Leadership Means Meeting People Where They Are

True leadership starts when we stop assuming the worst and start helping others do their best — from wherever they’re starting.

Most people are doing their best, even when you think they’re not.

I came across that line recently in a book and it brought me back to my first leadership role.

I was two years out of college, leading a software development team of 15 people, many with far more experience than I did. We’d just hired a new technical writer to create user guides, installation documentation, and help content for our applications.

After a month, she was struggling badly. I’d spent hours explaining the systems, workflows, and expectations. Then I gave her the instructions that so many new leaders think are empowering: “If you need anything else or have questions, just let me know.”

Weeks later, her first draft landed on my desk and it was a mess. A loose outline, placeholders, and half the document filled with comments like “Ask Joe about this.”

Frustrated, I went to my boss convinced she needed to be removed from the project. Instead of agreeing, he started asking questions:

“Did she understand what success looked like?”
“Did you give her a model to follow?”
“Did you check in along the way?”

And finally, he said something that’s stuck with me ever since:

“It’s your responsibility to help people do their best — and you need to meet them where they’re at.”

At the time, I didn’t want to hear it. But over the years, that feedback reshaped how I see leadership entirely.

Meeting people where they are isn’t lowering the bar. It’s leadership.

Not everyone operates at the same level of experience, confidence, or motivation. Some are balancing family commitments. Others are disengaged or unaligned with their work. Some haven’t had the coaching to unlock their potential.

If you expect people to give their best without understanding what “their best” looks like right now, you’ll always be disappointed.

Great leaders don’t start with judgment, they start with curiosity. They ask questions like:

  - What support do you need to do this well?
  - What part of this feels unclear or overwhelming?
  - What would “great” look like to you in this role?

When you do that, you uncover what’s holding them back and build trust that allows them to grow.

Leadership isn’t about demanding excellence. It’s about creating it.

It’s easy to lead when people are already high performers. The real test comes when they’re not. That’s when leadership shifts from delegation to development.

Over time, I’ve learned that my role isn’t to push everyone to be exceptional overnight. It’s to help them find their next step forward. Sometimes that means coaching a struggling performer. Sometimes it means realigning responsibilities to better fit their strengths. Sometimes it means helping them rediscover their purpose.

Because when you meet people where they are, you give them a chance to move closer to where they could be.

A simple practice for this week:
In your next one-on-one, ask one person on your team: “What would help you do your best work this week?”

Then listen. Really listen. You might be surprised by what they tell you.