The Power of Asking Why Like a 4-Year Old

The Power of Asking Why

Why do some founders and teams struggle to see growth opportunities? Often, it comes down to the questions they ask. When faced with a problem or decision, our instinct is to ask surface-level questions that lead to surface-level answers. Some leaders believe they already have the answers within themselves and fail to challenge their assumptions or listen to others who do so. Often, leaders are programmed to believe there is a “playbook” that always works. While these questions and best practice approaches are necessary and helpful, they rarely spur meaningful growth. 

When you dig deep to ask the right questions and are willing to accept challenges to the status quo, you have a much better shot at expending your precious and scarce resources for better outcomes. One of my favorite learnings from an executive strategy course I attended years ago is as follows:

Strategy is the allocation of scarce resources to achieve an intentional objective or outcome. ~ Stanford Professor at Business School

Strategy is the allocation of scarce resources to achieve an intentional objective or outcome.

~Stanford Business Strategy Professor

Without the right questions, the execution plans that result from the strategy are highly likely to misallocate precious, scarce resources. The best allocation of resources is particularly critical at that crucial timeframe that I refer to as “the knee of the growth curve.” The “knee of the growth curve” is when the product market fit is pretty solid, and it is time to apply investment to drive that curve up and dramatically to the right if possible. 

Bring Your Inner Four-Year-Old to the Process.

To find growth opportunities, bring forth that ever-curious inner four-year-old. Apply that voracious and unending curiosity unencumbered by pre-dispositions or prejudices that children demonstrate with glee and tenacity to get better answers and outcomes.

We need to ask “Why?” not once but repeatedly, just like a curious four-year-old. By doing so, we peel back the layers of the onion and reveal the root causes and real problems needing solutions along the journey to growing the company. 

  • Asking why opens up possibilities. 
  • Asking why repeatedly exposes assumptions so we can challenge them. 
  • Asking why repeatedly and applying the brainstorming ground rules (any answer is worthy of consideration, and no answer is “stupid”) sparks creativity and new ideas. 
  • Ultimately, asking why and other open-ended questions when formulating growth strategies can lead to better questions, which in turn lead to better answers, which in turn lead to better decisions on where and when to allocate resources.

Status Quo Questions

When a startup or team focuses on the next phase of growth, there is a tendency to ask questions based on a fixed perspective of what is possible. It often relies heavily on “playbooks” from consultants or investors.

How can we get more users to sign up?  How can we increase conversion rates? How can we speed up our sales process? How can we beat the competition? How can we refine our product roadmap?

The emphasis is on incremental improvements and optimizations. While there’s nothing inherently wrong with these questions or using playbooks to facilitate the exploratory effort, they are limiting. They stifle the deeper curiosity that opens up new possibilities for the business.  

While these questions have their place in day-to-day operations, relying entirely on them can limit a company’s imagination and obscure the bigger picture. 

Common flaws include:

Lack of Vision.

Status quo and “playbook” style questions keep teams locked into current models and metrics versus imagining future possibilities.

No “Why?” Understanding

Questions are tactical versus root cause focused. There needs to be more push to understand the deeper reasoning or motivation.

Narrow View of Solutions.

Existing perspectives and assmptions constrain answers.  When exploring GTM strategies, the participating teams should be broad and diverse. (Read more on this here._

Short-term Mindset.

Energy centers on immediate gains rather than sustainable growth and innovation.


Finding scapegoats and excuses for lack of results becomes too easy. Excuses like “Marketing did not create enough leads.” “We need to change out the sales team.” When deeper questions would have exposed a more profound opportunity to refine the ideal customer profile (ICP) or revamp critical elements of the software.

Connecting to Childhood Curiosity

As young children, we all went through a phase of asking “why” incessantly. We would not take an adult’s quick response as satisfactorily addressing our curiosity. 

Child: Why is it light during the day and dark at night?

Adult: Because the earth is spinning, sometimes we are on the side that faces the sun, and sometimes we are not. Thus, there is light and dark.

Child: But why does the earth spin? 

Adult: The earth spins because of gravity.

Child: What is gravity, and why does it spin the earth?

And on and on it goes!

This barrage of questions stems from an innate curiosity about the world. In early childhood, everything is new, and our minds are primed to explore, understand, and make sense of our experiences. Asking why helps us construct knowledge, draw connections, and develop intellectually. It comes from a place of openness, wonder, and motivation to learn.

Somewhere along the way to adulthood, this tendency dims for many of us. We assume we understand things or stop probing further. The deep curiosity gets buried. But that four-year-old with endless whys is still inside us. When we tap back into this inquisitiveness, we open ourselves up to new possibilities.

Power of Asking Multiple Whys When Developing a GTM Strategy

Asking “why” questions without preconceived expectations of what a correct answer looks like taps into a wealth of insights. Children notoriously ask “why” incessantly and glean a deeper understanding of the world around them. We can mimic that approach and begin to glean deeper insights about our businesses. We better understand the bigger picture and how we can best invest in our companies’ growth.

Rediscovering the power of asking “why” can provide many benefits:

  • It pushes us to think more critically instead of settling for apparent answers. 
  • It helps identify root causes instead of just dancing around symptoms. Rather than treating surface problems, we can see opportunities and challenges differently and diagnose core issues that create barriers to our success.
  • It sparks creativity by challenging assumptions. Questioning the status quo opens new possibilities. Being humble and open to challenges to our assumptions and thinking as leaders opens up a new source of potential great ideas to make our companies successful.
  • It uncovers unexpected insights. Often, the deepest whys reveal non-obvious solutions.
  • It builds understanding of motivations and goals. Asking why can get us closer to understanding our customer’s motivations. With greater customer empathy and understanding, we can reinvent our solutions or approaches for GTM to bring more value.

Asking Why for Growth 

Regarding growth, many founders and teams ask surface-level questions like “How can we get more users?” or “How do we increase conversion?”. While these questions are essential, they often lead to hackneyed answers like “Run more ads” or “A/B test the checkout flow.” 

Transformative growth requires digging deeper. Every answer you get should lead to another question and another, “But why?” 

For example, suppose you ask why your startup isn’t gaining users. In that case, you may get an answer like “our marketing isn’t effective enough.” 

But if you ask why again, you may realize “our messaging doesn’t resonate with our target audience.” 

After another why, it could be “we don’t fully understand our users’ needs.” 

Imagine the ability to allocate your precious scarce resources (time, money, human capital) to newly discovered opportunities rather than throwing more money into Google ads. Taking on this ever-curious and open-minded mindset to continuously improve your go-to-market strategy and execution can pay real benefits. The benefits include faster, more sustainable growth and increasingly delighted customers who will advocate for you in the marketplace.

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