Questions to Ask About Failure
Questions to ask about failure, for the times you want the real account from someone who has lived through one: a mentor, a boss, a guest on your podcast or panel, a student still sore from a bad result. They run in the order a good conversation does, from openers that let the other person choose what to tell, through what happened and what it cost, to what changed afterward. A group for a team's review and a last one to put to yourself after a failure of your own close the list.
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The questions
Each question, and why to ask it
Opening
Is there a failure you're comfortable talking about?
Why ask it
Asking it this way hands over two choices: which failure, and whether to tell one at all. A mentor or guest who picks their own example tells it better than one who is steered to the famous one. If the answer is 'not really', believe it and ask about something else.
What's something that didn't work out the way you planned?
Why ask it
Some people hear the word failure as a verdict, and this wording leaves it out. It suits a student, a new colleague or anyone still close to the event. A small example is the size they are ready for today, so take it seriously.
What's a failure you learned more from than any success?
Why ask it
This is the one a mentor or a guest expects, so the answer may arrive rehearsed. Let them finish, then ask which part of the lesson they only saw a year or two afterward. The late part is rarely in the rehearsed version.
What do you count as a failure, and what is just a thing that didn't work?
Why ask it
People draw this line in very different places: for one it is any missed target, for another only the times they let someone down. Once you know where theirs sits, every later answer is easier to read. Ask for one example from each side of the line.
What is the first thing you remember really failing at?
Why ask it
A driving test, a team tryout, a school play: early failures are safe ground because the stakes expired long ago. On a panel it makes a good first round, since every guest has one and nobody has to go deep. Notice who else is in the story and how they reacted.
Which failure is easy for you to talk about now, and which one still isn't?
Why ask it
The easy one tends to be old and to have an ending. You do not need the hard one told, only named, because knowing where it sits tells you where not to push. Before a recording or a panel, ask this off the air.
What happened
Take me back to the start: what were you trying to do?
Why ask it
Begin before anything went wrong, because people relax when the first thing they describe is the part that made sense. Then ask what they expected to happen. The gap between that and the real result is the whole story in outline.
When did you first suspect it wasn't going to work?
Why ask it
The suspicion tends to arrive well before the admission. Ask what they did with it: tested it, hid it, worked harder. That stretch between suspecting and saying so is where a listener can learn the most.
What warning signs can you see now that you couldn't see then?
Why ask it
Treat the answer with care, because hindsight makes signs look brighter than they were. The useful follow-up is whether anyone else noticed at the time, and what would have made the sign impossible to ignore.
Was there a point where you could have stopped, and what kept you going?
Why ask it
Money already spent, pride, a promise to someone, plain hope: the reason they carried on travels better than the details of the event. Whichever one they name is the pull to watch for in your own project.
What did you do to try to save it?
Why ask it
The rescue attempts are where much of the effort went, and the short version of the story drops them. Listen for the fix that nearly worked, and for whether they now count the rescue as part of the mistake.
How much of it was in your control?
Why ask it
Listen for a split, not a total. Someone who claims all the blame for a market that collapsed, or none for a deadline they set themselves, may still be working it out. 'Which part would you claim?' is a gentler second try than arguing with the first answer.
Who did you tell first, and what did you actually say?
Why ask it
The first telling is often the hardest part, and the exact words are something a listener can borrow. It also shows who they trusted when it counted. If they told nobody for a long time, ask what finally changed that.
How did you explain it to yourself back then, and how do you explain it now?
Why ask it
The early explanation is often about blame, their own or somebody else's, and the later one about causes. The distance between the two is what they learned, stated without a slogan. Two identical explanations may mean the story has never been tested, and 'has anyone seen it differently?' is a gentle way to find out.
Did anyone try to warn you, and why didn't it land?
Why ask it
A warning can miss because of who gave it, which week it came in or how vaguely it was put, and the reason this one missed is a lesson in giving one. For a mentor this often turns into what they now do when they see someone else heading the same way.
Was it one big mistake, or a lot of small ones?
Why ask it
A single cause makes a tidier story, so it is worth checking whether the tidy version is the true one. With a chain of small things, the link they would fix if they could fix only one is the answer to take away.
What part of the story do you usually leave out?
Why ask it
A bold one, so save it for when there is some warmth in the room and ask it with a smile. The missing piece is often the dull or unflattering part: boredom, an argument, money running out. 'The part I'm still leaving out' deserves a laugh from you, not a second try.
The cost
What did it cost you: money, time, a relationship, your confidence?
Why ask it
Listing the kinds of cost lets them choose one without you asking about money outright. Whichever they reach for first is often the one that hurt most. Do not press for figures; 'a lot' or 'two years' is enough to understand the weight.
Who else paid for it besides you?
Why ask it
Staff, family, teammates, people who put money in. This is the question that turns a tidy story into an honest one, and guilt often lives here, so ask it quietly and let a short answer stand.
What was the worst day of it?
Why ask it
One day produces a scene where 'it was a hard year' produces a summary. For a podcast, a class talk or a written profile, this is the answer the audience will remember. Stop where they stop.
How did it change the way you saw yourself?
Why ask it
Some people separate what happened from who they are within weeks, and for others it takes years. Neither needs correcting by you. A good follow-up is when that picture of themselves started to shift back, and what shifted it.
Did you lose anyone's trust, and were you able to earn it back?
Why ask it
Ask what the repair consisted of: an apology, a repayment, a year of turning up on time. Where trust never came back, that part of the story is theirs to give or keep.
What were you most afraid people would think?
Why ask it
Follow it with 'and did they?' Quite often the feared judgment came from one person or from nobody at all, which is worth hearing if you are dreading the same thing. With a teenager it can show that the real worry is one parent or one friend, and not the grade.
Who showed up for you, and who went quiet?
Why ask it
No names are needed for the second half. The first half is the practical part: what the people who helped actually did, whether that was a meal, a job lead or simply not bringing it up.
How long was it before you could tell this story without wincing?
Why ask it
A number of months or years is a real comfort to a listener who is in the middle of their own. If they say they still can't, thank them for telling it anyway and make your next question a lighter one.
Is there anything about it you still haven't made peace with?
Why ask it
It gives permission for a story with no neat ending. Keep it for a private conversation, late on; a stage or a recording rarely leaves room to answer it honestly.
What changed
What was the first thing that helped you get going again?
Why ask it
Expect something small where you were hoping for a turning point: a routine, a stopgap job, a friend who kept calling. Small is the useful answer, because a listener in the same spot can copy it this week.
What do you do differently now because of it?
Why ask it
Ask for a habit, not a moral: a checklist, a question they put before signing anything, a person they phone first. If no behavior is attached, the lesson may be one they admire more than follow.
What did you believe before that you no longer believe?
Why ask it
The beliefs that go tend to be the comfortable ones, such as hard work being enough or good people never letting you down. Ask what replaced it. A more careful belief is one thing and a bitter one is another, and you will hear the difference.
What lesson did you take from it at first that turned out to be the wrong one?
Why ask it
People overcorrect after a fall: never take a partner again, never take a risk again. Hardly anyone gets asked this, so the answer is seldom rehearsed. It is especially useful to someone drawing their own conclusions right now.
Did anything good come out of it that wouldn't have happened otherwise?
Why ask it
Hold this until the cost has been heard, or it sounds like a request to tie a bow on it. A new job, a friendship and a change of direction are common answers. If you get 'no, it was simply bad', take it at face value and do not go looking for a bright side on their behalf.
If someone you cared about were making the same bet, what would you tell them?
Why ask it
Check whether the advice is 'don't' or 'do it differently'. The first means they regret the attempt and the second only the way it was carried out, and those are different lessons for whoever is listening.
Would you do it again, knowing how it ended?
Why ask it
A yes means the attempt was worth more to them than the result, so ask what they would keep exactly as it was. A firm no deserves the same respect, and the reason behind it is the part to write down.
How do you decide now when to keep going and when to stop?
Why ask it
You are after the actual rule: a date, a budget, a number, one person whose opinion settles it. Someone who has been through a long failure may well have a rule that specific. A gut feeling counts as an answer too, provided they can describe what it felt like the last time.
Has it changed how you respond when someone else fails?
Why ask it
For a manager, teacher, coach or parent this may be the main thing the failure left behind. Ask about the most recent time a person on their team got something wrong and what they said in the first minute.
Are you more afraid of failing now, or less?
Why ask it
It goes both ways. Some people find the worst has happened and they are still standing, and others have grown more careful than they would like. Whichever it is, ask what they now turn down that they once would have tried, or the reverse.
What are you working on now that might not work?
Why ask it
It brings the subject into the present. Plenty of people talk easily about a failure from ten years ago and go quiet about the live risk, so a real answer here is a sign of trust. It makes a strong closing question for a mentor.
What would you say to yourself on the day it fell apart?
Why ask it
Narrower than advice to a younger self, because it fixes one day. The answer is often kinder and shorter than any lesson, and it doubles as something to say to a friend who is in that day now.
With a team
What did we expect to happen, and what happened instead?
Why ask it
Open a team review here and get both halves agreed before anyone discusses causes. Write them up where everyone can see. Groups often find they did not share one picture of the plan, and that is a finding in itself.
What did each of us know at the time that the others didn't?
Why ask it
This looks for gaps in information instead of a culprit. Go around the room and let the most junior person answer early, before the senior version of events hardens. Each gap you find points at a missing check-in or a message that was never sent.
What made our decision look right at the time?
Why ask it
It assumes sensible people under pressure, which is the fair starting point, and it draws out the deadline, the missing fact or the instruction that pushed the decision. With one student after a failed exam the same question works: what made skipping the review seem fine that week?
Did anyone have a doubt they didn't raise, and what would have made it easier to say?
Why ask it
The second half matters more, because it asks about the room and not the person. Whoever leads the group should answer last and resist explaining. If nobody speaks, offer a doubt of your own that you kept quiet.
What went right that we should keep?
Why ask it
A failed project still has working parts, and a review that skips them tends to throw those out too. Put it in the second half of the meeting, once the hard part has been said, so it does not read as changing the subject.
What is the one thing we will do differently next time, and who owns it?
Why ask it
One change with a name and a date on it stands a chance, where a list of ten tends to stay in the minutes. Put it on the agenda of the next meeting so someone has to report back.
What do you need from me before you try again?
Why ask it
For a coach, teacher, parent or manager to ask one person once the review is over. It moves you from judge to help. Be ready to give what they name, or to say plainly that you can't and offer what you can.
Ask yourself
What exactly failed: the idea, the plan, the timing or my part in it?
Why ask it
Taking it apart stops one failure from becoming a verdict on everything. Give each of the four a line on paper. Timing and luck are allowed on the list, as long as your own part is on it as well.
What am I telling myself this says about me?
Why ask it
Write the sentence out in full. 'I always ruin things' is easier to test against the record on paper than as a loop in your head, and the word 'always' rarely survives the test.
What would I say to a friend who had done exactly the same thing?
Why ask it
Say it out loud or put it in a short letter. You would probably give a friend the facts, some sympathy and a next step, in that order. Give yourself the same three.
Which part of this am I avoiding looking at?
Why ask it
It is usually something concrete: an unopened email, a bank balance, a conversation with one person. Naming it is half the job. Opening it for ten minutes with a timer running is a reasonable other half.
Who do I owe an apology, an explanation or money?
Why ask it
Make the list and start with the smallest item on it. Where money or a contract is involved, find out how the rules work where you live before you promise anything, and ask someone qualified if the sums are large.
What do I know now that I could only have learned this way?
Why ask it
A guard against the forced silver lining, since it asks for knowledge and not for gratitude. 'Nothing yet' is an acceptable answer in the first month. Put the question in your calendar for six months on and compare.
Do I want to try this again, and what would have to be different?
Why ask it
The second half is the test. If the only difference you can name is trying harder, you are describing the same attempt twice. Deciding not to go again is allowed, and it is a decision, not another failure.
What is the smallest next step that isn't a retreat?
Why ask it
Small enough to do this week, and pointed forward: one application sent, one page rewritten, one practice session booked. The size matters less than the direction. If every step you can think of is a retreat, you may not have settled yet whether you want another go at all.
How to ask about a failure and hear the real answer
Practical guidance for the conversation itself
Asking without prying
Ask first, and mean it
Before any of these, say what you would like to ask about and that 'I'd rather not' is a complete answer. People tell a failure more fully when they know the exit is open. If they take the exit, change the subject yourself so they do not have to.
Let them pick the failure
The questions under Opening leave the choice of story to the other person. Arriving with their best-known flop already in mind ('so, about the restaurant') puts them on the defensive before they have said a word.
Say why you want to know
'I'm about to start something and I'm scared of getting it wrong' gets a different answer than curiosity alone. A reason tells them which parts of the story will help you, and it shows you are not collecting gossip.
Offer one of your own
A short failure of yours, told plainly and without a moral, sets the level of honesty for the conversation. Keep it to a minute. The point is to go first, not to compete.
Leave some things alone
Do not ask for the sum lost, the name of the person at fault or the details of a dismissal or a lawsuit. If those are theirs to share they will share them, and some of it they may not be free to discuss at all.
Fitting the questions to the person
A mentor or a leader
They have told their failure before, so the first version will be smooth. Work through What happened in order and spend your time on The cost, which is the part a practiced story skips. Two or three questions from What changed are plenty to finish on.
A podcast or panel guest
Agree in advance which failure they are willing to discuss and send the two or three questions you most want answered. On a panel, give every guest the same opener and then follow one person's answer down instead of going along the row for each question.
A student or your own child
Wait a day. Ask in the car or on a walk, where nobody has to make eye contact, and start with the softest wording on the list. With a child or a teenager one or two questions is a whole conversation, and the grade or the score can wait until they bring it up.
A team after something went wrong
Take the With a team group in the order given, with someone other than the leader taking notes. Say at the start that the aim is to understand the work, not to rank the people. If the setback involved safety, money or a client, check what your organization requires for a formal review, since that differs from place to place.
While they answer
The polished version comes first
A failure that cost nothing and led straight to success has been told many times. Thank them for it, then ask one question from The cost. You are not catching them out; you are asking for the chapter the short version skips.
Do not fix it
Advice, silver linings and 'everything happens for a reason' all close a story down. 'That sounds hard' and 'what happened next?' keep it open. Hold your opinion back unless they ask for it.
Let a silence run
A pause after a hard question often means they are deciding how much to say. Count to five before you speak. If they are upset, tell them they can stop, and do not rush to cheer them up.
Keep what you hear
Unless you are recording with their consent, treat the story as told to you alone. Before repeating any of it to a class, a team or a friend, ask whether you may and which parts.
After a failure of your own
Give it a few days
In the first days the answers are mostly feeling, which is fair but not much use for deciding anything. Come to the Ask yourself group once you can describe what happened in two or three flat sentences.
Write the answers down
On paper an answer has to end. In your head it circles. A page per question is more than enough, and reading it back in a month shows what has moved.
Borrow a listener
Hand the list to someone you trust and have them ask you the What happened and The cost questions aloud. Being asked draws out things you would not write. If the failure is keeping you from sleeping or working for weeks, that is a reason to talk to a doctor or counselor, and no list of questions is meant to stand in for one.