Why we suck at asking better questions

I just came back from a weekend trip to Seattle (note: it’s so beautiful right now).

While wandering around, we stumbled into Half Price Books (yes, that’s literally the name) and a book caught my eye:

It was, “A more beautiful question” - the power of inquiry to spark breakthrough ideas.

I thought it’d be a quick, casual read.

Instead, it ended up changing the way I think, lead, and make decisions.

It also reminded me how bad we’ve become at asking good questions.

Here are 4 things I took away (plus my favorite questions at the end):

1/ We don’t ask enough questions

Did you know children ask 40,000 questions by age 5?!

Then it drops drastically…

Think about it. How often do you really ask questions?

And why is that the case?

It’s because we’ve been primed to:

• prioritize fixing > asking

• value answers over curiosity

• avoid looking stupid by not knowing

This is your sign to action less and ask more.

2/ Good questions spark clarity

Sounds simple but it’s true.

We’re so used to running on autopilot.

We’re moving so fast when we should actually be slowing down.

A good question forces us to pause, reflect and readjust.

That’s how you build with intention and focus on quality > speed.

3/ A simple but powerful framework

Why → What if → How

→ Why? (Why is this the way it is?)

→ What if? (What if there’s another way?)

→ How? (How might I bring it to life?)

Let’s say someone says:

Instead of jumping into action mode, try this:

→ Why?

This helps surface what’s actually not working.

→ Is it burnout?

→ Is it a values mismatch?

→ Do I actually want growth, not just a promotion?

→ What if?

Do I want more interesting projects? Do I want more flexibility?

→ How?

See the shift?

One reframe turns into three powerful, actionable reflections.

4/ 10 of my favorite questions

• What does failure mean to me?

• What is important to you and why?

• What if I do nothing? What if I succeed?

• What if we start with what we already have?

• What would an optimistic, confident person do?

• What’s truly worth doing, whether I fail or succeed?

• What if I made 1 small change today? What would it be?

• What has worked for me before and how can I bring more of that in my life?

• When I look back in 5 years, which of these options make for a better story?

• Is there something else you might want to do besides what you were told to do?

We spend so much of our lives chasing the “right” answers.

But sometimes, clarity comes from slowing down long enough to ask the right question.

Whether you're job searching, pivoting, building a business, or just navigating what’s next…

Don’t underestimate the power of a question.

Use the Why > What If > How framework.

You might be surprised with what you get :)

Love, Jean

📌Jean’s picks

My favorite finds to help you grow and think differently

• How she was articulated her layoff in interviews and got hired at Google

• 7 essays that had the most impact on Lenny’s product career (from Lenny’s Newsletter with over 1M+ subscribers)

• How Olivia landed her dream job as a Senior UX Designer at Walmart

💡 In case you missed it

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• This is my secret to becoming a PM at top tech companies WITHOUT the PM job title 🤫

• Every salary I’ve made since college (as a 8x career pivoter going from $50 to $200K+)

• Why not ❌ “anyone can be a program manager”

• 10-unofficial leveling guide for PM roles

📣 Job Board

Jobs that are 🔥 and new from my curated job board + network

• Insights Program Manager – Global Sales Insights, LinkedIn

• Project Manager, G2

• Senior Program Manager, Microsoft

• Senior Hardware Program Manager, Microsoft

• Program Manager, SAP Basis and Infrastructure, Google

• Accessibility Program Manager, Meta

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And you can read all the previous newsletters here 🎉