Questions to Ask New Leadership
Questions for employees when new senior leadership arrives, whether at an all-hands, a skip-level, or a small team session: what mandate they were given, what changes first and what is protected, how decisions and communication will work now, and what happens to people whose roles change.
The questions
Open any question for the note
What is your read on where the organization is right now?
Why ask it
Their diagnosis, stated early, is the best predictor of what they will do next. Compare it with what you see from the inside, because a wrong diagnosis in month one becomes a wrong strategy in month six.
What mandate were you given, in your own words?
Why ask it
Everyone arrives with a brief from a board, an owner or a chief executive, and that brief is usually narrower than the public announcement. Growth, cost reduction and turnaround produce very different years, and it is fair to ask which one this is.
What are you changing first, and what are you not touching?
Why ask it
The second half is what lets people keep working while the first half happens. Vagueness across both usually means the decisions have been made and are not yet being shared.
What does this organization already do well that you intend to protect?
Why ask it
Tests whether they have looked before deciding, and gives you a commitment you can hold them to later. An answer only about culture and people, with nothing operational in it, suggests they have not got far into the detail yet.
A year from now, what would tell you this worked?
Why ask it
Asks for measures rather than intentions, and the specific ones they name are what the organization will be steered by. Write them down, because official goals tend to be restated once results arrive.
Are changes to structure or headcount planned, and when will people be told?
Why ask it
The commitment to a timeline is the achievable part of this question, since legal and financial constraints often prevent an answer on substance. A leader who says they cannot comment yet but will announce by a given date is treating people better than one who says nothing.
What can you tell us about the financial position?
Why ask it
Whatever the answer, the way it is given tells you how much you will be trusted with. Watch for whether they distinguish between what they cannot disclose and what is simply uncomfortable.
How will decisions get made now, and who signs off on what?
Why ask it
New leadership usually redraws authority before it publishes an org chart, and in the gap everything slows down. Ask for named owners for the approvals your work depends on.
What happens to the work we are already partway through?
Why ask it
The single most practical question in the room, and the one most often left unanswered. Continuing to build something that has quietly been cancelled is the most common waste during a leadership change.
Where do you want us to move faster, and where would you rather we slowed down?
Why ask it
Gives teams something usable this week rather than a strategy for next year. If the answer is faster everywhere, that is a genuine signal about the pressure they are under.
What are you hearing from customers that we might not be hearing?
Why ask it
New leaders talk to customers and partners in their first weeks and hear things that never reach internal reporting. This question extracts real information rather than a position.
How do you want to hear from people who do not report to you?
Why ask it
You are asking for a specific channel: skip-levels, office hours, a mailbox, visits to sites. An invitation to reach out anytime with no mechanism behind it means the answer is effectively no.
When you cannot tell us something, will you say that rather than say nothing?
Why ask it
This asks for a communication standard rather than information, and most leaders will agree to it. Having it said publicly gives everyone something to point at when a silence stretches out.
How should we raise a problem we think is not reaching you?
Why ask it
Information traveling upwards gets smoothed at every level, and new leaders are the most exposed to this because they cannot yet tell what is missing. Ask for a route that does not depend on your own manager passing it on.
What is the plan for people whose roles change?
Why ask it
Redeployment, retraining and severance are three very different answers, and people deserve to know which is on the table. If it is too early to say, ask when it will not be.
Which part of the previous strategy do you disagree with, and why?
Why ask it
A direct question that most leaders will answer more openly than expected, because it lets them explain their reasoning. It also tells you which existing work is likely to be stopped.
What would make you change your mind about a decision you have already announced?
Why ask it
Asks for their conditions for reversal, which is a fair test of whether consultation is real. Watch whether they can name evidence that would move them, or only circumstances outside their control.
What do you expect to be hardest for us over the next six months?
Why ask it
Invites honesty about cost rather than a message about opportunity, and a leader who names something real is more credible than one who does not. It also tells you whether they understand what the change will feel like from where you sit.
Have you led through a change like this before, and what did you learn?
Why ask it
Experience is reassuring and the lesson they draw is revealing: some talk about communicating more, some about acting faster. That distinction usually predicts how the next few months will run.
What do you need from us in the next ninety days?
Why ask it
Ends with something people can act on, which is what most all-hands sessions lack. A specific answer also creates a fair exchange, since you have asked them for a good deal of candor.
Asking questions when leadership changes
Practical guidance for the conversation itself
How to ask so you get an answer
- Ask the narrow version. Are redundancies planned invites a non-answer; when will people be told invites a date.
- Ask one question at a time. Compound questions get the easiest part answered and the rest dropped.
- Submit it in writing beforehand if the format allows. Written questions are harder to skip and are often answered more carefully.
- Keep it non-accusatory. A question that sounds like an accusation gets handled as a public relations problem rather than answered.
- If your question is about your own team's work, ask it in a smaller room. All-hands answers are necessarily general.
Reading the answers
Distinguish cannot say from do not know
Both are legitimate and they mean different things. Cannot say implies a decision exists; do not know implies it does not. Leaders who blur the two are usually managing the room rather than informing it.
Note what is not mentioned
If a strategy presentation never mentions a product line, a site or a function, that omission is often the message. Ask about it directly rather than reading tea leaves.
Watch the gap between words and calendar
Within a month you can compare what was said with what actually got funded, staffed and reviewed. Spending and attention are the real strategy, and they will tell you more than any slide.
Afterwards
- 1Write down the specific commitments and dates that were given. Corporate memory for these is short and yours does not have to be.
- 2Send unanswered questions in writing to whoever ran the session and ask when an answer is likely.
- 3Tell your own team what you heard, separating what was stated from what you inferred. Rumor fills every gap left open.
- 4Keep delivering something visible. During a leadership change, teams whose work is legible are the ones that survive reviews.
- 5Update your own plans quietly. Taking a change seriously early is not disloyalty, and neither is keeping your options open.
What goes wrong
- Using the microphone to settle an old grievance. It burns the goodwill of everyone else who had a question.
- Reading silence as bad news in every case. In the first weeks, most silences are genuinely unfinished decisions.
- Waiting for certainty before doing anything. Restructures take longer than anyone predicts, and work stops long before jobs change.
- Assuming your manager knows more than you. Frequently they were told at the same meeting.