Reflections from 9 CEOs and the Journey to a Healthy Workplace Culture

I've been under nine CEOs in my career, and each has taught me unique lessons that have shaped my understanding of leadership, workplace dynamics, and, most importantly, how to cultivate a thriving organizational culture. Starting from the bottom, I worked my way up, navigating the nuances of corporate life and learning how to manage both my career and relationships. It’s been an eye-opening journey, watching the often hidden political plays unfold, feeling the competitive energy of the rat race, and observing the vast spectrum of personalities that define any company.

Understanding the Corporate Color Spectrum

Corporate culture is like a kaleidoscope, colored by a variety of personalities. Some colleagues are bold and driven, others calm and empathetic, and some bring a mix of creative unpredictability and steadfast loyalty. Managing and motivating people with diverse "colors" – red, blue, green, and orange – has been one of the biggest learning curves. Understanding the "love language" of each person you work with is essential. Whether it's a need for words of affirmation, acts of service, or a focus on professional growth, each individual comes to work with distinct motivators. A successful leader knows how to read these motivations and adapt their approach accordingly.

Navigating Promotion Dynamics: The Pushback Problem

Promotions, whether internal or external, always come with a degree of resistance. Internal promotions can lead to discontent among peers, each of whom feels deserving of that advancement or raise. Bringing in external hires can cause even greater unrest, sparking whispers and side conversations that can quickly erode morale if not addressed. Managing these optics is an art, one that requires transparency, empathy, and a clear understanding of each team member's aspirations. Balancing acknowledgment of individual efforts with a vision that champions collective growth has been vital in my leadership journey.

I can’t count the number of cafeteria conversations where colleagues vented frustrations, sometimes even directing their opinions toward leaders or fellow team members. Often, these discussions stem from unaddressed assumptions or lack of communication – things that, as a leader, I’ve learned must be managed proactively.

Assumptions, Theories, and “Shitty First Drafts”

In executive and VP-level roles, one of the most intriguing behaviors I’ve observed is the tendency of team members to make assumptions. When people lack concrete information, they try to connect dots and often fill in the blanks with what we call "shitty first drafts" – initial judgments or stories that aren’t fully formed and can be misleading. These assumptions can lead to misunderstandings and strained relationships within teams. For a leader, being aware of these narratives and actively countering them with clear, honest communication is critical to building trust and maintaining a healthy, inclusive culture.

The Curiosity Factor: Survival or Control?

Another pattern I’ve noticed is the need some employees have to be “in the know” beyond the confines of their own departments or roles. Rather than focusing exclusively on their designated responsibilities, they develop a curiosity about the inner workings of other teams and the decisions made by higher-ups. Initially, I couldn’t understand this drive, but over time, it became clear that it often stems from a survival instinct. In the corporate landscape, knowledge can equate to security; the more someone knows, the better they feel equipped to navigate change and mitigate uncertainties.

For some, this drive to gather information acts as a way to exert control over an otherwise unpredictable environment. By positioning themselves as gatekeepers or interpreters of information, they can elevate their influence, becoming valuable to colleagues who seek insights into company direction. Others may view this behavior as a strategy to stay relevant and aligned with power dynamics, feeling that knowledge offers a tactical edge in their climb up the ladder.

While this instinct for information-gathering can sometimes create friction or even distrust among team members, understanding its roots can help leaders foster a culture where people feel secure in their roles and recognized for their unique contributions. Encouraging open communication and ensuring everyone feels included and informed on major goals and strategies can redirect this curiosity in positive ways, turning it from a survival tactic into a shared team strength.

Creating a Culture of Family, Support, and Loyalty: The Secret Formula

The biggest question I’ve grappled with as a leader is this: how do you create a culture that feels like family, where support and loyalty run deep? How do you foster a work environment that celebrates collaboration over competition, that inspires people to see beyond their individual ambitions and feel like they’re part of something bigger?

Here’s what I’ve learned:

1. Transparent Communication: Openness is the bedrock of a supportive workplace culture. As leaders, we need to be transparent with our teams, sharing not only successes but also challenges and setbacks. When people feel that their leaders are authentic, it builds trust. Regularly updating team members on goals, changes, and decisions can eliminate the guesswork and reduce the tendency to fill in blanks with potentially damaging assumptions.
2. Recognition and Empowerment: Recognizing individual contributions goes a long way in creating a sense of belonging and loyalty. When people feel valued, they’re more likely to support their peers and invest in the organization. This isn’t just about monetary rewards – a simple acknowledgment or a word of appreciation can have a profound impact on morale and loyalty.
3. Inclusive Decision-Making: Whenever possible, including team members in decision-making processes fosters a sense of ownership and mutual respect. When they have a voice, even in decisions that don’t directly affect them, it sends a message that their perspectives matter, creating a culture of unity and respect.
4. Encouraging Growth Beyond the Rat Race: When people feel they are on a constant treadmill, competing for the next promotion or raise, the rat race becomes overwhelming. Leaders can alleviate this by providing opportunities for professional development, mentorship, and career path clarity. When team members see that growth is not limited to vertical promotions but also includes lateral opportunities and skill enhancement, they feel more secure and less competitive with their peers.
5. Addressing Gossip and Rumor-Mongering Head-On: Gossip and speculation can be toxic. By actively engaging in one-on-one and team discussions, leaders can help to dispel rumors before they take root. Setting the tone that we’re all in this together and ensuring that people have the information they need reduces the temptation to fill in the blanks on their own.

Building a Legacy of Trust

Every CEO I’ve worked under has taught me something about leadership. Some demonstrated the power of boldness, others the strength of compassion, and still others showed the necessity of resilience in the face of adversity. But if there’s one takeaway I carry with me, it’s the understanding that a leader’s ultimate role is to build a legacy of trust. Trust fosters loyalty, loyalty builds support, and support creates a sense of family – a feeling that everyone in the organization is working toward the same shared goals.

The journey to create a truly supportive and loyal culture is ongoing, filled with learning moments and growth. There’s no single “secret” to creating an ideal workplace. But with every step, by prioritizing transparency, recognition, inclusivity, and open communication, leaders can create an environment where every team member feels valued, supported, and inspired to contribute their best.

As I continue this journey, I remind myself that leadership is not about reaching a destination; it’s about evolving with each experience, learning from every CEO, and leaving a positive impact on everyone I work with. It’s a journey I’m proud of, and one I’m grateful to share with each new day.