Amy Endee

We Meet People Where They Are. And Yet... We Leave Them There.

We talk a lot about meeting people where they are.

People are carrying different experiences, different skills, different levels of confidence, different capacities, and different challenges. Good leaders understand that. Where someone is is a reality you can't ignore. Pretending otherwise doesn't create growth—it just creates frustration.

And yet...

Meeting People Where They Are

Somewhere along the way, "meeting people where they are" started getting confused with "lower the bar" or "don't push them." The purpose of meeting people where they are is not to stay there with them. It's to understand where the journey begins so you can help them get started.

If someone is learning a new skill, you start with what they know. If someone is struggling, you account for the challenge. If someone lacks experience, you provide training and support. In other words, you adjust your approach. What you don't do is adjust the destination.

Meeting people where they are means changing how you help them get there. It doesn't mean changing where they're going.

And yet, that's often what happens. We lower the bar and calibrate expectations instead of changing our methods. We confuse support with accommodation and empathy with avoidance.

We Weren't Meeting People Where They Were

I worked at an organization that communicated important information through unclear channels and inconsistent methods. When I asked why we were doing it that way, the answer was, "We need to meet people where they're at."

The underlying assumption was that employees lacked the professional maturity to use the proper communication channels and that we should accommodate that reality. We weren't meeting people where they were; we were redesigning the system around where they were and hoping they would grow anyway.

At first, this approach can sound—and feel—empathetic and realistic. But meeting people where they are is supposed to move the starting point, not the finish line. The moment we lower expectations instead of simply adjusting our approach, we've crossed into something else entirely.

We aren't helping people grow; we're protecting them from growth. That's not kindness. It's often just accountability avoidance disguised as compassion.

A better approach is to account for the barrier without abandoning the expectation. In the communication example, the answer isn't to stop using clear communication channels because employees aren't using them. The answer is to help employees use them more effectively.

Address the Obstacle Without Compromising the System

If your goal is to drive people to the company intranet to improve internal communication, then make the intranet easier to access. Make it the browser landing page. Create reminders. Simplify navigation. Remove the friction.

That's what meeting people where they are is supposed to look like. You acknowledge the challenge and adapt your approach, but you don't lower the expectation.

Meeting people where they are doesn't mean redesigning the system around current behavior. It means designing a path from current behavior to the behavior you're trying to create. In other words, address the obstacle without compromising the system.

I've seen the same logic show up in countless other places.

• "We know managers aren't reading the agenda ahead of time, so let's just not have one anymore."
• "We know people aren't following the process, so let's change it."
• "We know leaders aren't making decisions, so let's create another committee."

Every one of those decisions prioritizes short-term ease over long-term clarity. We tell ourselves we're meeting people where they are. But are we? Or are we simply taking the path of least resistance and calling it empathy?

The fatal flaw is that instead of helping people build better habits, we're building our systems around the absence of those habits.

We stop using the phrase as a way to understand growth and start using it as a way to avoid the hard things. "Meeting people where they are" can very quickly blur into "keeping people where they are."

Being Nice Often Means Removing Discomfort. Being Kind Sometimes Means Creating It.

If you're not paying attention, meeting people where they are can become an excuse for not doing things the correct—and often harder—way. Not because people are lazy, but because growth creates tension, and that's uncomfortable. It's supposed to be.

Being nice often means removing discomfort. Being kind sometimes means creating it.

Nice says, "Let's avoid the difficult conversation."

Kind says, "Let's have the difficult conversation because I believe you can do more."

Organizations often claim they want growth while systematically removing every condition that creates it.

• We want accountability, but not uncomfortable conversations.
• We want better communication, but not new habits.
• We want stronger leaders, but not the mistakes that come with learning.
• We want change, but we don't want the tension change creates.

And yet, growth has never existed without tension.

It's uncomfortable to hold someone accountable during a difficult conversation or to insist people learn a new system. It's uncomfortable to stop creating workarounds and let the consequences of poor habits play out in real time.

But sometimes that's what it takes—not asking the impossible, but creating the healthy tension that comes from being asked to take the next step beyond where you are now.

Recognizing When Being Supportive Becomes Enabling

A manager who only pushes may lose people through frustration, and a manager who only accommodates may lose people because of a lack of growth.

Recognizing when being supportive becomes enabling is the real work.

When does patience become avoidance? When does empathy become an excuse?

When does understanding someone's circumstances turn into accepting permanent limitations that even they haven't agreed to?

Because let's be clear: meeting people where they are can easily become making assumptions about someone else's ceiling. And frequently, those assumptions are never discussed openly because they're blind spots.

The best leaders I've worked with were able to walk that line—and walk it well. They recognized reality without resigning themselves to it. They could say, "I understand why this is difficult," and, in the same conversation, say, "And yet I still believe you can do it."

The balance is offering support alongside compassion and maintaining standards while holding space and accountability—without treating any of those as mutually exclusive.

Without the First, Leadership Becomes Detached

Meeting people where they are is critical because people don't grow from a reality you refuse to acknowledge.

Pushing them forward is equally critical because people don't grow by staying where they are.

Without the first, leadership becomes detached. Without the second, it becomes enabling.

Helping people move forward is essential because leadership is about ushering someone along a new path. Without the first, leadership becomes detached. Without the second, it becomes condescending.

People tend to rise—or fall—to the expectations you set.

The inconvenient truth is that there's something inherently insulting about deciding someone is incapable of growth and calling it kindness.

So the real question is this:

Are you meeting people where they are because you believe they can grow?

Or because you've already decided they won't?