Questions to Ask a New Leader
Questions for the first conversations with a leader who has just taken over your team, department or organisation, covering their mandate, what they were told before arriving, what they intend to change, and how they want to be challenged. Written for team members and managers reporting into a new arrival.
The questions
Open any question for the note
What were you asked to come and do here?
Why ask it
Every appointment carries a brief from whoever hired them, and it is often narrower than the vision they present publicly. Someone hired to cut costs and someone hired to grow will behave differently regardless of how they describe their approach.
What were you told about us before you arrived?
Why ask it
New leaders arrive with a version of the team's reputation assembled from other people. Hearing it lets you correct anything unfair early, before it hardens into the assumptions behind their first decisions.
What are you planning to spend your first ninety days on?
Why ask it
Distinguishes a leader who intends to listen first from one who arrived with a plan. Both exist and both can work, but you need to know which so you are not preparing a case for someone who has already decided.
What have you seen so far that surprised you?
Why ask it
The most useful question in the first month, because it shows what they are actually noticing rather than what they were briefed on. Surprises are also where the first changes tend to come from.
What would you like to know about how things currently work?
Why ask it
Turning the conversation around is more valuable than answering their questions passively. It also positions you as a source of context rather than someone waiting to be told what to do.
What are you going to leave alone?
Why ask it
Almost nobody asks this and it settles the anxiety running through the team. A leader who can name what is working has been paying attention; one who cannot is likely to change things for the sake of visible motion.
What do you think we are getting wrong?
Why ask it
Direct, and it invites the criticism that would otherwise reach you secondhand months later. How they deliver it also shows whether they can be candid without being dismissive of what came before.
How do you like to work: written, in meetings, or in the room?
Why ask it
Operating preferences change more about daily life than strategy does, and they are rarely stated unprompted. Ask specifically whether they read documents in advance, since teams waste months guessing.
How much detail do you want, and when should I escalate?
Why ask it
New leaders vary from wanting daily specifics to wanting only exceptions, and the mismatch produces the first accusations of either hiding things or flooding the inbox. Ask for an example of an escalation they would want.
How do you want to be disagreed with?
Why ask it
Almost every leader says they welcome challenge; the useful part is the mechanism, whether that is in the meeting, beforehand, or in writing. Asking now gives you something to point back to the first time you need it.
What does the person above you want from this team this year?
Why ask it
Their own boss's expectations explain which of your work will get support and which will quietly be deprioritised. It also reveals how much room the new leader actually has to make promises.
What are you being judged on, and by when?
Why ask it
New leaders are usually on a clock they did not set. Knowing the horizon tells you whether to expect fast visible changes or patient rebuilding, and it explains urgency that otherwise looks arbitrary.
How will you decide what to stop doing?
Why ask it
Most new leaders add before they subtract, and the team ends up carrying both. Asking about the process for stopping work is the most practical protection against a year of accumulating commitments.
Will the structure change, and when will people know?
Why ask it
Reorganisation is the question everyone is thinking about and nobody asks. Even an answer of not yet decided, with a date for when it will be, is worth more to a team than silence.
Who have you spoken to so far, and who haven't you?
Why ask it
Reveals whose account of the organisation they are working from. If they have only met leadership, offering access to the people doing the work is genuinely useful to them and to you.
What context are you missing that would change your mind about something?
Why ask it
Invites them to name where their picture is thin, and gives you a legitimate opening to supply it. Leaders who cannot identify any gap after a few weeks are usually the ones who make an avoidable early mistake.
Where have you done this before, and what did you learn the hard way?
Why ask it
Prior transitions are the best available evidence of how this one will go. Listen for a specific error and a specific correction rather than a general statement about listening more.
What should we do differently in how we work with you compared to your predecessor?
Why ask it
Gives them permission to be explicit rather than waiting for the team to guess. It also avoids the trap of everyone continuing habits built around someone who has gone.
What is the first thing you want from me specifically?
Why ask it
Narrows a broad conversation to a commitment you can act on this week. Delivering that one thing well is worth more than a good impression in the meeting.
How will you know in six months whether this has gone well?
Why ask it
A closing question that reveals what they genuinely value, and whether they think in terms of results, relationships, or their own standing. It also gives the team a shared understanding of what to aim at.
Working with a leader who has just arrived
Practical guidance for the conversation itself
Timing matters more than content
First fortnight: offer context, do not lobby
New leaders are met by a queue of people making cases, and everyone in it looks the same. Being the person who supplies useful background without an ask is what gets you a second conversation.
Weeks three to six: raise one issue, well prepared
By then they have enough context to understand it and have not yet locked in their plan. Bring the problem, what has been tried, and what you would do, in that order.
Ask the operating questions immediately
How they want detail, when to escalate and how to disagree can all be asked in week one and prevent most early friction. Save questions about your own progression for later.
Write a short handover of your own
One page on what you own, what is working, what is fragile and what decisions are pending. New leaders are drowning in information they cannot organise, and a clear summary from a direct report gets read.
Reading the transition
The mandate explains almost everything
Someone appointed to fix a problem behaves differently from someone appointed to steady the ship, and neither will announce it in those terms. Watch which meetings they keep and which they cancel.
Expect the predecessor to be re-evaluated
New leaders tend to reassess the previous regime's decisions, including ones you argued for. Being able to explain the reasoning behind a choice, without defending it as sacred, is what keeps your credibility.
Believe actions over stated preferences
A leader who says they want challenge and then shuts it down in a meeting has answered the question. Adjust to what happens rather than to what was described in the first one-to-one.
Common mistakes
Auditioning instead of informing
Trying to impress in the first meeting produces a list of your achievements and no useful exchange. Leaders remember the person who explained something they needed to understand.
Running down the previous leader
It is tempting when things were bad, and it lands badly nearly every time. Describe the situation and its consequences without a verdict on the person, and let the new leader draw their own conclusion.
Waiting to be asked
New leaders redistribute work in their first months using whatever information they have. Staying quiet means being allocated according to assumptions inherited from someone else.
Assuming the honeymoon lasts
Openness to being told things narrows as their plan forms. Anything you want considered should be raised in the first two months rather than saved for a better moment.