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7 Questions on Leadership with Jackson Bennett

Name: Jackson Bennett

Title: Facilities Manager

Organisation: Oracle

Originally hailing from the heartland of the Midwest in the US, I've had the privilege of experiencing the best of both worlds: the dynamic realm of the entertainment industry and the structured environment of corporate settings. Currently, I find myself balancing the roles of a devoted spouse and a proud parent to a delightful 4-year-old daughter, along with being the companion to three energetic Boston Terriers.

My journey has been a fascinating blend of creativity and professionalism. In the world of entertainment, I've delved into various facets, from working behind the scenes to front-and-center roles. These experiences have allowed me to witness the magic of storytelling and the power of artistry, enriching my understanding of how it shapes our lives and brings people together.

In my corporate endeavors, I've honed my skills in navigating the intricate structures of business. The challenges and successes in this arena have equipped me with valuable insights into effective teamwork, strategy, and problem-solving.

But it's not all business and responsibilities; I'm also passionate about fostering connections and inspiring individuals. I thrive on brainstorming and nurturing ideas that have the potential to spark inspiration and create meaningful connections among people. Whether it's through organizing events, producing content, or collaborating on creative projects, I'm driven by the belief that great ideas have the power to unite us and drive positive change.

Beyond my professional life, I find solace and creativity in my free time. One of my greatest joys is writing and recording music. The process of composing melodies and lyrics allows me to express my thoughts and emotions in a unique and cathartic way. Music has always been a cherished outlet for me, offering a space where I can explore the depths of my imagination and connect with others through the universal language of song.

In a world where diverse experiences converge, I embrace my background as a mosaic of many things, channeling it into a life filled with love, creativity, and the pursuit of inspiration. I am committed to making meaningful contributions and bringing people closer together through the power of ideas and artistry.

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

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


Jonno White

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

I feel that guiding teams through periods of change and uncertainty has always presented significant challenges, it’s often accompanied by resistance and apprehension about the unfamiliar. The pace of change has accelerated more than ever before, demanding increased support and resources for both teams and individuals as priorities evolve. Even managers themselves are not exempt from these challenges in their hierarchy.

Additionally, effectively managing conflicts within a team or organization while upholding morale and productivity is something I’ve found to be another intricate task. Amidst constant change, emotions often intensify, underscoring the growing significance of soft skills in these situations.

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

I've always had a natural inclination to collaborate with others toward achieving positive results. When I transitioned into a frontline management role, I discovered a passion for setting priorities and actively working alongside my team. With further education in leadership and coaching, I've come to deeply appreciate assisting others on their career journeys.

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

After waking up, my first task is to prepare lunch for my kiddo. Once I've dropped her off at school, I typically have a 30-minute commute to work. During this commute, I often listen to podcasts or dictate notes to myself, capturing ideas I don't want to forget.

At work, I prioritize tasks based on their importance and deadlines. As a front-line manager, my responsibilities involve a balance of tactical objectives, meetings, and handling emails. I schedule one-on-one meetings with my team once a week. During these meetings, we spend the first ten minutes discussing personal matters, followed by ten minutes on current project statuses, and we conclude with a discussion of what's on our agenda.

When I return home, my evening may involve making dinner, assisting with bath and bedtime routines for my kiddo, or tackling housekeeping chores. On nights dedicated to chores, I take the opportunity to review my notes, read inspiring materials, and work on my own content and projects that I want to get out in the world.

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

Being willing to take responsibility for your mistakes and, when necessary, offering apologies is crucial. Trust plays a significant role in effective leadership, and displaying vulnerability can be a remarkable strength. We all make mistakes, but how we address and rectify these errors can either strengthen or weaken our relationships. I've experimented with giving tough, uncompromising feedback in the past, and it typically yields limited results. It's essential to provide considerate and honest feedback, taking the time to navigate and resolve issues. Hastily rushing corrective actions due to discomfort will likely cause individuals to resist further, hindering the development of the trust needed for constructive progress.

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?

I'm currently reading: Holding Change: The Way of Emergent Strategy in Facilitation and Mediation, by Adrienne Maree Brown

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

One crucial piece of advice for a young leader in today's workplace is to prioritize continuous learning and adaptability. The modern workplace is evolving rapidly, with advancements in technology, changes in work dynamics, and shifting cultural expectations. By embracing a mindset of continuous learning, you can stay updated on industry trends, develop new skills, and adapt to the changing landscape effectively. Be open to feedback, seek mentorship, and proactively seek opportunities for growth and development. This not only enhances your leadership abilities but also sets an example for your team, fostering a culture of growth and innovation.

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

I don't have a story but I do know what's meaningful to me about management. My professional approach is not just about fulfilling tasks; it's a philosophy that imbues my work with profound personal meaning. I believe in a leadership approach that revolves around nurturing and developing my team members.

At the core of my approach is the belief in providing my team with assignments that push the boundaries of their abilities and encourage them to expand their knowledge. It's not merely about getting the job done; it's about enabling them to grow and evolve in their roles. The ultimate goal is to offer them a platform from which they can springboard into promotions or other career opportunities.

One key element of this approach is the emphasis on autonomy. I firmly believe in empowering my team members to take charge of their tasks and projects. I want them to apply their unique abilities, creativity, and problem-solving skills to manage these assignments. This autonomy not only fosters a sense of ownership but also allows them to develop their decision-making and leadership capabilities.

In essence, my approach is about fostering growth, independence, and personal development within my team. It's about creating an environment where everyone can thrive and, in doing so, find purpose and fulfillment in their work.

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