Questions to Ask an Older Woman
Questions for a younger person talking with an older woman she knows or admires, covering work, money, family, friendship, and the decisions she made against the expectations of her time.
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The questions
Each question, and why to ask it
What were you told a woman your age was supposed to want?
Why ask it
This gets at the expectations she was handed rather than the ones she chose, and the answer dates the era better than a year would. Where she matched the script and where she did not is the shape of the whole conversation.
What was the first big decision you made against advice?
Why ask it
Asking for a specific decision produces a scene: who objected, what they said, what happened next. General questions about courage get general answers.
What did your working life look like, and what did it cost at home?
Why ask it
Both halves are needed, because women of most generations were expected to absorb the cost privately. Listen for what she gave up rather than what she achieved.
Who taught you about money, and what did you have to work out alone?
Why ask it
Many women were kept away from accounts, mortgages, and pensions until a divorce or a death forced it. What she had to learn late is usually the most practical advice she can pass on.
When did you first feel you were being taken seriously at work?
Why ask it
The trigger is often a specific moment, such as being asked to present or being given a budget, rather than a promotion. It tells you what actually shifted her standing.
How did you handle being the only woman in the room?
Why ask it
Expect concrete tactics rather than sentiment: writing things down, getting the point onto the agenda in advance, finding one ally. Some answers will be about accommodation rather than resistance, which is honest and worth hearing.
What did you learn about friendship in your thirties that you did not know in your twenties?
Why ask it
Naming the decade prevents a generic answer. Answers usually involve dropping friendships that took more than they gave, and the reasoning transfers directly to a younger person's situation.
What did having children, or not having them, actually change?
Why ask it
Framing it both ways avoids assuming an answer and makes room for a decision that was not entirely hers. Watch for the difference between what changed in her life and what changed in how she was treated.
What did you keep from your mother, and what did you refuse to repeat?
Why ask it
The refusal is where the substance sits, and asking for both sides makes it possible to say without disloyalty. It also often explains how she raised her own family.
In your marriage or partnership, how did you end up dividing who does what?
Why ask it
Household division was rarely negotiated openly in her generation, so the answer describes how it settled rather than how it was agreed. Ask what she would arrange differently now.
What do you wish you had spent money on sooner?
Why ask it
Answers tend to be specific and unglamorous: help in the house, a better bed, a course, a lawyer. It is more useful than asking about regret in general.
What did you stop apologising for?
Why ask it
This names a change most women recognise without needing it explained, and the example given, whether about ambition, appetite, or taking up time, tells you what she had been carrying.
What has genuinely improved for women since you were young, and what has not?
Why ask it
The second half is the one worth waiting for, because it separates real change from changed language. Answers often distinguish law and workplace policy from what happens at home.
What advice about how you looked did you have to unlearn?
Why ask it
Rules about weight, hair, and dress were given to her as practical career advice, and hearing how firmly they were enforced explains a lot. Let her name it rather than raising her appearance yourself.
When something went badly, who did you lean on, and how did you ask?
Why ask it
The how is the useful part, since many women were raised not to ask at all. The answer often reveals a friendship or a sibling who carried more than the family credits.
What did you get wrong about ambition?
Why ask it
Asking for the error rather than the lesson gets something specific: staying too long, leaving too early, mistaking a title for influence. It also gives her room to be unsentimental about work.
What are you glad you said no to?
Why ask it
Refusals are rarely celebrated, so this is often the first time anyone has asked. Answers cover jobs, moves, and proposals, and the reasoning is usually clearer than for the things she said yes to.
What has become more interesting to you as you have got older?
Why ask it
It refuses the assumption of narrowing interests, and the answer gives you something to do together rather than only to discuss.
What do you think I should stop worrying about?
Why ask it
This asks her to advise you directly, which changes the register from interview to conversation. It also tells you what she thinks she can see in your situation that you cannot.
What would you like to be doing five years from now?
Why ask it
Asked of an older woman, this question is unusual enough that the answer is often surprising, and it makes clear you are not treating her life as finished. Practical obstacles she names may be ones a family can remove.
What are you working on or looking after at the moment?
Why ask it
Opening in the present avoids the assumption that her interesting years are behind her, which is the mistake most of these conversations start with. The answer is often a project, a garden, a committee or another person, and any of them gives you somewhere to go next.
What are you reading or listening to that would surprise people?
Why ask it
It puts you on equal footing and it reliably breaks whatever assumption you arrived with about her taste. It is also the easiest of these questions to return to next time you meet.
Where do you go when you want to be by yourself?
Why ask it
Women who have spent decades being available to a household often have a very precise answer, and it is rarely a room of their own. The specificity of the place tells you how hard-won it is.
Did you train for what you ended up doing, or fall into it?
Why ask it
For many women the answer involves a path that was closed, a course that was not available or a job that had to be left on marriage or pregnancy. It gets at her working life without making her summarise a career.
What did you teach yourself because nobody would show you?
Why ask it
Plumbing, accounts, driving, a trade, a language: there is usually something learned in the face of an assumption that she could not. This is where competence gets described plainly, which she may not have been invited to do in years.
Who taught you the most, and did they ever know it?
Why ask it
Often a teacher, an aunt or a colleague rather than a parent, and often someone who never found out. The unspoken gratitude is the part worth asking about.
Who were you at twenty five, and would she recognise you now?
Why ask it
More interesting than asking what she has learned, because it asks for a comparison rather than a lesson. Expect the answer to be about confidence or about how little of her own opinion she used to voice.
What are you better at now than you have ever been?
Why ask it
Most questions aimed at older women assume decline, and this one assumes the opposite, which tends to get a genuine laugh and then a serious answer. Follow up by asking when she noticed.
What did you have to fight for that people now assume was easy?
Why ask it
Depending on her age and where she lived, that could be a mortgage in her own name, a bank account, a place on a course or being taken seriously in a meeting. Listen without treating it as history, since much of it was recent.
What is the bravest thing you have done that nobody applauded?
Why ask it
Leaving, staying, telling the truth to family, taking on a debt, raising a child alone: courage in most lives is unwitnessed. Naming it aloud is the point of the question.
Which of your friendships has lasted longest, and what holds it together?
Why ask it
Long friendships between women often carry the practical history of each other's lives, including things no family member knows. Ask what has been forgiven, which is usually where the real answer sits.
What do people misjudge about you when they first meet you?
Why ask it
Direct, easy to answer, and it usually names something she has been quietly correcting for a long time: being read as timid, as unqualified, as somebody's wife. It also tells you what not to do for the rest of the conversation.
What do you no longer put up with?
Why ask it
Reliably the most enjoyable question in this list to ask, and the answers are specific rather than philosophical. Ask what happened the first time she said no, which is usually the story underneath it.
What would you want a younger woman to hear from you that is not advice?
Why ask it
Ruling out advice is what makes this different from every question she has already been asked a hundred times. You usually get an observation, a warning or a piece of solidarity instead of a maxim.
What would you like to be asked about that people never ask?
Why ask it
Ask it last. The answer often reveals a whole part of her life, a job, a talent, a person, that has gone unmentioned because everyone assumed the interesting subject was her children or her health.
How to ask well
Practical guidance for the conversation itself
Setting up the conversation
Ask about decisions, not eras
Questions about a period produce summaries; questions about one choice produce stories. Anchor each question to a moment: the job she took, the offer she refused, the year she went back to work.
Bring your own situation
Say what you are actually deciding before asking what she would do. Advice given in the abstract tends to be cautious, and advice given to a specific problem tends to be direct.
Give it more than one sitting
The questions about money, marriage, and refusal usually get their real answer the second time. Ask a few, leave the rest, and come back.
A sequence for a first proper conversation
Four questions in order
- 1What were you told a woman your age was supposed to want?
- 2What was the first big decision you made against advice?
- 3What did that cost you at the time?
- 4What do you think I should stop worrying about?
Common pitfalls
Making her a representative of her generation
Questions that begin with what women back then did invite a history lesson instead of her own account. Ask what she did and what she was told.
Asking only about being a woman
A conversation confined to gender leaves out the work, the ideas, and the interests she may most want to talk about. Mix in questions about what she is doing now.
Commenting on her age or appearance
Remarks meant as compliments, including surprise at what she still does, tend to land as condescension. Let her raise it if she wants to.
Treating advice as a verdict
Some of what she says will reflect constraints that no longer apply. Take the reasoning and leave the conclusion where it does not fit.