Hard Questions vs. Easy Questions: A Leadership Trap
- Fractional Insights
- May 9
- 5 min read
Inspired by psychologist Adam Mastroianni's brilliant article about how we humans substitute difficult questions with easier ones, we've been thinking about how this plays out in organizational leadership. Rather than ask the hard, meaningful question, we ask the one that is easy to answer and easier to jump to conclusions from.
The Substitution Trap:
Hard: Am I getting value from my human capital?
Easy: How many hours do people work?
Hard: Are people delivering optimal performance?
Easy: Are people exhausted?
Hard: Am I running this company well?
Easy: What's my turnover rate?
Hard: Are we making a difference in the world?
Easy: What's our YoY growth?
Hard: Are we truly solving customer problems?
Easy: Do people say they like what we sell?
Hard: Am I enough?
Easy: Do people like my LinkedIn posts?
Why We Avoid the Hard Questions:
This cognitive substitution is deeply ingrained in our human psyche. We are all predisposed to cognitive biases that drive us to seek closure and simplicity. These biases can lead us to favor easy, quick answers over more complex and nuanced ones, even when the latter may be more accurate and insightful. This tendency can be particularly problematic in situations that demand critical thinking and careful consideration.
As organizational psychologists, we have seen this play out for leaders, especially those leading people or making decisions about people. People can feel like a complex factor in the system of an organization. The human element is often viewed as an unpredictable variable in business, too complex or nuanced to measure precisely. This perception leads us to reach for simple metrics on people: performance ratings, engagements score, turnover rates. Simple metrics provide hard numbers to anchor to and use for decision making.
But what we don’t often measure or see are the factors beneath performance ratings, engagement scores, and turnover rates. What is driving those ratings? How can we predictably control and influence those metrics? Those are the harder questions.
But, here's what we know with scientific certainty: human behavior follows predictable patterns. Because human behavior follows predictable patterns with predictable drivers, we can measure, design for, and optimize human behavior.
Closing the Strategy-Execution Gap:
The greatest challenge in leadership isn't formulating strategy—it's executing it. And execution ultimately depends on human behavior and motivation.
Hard Question: Are we creating an environment that psychologically enables our strategy execution?
Easy Question: Did we communicate our strategy clearly in the all-hands meeting?
Where other approaches see the human element as an unpredictable or nuisance variable, we recognize it as the most powerful lever for turning strategy into reality. By designing environments aligned with fundamental human needs and motivations, we transform strategy execution into a predictable science. For example, while extrinsic motivators like compensation incentives can drive behavior, it's essential to balance them carefully with intrinsic motivators like recognition and appreciation to avoid counterproductive consequences and promote sustainable engagement over time, even if compensation has been maximized.
Taking a Systems-Level Approach
Human capital often represents the largest share of operating costs across organizations, yet it's frequently managed with less rigor than other business systems.
Hard Question: Is our entire human system optimized for performance and wellbeing?
Easy Question: Are individual team members hitting their KPIs?
The most effective leaders approach human capital as an integrated system governed by predictable psychological principles that can be measured, designed, and optimized. This systems architecture creates a unified framework that works across all business contexts, connecting psychological insights with business strategy to create sustainable momentum toward organizational goals.
Psychological Ergonomics by Design
Just as physical ergonomics revolutionized workplace efficiency, psychological ergonomics can transform organizational performance.
Hard Question: Have we engineered an environment that aligns with how humans actually think, feel, and perform?
Easy Question: Are we following influencer “best practices”?
Our foundational insight is that human psychology follows consistent patterns that can be designed for with scientific precision. By identifying and eliminating psychological friction points, we create environments where peak human performance becomes the natural state rather than the exception, driving measurable improvements in productivity, innovation, and execution.
The Psychology of Transformation
The greatest challenge in any organizational transformation isn't the initiative itself, but the human behavior change it requires.
Hard Question: Are we addressing the fundamental psychological needs that enable people to embrace change?
Easy Question: Have we rolled out the training for our new system?
Whether implementing AI technologies, restructuring teams, or shifting strategic direction, the focus must be on the human catalysts that unlock exponential impact. By addressing fundamental human needs for security, growth, and significance within changing environments, we create conditions where people naturally embrace and extend new capabilities.
Measuring What Truly Matters
Our expertise in psychological measurement allows us to quantify aspects of human performance that have traditionally been considered unmeasurable.
Hard Question: What are the root causes of underperformance or disengagement that need to be addressed to ensure we drive business outcomes?
Easy Question: What's our employee engagement score?
By bringing computational rigor and analytical precision to human capital measurement, we can diagnose, track, and analyze critical psychological and behavioral factors and their direct impact on key business outcomes. This transforms seemingly intangible human dynamics into concrete, actionable intelligence.
The Leadership Challenge
As psychologists working with CEOs and CHROs, we see this pattern repeatedly. We gravitate toward metrics we can easily measure as proxies rather than TRULY grappling with, sitting with, being deeply invested in the complex questions that actually matter.
Leaders who excel in today's environment demonstrate what I call "discomfort capacity" – the ability to hold difficult questions open long enough to discover valuable insights. They balance the tension between decisive action and thoughtful reflection.
Uncomfortable Truths
Working hard ≠ creating meaningful value
Customer satisfaction ≠ driving real outcomes
Having cutting-edge tech ≠ solving core problems
Employee engagement scores ≠ having a healthy culture
Meeting deadlines ≠ achieving strategic objectives
Making quick decisions ≠ making wise choices
The challenge for leaders isn't just recognizing these gaps – it's having the courage to sit with the uncertainty of those harder questions.
Engineering Better Questions
Here are practical steps to shift toward the harder, more meaningful questions:
Identify your substitutions - Notice where your organization substitutes easy metrics for hard questions. Map these substitutions explicitly.
Apply psychological precision - Leverage scientific understanding of human behavior to measure what actually drives performance, not just what's easy to count.
Design for human nature - Create environments that align with psychological principles, eliminating friction points that lead to disengagement or resistance.
Create systems-level measurement - Develop integrated measurement frameworks that connect psychological drivers to business outcomes across your organization.
Build transformation psychology - Address the fundamental human needs that enable people to embrace change rather than resist it.
To build truly effective organizations, products, and higher versions of ourselves, we need to be constantly checking ourselves (or having others check ourselves – which is WAY easier, by the way) - "Are we measuring what matters? And, are we interpreting that right?"
Your Turn
What hard question are you substituting with an easier one in your organization? Where might you be settling for comfortable metrics rather than psychological insights that truly drive performance?
Consider this: What would change if you engineered your environment for how humans actually work?
If this sparked something for you and you're curious about how to apply these insights in your own organization, we’d love to connect. Reach out to explore how we can support you in taking the next step.
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