any history you would otherwise walk into unaware.
How does work usually reach me: through you, or directly from others?
Why ask it
Determines whether you can be pulled in several directions and who resolves it. If requests come in directly, ask what you should do when two of them conflict.
What did my predecessor do well, and what would you like done differently?
Why ask it
The most efficient way to learn the unwritten expectations of the role. It also reveals whether the person left of their own accord, which changes how you read the rest of the answers.
What do you find frustrating in how people work with you?
Why ask it
Asked directly, most managers will answer honestly, and the answer is usually specific: long emails, meetings without an agenda, being copied on everything. These are cheap habits to change if you know them early.
How do you prefer to give feedback, and can I ask for it directly?
Why ask it
Establishes whether feedback arrives in the moment, in one-to-ones, or only at review time. Managers who default to the last of these will still give it if asked, but you have to ask.
How much of my job is fixed, and where is there room to change things?
Why ask it
Distinguishes the parts of the role you are expected to maintain from the parts you are expected to improve. Getting this wrong is why new hires either look passive or look like they are trampling on things.
What is the norm here for hours and for being reachable in the evening?
Why ask it
Ask what they do and what they expect, since those often differ. A manager who says they email late but does not expect a reply should be asked to confirm that plainly, because the team copies behaviour rather than policy.
How do meetings work here, and which ones should I be in?
Why ask it
Also worth asking which you can leave. New starters get added to standing meetings by default and spend months in rooms where their presence changes nothing.
When people disagree in this team, how does it usually get resolved?
Why ask it
Look for whether disagreement is aired in the room or handled privately afterwards. Getting this wrong in your first weeks is the most common way a new person acquires a reputation they did not intend.
What is the constraint on the team right now: people, budget, or something else?
Why ask it
The answer tells you which suggestions have any chance of being adopted. Proposing solutions that require the missing resource is how new hires get labelled unrealistic.
What growth is realistically available in this role over the next couple of years?
Why ask it
Ask for the actual mechanism: promotion cycles, the criteria, who decides. A vague answer about opportunity for those who perform usually means there is no defined path, and it is better to know now.
What do people take a while to work out about working with you?
Why ask it
A softer way of asking about their blind spots, and most managers enjoy answering it. What they volunteer, that they go quiet when thinking, or push back hard and then agree, saves you weeks of misreading them.
Early one-to-ones with a new manager
Practical guidance for the conversation itself
How to use these
Three at a time, not twenty
Bringing a list to a first meeting turns it into an interrogation and the answers get shorter. Pick three, spread the rest across your first six weeks, and open each one-to-one with one of them.
Ask the operating questions first
How they want bad news, what you can decide alone, and what they are measured on are the three that prevent early mistakes. Career and growth questions land better once you have delivered something.
Write down the answers and repeat them back
Send a short note after the conversation summarising what you understood. It catches misreadings while they are cheap and shows you treat their time as worth acting on.
Check the answers against what happens
Managers describe how they want to work, not always how they do. If someone says they want problems early and then reacts badly, believe the reaction and adjust.
If the manager is new to the team
Expect not to get answers yet
A manager in their own first month cannot tell you the team's priorities because they are still working them out. Offer context instead: what has been tried, what failed, and who knows what.
Do not lobby in the first fortnight
New managers are flooded with people making cases. Waiting a few weeks, then raising one well-prepared issue, gets a far better hearing than being early and indistinguishable from the queue.
Say plainly what you want to be doing
A new manager reassigns work in their first months and will use whatever information they have. If you never state a preference, you will be allocated according to the previous manager's assumptions.
Common mistakes
Asking only about yourself
A first conversation entirely about your objectives and progression reads as self-interest. Asking what pressure they are under changes the tone and usually produces more useful information anyway.
Taking the org chart at face value
Influence rarely matches reporting lines. Ask who actually needs to agree before something happens, because that is the answer that determines whether your work goes anywhere.
Treating an answer as permanent
Priorities move when the pressure above your manager moves. Re-ask what matters most every quarter rather than working from what you were told in week one.
Never asking about their frustrations
Most of the habits that damage a working relationship are small and easily fixed. If you never ask, you find out about them at a review instead.