My WHY, according to the WHY Institute, is Make Sense.

When I first encountered the WHY.os framework, I remember feeling a strange sense of recognition.

The WHY Institute describes a WHY as the fundamental motivation that drives a person’s behavior, decisions, and way of seeing the world.

In their model, the WHY is expressed through a HOW and ultimately delivered through a WHAT. My WHY is Make Sense. I express that through Mastery, bringing ideas to life through study, understanding, and refinement. What I ultimately deliver is Trust. The outcome I strive for is solutions, insights, and recommendations that people can depend on because they are grounded in careful thinking and accurate understanding.

The description explained something that had been present throughout my life. I have always been trying to understand what was really going on. Whenever an explanation was given to me, my mind would start pulling it apart. Did it actually explain the situation? Was there something missing? Did the explanation fit reality, or had people simply become comfortable repeating it?

“That doesn’t make sense” has probably been one of the most frequently used phrases in my vocabulary for decades.

Over time, that instinct evolved into a fascination with sensemaking itself.

I did not just want to understand events. I needed to understand how people arrived at their understanding of events. How leaders interpreted problems. How teams created narratives. How organizations explained success and failure. How entire groups of intelligent people can look at the same situation and arrive at completely different conclusions.

Looking back, it is probably inevitable that I became interested in sensemaking.

If your deepest motivation is to make sense of the world, eventually your attention shifts from understanding events to understanding how understanding itself is created.

I did not just want to understand what happened. I wanted to understand how people decided what happened. How leaders interpreted problems. How teams created narratives. How organizations explained success and failure. How entire groups of intelligent people could look at the same situation and arrive at completely different conclusions.

That curiosity eventually led me to Karl Weick’s seminal work on sensemaking. It felt like a natural next step in a journey I had already been on for decades. Early in the book, Weick references a line from Gilbert Ryle (1949) –

Conversion of knowledge of acquaintance into knowledge about is a risky exercise.

I immediately stopped reading and decided to make sense of it first and then write about it, because it describes something I see happening inside organizations all the time.

What I think Ryle is pointing to is the difference between knowing something because you have lived it and knowing something because you have described it.

Knowledge of acquaintance comes from direct experience.

It is the knowledge a leader develops after years of working with a team. The knowledge a parent develops raising a child. The knowledge an entrepreneur develops after surviving multiple cash flow crises. It is personal, lived, accumulated through contact with reality.

Knowledge about is different.

It is the explanation. The report. The summary. The framework. The theory. It is what happens when we attempt to translate experience into language so that it can be communicated to others.

Ryle’s warning is that something can be lost in that translation.

A leader spends years working alongside a team. They develop a feel for the culture. They can sense tension in a meeting before anyone says a word. They know which client is becoming frustrated. They know when a project is experiencing creep and taking far longer to complete than necessary. They know when a person is carrying more than they are admitting.

Then comes the weekly meeting, the bi-weekly report, the dashboard, the strategy session, or a consultant’s framework – and suddenly everyone is trying to explain what they already know.

The challenge is that lived experience and explanation are not the same thing.

A manager may know that a team is struggling because they have spent months observing interactions, conversations, missed handoffs, and subtle shifts in energy. The moment they try to convert all of that into a neat category such as communication problem, accountability issue, culture issue, or leadership issue, something can get lost. The description becomes smaller than the reality it is attempting to describe.

This is where organizations sometimes get themselves into trouble.

The language starts sounding more precise while the understanding becomes less complete.

• People begin discussing employee engagement scores instead of talking to employees.
• Customer satisfaction metrics start replacing actual conversations with customers.
• Performance indicators become proxies for realities that are far more textured, emotional, and complicated than any number on a dashboard can capture.

The result is often a strange kind of confidence.

Everyone feels as though they understand the situation because they have named it. Yet naming something and understanding it are two very different activities.

I suspect this is one reason why some business problems persist despite endless analysis.

The organization becomes increasingly skilled at talking about the problem while drifting further away from direct contact with the experience of the people living it every day.

There is tremendous value in models, frameworks, diagnostics, and measurement.

I use them myself. They help us organize information, spot patterns, and make decisions. Yet they work best when they remain connected to real human experience. Once the model becomes more trusted than the people experiencing the reality it was designed to describe, distortion starts creeping in.

Perhaps the deeper lesson in Ryle’s observation is one of humility.

Sometimes the first step toward understanding is spending more time with the thing itself before rushing to explain it. A customer complaint, a team conflict, a stalled initiative, or a leadership challenge often reveals more through careful observation than through immediate categorization.

Many of the alignment issues I encounter are not hidden because the information is unavailable. The information is usually present. People have seen it, felt it, and experienced it repeatedly. The difficulty begins when direct experience is translated into explanations that are tidy enough to fit a report, a meeting agenda, or a strategic plan.

In that translation, important details can disappear.

Strategic Reflection Prompt

Where in your business might explanations have started replacing direct observation, and what might you notice if you returned to the experience itself before trying to describe it?

About Giselle

I’m Giselle Hudson, a Pre-Decision Diagnostic Advisor. I work with leaders when something feels off — where results, decisions, or team response don’t match what was expected. I examine what’s shaping outcomes beneath the surface, so the next move is grounded, not reactive.

If this feels familiar, don’t rush your next decision. We can look at your situation properly before you take action.