In the wake of my recent viral LinkedIn post about a CEO’s attempt at creative messaging, I’ve been reflecting on the profound impact that communication (or miscommunication) can have within leadership—and quite frankly throughout the whole of an organization. The post sparked a mad flurry of reactions, many of which revealed how easily messages can be misinterpreted. As a leadership coach, I’m compelled to explore the patterns and trends that emerged from this conversation, and highlight the essential lessons for leaders striving to communicate effectively with their teams.

I started that exploration with a follow up post, and am continuing to dive into it here. As you read on, my goal it to provide valuable insight and perspective. But I also want us all to find the humor in this. Communication can be hard, and people can be hard— yet communication is a requirement on a daily basis, people are endlessly fascinating, and we can allow ourselves to seek the humor in most things.

Why Miscommunication Happens

Miscommunication occurs when there is a gap between what is said and how it is understood. I call it “the telephone effect.” Those times when you think you’re pretty friggin’ clear, and yet somehow they still don’t ‘get it.’ That comes from the gap between what you said and what they think you meant. And a major cause for that gap is perspective. In the case of my viral post, there were two primary reasons for this breakdown: (1) unclear messaging from the CEO and (2) emotional reactions from the audience.

1. Ambiguity in Messaging

The CEO’s message, written casually on a whiteboard, was open to interpretation. While his intention was to highlight a flexible, hands-off leadership style, the wording wasn’t specific enough to communicate that clearly. Many people saw the message as detached or even dismissive of employee needs.

In any leadership role, especially when addressing sensitive topics like autonomy or work-life balance, clarity is essential. Leaders must imagine that their audience comes with a range of perspectives, biases, and experiences that could color how the message is received. When there’s room for interpretation, people tend to fill the gaps with their own assumptions, which often leads to misunderstandings.

2. Emotional Reactions vs. Thoughtful Responses

A striking trend in the comments was the number of people who reacted emotionally, based on their initial gut reaction, rather than taking time to understand the intended message. Emotional reactions are fast, instinctual, and often shaped by personal experiences. This is why many saw the message as authoritarian, interpreting it through the lens of their own past interactions with unsympathetic leaders.

In contrast, thoughtful responses require a pause—time to gather information, ask questions, and reflect before responding. Leaders must be aware of this tendency toward emotional reactions and take steps to foster an environment where thoughtful responses are encouraged. This can be done by promoting transparency, asking clarifying questions, and encouraging dialogue, rather than leaving things up to interpretation.

The Role of Perspective in Interpretation

One of the most fascinating takeaways from the viral post was how differently people interpreted the same message. On one hand, most viewers (a quick calculation shows about 92% of 775 comments) immediately judged the message as harsh or unsympathetic. On the other hand, a smaller group understood that the CEO was advocating for employee autonomy (though perhaps not communicating it as effectively as he could have).

This demonstrates how much individual perspective shapes interpretation. People bring their own experiences, biases, and emotions to every interaction, and those factors heavily influence how they perceive communication. For instance, if someone has previously worked under an authoritarian leader, they might be quicker to interpret a vague or blunt message as another example of oppressive leadership.

Leaders need to be mindful that their teams are not blank slates. Different backgrounds, workplace cultures, and expectations will all play a role in how their messages are received. While it’s impossible to control how everyone will interpret a message, leaders can make efforts to account for these diverse perspectives by communicating with more intentionality, clarity, and compassion.

>>And here’s where I want us to find a bit of fascination and humor in all of this. Pause here and notice what reactions you’re having to this newsletter.

Perhaps you’re tempted to roll your eyes—to be annoyed and think “why do people have to be so sensitive?” or think “why can’t they just listen better?” Perhaps you’re also thinking to yourself, “if this is how a group of people react to just a virtual post, then it’s kind of hopeless to get my employees to hear me clearly at work…Why try?”

And I get it. Those are all reasonable reactions. But once you’ve had those thoughts and emotions, I want you to practice having a thoughtful response. Recognize that this kind of thing just happens; Fact. People are hard, weird, and unpredictable. And people are also dynamic, cool, and interesting. It’s the diversity in a company that creates real innovation, drives collaboration, and results in really awesome growth. And we can’t have one without the other. People are complex AND fascinating. Diversity causes miscommunication AND is a force for growth.

So let’s keep going here in this newsletter with that lens. Be curious about this situation, recognize your reactions and how you can respond, and then have a bit of a giggle at how abruptly challenging and excellent people can be.

Let’s continue… <<

Trends and Insights from Thoughtful Responses

While many comments on the viral post reflected emotional reactions, there were also some very thoughtful responses. These comments provide a deeper look at the dynamics of communication between leaders and employees and highlight key trends that are valuable for organizations to understand.

1. Trust Evolves with Longevity

A common theme in the responses was the role of trust and how it develops over time. Some commenters noted that newer employees might feel the need to seek approval or provide updates more frequently, while long-term employees might feel comfortable exercising more autonomy because trust has already been established.

Insight: Trust builds with tenure. For newer employees, establishing clear lines of communication is essential for ensuring they feel secure and understood. Over time, leaders can gradually reduce oversight as trust is earned, but early on, providing structure and open communication channels is necessary.

2. Ambiguity Breeds Misinterpretation

Many comments pointed out the ambiguity in the CEO’s messaging. Without clear wording or intent, people are left to interpret the message through their own lens—often leading to confusion or misinterpretation. As one commenter put it, the creative attempt at delivering a message got lost in translation because it wasn’t explicit enough. Starting with “Things I’m sick of hearing,” and ending with “I don’t care” were meant to be cheeky and creative, but really just missed the mark (even though the CEO wrote “I TRUST you” toward the bottom as well).

Insight: Ambiguity can lead to emotional reactions and misunderstandings. In this case, unclear communication left room for varied interpretations, which triggered different emotional reactions based on individual perspectives. Leaders must prioritize clarity, especially in sensitive matters, to ensure the message is received as intended. That’s not to say you can’t be creative or humorous at times, but there has to be some deeper forethought into when and where (and with whom) you choose to do so [more on this in #6].

3. Balancing Autonomy with Structure

Some commenters noted that a hands-off approach to leadership can be problematic without systems in place for communication. While autonomy is appreciated, employees still need ways to communicate when they encounter obstacles or need support. In the case of the viral post, several respondents mentioned that a framework for checking in or communicating challenges would be crucial for this approach to work effectively.

Insight: Autonomy doesn’t mean the absence of structure. Leaders need to ensure that there are frameworks in place for employees to communicate challenges or seek help, even if the day-to-day oversight is minimal. Regular check-ins, feedback mechanisms, and project tracking can strike a balance between autonomy and accountability. And to be honest, these are required in most work settings anyway. There are few industries where a hands-off approach works well, and even fewer where employees and teams are not reliant on one another for continuity and success.

4. Emotional Reactions vs. Thoughtful Responses

One of the recurring themes was how emotionally charged the responses were, especially when the message was perceived as uncaring or dismissive. Many comments highlighted the fact that people will react emotionally when they feel their personal situations are being disregarded. In contrast, more thoughtful responses came from those who paused to consider the intent behind the message.

Insight: Emotional reactions are often a result of unclear or insensitive communication. Leaders should aim to create environments where employees feel valued and understood, minimizing emotional reactions by encouraging thoughtful, informed responses. Taking the time to clarify a message or explain its intent can prevent unnecessary conflict.

5. Personal Perspective Shapes Interpretation

Many respondents highlighted that their own personal experiences influenced how they interpreted the CEO’s message. Those who had experienced dismissive leadership in the past saw the post in a negative light, while others who had more positive experiences viewed it as a message of trust and autonomy.

Insight: Communication is received through the lens of personal perspective. Leaders need to be aware that individuals will interpret messages differently based on their backgrounds and experiences. Providing context and making the intent behind the message clear can help bridge these gaps and create a shared understanding.

6. The Fine Line Between Creativity and Clarity

The CEO’s attempt to be creative with his message ended up being a double-edged sword. While some appreciated the humor or shock value, others felt it detracted from the message’s intention. Several commenters noted that the creativity backfired, leading to more confusion than engagement.

Insight: Creativity in communication is valuable, but it must be balanced with clarity. Leaders should ensure that their message is still clear, even if they choose to present it in a more creative or informal way. Otherwise, the creative delivery can undermine the intent, leading to misinterpretation.

7. Compassion and the Human Side of Leadership

A final trend that emerged was the need for compassion in leadership communication. Some commenters felt that the CEO’s message came across as uncaring, which made them question whether the leader valued the well-being of his employees. Others pointed out that while the intent may have been positive, the delivery was so unclear that it left room for assumptions about the leader’s compassion and empathy—or lack thereof.

Insight: Compassion is essential in leadership communication. Employees want to feel that their personal well-being is valued, not just their professional output. When communicating about work-life balance or personal matters, leaders should make it clear that they care about both aspects of their employees’ lives. This balance helps build trust and keeps employees engaged.

Conclusion: What This Viral Moment Teaches Us

The viral moment surrounding the CEO’s whiteboard serves as a powerful reminder of just how fragile communication can be. A single message, misinterpreted by many, sparked widespread discussion and emotional reactions. This same phenomenon plays out every day in organizations, where unclear messaging and emotional responses can lead to misunderstandings, conflict, and frustration.

For leaders, the key takeaway is simple: communication must be intentional, clear, and compassionate. It’s not enough to assume your audience will ‘get it.’ Leaders must take responsibility for ensuring that their messages are understood as intended, and they must foster environments where thoughtful responses—not knee-jerk reactions—are the norm.

As you reflect on your own leadership and communication style, consider this: how much miscommunication could you avoid by taking a moment to pause, clarify, and ensure understanding before the conversation moves forward?