Leadership Questions to Ask Yourself
These are questions for managers, founders and team leads to ask themselves about how they are actually leading, whether in a weekly review, after a hard week or before a promotion. The 51 questions start with taking stock of the kind of leader you are, then follow a review in order: where your week went, who you are developing, what you are putting off, how the team sees you and what to change next.
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The questions
Each question, and why to ask it
Taking stock
How would I describe the way I lead, and would my team use the same words?
Why ask it
Write your three words first, then guess theirs. Where the two lists match, you are being read the way you intend. If you wrote 'supportive' and suspect they would say 'hard to pin down', that gap is what to work on, and the questions under Their view give you ways to check it.
Why do I want to lead people at all?
Why ask it
Pay, the title and wanting a say in decisions are all honest answers, and none of them rules you out. The answer to worry about is one with no people in it. If the team is only a step toward your next job, they will have worked that out before you did.
What are my strengths as a leader, and which one do I overuse?
Why ask it
A strength pushed too far is usually the complaint people have about you: decisive turns into not listening, kind turns into never saying the hard thing. Name the strength, then the last time it cost someone on the team something.
What do I stand for as a leader, and when did holding to it last cost me something?
Why ask it
Name two or three values in plain words, such as fairness or telling people the truth early. Then look for a recent time when keeping one was inconvenient: a deadline you moved to protect the work, an unpopular call you stood behind. If no such time comes to mind, the value is still a slogan, and the useful step is deciding where it will next be tested.
Am I setting the example I expect the team to follow?
Why ask it
Pick one thing you ask for, such as meeting deadlines, answering promptly or taking time off, and check your own record over the past month. Where your record falls short of the request, expect the team to follow the record.
Does everyone on my team know what matters most right now?
Why ask it
The test is whether each person would name the same top priority without checking with you. If you are unsure, ask two of them this week and compare. Different answers mean the direction is clear in your head and nowhere else.
What do I believe about leading people that I have never tested?
Why ask it
Rules such as 'never show doubt' or 'good people do not need managing' are often borrowed from a first boss. Write one down and ask when it last proved true on this team. If you cannot find a recent case, try a week of doing the opposite in one small way.
Which boss from my past do I catch myself imitating, and is it the one I would choose?
Why ask it
Listen for a phrase you used this week that you once hated hearing. On a bad day it is easy to reach for whatever the manager you watched longest would have said. Decide what you would have wanted that boss to say in the same spot, and keep that sentence ready.
Your week
Where did my hours go this week, and which of them could only I have spent?
Why ask it
Go through the calendar and mark each block: only me, someone else could have, nobody needed to. In a good week the first pile is the biggest. A week made mostly of the second pile is a delegation list that has already been written for you.
What kept interrupting me this week, and why does it still need me?
Why ask it
Some weeks are all interruptions, and that is the job. Look for the repeat: the same kind of question or approval landing on you three times points to a process the team lacks, or a call you have not given anyone else the right to make. Take that one cause and decide who handles it from now on.
Which meeting would have gone just as well without me?
Why ask it
If you can name one, send someone else next time or ask for the notes. If you cannot name any, ask yourself a harder thing: has the team learned not to settle anything unless you are in the room?
What did I do this week that someone on my team should have done?
Why ask it
The usual culprits are the tasks you were promoted for being good at: fixing the spreadsheet, rewriting the draft, taking the client call. Once is a rescue. Every week means that person is not learning the work and your own job is going undone.
Who had most of my attention this week, and who had none?
Why ask it
Attention drifts to the loudest problem and to the people you find easiest. Write the names in two columns. Anyone in the second column three weeks running is being managed by absence, however well they seem to be doing.
What did I call a priority that got none of my time?
Why ask it
Compare what you said in the last team meeting with what the calendar shows. Either move an hour to it next week or stop calling it a priority. The team reads the gap, and takes it as permission to let the thing slide too.
When this week did I get an uninterrupted hour to think?
Why ask it
You are looking for one block with the inbox and chat closed. None at all is normal after a hard week. After a month of such weeks it is a warning, because the problems only you are placed to see coming are getting no attention.
How did I act this week when I was tired, late or under pressure?
Why ask it
One curt reply or a cancelled one-on-one is ordinary. What should bother you is a pattern the team can predict, such as snapping on deadline days. If you owe someone a sentence of apology, say it before the next week starts.
Your people
Who am I developing right now, and what did I do about it in the past month?
Why ask it
A real answer has a name and an action in it: a project handed over, an introduction made, comments on a specific piece of work. 'Everyone', with no examples, usually means no one. If the month is blank, choose one person and one action for next week.
Who could do my job a year from now, and what are they missing?
Why ask it
If a name comes to mind, the missing piece is your development plan for that person. If none does, look at whom you have hired and promoted lately, and whether you have been choosing people who are comfortable to manage over people who could outgrow you.
Could I say what each person on my team wants next?
Why ask it
Go down the list name by name and write only what they have told you, leaving out what you assume. A blank beside someone is simply the first item for your next conversation with them. Blanks beside most of the names mean your one-on-ones have turned into status updates.
Who is doing excellent work quietly that I have not acknowledged?
Why ask it
Think of the person who never causes a problem and so never comes up. Tell them this week and name the piece of work. 'Great job lately' is forgotten by lunch, while a comment about one particular report or call is remembered.
Who is struggling, and how long have I known?
Why ask it
The second half is the uncomfortable part. A week is noticing. A quarter means you have been hoping it works itself out, and the rest of the team has been watching you hope. Either way the next step is a private conversation that opens with what you have seen and leaves your conclusions for later.
Am I treating anyone differently because I like them more?
Why ask it
Check something you can count: who gets the interesting work, who gets the benefit of the doubt over a missed deadline, whose ideas you remember afterwards. Favorites are visible to everyone except the person who has them.
When did I last give someone feedback specific enough to act on?
Why ask it
Try to recall the sentence you said. If it named a piece of work and a change, good. If the most recent example is the last formal review, people on your team are finding out how they are doing only when the form comes around.
Whose work am I still checking that I could trust by now?
Why ask it
Choose one person and one kind of work, tell them you are stepping back from it, and stop reviewing it for a month. If the idea makes you uneasy, ask whether the unease comes from their record or from your habit.
Who have I privately given up on without telling them why?
Why ask it
A private verdict leaks out as duller assignments and shorter conversations, and the person feels it without knowing the cause. Tell them what would change your mind. If it has gone past that, ask your own manager or HR how performance concerns are handled where you work before doing anything else.
Putting off
What conversation am I avoiding, and with whom?
Why ask it
A name probably arrived before you reached the question mark. Write the first line you would say and choose a day this week. The same name coming up a month later is the worrying version, since by then the other person has usually guessed and is waiting too.
Which decisions are sitting with me, and who is waiting on each one?
Why ask it
List every decision more than two weeks old with the person stalled behind it. For each, decide, give the date you will decide, or say what you are waiting for. Silence is the one bad option, because people tend to take it as a no.
Where am I asking for more information when I already know the answer?
Why ask it
Asking for another report or one more round of opinions can be diligence or a way of not choosing. The test is whether any result would change your mind. If none would, you have decided and are only putting off saying so.
What am I tolerating that I would not accept from a new hire?
Why ask it
Typical answers: lateness from a longtime star, a meeting that always runs over, a rude tone in email. Whatever you let pass becomes the real standard, whatever the written one says. Pick the example the team would name first and raise it with that person.
What bad news have I softened or delayed on its way to my own boss?
Why ask it
A slipping date and a budget overrun are the common ones. Late news is worse news, and it arrives with the question of when you knew. Send the plain version this week, with what you propose to do about it.
What have I kept from the team because I decided they could not handle it?
Why ask it
Separate what you are not allowed to share from what would only be awkward to say. The second pile is usually the bigger one. People fill a silence with their own guesses, and the guesses tend to be worse than the facts.
What have I agreed to on the team's behalf that they have no room for?
Why ask it
A yes given upward is paid for by people who were not in the room. Go back with a trade: this can happen if that moves. If you have never once done that, ask what you think would happen if you did.
Which problem am I hoping will go away on its own?
Why ask it
Some do. A spat between two people after a deadline often fades without you. Give the problem a date, and if it is still there when the date comes, it is yours to raise.
What have I promised someone on my team and not delivered?
Why ask it
The raise you said you would look into, the introduction, the course. Do not wait to be reminded, because plenty of people will not ask their boss twice. Go back with the thing itself or with a straight account of why you could not get it.
Their view
What would my team say about me when I am not in the room?
Why ask it
Write it in their voice, including the joke they would make. If only compliments come out, you are guessing. Then ask one person you trust what the team finds hardest about working for you, and compare the two.
When did I last tell the team I got something wrong?
Why ask it
Recall the words you used. 'Mistakes were made' does not count; 'I called that wrong, and here is what I am changing' does. If the last example is more than a few months old, take the most recent call that went badly and own it at the next team meeting, since a team that never hears this from you has little reason to offer it about its own work.
What is it like to bring me bad news?
Why ask it
Think of the last person who did, and what your face and first sentence were. Problems that reach you early and small are a good sign. Hearing about things late, or from outside the team, suggests people have judged that telling you costs too much.
When did someone on my team last disagree with me in front of others, and what did I do next?
Why ask it
A recent example where the plan changed is the answer you want. If you cannot recall one, either you have been right for months or people have stopped trying. On the next decision, ask for the case against it before you give your own view.
How much of our team meetings do I spend talking?
Why ask it
Guess the share, then have someone time one meeting. If the timed figure is well above your guess, try speaking last on the next decision and notice what gets said that you would otherwise have talked over.
Which comment about my leadership keeps coming back, and what have I changed because of it?
Why ask it
Look through old reviews, exit interviews and offhand remarks for the point that repeats. Said once, it is one person's view; said three times by people in different jobs, it is a description of you. If the answer to the second half is 'nothing', that is next week's task.
Would I want to work for me?
Why ask it
Answer as yourself in the most junior seat on the team. Name the one thing that version of you would grumble about to a friend after work. It is often something small and fixable, such as late replies or plans that change without warning.
If my strongest person resigned tomorrow, what reason would they give?
Why ask it
You likely know it already: pay you have not argued for, a promotion that is slow, work they have outgrown. Act now on the part that is in your hands, before there is a resignation to answer. Find out how raises and promotion cases work at your employer before you promise anything.
Who tells me the truth about how I am doing, and when did I last ask them?
Why ask it
You need a name, and ideally one from below you as well as one beside you. If the last time you asked was more than a few months ago, the arrangement has lapsed. Ask a narrow thing, such as how one meeting went, since 'any feedback?' gets a polite nothing.
What next
What should I stop doing?
Why ask it
List what you do from habit: the report nobody reads, the approval step you added after one mistake, the weekly call you inherited. Pick one, tell whoever relies on it, and stop for a month. If nobody asks for it back, it is gone for good.
What am I doing to get better at leading, beyond just doing the job?
Why ask it
Count only what you did on purpose in the past quarter: a book finished, a course, time with a mentor, a skill you tried in a real meeting and asked about afterwards. Another year in the seat does not count, since it can as easily set a habit as fix one. If the quarter is empty, take the answer on this page that bothered you most and find one person who handles that thing well to learn from.
If I were promoted next month, what would fall apart without me?
Why ask it
Whatever you list lives only in your head: a client relationship, a judgment call, a process nobody wrote down. Much of being ready for the next job is getting that list close to empty. Start handing over or writing up the first item now.
What does the next level of this job need that I have not shown yet?
Why ask it
Ask the person who would decide, in more or less those words, instead of guessing. How promotions are judged differs from one employer to the next, so find out how it works where you are. Not knowing who would decide is the first thing to fix.
What do I need help with that I have not asked for?
Why ask it
It is easy to stop asking once you are the one others bring problems to. Name the thing, then the person: your own manager for cover or budget, a peer for how they handled the same problem, the team for the part they know better than you. What support is on offer, such as coaching or a mentor program, varies by employer, so ask what exists at yours.
Is this job making me better, or wearing me down?
Why ask it
Look at evidence from outside work: sleep, patience at home, how Sunday evening feels. A hard quarter is ordinary. If the answer has been 'wearing me down' for a year, tell someone you trust what would have to change, and see a doctor if your health is showing it.
What do I want this team to be able to do a year from now that it cannot do today?
Why ask it
A good answer names a capability, such as running a launch without you or handling its own hiring, where a weak one names a target number. If nothing comes to mind, you have been managing week to week. One answer is enough to change what you delegate next.
What is the one thing I will do differently next week?
Why ask it
One, with a day attached and a person who will notice. Three resolutions made after a hard week tend to be gone by Wednesday. Write it where you will see it at the next review, and begin that review by checking whether you did it.
How to run a leadership review on yourself
Practical guidance for the conversation itself
Setting up the review
Pick a fixed slot and keep it short
Twenty to thirty minutes at the end of the week is enough, at a time when the week is still fresh and nobody is waiting for you. Put it in the calendar as a meeting with yourself and protect it the way you would a one-on-one. A review that only happens when there is time happens in the quiet weeks, when you need it least.
Take five or six questions, not the whole page
One or two from Your week, one from Your people, one from Putting off and the last question on the page make a complete weekly review. Rotate the rest in. Keep any question whose answer bothered you until the answer changes.
Bring the evidence
Open the calendar, the sent folder and the list of your direct reports before you start. Most of these questions have a factual answer and a flattering one, and the record is how you tell them apart. Memory favors the afternoon you spent coaching over the three you spent in the inbox.
Write the answers down
A sentence each, in the same notebook or file every week. Written answers can be compared, and the comparison is where the use is: the same avoided conversation four weeks in a row is hard to argue with when it is in your own handwriting.
Which questions for which moment
The weekly review
Your week and Putting off are the core. They change every week and they produce actions you can take on Monday. Add one question from Your people so that nobody on the team goes a month without your having thought about them.
After a hard week
Start with how you acted under pressure and what it is like to bring you bad news, while the examples are fresh. Leave Taking stock for another day. A tired person asked why they lead at all tends to give an answer they would not stand by on Tuesday.
Before a promotion or a new team
Taking stock and What next are written for this. Answer who could do your job, what would fall apart without you and what the next level needs, then take the answers to your own manager. How promotion decisions are made differs by employer, so ask what the process and the criteria are where you work.
Once a quarter
Go through Their view slowly, and check at least one answer against a real person: a report you trust, a peer, a mentor. These are the questions where your own guess is least reliable.
Turning answers into action
One change per week
Finish every review with the last question on the page and a single action with a day on it. A small thing done, such as one overdue decision made or one piece of praise delivered, is worth more than a plan to become a different kind of leader.
Name names
'I should delegate more' changes nothing. 'Sam runs the Thursday client call starting next week' does. If an answer has no person, date or piece of work in it, it is not finished.
Check your guesses with someone
Several questions ask what other people think of you, and you are answering for them. Now and then, ask. One trusted report, asked one narrow question, will correct more than a month of reflection. A coach, a mentor or a peer on another team can do the same for the questions about your boss and your next step.
Look back before you look ahead
Begin each review by reading last week's answers. You are looking for two things: whether you did the one thing, and which answers have not moved. An answer that repeats for a month has stopped being a reflection and become a choice you are making.
Mistakes to avoid
Answering with intentions
'I value developing people' is an intention. The question asked what you did. If you notice an answer in the future tense, or one about what you believe, go back to the calendar.
Using the review to beat yourself up
The aim is to find one or two things to adjust. A list of everything wrong with you is a different exercise and a less useful one. If a session leaves you only feeling worse, you took too many questions. Do three next time, and include the one about quiet excellent work, which ends in something pleasant to do.
Using it in place of asking the team
Self-review finds what you already half know. It cannot show you what you have no way of seeing, such as how a decision landed or what people have stopped asking you for. Questions to put to the team are a separate list, and this one works best alongside it.
Keeping every answer to yourself
Some answers need another person: a struggling report, a decision above your level, a job that is wearing you down. Take those to your manager, HR, a mentor or, where your own health is involved, a professional. What support exists depends on where you work, so ask what is available.