How Leaders with Curiosity Can Drive Organizational Success

I am a strategic advisor for both the public and private sectors. Unlike a business coach, my job is to help organizations define clear missions and gather intelligence. This allows us to create strategies to navigate complex challenges and achieve measurable results.

In contrast, a business coach typically works on individual growth, offering guidance to improve personal skills, mindset and leadership abilities within a business context. I work behind the scenes to advise my clients on both day-to-day operations and during a crisis.

The questions that begin with “How?” are the most common. Examples include, “How do we get through this supply chain nightmare?” “How will we ever live down this scandal?” and “How can we increase our earnings exponentially despite being in a recession?”

Not a prescriptive person by nature, I will suggest two things:

1. It’s all about the intelligence gathering you do
2. But in order to get to that stage, are you asking the right questions?

There is no doubt that running a business nowadays is complicated… to say the least. Some of it has to do with our global connectedness, along with regulations that had far fewer reasons to exist in our parents’ and grandparents’ day.

Indeed, geopolitical strife and regulations can and will cause supply chain disruptions. There is also the constant threat of data breaches, and then there are the day-to-day issues all companies contend with that seem magnified in our new normal.

Related: 3 Business Models That Will Shape the Future of Entrepreneurship in 2025 and Beyond

Why asking the right questions matters

I have to remind my clients that surviving and even thriving amid these obstacles isn’t necessarily about having all the answers or the latest technology but about knowing the right questions to ask. For leaders, executives and advisors who are helping them navigate these complexities, mastering the art of inquiry may be the game-changing advantage you need.

Although my clients and all business owners face numerous struggles, I’d like to focus on remote working and the ease with which many remote workers cheat the system.

While freelancing has been around since the 1970s, until the pandemic, it was still a relatively novel approach to making a living. Once the world shut down in an instant and we embraced sheltering in place and social distancing, employees working remotely became somewhat of a norm.

One of my clients recently dealt with a unique issue. When the company moved to remote working during the pandemic, there was initially a spike in productivity. Staff members quickly took to casual Fridays, which were a daily occurrence, and they did not have the oversight of their micromanaging supervisors monitoring their every move. Stress was down, and productivity was up — an ideal scenario, wouldn’t you say?

But over the last nine or so months, she noticed that productivity was waning, and her first thought was to fire everyone and start all over. I explained some realities about her situation. Attrition is not just a line item on an HR report; it’s a symptom of a deeper dysfunction within the organizational fabric.

In 2022, Gallup published a survey revealing that disengaged employees cost the global economy $8.8 trillion annually, a testament to the high price of ignoring employee happiness. In other words, the solution is to engage her employees.

But, and this is a big problem, sometimes it’s not just about pacifying employees but also recognizing there are indeed some bad apples, and it’s important to know which situation she had to work through.

A trend that’s growing in numbers

In January 2024, so nearly four years after the pandemic began, the Canadian government revealed that 43% of their workforce who are still working remotely are not dedicating their full-time work exclusively to their main job.

This unfortunate reality isn’t unique to the government. People working remotely in the private sector are also gaming the system. Yegor Denisov-Blanch is a student at Stanford Business School whose research describes a tool that helps software developers review code more efficiently by automating some of the tedious or subjective tasks that are often skipped.

Seemingly obscure to the rest of the world outside of school and maybe some scholars in his field, in November of this year, Denisov-Blanch shared an observation that he posted on X that has since gone viral. “I’m at Stanford and I research software engineering productivity. We have data on the performance of >50k engineers from 100s of companies.” … “Our research shows: ~9.5% of software engineers do virtually nothing.”

He went on to suggest that some in this group were contributing such little code that he suspected they may be working multiple jobs to boost their pay. However, these aren’t people making minimum wage. According to many published accounts, these engineers make close to or above $300,000 annually.

Related: Why Are Remote Work Trends So Different in the US and UK?

PopSugar, which focuses on trending topics like celebrity gossip and pop culture, concurs. They ran an article recently entitled, “HR Weighs in on “Quiet Vacationing,” which illuminates another issue with remote working: taking vacation but not using vacation days/PTO. Instead, they are sitting on a beach at a resort, squeezing in time between sipping drinks with cute umbrellas, activities and catching some rays.

Given how widespread this issue is, rather than give my client the answers that she hoped would solve her problem, I suggested a different approach. “You’re not asking the right questions,” I told her.

I posed these two questions:

1. “What data can we collect to better understand how employees allocate their time?”
2. “How can we use this information to ensure fairness and productivity?”

To address the challenge of remote workers splitting their focus between multiple employers during company hours, I suggested she focus on improving how we gather and analyze intelligence. The solution, I assured her, begins with asking the right questions to uncover patterns that might otherwise go unnoticed.

Mind you, this wasn’t a quick endeavor. It took us weeks to complete this intelligence gathering.

Once we had the data, I analyzed it to identify inefficiencies and any behaviors that suggest misuse of company time. This allowed me to consider and suggest tailored accountability measures, such as clear productivity benchmarks and periodic but unplanned reviews. By focusing on these insights, I helped her refine the organization’s remote work policies, ensuring they balanced trust with accountability and enabled their employees to work effectively while maintaining integrity.

In times of crisis or upheaval, the instinct to seek immediate answers is natural. But the leaders who thrive are those who first pause to explore deeper, more insightful questions. Why? Because asking the right questions:

1. Clarifies the Mission: It helps identify the real objectives and avoid distractions.
2. Surfaces Hidden Assumptions: It challenges what is taken for granted and uncovers blind spots.
3. Guides Effective Intelligence Gathering: The quality of your data depends on the quality of your inquiry.
4. Informs Decisive Action: Clear questions lead to clear, actionable strategies.

Curiosity: the foundation of effective intelligence gathering

Curiosity is more than a trait — it’s a strategic tool. In environments where the situation is evolving rapidly, a mindset of curiosity-driven inquiry keeps organizations agile and adaptive. Instead of reacting to surface-level disruptions, strategic curiosity digs deeper.

In The Art and Science of Intelligence Gathering, my forthcoming book and follow-up to my first book, From War Zones to Boardrooms: Optimize the Moment When Strategic Planning Fails, I outline how curiosity drives effective intelligence.

Leaders who ask, “What are we missing?” or “What assumptions underlie our current strategy?” open the door to insights that transform challenges into opportunities.

In times of disruption, answers may be scarce — but the right questions are always within reach. Embrace curiosity, challenge assumptions, and let intelligence gathering guide your path to success. After all, the most powerful strategies begin not with the right answers but with the right questions.