Questions to Ask Your Siblings About Yourself
For anyone who wants an honest read on themselves from the people who saw the early version. Twenty questions to ask a brother or sister about your patterns, your blind spots and the parts of you that have and have not changed.
The questions
Open any question for the note
What is a childhood story about me that you think sums me up?
Why ask it
Starts with a story rather than an assessment, which is much easier to answer honestly. The detail they choose to include, and what they clearly remember better than you do, is the actual information.
What was I like before I could have been performing for anyone?
Why ask it
Siblings are the only witnesses to the version of you that existed before self consciousness. Their answer often describes a trait you now think of as an adult decision.
What did you think my role was in our family?
Why ask it
Expect the responsible one, the peacemaker, the difficult one, the invisible one. Hearing a label you did not know you had been given explains a surprising amount about how you still behave at family gatherings.
Where do you think I have changed most in the last few years?
Why ask it
Change is hard to see from the inside because you only ever have today's vantage point. A sibling who sees you a few times a year notices the difference in a way that daily company cannot.
What about me has not changed at all?
Why ask it
The harder half, and usually the more useful. If they name something you have spent years working on, that is worth sitting with rather than arguing about.
What is one strength of mine you think I underrate?
Why ask it
People tend to discount whatever comes easily to them, so the answer is often something you assumed everyone could do. Ask for an example of you doing it, or the compliment stays abstract.
What is a blind spot you have noticed, and where does it show up?
Why ask it
The where matters more than the what. A blind spot without a situation attached is just a character judgment, while one tied to specific moments, in meetings, with our mother, when you are tired, is something you can watch for.
How would you describe me to someone who is about to meet me?
Why ask it
Gets you the summary version, which is closer to how strangers experience you than to how you experience yourself. Note which of your qualities they think need warning about.
What do I do that makes people feel looked after?
Why ask it
You are asking for the mechanism, not the sentiment. Answers tend to be small and repeatable, remembering dates, following up two days later, noticing when someone goes quiet, which means you can do them on purpose.
When do I get most difficult to be around?
Why ask it
Better than asking what your flaws are, because it points at conditions rather than character: short of sleep, out of control of the plan, around a particular person. Conditions can be managed.
What do you think I am like when things are going well for me?
Why ask it
Most self examination focuses on the bad weeks. A description of you at your best gives you something to recognize and recreate, rather than only faults to avoid.
What is something about me people misread?
Why ask it
Gets at the gap between what you intend and how it lands, which is nearly always about pace, tone or silence rather than substance. Siblings have watched other people misread you for decades.
What is a decision of mine you thought was better than I did?
Why ask it
You will hear about a choice you still classify as a mistake or a piece of luck. Their outside reading of it is a useful correction to a story you may have settled on too early.
What is a decision of mine you were worried about at the time?
Why ask it
Ask for both sides or you only get the flattering half. Worth asking whether they said anything at the time, and if not, why they did not.
What can I do that you cannot, and the other way round?
Why ask it
Comparison between siblings is usually unspoken and slightly sore, so putting it into an explicit trade defuses it. It also tends to produce an accurate list, because you have both been keeping score quietly for years.
Do you think I am more like our mother or our father, and in what way?
Why ask it
Expect an answer you will want to dispute, which is the point. The specific behavior they name is usually harder to deny than the comparison itself.
What do I do that reminds you of how we were treated growing up?
Why ask it
A serious question, so pick your moment. Inherited habits around money, conflict, apologizing or going quiet are the ones a sibling can identify precisely, because they were in the same house when they formed.
When have I let you down?
Why ask it
The hardest one on the list and the one that most changes the conversation. Do not explain or defend on the spot: ask a clarifying question, say you will think about it, and then actually think about it.
What do you need from me that you have not asked for?
Why ask it
Turns the conversation from information gathering into something reciprocal, which is what stops the whole exercise feeling self absorbed. The answer is often smaller than you fear: more calls, fewer opinions, help with a parent.
What do you think I will be like in twenty years?
Why ask it
Closes on speculation rather than judgment, so it lands lightly after the harder questions. The version they describe tells you which of your current habits they expect to compound.
Asking Family for an Honest Read
Practical guidance for the conversation itself
Setting It Up
Say why you are asking
A sibling who does not know the purpose will assume something is wrong, or that a criticism is being set up. One sentence, that you are trying to see yourself more accurately and they have known you longest, is enough.
Pick five questions, not twenty
This works as a conversation, not a questionnaire. Choose a couple of easy ones about childhood, one about a strength, one about a blind spot, and stop while it is still going well.
Choose a side by side setting
A drive, a walk or doing the dishes produces franker answers than sitting across a table. Anything that involves eye contact for an hour will make both of you perform.
Offer to answer too
Say up front that they can ask you the same questions. It converts an interrogation into a trade, and their answers get noticeably more honest once they know it runs both ways.
Taking the Answer Well
- Ask when they first noticed it rather than whether they are sure. Detail is more useful than debate.
- Do not correct their memory of an event. Two accounts can both be true and the disagreement will eat the conversation.
- Wait out the pause. The second thing they say is usually the one they were deciding whether to mention.
- Say thank you for the uncomfortable answers specifically. It is the only way you get another one.
- Name one thing you are going to do differently, then leave it there. Over-promising in the moment reads as deflection.
What Tends to Go Wrong
- Asking during or straight after a family argument, when every answer arrives with a charge on it.
- Turning it into a comparison between siblings, or asking who our parents preferred. That is a different conversation and a longer one.
- Treating one sibling's view as the verdict. It is one well informed perspective from a particular angle.
- Fishing for reassurance and then rejecting it. If you only wanted the compliments, ask a different set of questions.
- Repeating what they told you to other family members. Nothing closes this down faster.