Leadership Requires Different Kinds of Knowing

A month ago, a senior executive told me, “I have more data than ever—and less clarity about what actually matters.”

After a pause, he added, “Now that we’re trying to infuse AI in some core areas and into three different business units, I feel even less certain about which paths will pay off.”

As AI moves into core operations, leaders gain access to more insight while feeling less certain about direction. Systems that promise efficiency often introduce new layers of complexity, dulling our humanity in turn. What matters becomes harder to see in the middle of it.

Beneath the dashboards and decisions sits a potent question: what kind of knowing leads to wise action?

English gives us one verb—to know—and it carries a lot of weight.

Spanish offers two: saber and conocer.

Saber refers to facts and informed judgment.
Conocer is knowing through relationship and lived experience.

You can saber that your partner’s birthday falls on February 13th.

You conocer your partner through shared history and experience with them. You know their quirks, rhythms, passions, prides, and the way they laugh at your worst dad jokes. And because of that, you can know what to get them for their birthday.

You can saber that your team is made up of high performers.
You conocer your team by working alongside them long enough to notice how they respond to stress, what energizes them, and when they need support versus space.

That difference shows up quickly in leadership.

Leaders who rely mostly on saber tend to move quickly and build confidence through accumulation—more data, more inputs, more answers.

Leaders who develop conocer spend time in the work itself. They pay attention to how things actually unfold. Culture takes shape in those moments—how a leader listens, where they stay present, what they do when tension shows up.

Many of the technology systems we rely on today promise connection at scale, and often fail. Algorithms attempt to mirror real conversation. Platforms compete for attention, while “influencers” compete for clicks. The rise of AI companions points to something very human beneath it all: people want to feel known.

We have more access to information than ever, and still find ourselves searching for clearer judgment.

Robin Wall Kimmerer writes that “all flourishing is mutual,” a perspective grounded in close observation of the natural world. Spend time in a forest, and you begin to notice how much it depends on exchange—nutrients moving between trees, growth shaped by what surrounds it.

Human development follows a similar rhythm, shaped by the experiences we encounter. Gloria Anzaldúa names this deeper form of knowing, conocimiento, as an awareness that involves the whole person and grows through experience with others.

Seen over time, the pattern becomes clear: Wisdom grows in relationship.

That kind of knowing asks something of us.

It asks for presence. Growth takes time to reveal itself.
It asks for a relationship. Understanding deepens through conversation.
It asks for reciprocity. People and systems respond to how they are engaged.
It asks for change. We are shaped by the people and environments we stay close to.

AI is very good at saber. It processes data, identifies patterns, and accelerates some analysis. Leadership carries a different responsibility. It involves making sense of what matters, choosing direction, and staying accountable for the impact of those choices.

Over time, leaders evolve their ways of knowing. Early years are often driven by learning, building, and proving capability. Later, attention turns toward judgment—what to prioritize, what to hold, what to let go. That shift is shaped through experience with people, not just exposure to information.

The question becomes: how do we choose to know?

Can we approach our work and the people we work with as something we stay in relationship with?
Can we stay close enough to people and problems to understand how they are actually changing?

Leadership asks us to move beyond collecting answers and to stay engaged long enough for understanding to take hold. Because in the end, the quality of our decisions reflects how well we know the people and problems in front of us.

If you want a more trusting team, a culture of belonging or a magnetic brand that attracts more of the right customers, I can help. If you'd like to explore if working together makes sense, drop me a line.

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