How to Listen to Older Generations

You ask an older colleague for advice about a difficult decision.

Instead of giving you an answer, they begin telling you a story. It starts years before the situation you asked about. They mention people you’ve never met and details that don’t immediately seem relevant.

You wait for the point.

And while you wait, you begin wondering whether you should have asked someone else.

When I’m in that situation, I often sense there is something useful in the story. The difficulty is that the useful thing hasn’t yet come in a form I recognise.

That’s a communication principle to keep in mind when speaking to older generations.

A person’s experience doesn’t come neatly organised around your questions. They may remember a decision through the people involved or a small event that changed how they understood the situation. What seems like a detour to you may be an important part of the story to them.

So, if you want to learn from someone older, you need more than a good question. You also need to listen in a way that helps both of you discover what is important.

Ask for a story, then find your way into it

Let’s say you’re considering a career change. You could ask an older colleague:

‘What should I do?’

They might give you a useful answer. But they may also tell you what they would do based on their own priorities and responsibilities. Those may be different from yours.

I think you can ask a better question:

‘So, Professor Dumbledore, could I ask you something? Have you made a career decision you weren’t sure about at the time?’

Now you’re inviting them to share a story you can explore. You can ask what options they had and what happened after they made their decision.

The story may still contain advice. But you can see more of the experience behind it. And that makes it easier to decide what, if anything, applies to you.

Listen for the decision inside the story

As you listen, try to identify the decision or difficulty at its centre.

What was the person trying to do? What made it difficult? And what happened afterwards?

Sometimes an older person mentions something briefly and then moves on. You may be curious about it, but feel that interrupting would be rude.

You don’t have to interrupt immediately. You can wait for a pause and return to it:

‘Wait, you said your wife wasn’t happy with that career change, right? What happened when you spoke to her?’

A question like this does two things. It shows that you’ve been listening, and it helps the speaker return to a part of the story that might otherwise disappear.

That doesn’t mean directing every sentence towards your own interests. Some details are important because they help you understand the person, even when you can’t immediately use them. A conversation becomes richer when you’re willing to understand the situation before extracting a conclusion from it.

Check what you think you heard

What I usually practise is saying their point back in my own words.

For example:

‘It sounds like you weren’t only worried about changing jobs. You were also worried about disappointing the people who depended on you. Is that right?’

Now, remember that these are our interpretations. We draw them through a process of reasoning called inference.

Inferences can miss something important. That’s why I like to check at the end with a question.

If the person corrects you, listen to the correction. You may discover that the part you assumed was central wasn’t central to them at all.

And if they agree, you can go further:

‘How did that change the way you made similar decisions later?’

Now you’re moving from what happened to what they learned from it.

Don’t rush to turn their experience into a rule

Because I studied natural science, when I was much younger, I wasn’t patient when an older person told me a story. ‘Urghh, can’t they just get to the point?’

I wanted older people’s wisdom to be structured like an immunology research paper.

Only later, after I studied philosophy of science, did I learn how a story can be valuable without providing a universal lesson.

Someone may tell you a story about taking a risk that worked out well.

You can learn from the facts, such as the information they had and the consequences of their decision.

But that outcome alone doesn’t tell you that the same decision will work for you.

The story surrounding it can help you answer a crucial question:

‘What was different about your situation from mine?’

By not restricting them to telling you ‘just the facts’ of what happened, you also give the person room to reflect on their own story. What they once saw as a mistake may now look different. What they once regarded as a success may have come with painful costs you didn’t know about.

Final thoughts

Listening skills can be more important in communication than speaking skills. So listen to the person before deciding what you want to say next.

And if the story begins to wander too much, guide it without dismissing it:

‘So, wait, let’s go back to make sure I understand. What was the most difficult part of that decision for you?’

You’re not asking them to package a lifetime of experience into a perfect answer. You’re helping them find a place to begin.

So, the next time you speak with an older colleague, teacher or relative, try asking about one decision they remember clearly. Follow one detail that interests you. Then check whether you’ve understood what mattered to them.

You may come away with an idea you can use. You may also come away knowing the person a little better.

Both are worth the conversation.