What a Plantation Retreat Reveals About Leadership Blind Spots

Last week, a post from a Black surgeon on LinkedIn stopped me in my tracks.

She shared that leaders in her organization had planned a retreat at an old plantation. To their credit, when she spoke up, the location was changed. But the larger issue remains: the fact that this location was ever considered acceptable in the first place.

This wasn’t about bad intentions. It was about a lack of awareness, and the cost of that gap.

Why this matters more than people want to admit

Corporate retreats are often positioned as moments of alignment, trust-building, and renewal. They’re meant to bring teams closer together.

But place matters. History matters.

And context matters, especially when you’re bringing together people from different backgrounds, identities, and lived experiences.

For many Black employees, plantations are not “charming venues” or “historic backdrops.” They are sites of trauma. Symbols of brutality. Physical reminders of generational harm.

Choosing a plantation as a retreat location—especially without questioning it—signals something deeply problematic: That comfort for some is prioritized over psychological safety for others.

And when leaders miss that, it erodes trust before the retreat even begins.

This is what happens when leaders don’t do the work

Situations like this reveal a broader pattern I see often in organizations:

• Leaders planning experiences through their own lens only

• Decisions made without diverse perspectives in the room

• A belief that “we didn’t mean harm” is enough (spoiler alert: it isn’t.)

In today’s workplace, leadership requires more than good intent. It requires cultural competence, empathy, and a willingness to pause and ask harder questions before decisions are finalized.

Because when employees have to be the ones to speak up—again and again—to prevent harm, the emotional labor is exhausting. And the damage is already done.

Why retreats can either heal or harm

Retreats are powerful tools. I believe deeply in their value. But they are not neutral by default.

A poorly designed retreat can:

• Alienate employees

• Undermine trust

• Signal whose comfort matters most

• Reinforce existing power dynamics

A well-designed retreat does the opposite:

• Creates psychological safety

• Acknowledges different lived experiences

• Builds shared understanding

• Strengthens trust instead of testing it

The difference isn’t the venue alone. It’s the intentionality behind every decision.

What leaders should be asking before planning an offsite

Before you book a location, design an agenda, or send a calendar invite, ask:

• Who might feel excluded or unsafe in this space?

• Whose perspective is missing from this planning process?

• What messages are we sending—intentionally or not?

• Are we building connection, or assuming it?

If those questions feel uncomfortable, that’s the work.

Leadership is revealed in moments like this

The surgeon who spoke up showed courage. The organization that changed course showed responsiveness.

But the real test of leadership is what happens before someone has to raise their hand and say, “This isn’t okay.”

At Simetras, we help leaders design retreats and offsites that are not just effective—but thoughtful, inclusive, and worthy of the teams they’re meant to serve.

Because alignment without awareness isn’t alignment at all.

If this story made you pause, I invite you to reflect on how your organization plans its most important moments of connection—and whether they truly serve everyone in the room.