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Home Leadership

Why Communicating With Context Is The Practice Most Leaders Get Wrong

It is one of the six differentiators that separates exceptional leaders from good ones. Critically, the way most leaders define it is missing what actually matters.

David GrossmanbyDavid Grossman
May 21, 2026
in Leadership
Reading Time: 5 mins read
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Why Communicating With Context Is The Practice Most Leaders Get Wrong

Most leaders misunderstand what it means to communicate with context, focusing only on delivering information while failing to account for what their audience is already experiencing.

This is the fifth article in a leadership series exploring the six practices that create exceptional leaders. Read the introductory article here: The Future Of Work Has Outgrown โ€œGood Enoughโ€ Leadership. Your 6-Part Playbook To Become An Exceptional Leader Starts Hereย 

Ask most senior leaders what it means to communicate with context and you will get some version of the same answer. It means giving people the background they need to understand a decision. The financials, strategic rationale, and the why behind the what. Good leaders can usually do that well.

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And yet the research says thatโ€™s simply not enough.

When we partnered with The Harris Poll to survey 2,206 employed Americans on what separates exceptional leaders from good ones, communicating with context was one of the six differentiators we identified. Exceptional leaders were 2.20 times stronger at communicating with context than good leaders. But when we looked closely at what exceptional leaders actually do differently, the pattern was consistent. They define context more broadly than their peers do, and they do the harder half of the work that most leaders skip.

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Context is two things, and most leaders only deliver one

Good leaders think of context as what they know that the audience does not. Exceptional leaders think of it as that, plus something more: the history, experiences, and assumptions the audience brings into the room before the leader says a word. Itโ€™s what I often refer to as truly โ€œknowing your audience.โ€

Both halves matter. One is information the leader provides. The other is information the leader has to understand about the audience before any message will land.

Most leaders do the first half well and skip the second half entirely. They prepare carefully, walk into the room with their data, and explain the rationale. And then they are surprised when people do not respond the way they expected.

What they missed is that their audience walked in with its own context, and the leader never accounted for it.

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A leader who understood what his audience was carrying

In early 2020, healthcare systems across the United States were preparing to roll out COVID-19 vaccines. Dr. Chuck Wallington, EVP and Chief Marketing & Communications Officer at Cone Health in North Carolina, was part of the team planning those communications in his region.

In one leadership meeting, Wallington shared something his colleagues had not fully registered. Not everyone in the community was going to be eager to get vaccinated, and in minority communities, the hesitation had specific historical roots, including the Tuskegee Study and decades of documented inequities in how African Americans have been treated by the U.S. healthcare system.

Wallingtonโ€™s point to his leadership team was not that any single historical event explained everything. It was that if Cone Health rolled out a standard vaccine communication campaign without accounting for what their audience was carrying, the information could be correct and the message could still fail.

So Cone Health took a different approach. The team built vaccine communications grounded in authentic leadership. They worked with community voices the audience already trusted. They acknowledged the history rather than avoiding it. They answered questions most vaccine campaigns were not even asking.ย 

That is what communicating with context looks like in practice.

Why good leaders skip the audience half

Good leaders usually do not ignore audience context on purpose. They skip it because their training pointed them somewhere else.

For more than three decades, I have watched a consistent pattern. Leaders get promoted on the strength of their ability to process information and make sound decisions. They learn to communicate by preparing material, organizing it, and delivering it clearly. That is a real skill, and it serves them well.ย 

What it does not teach them is how to account for the fact that every audience is already coming in with their own perspective and the very real challenges they face in making change happen within their roles.

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When the leader does not do the work to see where their audience is, communication turns into a one-way delivery. The message goes out, and the audience receives it through whatever filters they were already wearing. The leader wonders why the message did not land.

Exceptional leaders start in a different place. Before they prepare their content, they ask what their audience is already carrying, what they have lived through recently, and any assumptions theyโ€™re struggling with.ย 

In doing this pre-work, leaders know what kinds of concerns and questions to work through first before any of the actual information can get through.

What to do starting Monday

Three practices bring the audience half of context into your communication.

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1. Audit what your audience is already carrying.

Before your next significant message, ask yourself two questions. What has this audience lived through recently that is shaping how they will hear this? And what is the last big message they received from leadership that went well or badly? The first is context. The second is trust history. Both matter.

2. Name what is not being said.

The most powerful thing a leader can do in a moment of uncertainty is name the emotional reality in the room before naming the business reality. โ€œI know this raises real questions for people.โ€ โ€œI know the last reorganization is still fresh for some of you.โ€ That kind of acknowledgment does not slow things down. It clears the path for everything else you are about to say.

3. Do not wait until you have everything.

When something is changing, the worst move is waiting until you have the full picture before communicating to your teams. Say what you know, what you do not yet know, and say when you expect to know more. People can live with uncertainty, but not silence.

Why this matters right now

Employees today are processing more change at once than most workforces in recent history. Artificial intelligence is rewriting their job descriptions. Hybrid arrangements have changed their relationship to the office. Economic volatility has changed their sense of security. Every major organizational announcement now lands on top of all of that.

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In that environment, communicating with context, including the context the audience carries into the room, stops being a nice-to-have. It becomes the thing that decides whether your message lands, gets ignored, or actively backfires.

Communicating with context was one of the six differentiators in our research for a reason. It is the skill that determines whether all the other good things a leader does actually reach the people they lead. The gratitude, the listening, the inclusion, the growth, the enablement. None of it translates if the leader cannot meet their audience where their audience already is.

Next article: Connecting strategy to employee growth, and the one question every employee is silently asking during every period of change.

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David Grossman

David Grossman

David Grossman is an author, consultant, speaker, and one of America's foremost authorities on leadership and change communication inside organizations. He is the Founder and CEO of The Grossman Group, an award-winning internal communications consultancy that works with Fortune 500 organizations. His work focuses on helping leaders align business and communication strategy, strengthen workplace culture, and improve employee engagement and performance, particularly during periods of uncertainty and organizational change. An award-winning, six-time author, Davidโ€™s latest bestselling book is The Heart Work of Modern Leadership: 6 Differentiators of Exceptional Leaders.

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