Questions to Ask About Goals
Questions about what someone is aiming at, what they quietly gave up on, and what keeps getting in the way. Suited to a friend, a partner, or a long conversation with yourself, and phrased to avoid the language of five-year plans.
The questions
Open any question for the note
What are you working on at the moment that you actually care about?
Why ask it
Present tense and low stakes, so nobody needs a plan to answer. What they name first is where their attention really is, which is often not what they would list as a priority.
What did you expect to have done by now?
Why ask it
Reaches the private timetable most people carry and rarely state. Expect an age, a job title, or a milestone, and expect the size of the gap to explain a good deal about their current mood.
What has been on your list for years?
Why ask it
A goal that survives years without progress is either genuinely wanted or borrowed from someone else. Asking what happened the last time they tried usually settles which of the two it is.
What would you do with a free month and no obligations?
Why ask it
Removing obligation rather than money makes this sharper than the usual lottery question. Time is the real constraint for most people, and the answers tend to be modest and very specific.
What skill do you wish you had started earlier?
Why ask it
Regret about skills is easier to admit than regret about decisions, and it usually points at something still available to them. Notice if they describe it as closed off, because that belief is often the whole obstacle.
What did you give up on, and how did you decide?
Why ask it
Abandoned goals are the most honest part of anyone's history. Whether it ended in one clear moment or faded over two years predicts how they will handle the next dead end.
What are you aiming at that other people find odd?
Why ask it
Ambitions that earn no social credit are usually held for the person's own reasons. The answer tends to carry more conviction than anything they would put on a formal list.
What would you try if you knew you would not be embarrassed?
Why ask it
Names the real barrier. Looking foolish stops far more people than failing does, and phrasing it this way tends to get a truer answer than asking what they are afraid of.
What would enough look like: money, work, where you live?
Why ask it
Hardly anyone has defined enough, which is why the target keeps moving. A specific figure or a described ordinary week marks someone who has thought about it rather than absorbed a default.
Where do you want to be living in five years?
Why ask it
Place quietly decides most of the rest: the work available, the cost of living, who is within reach. It is also easier to answer than a question about identity and reveals nearly as much.
Whose life looks close to what you want?
Why ask it
Envy is useful once it is examined. Most people can name someone, and what they actually envy is narrow, usually the schedule or the independence rather than the whole life.
What are you doing this week that moves any of that forward?
Why ask it
This is where ambition and action separate. If nothing in the week connects to anything described so far, that is worth noticing quietly rather than announcing.
What keeps getting in the way, honestly?
Why ask it
The word honestly gives permission to skip the respectable answer about being busy. What follows is usually money, one particular person, or a fear they have not said aloud before.
Is there a goal you have kept to yourself, and why?
Why ask it
Private goals are protected either from ridicule or from accountability. Which one it is tells you whether the person needs encouragement or a deadline, and those are opposite kinds of help.
What have you achieved that took the longest?
Why ask it
Duration measures character better than difficulty does. Whatever kept them going, a person, a habit, or plain stubbornness, is the resource they will need again for anything ahead.
What did you want at twenty that you no longer want?
Why ask it
Change is easiest to see in what got dropped. It also relieves the pressure of the earlier questions, since it demonstrates that letting something go can be the right decision.
What would you have to stop doing to get the thing you want?
Why ask it
Almost every new goal requires giving something up, and that half is rarely planned. Vagueness here is the most reliable sign that a plan will not survive past February.
Who would you want to tell first?
Why ask it
The audience reveals the motive. Wanting to tell a parent, a former boss, or somebody who doubted them is a different engine from wanting to tell nobody at all.
What do you want to be different about you in five years, rather than about your circumstances?
Why ask it
Turns the conversation from situation to character, which is where most dissatisfaction actually sits. It usually produces the longest pause of the conversation and the best answer.
If nothing changed and you carried on exactly as you are, where would you end up?
Why ask it
Extrapolation is less comfortable than aspiration and far more useful. Some people are content with the trajectory. For those who are not, this is the question that tends to get acted on.
How to use these questions
Practical guidance for the conversation itself
How to ask without turning into a coach
Ask about the past as well as the future
What someone abandoned, and what they no longer want, is easier to talk about than what they are attempting now. It also builds enough trust for the harder questions later in the list.
Do not solve it
The moment you suggest a course of action, the other person starts defending their situation instead of describing it. If you have an idea, hold it until they ask, or until the conversation is over.
Follow the obstacle, not the ambition
The interesting material is almost always in what keeps getting in the way. Asking what happened last time they tried gets you further than asking how much they want it.
Offer something specific or nothing
An introduction, a lent tool, or two hours of childcare is worth more than encouragement. Vague offers to help are heard as politeness and change nothing.
What tends to go wrong
Asking someone who is in a hard season
During illness, a layoff, or the first year with a baby, questions about ambition land as pressure. Ask what would make this month easier instead, and come back to goals later.
Comparing quietly
People notice when a question is really about measuring them against you. Keep your own progress out of the exchange unless they ask, and resist the urge to match their answer with a bigger one.
Mistaking articulacy for progress
Some people describe plans fluently and never start. Others cannot explain what they are doing and are three years in. The week-by-week question separates the two more reliably than any amount of vision talk.
Repeating it back later as accountability
Bringing up something they told you in confidence, months on, reads as a check rather than as interest. Wait for them to raise it, unless they explicitly asked you to remind them.
Two ways through the list
With a friend, over an evening
- 1What they are working on now, then what has been on the list for years.
- 2What they gave up on, and what they wanted at twenty that they no longer want.
- 3What keeps getting in the way, honestly.
- 4Who they would want to tell first, which usually ends the conversation somewhere warm.
On your own, with something to write on
- 1What did you expect to have done by now, and what would enough actually look like?
- 2What would you have to stop doing to get the thing you say you want?
- 3What are you doing this week that moves it forward?
- 4If nothing changed, where does the current path end up? Write the answer as a sentence, not a feeling.