Questions to Ask Other Leaders
Questions for a peer conversation between people who both manage teams: a coffee with a counterpart, a peer group, or a leadership offsite. Written for exchange rather than interview, so most of these work in both directions.
The questions
Open any question for the note
What is taking up most of your week right now?
Why ask it
A low-stakes opener that lands on something real, because most managers are absorbed by one thing at any moment. It also tells you which of the questions below are worth asking and which will fall flat today.
What part of the job did you not expect to be this hard?
Why ask it
Invites honesty without requiring a confession of failure, and the answer is usually specific: performance conversations, saying no upward, being liked less than before. Once one person names theirs, the conversation stops being polite.
How do you actually spend your one-to-ones?
Why ask it
Practical and comparable. Some use them for status, some for coaching, some ask the person to set the agenda entirely. Hearing a different structure is one of the few things you can borrow and try next week.
Who on your team are you worried about, and what have you tried?
Why ask it
Peers can help with this in a way that nobody in your own reporting line can, because they have no stake in the outcome. Keep it anonymous, and expect the useful part to be the list of things already attempted.
What is your read on when to intervene and when to let someone struggle?
Why ask it
This is the daily judgement call of managing, and there is no consensus answer. Comparing thresholds tends to reveal that one of you steps in too early and the other too late, which is more useful than any principle.
How do you handle the conversation where you have to say no to your own boss?
Why ask it
Ask for the last real instance and the words used. Managing upward is rarely taught and mostly learned by watching, so a peer who does it well is a genuine source of technique.
What did you get wrong recently, and what did it cost?
Why ask it
Sharing a mistake first is the fastest way to make this reciprocal. Listen for whether they know the cost, since leaders who can quantify the damage of a bad hire or a delayed decision usually make the next one faster.
How do you keep people who are not in the room from being forgotten?
Why ask it
Relevant for remote teams, night shifts, satellite offices, and quieter team members. Answers are usually concrete practices rather than principles: written updates, rotating meeting times, deliberately asking the silent person first.
What have you stopped doing since you took the role?
Why ask it
Most managers add responsibilities and remove nothing, then wonder where the week went. Someone who can name a specific thing they gave up, and how they handed it over, is describing a skill worth copying.
How do you tell whether your team is actually all right?
Why ask it
Survey scores lag and skip the individual. Ask what they watch instead: who has stopped speaking in meetings, who is working at midnight, who has stopped disagreeing. These early signals are specific to each team.
What is the hardest feedback you have had to give, and how did you open it?
Why ask it
The opening sentence is the part people struggle with, so ask for it word for word. Also ask what happened next, since the technique matters less than whether the behaviour actually changed.
How do you decide who gets the opportunity when two people want it?
Why ask it
Reveals whether promotion and stretch work are allocated on readiness, visibility, or turn-taking. Comparing criteria with a peer is often uncomfortable and usually exposes a bias one of you had not examined.
What is your team currently working on that you privately doubt?
Why ask it
Peers can say this to each other and rarely can say it internally. It tends to surface work that continues because of sunk cost or a commitment nobody wants to revisit, and hearing yourself describe it aloud often settles the decision.
How do you handle a project you inherited and would not have started?
Why ask it
A common and awkward position. Answers range from finishing it out of respect to killing it quickly to renegotiating scope, and the reasoning behind whichever they chose usually applies to something on your own list.
Who do you go to when you are stuck, and why them?
Why ask it
Shows how deliberately they built support outside their reporting line. If the honest answer is nobody, that is worth naming, and it is often the point where a peer conversation turns into an ongoing one.
What do you do in the ten minutes before a conversation you are dreading?
Why ask it
Small, practical, and rarely discussed. Answers range from writing the first line down to walking outside to rehearsing the worst response. This is the sort of thing peers exchange easily and nobody documents.
Where does your team's workload come from, and can you actually turn any of it off?
Why ask it
Distinguishes leaders who control intake from those who absorb whatever arrives. Ask what they have successfully refused, and how they said it, since the phrasing is the transferable part.
What are you doing to stay employable outside this organisation?
Why ask it
An unusually direct question that peers can ask each other. Long tenure in one place narrows options quietly, and comparing notes on external networks, speaking, or side projects is useful to both of you.
What would you want someone to tell you honestly about how you lead?
Why ask it
Best kept until trust exists in the conversation. It invites an exchange of observations rather than compliments, and if you are willing to answer it first, you will usually get something you had not heard from anyone reporting to you.
What should we make a habit of, rather than doing this once?
Why ask it
Closes with a decision instead of vague goodwill. Peer conversations that continue on a schedule are more valuable than any single one, and one of you has to propose it before both drift back into the week.
Making peer conversations worth repeating
Practical guidance for the conversation itself
Setting it up
Choose a peer with no stake in your outcomes
Someone in a different function, division, or organisation can hear about a struggling report or a doubtful project without it affecting how you are assessed. The same conversation with a direct competitor for the next promotion will stay superficial.
Agree what stays in the room, out loud
One sentence at the start is enough. Without it, both of you will keep the specifics vague, and specifics are the only part that helps.
Bring one live problem, not a general interest in leadership
Arriving with an actual decision you are stuck on gives the conversation something to work on. It also makes it easy for the other person to reciprocate with theirs.
During the conversation
Go first on anything uncomfortable
If you want to hear about a mistake, describe yours before you ask. Peer conversations calibrate to whoever is most candid, and that has to be someone.
Ask for the words, not the principle
"How do you approach difficult feedback" gets you a philosophy. "What was your opening sentence" gets you something you can use on Thursday.
Resist solving it immediately
The instinct between managers is to trade advice quickly. Asking two more questions before offering anything usually reveals the problem is not the one first described.
How these go wrong
Turning into a complaint session
Shared frustration feels good and changes nothing. If twenty minutes have passed with no decision or experiment named, ask what either of you is going to do differently.
Competing on how busy you are
Status displays about workload crowd out the actual exchange. Notice it, name it lightly, and move to the specific problem.
Never scheduling the next one
The value compounds when you can report back on what you tried. Set the next date before you leave rather than agreeing to do this again sometime.
Afterwards
- Write down the one practice you are going to try, and by when.
- Note what you said out loud that you had not admitted to yourself.
- If they gave you a phrase for a hard conversation, keep it verbatim.
- Send anything you promised within two days, or say you cannot.
- At the next meeting, open with what happened when you tried it.