What Pivotal Moment Influenced Your Leadership Style?
Delve into the defining moments that shape exemplary leadership, guided by the wisdom of seasoned professionals across industries. This article unpacks critical strategies for empowering teams, fostering collaboration, and driving impactful results. Gain a competitive edge with expert insights on transforming leadership approaches to thrive in dynamic business landscapes.
- Lead, Not Do
- Empowering Team Through Clear Processes
- Adopt Transparency and Collaboration
- Importance of Strategic Partnerships
- From Micromanaging to Empowering
- Trust Editors for Better Content
- Trust Team to Own Their Work
- Empathy Over Profit
- Lead by Example
- Adapt and Collaborate
- Empower Team for Faster Deals
- Focus on Relationships
- Empathy and Practical Experience
- Trust and Empower Team
- Collaborative Problem-Solving
- Listen and Empower Team
- Lead with Empathy and Vision
- Adaptability and Transparent Communication
- Collaborative Problem-Solving
- Value Diverse Perspectives
- Empower Team Through Communication
- Empower Team for Better Outcomes
- Mentorship Builds Stronger Teams
- Empower Team for Better Decisions
- Empower Team for Better Outcomes
Lead, Not Do
A pivotal moment for me as a CEO happened early in my leadership journey. We were in the middle of a critical product launch, and I was in full "hands-on" mode—micromanaging every detail, from marketing to logistics. I thought I was being thorough, but instead, I created bottlenecks and stifled my team.
One day, my operations manager pulled me aside and said, "We need you to lead, not do." It stung, but I realized she was right. I was so focused on doing everything perfectly that I wasn't empowering my team to shine.
That week, I called a meeting and laid it all out. I told the team, "I've been holding on too tight. From now on, I'll trust you to take the lead in your areas, and I'll be here to support you." It was a shift from being the fixer to being the enabler.
The results were incredible. The launch was a success—not because of me, but because of the team's collaboration and ownership.
That experience taught me that leadership isn't about control; it's about trust. When you give people the space to excel, they'll often exceed your expectations. It's a lesson I carry with me every day.
Empowering Team Through Clear Processes
A pivotal moment that shaped my leadership style as a CEO occurred during the early years of my telecommunications company. We were rapidly expanding, and I faced a crisis when a key project with a major client began to unravel due to communication breakdowns within my team. The stakes were high, as the client represented a significant portion of our revenue, and I knew losing their trust could be devastating. I realized the root of the problem wasn't technical expertise but a lack of clarity in roles and accountability. My military training in telecommunications and leadership under pressure became invaluable here. In the army, we were trained to thrive on structure and clear communication, and I applied those principles immediately.
I called an emergency meeting, streamlined the decision-making process, and introduced systems to enhance transparency and efficiency. My MBA in finance also came into play, as I realigned the budget to prioritize resources where they were needed most, allowing the project to move forward without delays. As a result, not only did we salvage the client relationship, but the project exceeded their expectations. This incident taught me that leadership is about empowering people with clear processes and accountability while maintaining a calm, solution-oriented mindset. It became a defining approach that I've carried forward in helping hundreds of other business owners navigate their challenges with precision and confidence.
Adopt Transparency and Collaboration
One pivotal moment that significantly influenced my leadership style as a CEO occurred during a period of rapid growth in our company. As we scaled, I noticed a disconnect between leadership and the team, resulting in misaligned priorities, waning morale, and delayed project outcomes. This prompted me to reassess my approach to leadership and how I communicated with and empowered the team.
The Turning Point
During a quarterly meeting, a team member bravely voiced their frustration about unclear expectations and the lack of involvement in decision-making. It was a humbling moment that made me realize I was too focused on driving results and not enough on fostering clarity, collaboration, and inclusion.
The Change
In response, I adopted elements of the Entrepreneurial Operating System (EOS) to restructure how we operated and interacted as a team. This moment reshaped my leadership style in three key ways:
Prioritizing Transparency
I began hosting weekly check-ins and quarterly town halls to share company goals, challenges, and achievements openly. This gave the team a clear vision of where we were heading and their role in achieving it.
Empowering Team Ownership
Through EOS practices, such as the Accountability Chart and assigning Rocks (priority goals), team members were given clear responsibilities and autonomy. This approach encouraged ownership and accountability, fostering a sense of pride in their contributions.
Active Listening and Inclusion
I made it a priority to seek input from the team, both in formal meetings and informal conversations. By listening actively and incorporating their insights, I built trust and improved decision-making.
The Outcome
This shift transformed our company culture and boosted overall performance. One notable example was during a product rollout that required cross-departmental collaboration. By empowering the team with clear goals and open communication channels, we delivered the project ahead of schedule, exceeding client expectations. The experience reinforced the power of transparency and collaboration in driving success.
Conclusion
This pivotal moment taught me that leadership isn't about dictating direction but enabling the team to thrive through clarity, empowerment, and trust. It's a lesson I carry forward, continually shaping my leadership style to adapt and grow with my team.
Importance of Strategic Partnerships
A pivotal moment that significantly influenced my leadership style as a CEO was during the early years of running Jones Ideal Limousine in Chicago. Building the business from a single vehicle to a fleet of six taught me the importance of strategic partnerships and leveraging community networks-skills I later applied when founding Detroit Furnished Rentals LLC. By cultivating strong relationships with local businesses, such as hotel concierges, I ensured a steady stream of clients, demonstrating the power of networking and collaboration.
Another critical experience was managing operational pivots, such as when transitioning from the limousine business to over-the-road trucking with Sonic Logistics, Inc. During this time, I learned the importance of alignment and adaptability, ensuring my team understood and adapted to new business landscapes. This adaptability was put to the test again in the short-term rental market, where unforeseen property issues required quick decision-making and relocation to better-suited environments, ultimately improving guest satisfaction.
Additionally, my venture into the short-term rental market highlighted the critical role of customer feedback and digital tools. Incorporating guest reviews to improve service offerings and using AI-driven tools to improve customer interactions have proven essential for growth and engagement. These experiences emphasized the need for a customer-centric approach and the integration of technology to streamline operations and provide outstanding service.
From Micromanaging to Empowering
From Micromanaging to Empowering as a Leadership Transformation Journey
As the founder, one pivotal moment that significantly influenced my leadership style came during a challenging project early in the business. We had a tight deadline for a large-scale document review, and I initially took a hands-on approach, managing every detail to ensure perfection.
However, this created bottlenecks and left my team feeling micromanaged. One of my senior team members candidly told me they felt their skills weren't being fully utilized.
That conversation was a turning point. I realized that effective leadership isn't about controlling every outcome but empowering others to take ownership. I began delegating responsibilities, trusting my team's expertise, and focusing on guiding rather than doing.
The result was remarkable-our project finished ahead of schedule, with higher morale and a stronger team bond. This experience taught me that true leadership lies in enabling others to excel, a lesson that continues to shape how I lead today.
Trust Editors for Better Content
When we launched TheStockDork.com, I initially tried to micromanage every article and market analysis that went out. After burning out and seeing team morale drop, I learned to trust my editors' expertise and focused instead on providing clear guidelines and feedback. This shift from controlling everything to empowering my team not only improved our content quality but also helped us grow from 50,000 to 500,000 monthly readers within a year.
Trust Team to Own Their Work
There's one moment I'll never forget—I had just spent hours redoing part of a feature my team built, thinking I was 'fixing' it. The next day, my lead engineer came to me and said, 'If you don't trust us to own this, how will we ever grow?' That hit me hard. I realized my job wasn't to fix everything but to give my team the space to take ownership. From that point on, I made it a priority to step back, trust them, and focus on leading instead of micromanaging. It completely changed how I work.
Empathy Over Profit
I remember when the housing market crashed in 2020, and many of our clients were panicking about selling their homes during such uncertainty. Rather than pushing for quick sales, I decided to pause operations for two weeks to retrain our entire team on crisis communication and create flexible payment options for stressed homeowners. Looking back, choosing empathy over profit during that tough time completely transformed how I lead - it showed me that putting people first actually creates better business outcomes.
Lead by Example
One pivotal moment that significantly shaped my leadership style as a CEO occurred early in my career when we faced a major storm in the Dallas-Fort Worth area. The volume of emergency calls was overwhelming, and we had to prioritize safety while addressing each client's urgent needs as quickly as possible. At that time, we were a smaller team, and the pressure to deliver excellent service without compromising safety was immense. I leaned on my experience as a certified arborist and the work ethic I developed playing competitive soccer to organize and motivate the team. By strategically dividing tasks, staying calm under pressure, and personally leading the most critical jobs, we managed not only to complete the work efficiently but also to earn the trust and gratitude of our clients. That experience solidified my commitment to leading by example and instilled the importance of clear communication during high-stress situations.
This moment also taught me the value of preparation and adaptability, two qualities I've honed throughout my career. My TRAQ certification and years of hands-on experience allowed me to quickly assess hazardous trees and make informed decisions, while my leadership ensured the team stayed focused and collaborative. Today, I use those lessons to empower my employees, ensuring they feel supported and prepared for challenges, which has helped Ponce Tree Services grow into a trusted name in our community.
Adapt and Collaborate
A pivotal moment that significantly influenced my leadership style came early in the life of Ozzie Mowing & Gardening, when I had to manage a project for a large-scale community garden. The project was complex, involving several stakeholders with competing visions, a tight budget, and a short timeline. One of the challenges was bringing together volunteers, council representatives, and contractors to create a cohesive plan. My years of experience as a certified horticulturist and over 700 completed projects gave me the technical confidence to address the practical issues, but the real turning point was learning how to lead a diverse group toward a shared goal.
I realized the importance of active listening and clear communication during that project. By hearing each stakeholder's concerns and finding common ground, I was able to guide the group toward decisions that benefited the entire community. My theoretical knowledge from studying horticulture allowed me to propose sustainable solutions that satisfied environmental goals, while my hands-on experience gave the team confidence in the plan's practicality. The project was completed on time and became a space that continues to bring people together, but it also taught me that leadership isn't about having all the answers; it's about empowering people to collaborate effectively. That experience shaped how I lead my team today, ensuring that every voice is valued and every challenge is met with a balance of expertise and empathy.
Empower Team for Faster Deals
When I started Coastal Edge Homebuyers in 2018, I tried to micromanage everything until a major deal almost fell apart because I wasn't trusting my team's expertise. That wake-up call showed me that true leadership means empowering your people to make decisions and supporting them even when things don't go perfectly - now we close deals faster and my team is more confident.
Focus on Relationships
When I was first starting out as a real estate agent, I came into a challenging deal. I was committed to completing the deal because the client was demanding and the property was upscale. Nothing appeared to work despite my endless hours of bargaining and showing the house to prospective buyers. Consequently, I was experiencing unprecedented amounts of stress and was close to giving up.
But suddenly something clicked inside of me. It became clear to me that I needed to step back from the situation and change my strategy. I chose to put more of an emphasis on developing a relationship with the client than just closing the deal. I took the effort to understand their requirements, concerns, and expectations. I was able to establish rapport and trust with the client as a result of this shift in perspective and strategy, and the sale was ultimately closed successfully.
In addition to being a turning point in my career as a realtor, this experience profoundly affected my leadership approach as a CEO. I discovered that developing relationships and being aware of the needs of those around you are just as important to being a successful leader as closing deals and accomplishing goals.
Building trusting relationships with my team and clientele is now a top priority for me as CEO. I make certain that their needs are met and that their opinions are heard. As a result, we now have a productive workplace where everyone feels appreciated and inspired to strive toward our shared objectives.
The value of flexibility was yet another important lesson learned from this experience. I had to modify my strategy as a realtor to fit the client's wants and the circumstances. This ability has been essential to my work as a CEO, particularly in the dynamic corporate environment of today.
I learned the importance of building relationships, being aware of others' needs, and being flexible during this crucial period in my career. These abilities have helped me become a strong and successful CEO in addition to a successful realtor.
Empathy and Practical Experience
A defining moment in my leadership journey happened during my transition from Deloitte to founding spectup. I initially tried to replicate the structured, corporate approach I'd learned at larger companies, but quickly realized it wasn't working for our startup environment. One particular client meeting stands out - we were presenting a detailed, Deloitte-style analysis when the client stopped us and said, "This is great, but what I really need is someone who understands what it's like to be in my shoes." That conversation completely changed my approach to leading spectup. I started focusing more on empathy and practical experience, drawing from my time at N26 and my journey through various roles in different companies. This shift made our team more approachable and effective - we began sharing our own startup struggles and successes openly with clients. Now at spectup, I encourage our team to bring their personal experiences to the table, knowing that authentic leadership creates stronger connections with our clients. It's not just about the analysis anymore; it's about understanding and relating to the entrepreneurial journey.
Trust and Empower Team
Let me recall a defining experience that has transformed my leadership. Early in my career, I was very opinionated that no one could understand the importance of controlling every tiny detail to excel. However, during one of the major projects, I realized that my experienced team members were becoming disengaged. They had years of experience but were not taking initiative or suggesting improvements. One day, instead of pushing them harder for compliance, I paused and really listened to their perspectives. True leadership is not control, but rather trust and empowerment. People took ownership of their work, innovation thrived, and our performance exceeded expectations. This experience really changed my command-and-control-based leadership philosophy into one based on trust, open communication, and shared responsibility. I learned that when people are valued and empowered, they perform with excellence as a natural act.
Collaborative Problem-Solving
I've learned my biggest leadership lesson when one of our house flips went terribly wrong - we discovered major foundation issues after demolition that weren't in the inspection. Instead of trying to cut corners, I gathered my team, openly discussed the $50,000 setback, and we brainstormed solutions together rather than me just dictating next steps. That moment taught me that transparent leadership and collaborative problem-solving build stronger teams than always trying to have all the answers myself.
Listen and Empower Team
One pivotal moment that significantly influenced my leadership style occurred during a critical growth phase for one of my early ventures.
We were scaling rapidly, and I believed that setting clear directives was the key to keeping everyone aligned. However, during a company-wide meeting, a junior team member spoke up about feeling unheard in the decision-making process. Their perspective highlighted an operational flaw I had completely overlooked. That moment was humbling and forced me to rethink how I approached leadership.
Instead of relying solely on top-down communication, I shifted to creating more collaborative spaces for feedback. Regularly scheduled brainstorming sessions and anonymous suggestion channels became part of our culture. As a result, team members felt more empowered to contribute, which improved morale and led to more innovative solutions. For instance, one suggestion from a junior developer saved us thousands by optimizing a backend process.
This experience taught me the importance of listening deeply and recognizing that great ideas can come from anywhere. Leadership is about creating an environment where every voice feels valued. If you're exploring ways to refine your own leadership approach, I'd be glad to share further insights.
Lead with Empathy and Vision
Another significant learning for my leadership style was when I started growing my team, and things were difficult. I assumed I could be sure of leadership, but I soon realized building trust and working together was much more effective. One afternoon, an employee told me something I didn't even know he was proposing. I didn't dismiss it but listened—that concept was fundamental to how we worked. It also taught me how to be humble and have a room where everyone can feel heard. Today, I lead a team where I am supporting rather than bossing. This change of mindset bolstered my team and taught me how to lead—empathetically, openly, and with a vision for what success looked like. I learn that every day.
Adaptability and Transparent Communication
A pivotal moment that influenced my leadership style as a CEO was when I transitioned from managing tasks to leading with empathy and vision. Early in my career, I focused heavily on the operational side of running a business, ensuring that every detail was executed perfectly. However, as we grew, I realized that my most important role wasn't micromanaging but empowering my team to thrive.
One defining experience came during a high-pressure launch. Instead of directing every step, I stepped back and trusted my team to own their areas of expertise. I focused on supporting them with clear goals, open communication, and encouragement. The results were not only successful but also revealed trust and collaboration. That experience shifted my approach to leadership—I now prioritize creating an environment where my team feels inspired, valued, and empowered to take initiative. This shift has not only strengthened our company culture but also reinforced the importance of leading with both strategy and empathy.
Collaborative Problem-Solving
I remember when the 2008 housing crisis hit Columbus, and I had to completely rethink how we operated - it was a wake-up call that taught me the importance of adaptability and transparent communication with my team. We shifted from just buying properties to helping homeowners find creative solutions, like rent-to-own options and renovation partnerships, which not only kept us afloat but also showed me that true leadership means putting people's needs first.
Value Diverse Perspectives
A pivotal moment that shaped my leadership style was during a challenging real estate project where unforeseen obstacles threatened to derail our timeline and budget. Instead of making decisions in isolation, I gathered my team, openly shared the challenges, and invited input on solutions.
This collaborative approach not only resolved the issues but also unknowingly highlighted key performers outside of my usual leadership circle. Bringing more voices to the table revealed talent that might have otherwise gone unnoticed, accelerating their recognition and growth within the company. It taught me the value of transparency, listening, and empowering others, which has consistently led to better outcomes and a stronger, more cohesive organization.
Empower Team Through Communication
Early in my tenure as CEO of SuperDupr, a pivotal moment came when we revamped the website and digital magazine for "The Unmooring." Our goal was to amplify voices that are often underrepresented, which taught me the value of inclusion and how unique perspectives can drive business change. This project not only expanded client engagement but also significantly increased our referral rate by 35% within a few months.
This experience solidified my belief that leadership thrives when it values diverse perspectives and drives innovation through them. I started integrating more diverse voices into our strategy and operations, resulting in a more creative and responsive team environment. Understanding and addressing the unique needs of each project have consistently helped us exceed client expectations.
Additionally, leading the restructuring project for Goodnight Law highlighted the importance of adaptability in swiftly resolving technical challenges. We overhauled their UI and integrated an automated follow-up system, increasing their client conversion by 20%. It's these experiences of turning challenges into growth opportunities that have profoundly shaped my leadership style.
Empower Team for Better Outcomes
A pivotal moment that significantly influenced my leadership style as a CEO occurred during a particularly challenging period when our company faced a major setback. We were in the middle of a product launch, and despite months of preparation, we encountered a series of technical failures that delayed the rollout. Our team was frustrated, morale was low, and I could sense a sense of uncertainty among everyone.
As the leader, I initially felt the weight of the situation and was tempted to jump in and direct everything myself. However, I realized that this approach wasn't going to help the team grow or solve the issue at hand. I decided to step back and focus on fostering open communication within the team. I held a company-wide meeting where I acknowledged the setback, took full responsibility as the leader, and reassured everyone that failure was a part of the process. I encouraged each department to openly share their challenges and brainstorm solutions collaboratively.
This moment taught me the value of transparency, vulnerability, and empowering the team. Instead of micromanaging, I learned to trust my team to handle the situation, offer their insights, and take ownership of their roles. By leading with openness and inclusivity, we were able to pivot quickly, resolve the issues, and successfully launch the product, even if it was later than originally planned.
Since then, I've adopted a leadership style that emphasizes shared responsibility, honest communication, and trust in the capabilities of my team. This experience reinforced that effective leadership is about empowering others and creating an environment where everyone feels heard and valued.
Mentorship Builds Stronger Teams
A pivotal moment that significantly influenced my leadership style was when we handled a complex high-stakes case involving multiple team members. Early on, I realized my tendency to micromanage was stifling creativity and slowing decision making. To address this, I stepped back, trusted my team's expertise, and focused on providing guidance rather than control.
The results were incredible. Not only did we achieve a favorable outcome for the client, but the team also grew more confident and collaborative. This experience taught me the importance of empowering others, which has since become a cornerstone of my leadership style.
Empower Team for Better Decisions
I recently faced a challenging situation where one of my team members made a costly mistake on a property valuation, and instead of immediately reprimanding them, I took them under my wing for mentorship. That moment taught me that leading with empathy and turning setbacks into teaching opportunities not only builds loyalty but also creates a stronger, more confident team at House Buying Girls.
Empower Team for Better Outcomes
I recently faced a challenging situation where half our rental portfolio was draining our resources with constant repairs, and that's when I learned the importance of empowering my team to make decisions. By trusting my property managers to implement a systematic renovation approach and giving them authority to make quick decisions under $500, we transformed our struggling properties into profitable assets while building a more confident, autonomous team.
