5 Questions to Ask When Starting a New Job
The five questions to get answered in your first week, followed by fifteen more for the first three months. Aimed at your manager, your teammates and whoever has been there longest, covering expectations, feedback, who decides what, and the rules nobody writes down.
20 questions, each with the reason to ask it · includes a conversation guide
The questions
Open any question to see why it works.
- 1
What does good look like for me in ninety days?
Ask this in your first conversation with your manager and write the answer down verbatim. If they cannot describe it, that is the finding: it means your review will be based on impressions, and you will need to define the target yourself and get it agreed in writing.
- 2
How do you prefer to hear from me, and how often?
Managers vary between wanting a weekly written summary and wanting to be left alone until something breaks. Getting this wrong is the most common early friction, and it reads as judgement about you rather than a mismatch of format.
- 3
What is the one thing that would make your week easier if I took it off you?
It gives you an early, visible win and it tells you what your manager is actually drowning in, which is rarely what the job description said. Ask again at week six, because the answer will have changed.
- 4
Who do I need to know, and who will not appear on the org chart?
Every organisation has people whose influence exceeds their title: a long-serving coordinator, an engineer everyone consults, an assistant who controls calendars. Ask for the names and ask for an introduction rather than finding them yourself over six months.
- 5
What happened with the last person in this role?
Ask it neutrally and listen for whether the answer is a promotion, a restructure or a silence. A role that has turned over twice in two years has a structural problem, and it is better to know which one before you inherit it.
- 6
How does work actually arrive here: a queue, a meeting, or someone tapping me on the shoulder?
The official process and the real one differ almost everywhere. If most work arrives informally, your calendar will not reflect your workload, and you will need a way to make what you are doing visible.
- 7
Which meetings matter, and which could I stop attending without anyone noticing?
New people are invited to everything and nobody tells them which invitations were courtesy. Ask a peer rather than your manager, and wait until week three so you have seen the meetings for yourself.
- 8
What can I decide on my own, and what needs you?
Ask for the boundary in terms of money, risk and who else is affected rather than in principle. Getting this wrong in either direction is costly: escalating everything reads as incapable, escalating nothing reads as reckless.
- 9
How is my performance reviewed, by whom, and against what?
Find out whether your manager writes it alone or collects input, whether there is a rating scale, and when the cycle falls. Joining shortly before a review cycle often means a partial assessment, which is worth knowing early.
- 10
What does the rest of the company judge this team on?
Internal metrics and external reputation rarely match. The answer tells you what your team is defensive about, which explains a surprising amount of behaviour you would otherwise find baffling.
- 11
What is this team currently bad at?
Ask a teammate, not your manager, and ask after a few weeks rather than on day one. Willingness to answer honestly tells you how safe it is to raise problems here, which is more useful than the answer itself.
- 12
Where is the documentation, and how out of date is it?
The second half is the real question. Someone who tells you which pages to trust and which to ignore has just saved you a month, and they are usually the person worth asking things in future.
- 13
What does everyone here complain about that has never been fixed?
Long-running complaints are either genuinely hard or politically protected, and new starters often propose fixes for them in week two. Knowing the history stops you spending your early credibility on it.
- 14
What changed after the last reorganization, and who was here before it?
Reporting lines and grudges outlive restructures. The people who were there before it can tell you why a process looks illogical, which is nearly always because it was designed for a structure that no longer exists.
- 15
How do people here disagree with each other in public?
Some places argue openly in meetings and consider it healthy, others settle everything beforehand and treat public disagreement as an attack. Misreading this is how a competent new hire acquires a reputation in their first month.
- 16
What should I not change in my first six months?
An unusual question that people answer honestly, because it invites them to protect something. It surfaces which processes have a history behind them and which colleague owns them personally.
- 17
What do you wish someone had told you in your first month here?
Ask everyone you meet in your first few weeks. The answers cluster, and the thing three people mention independently is the real induction, which no formal onboarding process ever contains.
- 18
What am I likely to get wrong because of where I worked before?
Assumes the problem exists, which makes it easier to answer honestly. Habits from a previous employer around tooling, tone and how much you announce your own work are the usual answers.
- 19
In a year, what would make you glad you hired me?
Ask your manager this at the end of your first month, once you both know more. It often produces a different and more honest answer than the ninety-day question, because by then they have seen you work.
- 20
Is anything about this job different from how it was described to me?
Ask it directly and early, while raising it is still normal. Scope drift between the advert and the reality is common, and the moment to renegotiate title, level or remit is in the first weeks rather than at your first review.
The first three months
Practical guidance for the conversation itself.
Who to ask what
Who to ask what
- Your manager: expectations, decision rights, how you are reviewed, and what would make them glad they hired you. Keep these formal and write down the answers.
- Your peers: which meetings matter, what the team is bad at, and how people disagree here. Ask these one to one, never in a group.
- The longest-serving person: why things are the way they are, what was tried before, and who to avoid blindsiding. This conversation is worth requesting explicitly.
- Whoever left the role, if you can reach them and it is not awkward. Former occupants are candid in a way current staff cannot be.
When to ask
When to ask
- 1Week one: expectations, communication preferences, and the names you need. Do not ask about problems yet, because you have no standing to hear the answer.
- 2Weeks two to four: how work arrives, what you can decide, where the documentation is, and what your colleagues wish someone had told them.
- 3Week four: go back to your manager with what you have learned and check your ninety-day target still matches.
- 4Months two and three: the harder questions about what is broken, what not to change, and anything that differs from how the job was described.
- 5End of month three: ask for feedback in specific terms, since the general version is always fine and tells you nothing.
Listening for the answer behind the answer
Listening for the answer behind the answer
- A long pause before an answer about the last person in your role is information. So is a rehearsed one.
- If several people give the same warning about one colleague, treat it as a pattern rather than as gossip, and still form your own view.
- When a manager cannot describe what good looks like, propose your own version in writing and ask them to correct it. Getting agreement on paper protects you at review time.
- Ask for examples whenever you get an adjective. Fast moving, collaborative and high performing mean completely different things at different employers.
- Keep a private note of everything you were told in your first month. By month six you will have absorbed the local assumptions and stopped being able to see them.