Question Your Assumptions: Challenge What You Know

Why is ‘we have always done it this way’ the most dangerous phrase in business?

I remember sitting in a boardroom surrounded by stacks of paper and tired faces. We were trying to fix a broken process that was costing us time and money.

I asked a simple question: ‘Why do we print these forms in triplicate?’

The room went silent. Finally, a colleague shrugged and said, ‘That is just how we do it.’

It was a moment that stuck with me. We were not making decisions based on facts. We were running on autopilot, fuelled by old assumptions.

In my years working with teams across various sectors, I saw this pattern repeat itself constantly.

I advised an education technology group. I also worked on a project for a judicial organisation. I found that the biggest barrier was rarely technology. It was the invisible script in our heads.

We assumed we knew what the customer wanted. We assumed the old methods were the safest.

These assumptions often led to wasted effort and missed opportunities.

Challenging what you know is uncomfortable. It requires you to admit that your experience might be outdated.

During a complex integration project I worked on, I realised I had to let go of my own ‘best practices’. I needed to find a solution that actually fit the context. It was humbling, but it was necessary.

To lead effectively, you must learn to spot these mental traps. You need to stop predicting the future based on the past. Start looking at the raw data right in front of you.

Key Takeaways

• The danger of autopilot: Relying on past successes and ‘the way things are done’ creates a blind spot. This blind spot stifles innovation.
• The Ladder of Inference: Understanding this mental model helps you pause, check your data, and avoid jumping to incorrect conclusions.
• First Principles Thinking: Breaking problems down to their fundamental truths lets you rebuild better solutions from the ground up.

The Cautionary Tale

History is full of giants who fell asleep at the wheel.

We all know the stories of Blockbuster and Kodak. They did not fail because they lacked smart people or resources. They failed because they held onto a rigid assumption.

Blockbuster assumed people wanted the physical experience of a store. Kodak assumed digital photography would not replace film quality.

This happens because of a biological trait called Predictive Processing. Our brains are efficiency machines. To save energy, the brain predicts outcomes based on past patterns. It does not analyse every new piece of information.

• Efficiency: The brain takes shortcuts to process the world quickly.
• Pattern Matching: It looks for familiar shapes and routines.
• Blind Spots: It ignores data that does not fit the established pattern.

In business, this evolutionary advantage becomes a liability.

The market changes faster than our internal patterns do. When we treat our interpretations as objective facts, we create an ‘illusion of objectivity’. We stop seeing reality.

To stay agile, leaders must fight this natural urge. You must build systems to ‘fact-check’ your intuition. This skill is essential for escaping cognitive traps that lead to bad decisions.

The Framework: Understanding the Ladder of Inference

Chris Argyris, an organisational psychologist, created a model to explain our tendency to draw hasty conclusions. It is called the Ladder of Inference. It visualises the split-second steps our brains take from seeing data to taking action. Understanding this ladder is the first step in regaining control.

Here are the rungs of the ladder, starting from the bottom:

• Raw Data: The objective reality (e.g., a team member misses a deadline).
• Selected Data: We subconsciously filter data (e.g., noticing they also missed a meeting).
• Added Meaning: We interpret this culturally or personally (e.g., ‘They do not care about this project’).
• Assumptions: We formulate a theory (e.g., ‘They are unreliable’).
• Conclusions/Beliefs: We solidify this into a mindset (e.g., ‘I can’t trust this person’).
• Action: We act on the belief (e.g., stop delegating work to them).

The most dangerous part is the Reflexive Loop. Once you form a belief, it influences the data you select next time. If you believe someone is lazy, you will only notice when they take a break. You will miss the times they stay late. This creates a self-fulfilling prophecy.

The solution is ‘Climbing Down’. You must consciously pause before you act.

Ask yourself: ‘What data am I basing my decisions on?’ and ‘Is there another interpretation?’

In my experience, this pause often prevents unnecessary conflict and bad strategy.

The Methodology: First Principles Thinking

To truly innovate, we need to go deeper than just checking our biases. We need a method to strip away the noise. This is where First Principles Thinking comes in.

Most people reason by analogy. They look at what competitors are doing or what worked last year. They try to make small improvements to existing models.

First Principles Thinking is different. It requires you to boil a process down to its fundamental truths.

• Identify the problem: clearly state what you are trying to solve.
• Break it down: list the physical realities or facts that can’t be changed.
• Reconstruct: Build a solution based solely on those facts.

Aristotle defined this approach centuries ago, and Elon Musk uses it today to build rockets.

Instead of asking, ‘How do we make this battery cheaper?’, Musk asked, ‘What are the material constituents of a battery and what is their market value?’ He realised that the raw materials were cheap. The cost was in the process.

This shift changes your perspective:

• Incremental: ‘How do we make this form easier to fill out?’
• Exponential: ‘Is this form even necessary?’
• Agile: ‘Does this meeting add value, or is it just a habit?’

This type of thinking is vital for problem-solving in complex environments. It moves teams away from blindly following ‘best practices’ and towards creating context-specific solutions.

The Mindset: Intellectual Humility and Unlearning

Tools are useless without the right mindset. You need intellectual humility. Such humility is not about lacking confidence. It is about having high openness. It is a distinct recognition that ‘the things I believe might be wrong’.

In the past, leaders were expected to have all the answers. The ‘gut feeling’ of a senior executive was law. Today, data analytics and AI are challenging that reliance.

• Data over instinct: Hard numbers often contradict experienced intuition.
• Openness to change: Being willing to change your mind when presented with new evidence.
• Curiosity: Asking ‘why’ instead of stating ‘how’.

The World Economic Forum has highlighted unlearning as a critical skill. The ability to let go of obsolete methods is now more valuable than learning new ones.

In a project I worked on that involved a major system overhaul, identifying the necessary technical skills was straightforward. The hard part was getting the team to unlearn their old workflow habits.

The same principle also applies to diversity and inclusion. Assumption-checking is critical for Diversity, Equity, and Inclusion (DEI).

• Combat bias: It helps us question the scripts we run about other people.
• Reduce microaggressions: we stop assuming intent and start asking for clarification.
• Broaden views: It encourages seeking diverse perspectives rather than relying on an echo chamber.

Actionable Strategies: Tools to Break the Cycle

You can’t just tell people to ‘think better’. You need practical tools to force the shift. I have employed three strategies to help teams in descending the hierarchy and achieving clear thinking.

Tool 1: The ‘Five Whys’

This is a simple method to drill down past surface-level assumptions. When a problem occurs, ask ‘why’ five times.

• Why did the server crash? Because it ran out of memory.
• Why did it run out of memory? Because it was misconfigured.
• Why was it misconfigured? Because the engineer used an old script.
• Why did they use an old script? Because the new one was not documented.
• Root Cause: Lack of documentation, not ‘human error’.

Tool 2: Red Teaming

This involves assigning a specific team member to play ‘Devil’s Advocate’.

• Formalise dissent: make it someone’s job to challenge the plan.
• Remove friction: Since it is a role, it is not viewed as personal conflict.
• Test weaknesses: Find the holes in your logic before execution.

Tool 3: Data-Driven Debate

Implement a rule where opinions must be backed by raw data. This compels the team to collaboratively navigate the Ladder of Inference. It moves the conversation from ‘I think this won’t work’ to ‘The data shows a 20% drop in engagement’.

This process promotes critical thinking and keeps meetings focused on reality.

Conclusion

True growth requires vulnerability. You must be willing to admit that your current mental map might be wrong.

Authenticity includes being honest about what you don’t know. It takes courage to stand in front of a team and say, ‘I am operating on an assumption here; let’s test it.’

I challenge you to identify one ‘fact’ about your role that you have not questioned for over a year. Maybe it is a weekly report, a standing meeting, or a client interaction rule. Subject it to the Ladder of Inference. Ask if it is based on raw data or old beliefs.

Remember the old Zen proverb: ‘You can’t fill a cup that is already full.’

Innovation requires emptying the cup of assumptions. Only then can you make space for something new.

Wrapping Up

Challenging assumptions is not just about fixing business processes; it is about sharpening your mind. By using tools like the Ladder of Inference and First Principles, you move from reactive habits to proactive leadership.

The most effective leaders are those who never stop asking ‘why’, even when the answer seems obvious.

🌱 Question Your Assumptions: The Growthenticity Connection

The core ideas explored in this article aren’t just isolated concepts; they deeply resonate with the principles of what I call ‘Growthenticity’:

‘The continuous, integrated process of becoming more oneself (authentic) through leading with questions, learning through action, and growing by embracing uncertainty and imperfection, all fuelled by curiosity.’

Growthenticity requires the courage to admit you do not have all the answers. When you question your assumptions, you are embracing uncertainty and leading with questions rather than directives.

This openness lets you learn through action, testing your beliefs against reality. It is a fundamental step in moving away from the ‘perfect’ leader facade and becoming a more authentic, curious learner.

👉 Check out my free and paid Substack offerings at Lead, Learn, Grow. You can further explore concepts like ‘Growthenticity’. You will also gain access to practical tools and connect with a supportive community. This community focuses on encouraging authentic and impactful growth.

Join us as we unpack these ideas and support each other on our journeys.

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Your Turn

What is one ‘best practice’ in your current role? Do you suspect it might actually be a ‘bad habit’? Could this be based on an outdated assumption?