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Asking Better Questions Is Overrated
The Power Of Improvisation And Spontaneous Inquiry
Read time: 5 min
Welcome to Agua, a weekly newsletter where I provide tactics and stories to help founders magnify their potential.
Today’s Top Takeaways:
The ability to ask good questions is essential for effective leadership, decision-making, and problem-solving. However, over-reliance on questioning can lead to dependence and slow down decision-making.
Instead of solely focusing on asking better questions, improvisation, and spontaneous inquiry can help promote flexibility, collaboration, and experimentation.
Four tactics to integrate improvisation and spontaneous inquiry into your day include encouraging experimentation, promoting flexible thinking, fostering collaboration, and practicing presence. By implementing these tactics, individuals and teams can become more creative, innovative, and better equipped to solve complex problems.
Asking Better Questions Is Overrated
The Power Of Improvisation And Spontaneous Inquiry

Illustration by Michelle D'Urbano
The underrated skill, that hopefully isn’t underrated anymore: Asking good questions.
Underrated skill: Knowing which questions to ask
— Ryan Hoover (@rrhoover)
8:31 PM • Dec 21, 2017
From making difficult decisions to balancing priorities to delegating responsibilities, your day is in a constant state of flux. Forming the right approach is essential. Like you, I’ve spent countless hours preparing for meetings making sure I ask the right question(s).
Understanding how to ask good questions is essential, yes. But, it has its setbacks.
There’s a fine line when crafting a motivated team between dependence and autonomy. Folks on your team need to beware of leaning too much on others for answers and insights. And, relying too heavily on questioning can lead to dependence rather than developing individual creativity and problem-solving skills.
In your case, if questioning is your primary mode of inquiry, it can result in a lack of ownership. Thus, leading you to take less initiative to drive change and make decisions. While questions are essential for information gathering, they can slow down decision-making if used too much.
Instead of prioritizing asking better questions, explore improvisation and spontaneous inquiry.
Before diving in, let’s align on meaning:
Improvisation: The ability to adapt and adjust at the moment, react to changes, and make decisions on the spot.
Spontaneous inquiry: A more unstructured and informal approach to questioning, where you ask questions as they come to mind, without a predetermined plan.
Integrate improvisation and spontaneous inquiry into your day with these 4 tactics:
Encourage Experimentation
One of the best examples of improvisation and spontaneous inquiry are from cultures of experimentation. An example of this is Booking.com.
In 2017, the product and design team wanted to introduce changes to the UI before the busy holiday booking season. There was pushback from the CEO. Yet, one of Booking.com’s core tenets is: Anyone at the company can test anything—without management’s permission.
Booking.com runs more than 1,000 rigorous tests simultaneously and, by my estimates, more than 25,000 tests a year. At any given time, quadrillions (millions of billions) of landing-page permutations are live, meaning two customers in the same location are unlikely to see the same version. All this experimentation has helped transform the company from a small Dutch start-up to the world’s largest online accommodation platform in less than two decades
Why did this work?
Safe environments of experimentation lead to new solutions, ideas, and approaches. All while, recognizing, only some things will go according to plan.
When you encourage experimentation, folks will be inspired to take risks and try new approaches. People are more likely to act in this way when they feel supported and encouraged to do so.
Promote Flexible Thinking
The thoughts and stories streaming through your head are entirely unique to you.
Take a moment, and read that again. Really think about it.
Thus, the way I look at a situation is utterly different than the way you look at a situation. While overlaps are based on shared identities, backgrounds, values, shared interests, etc, we all look at the world through a lens.
When you’re solving a problem, sharing a solution, or simply collecting information, allowing your thinking to be malleable is a superpower. To best understand the situation at play, world-class players adjust their thought processes and perspectives in response to changing circumstances or new information.
To put this into action it's essential to stay open-minded by seeking out diverse perspectives, active listening, and practicing curiosity. Over time, you’ll see yourself, your team, and others who put this into practice start to be more creative, innovative, and better equipped to solve complex problems.
Foster Collaboration
Improvisation and spontaneous inquiry are dampened when siloed. These skills blossom when folks feel comfortable working together, sharing ideas, and building off each other’s thoughts.
Encourage teamwork and collaboration by creating more opportunities to work with others.
A collaborative environment can lead to more improvisation and spontaneous inquiry as employees are more likely to come up with new ideas and approaches when they feel comfortable sharing and building on each other's thoughts.
86% of employees and executives cite a lack of collaboration or ineffective communication for workplace failures.
Simply put, when you foster a collaborative environment, you’ll arrive at more creative and innovative solutions.
Practice Presence
You’re in a meeting right before lunch. Your stomach starts to growl. You look down at your phone and open up your favorite delivery app. It wasn’t a cook-at-home kinda day. Your order is running late– still over 30 minutes out. You skipped breakfast because you overslept and needed to hop right into the day. So, you’re, well, starving.
The next moment, someone in the meeting asks, “So, [your name], what do you think about that?”
Your stomach drops. You look up at your screen. You’re luckily familiar enough with the content to put the pieces together enough and add just enough value to get by. But, tbh, you completely made something up.
Presence is the foundation for each prior tactic. Without focusing on what’s happening right now, you’ll respond slower and miss changes at play.
When you’re present you can better understand your own thoughts, feelings, and behaviors, and make more informed decisions.
This allows you to answer with whatever comes to mind rather than getting caught in a pre-determined plan that doesn’t fit the situation anymore. How to be present? That’s for another post. But, start with noticing your breath. Notice what’s happening within your senses. There’s so much to learn and notice when starting, simply, there.
Experiment and discover the game-changing secret to unlocking creativity, innovation, and success in your team: embracing the power of improvisation and spontaneous inquiry.
See you next week,
Rachel
Whenever you’re ready, here are 3 ways I can help you:
CEO Coaching: CEO coaching for high-growth founders. I work with top CEOs and founders to unleash their superpowers, surpass their goals, and thrive in the process while scaling their companies. Learn more here.
Self-Paced Courses: Learn proven strategies, systems, and tactics to perform at your best, maximize your potential, and achieve lasting results. Check out Master Your Inner Game and Magnify Your Potential Masterclass.
Speaking: Inspire and motivate your organization with the power of creativity, decision-making, productivity, innovation, leadership, and mindfulness. Get in touch here.

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