Structure & Systems

When the Message Is Right but the Communication Still Fails

When the Message Is Right but the Communication Still Fails

I witnessed something recently that stopped me in my tracks.

An executive director was heading out for the day when a team member caught her with a question about a task. What followed was a five-minute exchange that, on the surface, looked like a communication breakdown. The director kept saying, "No, that's not what I mean," only to restate — almost word for word — exactly what the team member had already said.

The team member's understanding was correct the entire time.

They eventually landed on "Okay, I got it," and the director walked out. Less than ten minutes later? The director called back and repeated the entire exchange by phone.

As an observer, I watched tension build in real time. What I saw was frustration on both sides and a noticeable lack of trust — specifically, the director's trust that her team member had understood the instructions and would follow through.

As a consultant, I saw something deeper.

The Real Issue Wasn't Communication. It Was Clarity and Confidence.

That director wasn't just struggling to communicate her message. She wasn't fully clear on what she wanted in the first place. And when you aren't clear on what you want or how you want it done, it becomes nearly impossible to deliver that message with confidence — no matter how many times you repeat it.

This is more common than most leaders want to admit. According to McKinsey, ineffective communication and unclear direction are among the top factors that reduce organizational productivity. And Deloitte research has found that unclear expectations from leadership directly impact employee engagement and performance outcomes.

The team member in this scenario had been on staff for over a year. She wasn't new. She wasn't underperforming. Yet the interaction communicated something unintended — I don't trust that you can handle this.

That has a cost.

Two Opportunities Every Small Organization Leader Should Seize

1. Get clear before you communicate.

If you find yourself restating the same instruction multiple ways, that's a signal worth paying attention to. It may not be a delivery problem — it may be a clarity problem. Before assigning a task or delegating a project, take a moment to define, for yourself, what a successful outcome looks like. What specifically needs to happen? By when? What does done look like?

When you have that clarity internally, your communication becomes more direct, more confident, and far less likely to create confusion on the receiving end.

2. Create a system for delegation — and protect the space for it.

Giving instructions as you're walking out the door is one of the most common and costly communication habits in small organizations. It leaves too many gaps. There's no room for the recipient to fully process the information, make sense of it, or ask meaningful clarifying questions.

Effective delegation isn't just about passing off a task. It's about creating a structured moment — however brief — where information is exchanged clearly, questions are welcomed, and both parties leave the conversation aligned. When that space is consistently held, something powerful happens: your team builds confidence in their own understanding, and you build confidence in them.

That's where trust is built. Not in the big moments — but in the ordinary, everyday exchanges that either strengthen or quietly erode your team's sense of direction.

What This Means for Your Organization

If your team regularly asks the same clarifying questions, or if you find yourself following up shortly after giving instructions, it's worth pausing to examine the system — or the absence of one.

Small and mid-size organizations often run on the momentum of their leaders. When that leader is unclear or rushed, the entire team feels it. And over time, that uncertainty doesn't just slow down tasks — it chips away at the culture of trust you're trying to build.

The good news? This is fixable. It starts with honest reflection about how instructions are currently given, received, and followed up on inside your organization.

Ask yourself:

  • Do your team members leave conversations knowing exactly what's expected of them?
  • Do you have a consistent approach to delegation, or does it depend on the day?
  • When a task isn't completed the way you envisioned, where does the breakdown usually start?

If you're not sure — or if you know the answer and it's uncomfortable — that's your starting point.

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