A conversation with Carolyn Swinton, Leadership Coach at BenchStrength Coaching

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Most leadership advice focuses on behavior.

What to say in difficult conversations.
How to motivate teams.
When to step in or step back.

But beneath every leadership behavior is something far more influential: How you see the world.

In a recent conversation with executive coach Carolyn Swinton, we explored a powerful and often overlooked concept in leadership development: the observer. It’s just what you do as a leader, but who you are being as a leader.

The way you interpret situations often determines how you lead through them.

From the Front Lines to the Coaching Chair

Carolyn’s path to coaching began in nursing, where she spent more than three decades in healthcare leadership, including serving as a Chief Nurse Executive.

Early in her career, she noticed something important about herself: she thrived in complexity.

“I loved chaos,” she shared. Not dysfunction, but the energy of real problems, heightened emotion, and human stakes. She discovered she had a natural ability to engage patients, families, and colleagues in ways that shifted charged situations into calmer, more productive ones.

That ability followed her throughout her leadership journey. But it wasn’t until she experienced executive coaching herself that something truly shifted.

“It changed my life,” she said. “And I knew that’s what I wanted my next chapter to be.”

What Is the Observer?

Carolyn describes the observer as something deeper than personality or leadership style. It is shaped by lineage, culture, and lived experience.

“When I’m talking to you,” she explained, “I’m not just talking to you. I’m talking to your grandmother, your great-aunt, your ancestors.”

Our observer is influenced by how we were raised, how conflict was handled in our homes, what was celebrated, and what was avoided. These experiences quietly form the lens through which we interpret situations, especially under stress.

The challenge? We often mistake our perspective for reality.

“As leaders,” Carolyn said, “we see the world the way we are, not necessarily the way the world is.”

Why the Observer Matters in Leadership

At its core, the observer is how we see the world and how that perspective shapes how we think, decide, and show up.

Carolyn believes effective leaders stay grounded in their values while remaining flexible enough to meet others where they are.

One of her favorite metaphors is entering conversations as an “empty cup.”

“As leaders, we’re supposed to know,” she said “S.o, we often come in full, full of answers, opinions, and conclusions. But if we come in as an empty cup, we give others space to pour in.”

That pouring in creates connection. It expands perspective. And it reminds leaders of an essential truth: We see a lot, but not everything.

From Reaction to Intention

A fixed observer often leads to habitual reactions.

Carolyn shared a familiar leadership scenario: a text message goes unanswered. Silence gets interpreted through past experiences, assumptions start forming, and emotion fills in the gaps.

Before long, a story takes hold, one that feels real but may not be true.

“The trouble starts when we don’t test our assumptions,” she said. “We pay more attention to what we believe than to what we actually know.”

Expanding the observer allows leaders to pause, ask better questions, and respond with intention rather than emotion.

Instead of thinking, “What does this mean about me?”

They begin asking, “What else might be going on here?”

A Coaching Moment That Changed Everything

Carolyn shared a story about a leader who entered coaching reluctantly. She believed the coaching referral was a punishment rather than an opportunity.

Together, they explored a different question: What if this situation is here to teach you something?

As the leader began expanding her observer, her leadership shifted.

She discovered she could be both direct and empathetic.
She could hold people accountable and stay fully present.
She stopped trying to prove she was right and started learning.

“Her  concerns were resolved,” Carolyn said. “But more importantly, she came full circle as a leader. She became more grounded, more self-aware, and more effective.”

The Cost of a Narrow Observer

When leaders are unwilling, or unable, to expand their perspective, the cost is significant.

Carolyn named it plainly:

• Curiosity is traded for certainty
• Connection is traded for control
• Presence is traded for performance

In the pursuit of being right, leaders often sacrifice trust, growth, and impact.

Curiosity as a Leadership Practice

Curiosity, Carolyn emphasizes, is an important leadership skill, not a personality trait.

It’s a moment-to-moment leadership practice.

It starts with self-awareness: noticing triggers, recognizing patterns, and learning when to pause. It shows up through simple but powerful questions:

• What am I missing?
• What else is possible?
• Is there another way to see this?

Curiosity allows people to feel seen, heard, and valued. It reveals blind spots and opens leaders to perspectives they could never access alone.

Expanding Choice, Expanding Impact

When leaders expand their observer, they expand their range of choices.

• Scarcity gives way to abundance
• Rigidity gives way to flexibility
• Certainty gives way to possibility

“Life isn’t linear,” Carolyn reminded us. “There are curves, valleys, and mountains. Expanding your observer helps you know when to keep going and when to shift.”

A Reflection for Leaders

Before your next conversation, pause and ask yourself:

• What story am I telling about this situation? About this person?
• What assumptions might I be making?
• What perspective might I be missing?
• How could curiosity change this interaction?

If this idea resonates, start with one moment this week: enter the conversation as an “empty cup,” test one assumption, and ask one question that creates space for the other person’s reality. That small shift is often where trust, influence, and better outcomes begin.

In our work at BenchStrength Coaching®, we help leaders notice the “observer” they bring into high-stakes conversations, expand perspective before they escalate, and lead with curiosity without losing clarity. 

Leadership isn’t just about the actions you take. It’s about the lens through which you see the world. 

And when leaders expand the observer they are, they don’t just change their leadership, they expand what becomes possible for themselves and for the people they lead.

In our work at BenchStrength Coaching®, we help leaders notice the “observer” they bring into conversations, expand their perspective and grow in effectiveness, and lead with curiosity without losing clarity. om self-trust looks like. And it’s available to every leader willing to build it.