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7 Questions on Leadership with Corilynn Bailey

Name: Corilynn Bailey

Title: Global SVP, Sales/Customer Success

Organisation: Semy

Meet Corilynn Bailey, a dynamic and inspirational figure based in Dallas, Texas. Corilynn's life is a beautiful tapestry woven with the threads of leadership, compassion, and relentless pursuit of growth. As the heart of her bustling household, she shares her life with her devoted husband and their four wonderful children, creating a home filled with love, laughter, and endless energy.

Professionally, Corilynn stands tall as the Senior Vice President of Sales and Customer Success at Semy, where her leadership skills shine brightly. Her role is not just a job; it's a platform where she combines her expertise in sales with her innate ability to connect with people, guiding her team towards remarkable achievements.

But Corilynn's journey extends beyond the corporate arena. Driven by a deeply personal and poignant mission, she founded the Be Fearless You Foundation. This foundation is a tribute to her beloved younger sister, a bright soul who tragically lost her life to suicide in 2019. Through this foundation, Corilynn channels her loss into a source of strength, empowering others to face their fears and embrace life with courage and hope.

Leadership for Corilynn is not just a role but a calling. It's an ever-evolving journey of learning, growing, and improving. She believes in leading by example, inspiring those around her to reach their highest potential. Her passion for leadership is not confined to the boardroom; it resonates in every aspect of her life, making her a beacon of inspiration for her family, team, and community.

Corilynn Bailey's story is one of resilience, dedication, and the power of a fearless heart. In Dallas and beyond, she continues to make a profound impact, touching lives and shaping futures with her indomitable spirit.

Thank you to the 2,000 leaders who’ve generously done the 7 Questions on Leadership!

I hope Corilynn's answers will encourage you in your leadership journey. Enjoy!


Jonno White

1. What have you found most challenging as a leader?

One of the most challenging aspects of leadership I've encountered is balancing the fine line between driving results and nurturing the well-being of my team. In the fast-paced, result-oriented world we operate in, it's easy to get caught up in the pursuit of objectives and KPIs. However, true leadership extends beyond just achieving targets; it involves recognizing and caring for the human element in the workplace.

Ensuring that each team member feels valued, heard, and supported is crucial, but it's not always straightforward. Different individuals have diverse needs, motivations, and stress thresholds. Tailoring my approach to meet these varied requirements, while keeping the team aligned with our collective goals, can be a complex task. It requires a deep understanding of each person, a high level of emotional intelligence, and the ability to adapt my leadership style accordingly.

Another significant challenge is maintaining a culture of open communication and psychological safety, especially during times of change or uncertainty. Encouraging team members to voice their opinions, concerns, and ideas without fear of judgment or reprisal is essential for fostering innovation and continuous improvement. However, creating and sustaining this kind of environment demands constant effort and vigilance.

Lastly, self-leadership is a continuous challenge. As a leader, I must be cognizant of my actions, decisions, and how they impact those around me. Balancing my professional responsibilities with personal well-being is key to maintaining the energy, clarity, and focus needed to lead effectively. It's a journey of ongoing learning and self-improvement, where I have to be as committed to my own growth as I am to that of my team.

In summary, the greatest challenge in leadership for me has been mastering the art of people management in a way that is both empathetic and effective, while also maintaining a commitment to my own personal and professional development.

2. How did you become a leader? Can you please briefly tell the story?

My journey to becoming a leader was not a straightforward path, but rather a series of pivotal moments and insightful experiences that shaped my understanding of what true leadership means.

It all started in the early stages of my career. Initially, I was more of a team player than a leader. I focused on excelling in my tasks, supporting my colleagues, and learning as much as I could about our industry. However, I soon realized that my natural inclination was to take initiative, guide, and support others in their work. This realization was the first step towards leadership.

The turning point came when I was given the opportunity to lead a small project team. This experience was both exhilarating and daunting. I found myself responsible not only for the project's success but also for the growth and well-being of my team members. This role opened my eyes to the true essence of leadership – it's not just about managing tasks, but about inspiring and empowering others.

I made plenty of mistakes along the way, which became valuable learning experiences. Each misstep taught me something new about communication, decision-making, and empathy. I learned that effective leadership is not about having all the answers, but about asking the right questions and listening to the insights and needs of your team.

Over time, I embraced more significant leadership roles, each with its own set of challenges and learning opportunities. I actively sought feedback, invested in professional development, and learned from other leaders whose styles I admired. This continuous learning and adaptation helped refine my leadership approach.

Throughout my journey, I've realized that becoming a leader is not a destination but an ongoing process. It involves constant self-reflection, learning, and a commitment to fostering an environment where everyone can thrive and contribute their best.

In essence, I became a leader by embracing opportunities, learning from my experiences, and maintaining a steadfast commitment to supporting and empowering those around me. This path has been both challenging and rewarding, and it continues to evolve with each new experience and responsibility I undertake.

3. How do you structure your work days from waking up to going to sleep?

Effective time management is the cornerstone of my daily routine, enabling me to navigate through my responsibilities efficiently while maintaining a healthy work-life balance. Here’s how I structure my workdays, emphasizing the criticality of time blocking, prioritization, and strategic planning:

Morning (Waking Up to Noon):

Early Morning (Waking Up - 8:00 AM): My day begins early, with personal time dedicated to exercise or meditation. This sets a positive tone for the day and boosts my focus.

Priority Planning (8:00 AM - 9:00 AM): The first hour of my workday involves reviewing my tasks and categorizing them based on the Eisenhower Matrix: urgent and important, important but not urgent, urgent but not important, and neither urgent nor important. This helps in aligning my day’s priorities.

Focused Work Block (9:00 AM - Noon): I reserve my mornings for tasks that are urgent and important. This time is protected from distractions, allowing me to tackle high-priority projects when my energy is at its peak.

Afternoon (Noon to Evening):

Lunch and Short Break (Noon - 1:00 PM): A dedicated break for lunch helps in recharging. It's also a time for mental rest, essential for maintaining productivity.

Scheduled Meetings and Collaborations (1:00 PM - 4:00 PM): I schedule meetings and collaborative work during the afternoon. This period is ideal for addressing important but not urgent tasks, such as strategic discussions and team check-ins.

Evening (Post-Work Hours):

Family Time (End of Work - 7:00 PM): Post-work hours are reserved for family, an essential aspect of my work-life balance.

Dinner and Relaxation (7:00 PM - 9:00 PM): Dinner is family time, followed by relaxation activities which help in unwinding from the day's stress.

Night (Post-Dinner to Bedtime):

Addressing Lower Priorities (9:00 PM - 10:30 PM): I use this time to address tasks that are either not urgent and not important or urgent but not important. This includes responding to low and medium-priority emails and planning for the next day. This strategy ensures that my next day starts off ahead, rather than playing catch-up.

Wind-Down Routine (10:30 PM - Bedtime): A wind-down routine is crucial for a good night’s sleep, preparing me both mentally and physically for the next day.

By strategically blocking out my time and prioritizing tasks based on their urgency and importance, I maintain a high level of productivity while ensuring that I don't overlook my personal life and well-being. This approach of dealing with less critical tasks at night ensures that I am always a step ahead, reducing morning stress and allowing for a more focused start to the day. It’s a system that requires discipline and regular reassessment but has proven to be highly effective in managing a busy schedule.

4. What's a recent leadership lesson you've learned for the first time or been reminded of?

A recent leadership lesson that has resonated deeply with me, both as a new realization and a poignant reminder, is the profound importance of empathetic listening in leadership. This lesson was brought home to me in a particularly challenging situation with my team.

We were navigating a complex project with tight deadlines and high stakes. Amidst this, one of my key team members was visibly struggling, not just with the workload, but on a personal level. In my initial approach, I focused on offering solutions and advice, trying to steer them back on track quickly. However, I soon realized that this method, though well-intentioned, was not what they needed at that moment.

The turning point came when I decided to simply listen – really listen – to what they were experiencing and feeling, without the immediate intent to fix the problem. This act of empathetic listening opened up a new level of understanding and trust between us. It became clear that the support they needed was not just in the realm of task management, but in feeling understood and valued as a person going through a tough time.

This experience was a powerful reminder that leadership is not just about guiding a team towards goals and objectives. It's equally about being attuned to the emotional and human side of the people I lead. Empathetic listening goes beyond hearing words; it involves understanding emotions, perspectives, and underlying challenges. It's about creating a space where team members feel safe to express themselves, knowing they will be heard and understood.

This lesson has impacted how I approach leadership. It has underscored the importance of building genuine connections with my team, recognizing that each member is not just a part of a professional machinery, but a human with unique experiences and emotions. It's a reminder that sometimes, the most powerful thing a leader can do is listen, empathize, and support, rather than just direct and advise.

Incorporating this lesson has not only enhanced my effectiveness as a leader but has also deepened the sense of trust and cohesion within my team. It's a testament to the fact that the heart of impactful leadership lies in the human connection.

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

One book that profoundly shaped my leadership journey is "Dare to Lead" by Brené Brown. This book struck a chord with me at a crucial point in my career, fundamentally altering my approach to leadership.

"Dare to Lead" delves into the power of vulnerability in leadership. Brown's central thesis is that true leadership courage isn't about armored toughness; it's about the bravery to show up, be seen, and engage openly, even when you can't control the outcome. This concept was a revelation to me. Until then, I had always equated leadership with unwavering strength and certainty. The idea of incorporating vulnerability into my leadership style was both intriguing and intimidating.

Reading Brown's insights prompted a period of self-reflection. I realized that in my efforts to be a strong leader, I often kept a rigid facade, hesitant to show any form of vulnerability to my team. This approach, while well-intentioned, was inadvertently creating a distance and a lack of deep connection with my team.

I decided to implement Brown's principles in my leadership. Gradually, I started sharing my own challenges and uncertainties with my team. This didn’t come naturally at first; it felt like stepping into uncharted waters. However, the response was overwhelmingly positive. My openness encouraged others to share their thoughts and concerns more freely, fostering a culture of trust and psychological safety within the team.

This shift also helped me recognize and appreciate the unique strengths and vulnerabilities of each team member, leading to more empathetic and effective leadership. I learned that vulnerability is not a weakness, but a courageous step towards building authentic connections and a resilient team.

"Dare to Lead" didn't just change my leadership style; it transformed my entire perspective on what it means to be a leader. It taught me that the heart of impactful leadership lies in the courage to be vulnerable, to connect, and to embrace the imperfect journey of leading with authenticity. This book remains a touchstone in my leadership philosophy, constantly reminding me of the power of vulnerability in forging strong, effective, and human-centered leadership.

6. If you could only give one piece of advice to a young leader, what would you say to them?

If I were to offer a single, heartfelt piece of advice to a young leader, it would be this: Cultivate the art of active listening. In the realm of leadership, the ability to listen – truly listen – to others is a skill of immeasurable value, yet it's often undervalued or overlooked.

Active listening goes beyond simply hearing the words spoken by others. It involves engaging with and understanding their perspectives, thoughts, and emotions. It's about giving your undivided attention, showing genuine interest, and seeking to comprehend the message behind the words. This kind of listening builds trust, fosters open communication, and creates a foundation for meaningful connections.

In your leadership journey, you will encounter diverse opinions, complex challenges, and a myriad of ideas. The ability to listen actively will enable you to navigate these waters with greater empathy, clarity, and insight. It will help you understand the needs and motivations of your team, identify underlying issues, and collaborate more effectively. Moreover, it will encourage your team members to voice their thoughts and ideas, leading to a more inclusive and innovative environment.

Remember, leadership is not just about providing direction and making decisions. It's equally about being receptive and responsive to those you lead. By honing your listening skills, you not only empower others but also enrich your own understanding and perspective.

In a world where everyone is eager to speak and be heard, being a leader who listens, understands, and connects deeply can make all the difference. This is a skill that will not only enhance your effectiveness as a leader but will also leave a lasting impact on the people you lead and the culture you foster. So, as you embark on your leadership journey, make active listening a cornerstone of your leadership style. It is a tool that will serve you well in every aspect of your career and life.

7. What is one meaningful story that comes to mind from your time as a leader, so far?

One meaningful story that stands out from my leadership journey involves a young team member, whom I'll call Alex. This experience not only taught me a valuable lesson about leadership but also left a lasting impact on how I view the potential within each individual.

Alex joined our team as a fresh graduate, brimming with enthusiasm but noticeably lacking in confidence. He was bright and had great ideas, but he often hesitated to speak up in meetings or take initiative. It was clear that he doubted his abilities and place within the team.

I remember a specific project where I saw an opportunity for Alex to shine. The project was in an area where he had expressed interest, but it was also challenging and required stepping out of his comfort zone. I decided to assign him the lead role, despite some initial reservations from other senior team members. I believed in his potential, even if he hadn't fully realized it himself.

The turning point came during a crucial team meeting. Alex, who usually shied away from the spotlight, presented his ideas with a level of insight and creativity that took everyone by surprise. His plan was not only innovative but also meticulously thought out, addressing potential challenges we hadn't considered.

However, the real success of this story lies beyond that meeting. Leading this project became a transformative journey for Alex. It was not without its challenges, but with each obstacle, he grew more confident and capable. As a leader, I provided guidance and support, but I also stepped back to allow him the space to navigate, make decisions, and learn from his experiences.

By the project's completion, Alex had not only delivered exceptional results but had also undergone a remarkable personal transformation. He had found his voice and confidence. The trust and responsibility I placed in him acted as a catalyst for his growth.

This experience taught me the profound impact a leader can have by believing in someone's potential and giving them the opportunity to rise to the occasion. It reinforced my belief that leadership is as much about nurturing growth in others as it is about guiding them. Alex's journey was a reminder that sometimes, all a person needs is a vote of confidence and the right opportunity to unlock their true potential. Witnessing his transformation remains one of the most rewarding experiences of my leadership journey.

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