The Questions That Keep Finding You

Every so often, life hands you a question you swear you've already answered.

You expect to revisit it for old time's sake.

Instead, you realize it has been waiting for you to catch up.

That's what happened to me last week.

I was invited to give a talk about altmetrics and Plum Analytics, the company I co-founded fifteen years ago.

As I started preparing, I expected to spend time looking backward.

Instead, I found myself staring at the exact same question that started the company.

How do we know whether research is making an impact?

That question actually began years before Plum Analytics.

I was leading the development of a research discovery platform called Summon. Our job was deceptively simple: help researchers find the most relevant papers from millions of possibilities.

At the time, citation counts were the dominant measure of research impact. And they weren't wrong. They answered one question extremely well:
What has already become influential?

But they couldn't answer the one that kept nagging at me.

What is happening now that is likely to become influential?

By the time a paper accumulated enough citations to stand out, years had passed. Citation counts were reliable at spotting research that had already proven its impact, and much less useful for spotting research shaping the conversation in real time.

I became convinced the future was already leaving traces.
Downloads.
Mentions.
Saves.
Tweets.
Shares.
Recommendations.

No single signal could replace citations. But together, they painted a richer picture of research impact as it was unfolding.

That idea became Plum Analytics.

What eventually became known as altmetrics wasn't an attempt to replace citations. It was an attempt to answer a bigger question.

How do we measure the full picture of what matters?

For years, that question shaped my work. Then Plum Analytics was acquired, I moved into new roles, and I mentally filed that chapter under “complete.”

Until last week.

Preparing for that talk, I realized I wasn’t revisiting an old question.

I was standing in front of it again.

Only this time, AI had changed almost everything around it.

Researchers increasingly discover, synthesize, and interact with knowledge through AI systems instead of traditional search. The front door of research is changing, and that raises a new version of the same challenge.

How do we understand research impact when the way people discover and use knowledge has fundamentally changed?

I used to think returning to an old question meant I hadn’t finished the job.

Now I think it’s the whole point.

The questions that actually matter rarely disappear.

They return.

We often treat repetition like failure.
Back to square one.
Reinventing the wheel.

But there’s a difference between a circle and a spiral.

A circle brings you back to the exact same spot.

A spiral brings you back to the same place at a different altitude.

The question hasn’t changed.

You have.

You return with different experiences.
Different failures.
Different successes.
Different tools.

You notice patterns you couldn’t have seen before because you hadn’t lived them yet.

The same question I asked at Plum Analytics is back, but I’m not the same person who asked it.

I’m answering it with fifteen years of experience watching measurement systems get built, adopted, gamed, and misunderstood.

The question is the same.

The perspective isn’t.

And this pattern isn’t unique to research.

It shows up in leadership too.

Most people assume experienced leaders succeed because they’re constantly solving new problems.

I think the opposite is closer to the truth.

The biggest leadership questions rarely change.

How do you motivate people?
How do you decide what to build?
How do you measure success?
How do you earn trust?

What changes is your ability to answer them.

Experience doesn’t eliminate important questions.

It changes the quality of the answers you’re capable of giving.

I’ve come to believe this is one of the defining characteristics of breakthrough leaders.

They don’t obsess over finding entirely new questions.

They recognize when an old question deserves a fundamentally new answer.

Eventually every breakthrough becomes today’s normal.

The ideas that once felt revolutionary become assumptions.

Markets mature.
Technology changes.
Expectations shift.

Then the original question opens back up.

Not because you failed.

Because the world moved.

The Trap on the Other Side

There’s a darker side to all of this.

The spiral only works if you actually climb.

AI isn’t the only system that learns from the past.

Experienced leaders do too.

That’s both our greatest advantage and our greatest risk.

When a familiar problem returns, you can approach it with curiosity.

Or you can reach for the answer that worked last time.

Experience is incredibly valuable, until it becomes “I’ve seen this before.”

That’s when yesterday’s insight becomes today’s limitation.

A spiral climbs. A loop just repeats.

The difference isn’t whether the question returns.

The difference is whether you allow your previous answer to become the default.

Returning to an important question is a gift when you bring everything you’ve learned.

It’s a trap when you assume there’s nothing left to learn.

Practical Application

Think about a challenge that feels strangely familiar.

Not because nothing has changed.

Because everything has.

Maybe it’s how to structure your team.
How to measure whether your work is having an impact.
How to keep people motivated through uncertainty.
How to decide what deserves your attention.

Before you answer it, ask yourself:

What answer am I carrying forward simply because it worked before?

Then ask yourself:

What do I know now that I couldn’t have known the last time I faced this question?

That’s the altitude.

That’s the advantage experience is supposed to give you.

The failure isn’t seeing the same question twice.

The failure is answering it the same way without noticing that both you and the world have moved on.

Key Takeaways

✅ The questions that matter don’t disappear. They return throughout your career because the work keeps evolving.

✅ Experience compounds when you revisit old questions with fresh perspective. Your advantage isn’t solving brand-new problems. It’s recognizing familiar ones and seeing what you couldn’t see before.

✅ A spiral climbs. A loop repeats. The difference is whether you let yesterday’s answer become today’s default.

Wrapping Up

I said yes to that talk expecting a trip down memory lane.

Instead, it reminded me that the most meaningful work of our careers isn't about leaving our biggest questions behind.

It's about meeting them again with everything we've learned since.

Because the question isn't whether you've seen it before.

The question is whether you've become someone capable of answering it differently.

What question keeps finding you?

Hit reply and let me know. I read every one.