Advice Questions to Ask
Questions for when you are stuck and want someone else's judgement: a mentor, a former manager, an older relative, or a friend who has been through it. They cover what you may be getting wrong, what they would rule out, and what to do next week.
The questions
Open any question for the note
Can I describe something I am stuck on and get your honest read on it?
Why ask it
Asking permission first tells the other person how much attention you want, which is why it gets better answers than launching straight in. It also gives them a graceful way to say they are not the right person today.
What would you do if you were in my position?
Why ask it
The most direct version of the question, and worth asking early. Notice whether they answer from your constraints or from theirs, because advice built on resources you do not have is only entertainment.
What am I getting wrong about this?
Why ask it
Most people soften criticism unless you invite it explicitly, and this phrasing makes disagreement the polite response. If they say nothing at all, you have probably described the situation too persuasively for them to argue with.
Which part of what I described worries you most?
Why ask it
It asks for a single priority instead of a general reaction, and the part they pick is often not the part you thought was the problem. That mismatch is usually the most valuable thing in the conversation.
Have you seen this go badly, and what did that look like?
Why ask it
Concrete failure stories are more useful than principles because they include the sequence of events. Anyone with real experience of the situation has at least one, and the details tell you which warning signs to watch for.
What would you have wanted someone to tell you at this stage?
Why ask it
This gets past general encouragement to the thing they actually learned the hard way. It also lets a person who is reluctant to instruct you talk about themselves instead.
Which of my options would you take off the table straight away?
Why ask it
Ruling out is easier and more honest than ranking, so people answer this more decisively. If they eliminate the option you were leaning towards, ask what they know that you do not.
What would you need to know before you could give me a straight answer?
Why ask it
It surfaces the facts you have skipped over, and those gaps are often the reason you are still undecided. A good adviser will name two or three things you can go and find out.
Am I solving the right problem, or is there a bigger one behind it?
Why ask it
Outsiders spot the substituted problem quickly: the job search that is really about a relationship, the money question that is really about status. Expect to resist the answer if it lands.
How much of this is a decision, and how much is discomfort I need to sit with?
Why ask it
Not everything unpleasant is a problem to be solved, and treating it as one produces unnecessary upheaval. Someone at a distance can usually tell which of the two you are describing.
Who else should I be talking to about this?
Why ask it
It respects the limits of one person's experience and often produces a specific introduction rather than a category. It also relieves the pressure on them to have the whole answer.
What did you get wrong the first time you faced something like this?
Why ask it
Mistakes are remembered in far more detail than successes and are less likely to have been tidied up in the retelling. This tends to be the question that changes the tone of the conversation for the better.
If I do nothing for six months, what happens?
Why ask it
It makes the cost of waiting visible, which is what most people ignore. Sometimes the honest answer is that very little happens, and that is worth knowing before you upend anything.
What is the smallest step I could take this week to test my thinking?
Why ask it
It converts a large decision into something reversible: one conversation, one application, one week of trying it. If nobody can name a small step, the decision may genuinely be all or nothing, which is itself useful to establish.
How would you tell the difference between patience and avoidance here?
Why ask it
Both look identical from the inside and feel like the same thing. Asking someone to draw the line usually produces a practical test, such as whether you have a date in mind or only a hope.
What would you expect me to regret, whichever way I go?
Why ask it
It accepts that both paths have a cost, so the answer is not a sales pitch for one option. Naming the likely regret in advance makes it much easier to live with later.
Is there a version of this I have not considered?
Why ask it
People arrive at these conversations with two options and a preference. Outsiders routinely see a third, usually a partial or staged version that neither of the original two allowed for.
What would you want me to come back and tell you in a month?
Why ask it
It commits you to something specific and gives the other person a stake in the outcome. It also quietly reveals what they think the real next step is.
Can I check in with you again once I have decided, or is this a one-off?
Why ask it
Asking directly avoids the awkwardness of assuming an ongoing arrangement that does not exist. Most people say yes, and the ones who do not have told you something useful about their capacity.
What have I not asked that you expected me to?
Why ask it
A closing question that catches whatever they held back out of politeness. It is often where the most direct advice of the whole conversation arrives.
Asking for advice you can actually use
Practical guidance for the conversation itself
Choosing who to ask
Prefer someone who has faced the specific situation
General wisdom is easy to find and rarely decides anything. Someone who has made the same decision, even if they made it differently, can tell you what the second and third months were like.
Ask one person at a time
Collecting five opinions in a week tends to produce paralysis rather than clarity, because each one reframes the problem. Take one conversation, act on part of it, then go back or go elsewhere.
Notice when you are looking for permission
If you already know what you intend to do, say so and ask them to argue against it. Disguising a decision as a question wastes their time and gets you agreement you cannot trust.
How to ask
- Give the context in two or three minutes, then stop. Long preambles teach the other person which conclusion you want.
- Include the detail you would rather leave out. Advice built on an edited version of events is worthless, however kindly it is given.
- Say what you have already tried, so they do not spend their answer on ground you covered.
- Ask for a decision, not for support, if that is what you want. The two requests need different conversations and mixing them frustrates both.
- Write down what they said soon afterwards. Specific phrases fade within a day and the specifics are the part worth keeping.
After the conversation
Separate the diagnosis from the prescription
Someone can read your situation accurately and still recommend something that suits their temperament rather than yours. Keep the first part even when you discard the second.
Do one thing within a week
Advice acted on slowly turns into advice sought again from someone else. A single small step also gives you something real to report back, which is what keeps people willing to help.
Tell them what happened
Most people never hear the outcome of the advice they gave. Closing the loop is the main reason someone takes your call the next time, and it costs one message.