The life-changing magic of asking good questions

“I want to invest in RadReads.”

Wait, say wutt?

“Would you take my $300,000 investment?”

This question landed like a Jake Paul haymaker. I was totally blindsided.

After all, we were just two friends sipping some Skinny Margaritas (pro tip: swap out Triple Sec with Giffard Pamplemousse Liquer) catching up on summer gallivanting. The mosquitos in Austin. Luxury high-rises going up on the Gowanus Canal. And what the “mask scene” looks like at the local elementary school pickups.

But no. RadReads is not looking for investors. It’s not structured to take on investors. Heck, it doesn’t even have a business plan.

It’s a bootstrapped lifestyle business. Full stop.

“Sounds good,” he said. “But you know if you took it, you wouldn’t have to change your life one bit. You could still spend summers traveling, surf every morning, eat dinner with the fam every night. Just sayin.”

The friend left, but the question simmered in my psyche. Had I really created something of value? Who would we hire? Did we have the infrastructure to scale? What would it feel like to go from working in the business to working on the business? These were all $10K Questions that could dramatically move the needle on our 6 year old business.

I officially rejected the offer via text, but that simple question created a web of possibility, creativity and innovation that continues to linger weeks later.

“The quality of your life is a direct reflection of the quality of the questions you are asking yourself,” wrote Tony Robbins in Awaken the Giant. Yet in a react-first world where we are bombarded with inputs and information, searching for answers seems to be our default setting. Questions, are merely a distraction.

Or are they?

Why we fail to ask good questions

It finally happened.

“Where do babies come from?” asked our seven year old asked my wife Lisa. (She’d also asked What’s WAP, so at least her inquiry has a consistent through-line.)

And while Lisa didn’t go full stork with her answer, she hemmed and hawed to buy herself a bit more time to reflect.

One friend suggested going the full truth route as exemplified by the book My Mom’s Having a Baby.

But I digress. Any parent knows that kids are mini-question-asking-machines. They’re relentless in their “Whys” and are only satiated when they land upon the deepest kernel of truth. Kids are wellsprings of curiosity.

But here’s a sad truth.

As we “grow up,” our question-asking prowess falls off a cliff.

Here’s what the Harvard Business Review article Relearning the Art of Asking Questions found after surveying 200 workers about their rate of asking questions:

[The poll] found that those with children estimated that 70-80% of their kids’ dialogues with others were comprised of questions. But those same clients said that only 15-25% of their own interactions consisted of questions.

What holds grown-ups back from asking good questions? (And why had I never considered growing RadReads without the nudge from a friend?)

First, society rewards answering questions. In the book A More Beautiful Question, Warren Berger describes that from a young age “questions are viewed as a distraction” and “inefficient.” At school and in business, we tend to reward the question-answer-er; not the person who asked the question.

Next, the curse of knowledge comes into play – conspiring against asking more questions. This can lead to overconfidence in one’s own knowledge. Here’s Berger again on Shane Parish’s Knowledge Project Podcast:

Knowledge is if we feel we know something and we don’t have to ask. And so as you get older, you start to feel like, oh, I know, I know what this is all about.

Berger adds that in today’s environment expertise “tends to become outdated and obsolete” and a questioner keeps adding to (or rethinking) what they “actually know.” As Einstein said, “never lose a holy curiosity.”

But maybe the biggest obstacle to asking good questions is plain old ignorance. We don’t understand the transformative effect that questions can have on our lives and careers.

A framework for asking good questions

I took the $300,000 investment question and re-framed it into: What does RadReads look like without me?

Not because I’ve got any plans on going anywhere. On the contrary, we’re growing our team and expanding our product offerings.

Now, at the beginning of each the day and before any new project or task, I repeat the question to myself. The 7-word question is like a delicious layer cake — constantly revealing new insight, flavor, texture, perspective and complexity with every bite.

That question alone has helped me consider:

  • Who to recruit tomorrow, next year and in 3 years
  • How to train, retain and attract the brightest and kindest group of colleagues
  • What systems and tools we would need to invest in
  • How a brand identity could evolve (Is RadReads even the right name)
  • Designing automated sales pipelines
  • Creating a board of advisors
  • Considering different sources of funding (i.e. debt, community-based)
  • Could we acquire a company, platform, or an app
  • Team-wide and company wide OKRs
  • Mission statements, internal values and DEI policies

Before that question, I rarely thought about these things. The list could goes on and on, and each morning I journal on this $10k Question.

Being a sucker for a good framework, I went on the hunt for tools to help y’all come up with your $10k Questions — both in work and in life.

In How to Ask Great Questions, the authors present (yet another) 2×2 framework for asking questions. On the Y-Axis, you’ve got the The View Of the Problem (Wide or Narrow) you’re looking to solve; and on the X-Axis The Intent of The Question (Affirming, Discovering).

“What does RadReads look like without me?” is an Elevating Question. It’s wide and sole purpose is discovering something new.

And boy does it deliver.

$10k Questions are a compass for life

But enough about my itty-bitty company and its imaginary growth plans.

Remember, Tony Robbins’ “The quality of your life is a direct reflection of the quality of the questions you are asking yourself.”

Let’s take that even further, courtesy of a true OG — Socrates. In the Apology of Socrates, he wrote:

The unexamined life is not worth living.

(Which btw, inspires our mission to help RadReaders lead productive, examined and joyful lives.)

A great starting point for an examined life are Elevating Questions.

But these questions are often overlooked. Instead of asking “the why,” we get preoccupied with “the how.” Which leads us down rabbit holes of Notion Dashboards, GTD, and Big Hairy Audacious Goals. But if you don’t know where you’re heading, might you be shooting an arrow without a target?

How can we develop a practice of asking wide questions that help us discover something new?

Start your inquiry with something you’re genuinely curious about. Do you truly want to discover what it means to “make an impact?” (Or is it something you just throw around at a cocktail party?)

Demonstrate a hunger and commitment to go deeper. A $10k question is multi-layered. Be prepared to deepen the inquiry with methods like the 5 Whys.

Be self-compassionate. Your answers may not always be what you want to hear — they may reveal hurt, sadness, arrogance or insecurity. Acknowledge these uncomfortable feelings, without judging them.

Engage others. If you’ve found a juicy $10k question, there’s a high probability that it will evoke emotion in someone else.

In nearly three years of teaching Supercharge Your Productivity, we’ve watched students apply $10k questions across all dimensions of their lives. While asking these questions is definitely more art than science, we’ve found that two types of questions tend to emerge: Alignment and North Star questions.

To continue our maritime analogy, Alignment Questions are the ship’s rudder and serve as a gut-check on the present moment. North Star Questions are the lighthouse – a distant and abstract future version of you capturing your dreams and aspirations.

Alignment Questions

  • Am I living the life I choose for myself?
  • Am I off center?
  • Does how I spend my time align with what I value?
  • Why am I actually doing this work?
  • Did I love well?
  • Am I utilizing my strengths?
  • How can I foster curiosity and compassion?
  • Where is there unnecessary struggle?
  • What if it were easy?
  • What am I avoiding?
  • What makes me proud?

North Star Questions

  • What does success mean to me?
  • If I had 1 year to live, what (if anything) would I change?
  • Am I playing the right game?
  • What is happiness? (And am I happy?)
  • When well I know that I have enough?
  • How would life be different if there weren’t criticism in the world?
  • Who am I?

Human beings are quite complex, so this list and categories is by no means definitive nor exhaustive. But as you read through them, some will have a little flavor – a little zest – to them. Others will fall flat. And a select few might make the hairs on the back of your neck stand. Pay close attention, these are clues from your heart – and your soul.

We’ll be covering $10k questions with James Clear, Rachel Rodgers, Anne-Laure Le Cunff and many other Rad Guests at the upcoming $10k Summit beginning on October 5th.

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