Episode 99 - Founder, Facilitator and Life & Leadership Coach, Gillian Smith

31 July

Written By Jane Anderson

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🎙️In this empowering episode of The Jane Anderson Show, we’re spotlighting Gillian Smith, founder of Connect Lead Coach and a passionate advocate for compassionate, sustainable leadership. With over 20 years of experience working across the UK, Europe, US, Australia, and New Zealand—including with FTSE 100 and ASX-listed organisations—Gillian brings a fresh, human-centred approach to leadership development and workplace culture.

Meet Gillian Smith

Gillian isn’t just a coach—she’s a bridge-builder. Her vibrant energy and deep HR expertise shine through in her coaching, facilitation, and speaking. After navigating her own experiences of corporate burnout, she launched Connect Lead Coach in 2021 to help leaders and teams foster safer, kinder, more connected workplaces—starting with her own transformation journey.

Cultivating Connection and Courageous Leadership

In a world craving meaning and authenticity, Gillian believes true leadership starts with making people feel seen and heard. Her signature style blends introspection, empathy, and cultural insight to guide leaders in creating inclusive, engaged environments where everyone thrives.

Tools and Stories That Inspire Growth and Trust

In this episode, Gillian shares real-life strategies that leaders can use to build connection and resilience—whether you're leading a global team or mentoring a new manager locally in Brisbane. From designing purposeful workshops to coaching leaders through change, she brings practical insights to the heart of complex challenges. Her goal? To turn everyday leadership into meaningful action.

Here’s what you can expect:

Warm, human-first frameworks for reconnecting with your people
Practical techniques to foster psychological safety and trust
Wisdom shaped by global experience and real transformation—including burnout and renewal

✨ Tune in to hear how Gillian is helping leaders lead with heart and authenticity—creating cultures where everyone belongs, contributes, and flourishes.

Key Takeaways from Today’s Episode:

The podcast opens with a warm welcome from the host, who introduces the guest, Kylee Leota, as a leadership expert, author, and speaker. Kylee transitioned from a long-standing career in education into her own thriving thought leadership practice during the COVID era. She has since written books, travelled to New York City to promote her work, and even had her book featured in Times Square. The host sets the scene for a discussion about Kylee’s journey from the education sector into corporate and entrepreneurial spaces, leveraging her specialised expertise. Kylee joins the conversation and reflects on her origins, describing herself as an “accidental” business owner. Although she had aspired to be an educator from a young age, her creative, out-of-the-box thinking—particularly in supporting students with disabilities, trauma, and complex behaviours—foreshadowed her current work. While she didn’t initially see herself as a thought leader, hindsight revealed she had always approached problems innovatively, even in structured systems.
Kylee shares that after 20 years in various leadership roles across the education sector, it was an injury in 2019 that forced her to reconsider her career path. Unable to continue in the same way, she asked herself what parts of her job she truly loved and how she might create something new. What began as quiet experimentation—letting a few people know what she was doing—soon evolved through word-of-mouth into a full-blown practice. Connecting with mentors and engaging in personal growth enabled her to sharpen her business model. Today, she primarily works with executive and aspiring leaders, including educational professionals, offering coaching in self-leadership and alignment. Her business, Elements to Success, is inspired by Earl Nightingale’s definition of success and focuses on identifying the “elements” individuals and organisations need to realise their goals. Kylee’s offerings are deeply personalised, supporting clients in bridging the gap between their current reality and their envisioned future.
She also discusses the impact of writing and publishing her book, Infinite Leadership: Driving Continuous Improvement to Create Excellence for Everyone. Initially plagued by imposter syndrome and doubts about her authority compared to renowned thought leaders like Simon Sinek or Adam Grant, Kylee eventually embraced her place as an author. The writing process was empowering rather than exhausting, and having now contributed to multiple books—Infinite Leadership, Impact (a co-authored book), and Business Goddesses—Kylee feels confident to keep publishing. She speaks passionately about her “ecosystem” of support and how it bolstered her confidence. A serendipitous moment in New York underscored her growing influence: she met a reader from Pennsylvania who had devoured her book, reaffirming the unexpected global reach of her work and the profound impact a book can have.
As the conversation moves behind the scenes, Kylee is candid about the challenges she has faced. Despite appearing calm and composed on the outside, she likens herself to a duck on water—serene above but paddling frantically below. She shares a humorous anecdote about her “ducks” not being in a row but rather “in the back of a police car,” illustrating the chaos she has sometimes managed behind the scenes. Kylee is a single mother of three and launched her business in 2020 during the peak of COVID—a move many people around her thought was irrational. Yet she believed in her vision, even when others couldn’t see it, and this required deep courage and conviction.
Kylee reflects on the ongoing self-doubt she experiences and the importance of having her own back. She recently received a message from someone who only now appreciated the bravery it took for her to leave a secure government role. As a fast-thinking visionary, Kylee admits that administrative or operational tasks drain her energy. One of her biggest breakthroughs was recognising she couldn’t—and shouldn’t—do everything herself. She prioritised outsourcing the tasks that fell outside her “zone of genius” and building a supportive team. Delegating allowed her to focus on her strengths and grow her business strategically. However, she notes that this is an ongoing journey; what serves a business at one stage may not serve it at the next. She underscores the importance of recalibrating and evolving one’s business mindset. Instead of viewing challenges with resentment, Kylee now sees them as signs of progress, much like being grateful for a high tax bill because it signifies financial success.
Kylee reflects on the critical role of mindset in her journey, drawing from her education background, particularly the influence of Carol Dweck’s work on growth mindset. While she acknowledges her ability to reframe challenges and move forward, she’s quick to clarify that it’s not always easy. She still experiences moments of frustration and self-doubt but has developed the resilience to keep getting back up—what she humorously likens to “fall down 777, get up 888.” This tenacity stems from recognising that the world is inherently complex, and waiting for perfect conditions is futile. Instead, she’s learned to act amid uncertainty.
The conversation shifts to the value of the Women With Influence community in her personal and professional growth. Kylee shares that this community has allowed her to fully step into her authentic identity—something she previously struggled with in environments that weren’t receptive to her visionary thinking. She describes how being surrounded by like-minded peers who celebrate ambition rather than diminish it has been transformative. This safe, supportive ecosystem contrasts sharply with past experiences where others tried to limit her because of their discomfort with her success.
She particularly values how the community embraces and celebrates success without falling into the cultural trap of tall poppy syndrome. In this group, wins are openly shared and supported. This camaraderie helps members—herself included—believe in what's possible, ask questions freely, and draw inspiration from one another’s journeys. Kylee praises the generosity, kindness, and intentionality of the group, noting how rare and powerful it is to be surrounded by people who lift each other up regardless of where they are in their business journey. She credits the host, Jane, with carefully curating this environment, avoiding a one-size-fits-all approach and instead creating a cohesive, aligned collective.
Reflecting on her five-year journey, Kylee shares several lessons she’s learned in hindsight. One of the biggest was not prioritising systems early enough. Although her business was successful, it operated in “organised chaos” for a while before she streamlined her operations. She also highlights the importance of having trusted advisors—her “board of directors”—but admits she wasn’t initially discerning enough in choosing them. In the early days, she was vulnerable to believing people who promised quick fixes. Over time, she’s developed sharper discernment and become more selective about whose advice she follows and who she invites into her inner circle.
Another powerful insight Kylee shares is the importance of consistently backing yourself—not just at the start, but at every stage. While she took a bold step in leaving government to launch her business, she noticed that at each new phase of growth, she needed to renew that self-belief. Despite consistent year-on-year business growth, her confidence sometimes wavered, which she’s learned to address through self-compassion and breaking down big ideas into smaller, actionable steps. As a visionary, she’s learned the importance of translating large-scale ideas into manageable chunks to avoid becoming overwhelmed or paralysed by comparison.
She also offers guidance for others building thought leadership businesses: focus first on understanding your identity. Only when she was clear on who she was and aspired to be could she attract the right people into her ecosystem. She introduces the metaphor of being a thermostat (setting the temperature) versus a thermometer (reacting to the temperature), advocating for leaders to become thermostats who create and maintain the conditions they want to thrive in. That clarity of identity and aspiration influences who you attract and how effectively you grow.
Looking ahead, Kylee shares her excitement about a new development in her practice—the creation of the Infinite Leadership Profile Diagnostic. Over the weekend, she finalised both a short and long-form version of the diagnostic, which she plans to introduce first within her community and then more broadly. The tool is designed to help educational and corporate leaders identify where they are in their leadership journey and what steps to take next. It builds on the core philosophy of her Infinite Leadership framework, which sees leadership development as an ongoing evolution.
The diagnostic has already been piloted with a few individuals, who reported that its insights were remarkably accurate. Kylee sees it as a way to add value to clients at any stage in their leadership growth, helping them self-assess and move forward intentionally. Jane responds with enthusiasm, affirming the power of diagnostics in making leadership frameworks more relatable and actionable for individuals.
Kylee shares how much joy and fulfilment she derives from her thought leadership practice, particularly when working on projects that excite her—even on weekends. Far from feeling burdened, she describes how choosing to work during her downtime is energising because she’s immersed in work that’s deeply meaningful and aligned with her purpose. For her, the process of developing tools like the Infinite Leadership Diagnostic is not only intellectually stimulating but also a way to serve more people at a deeper level.
Jane affirms this passion, drawing parallels with entrepreneur Simon Baird—co-founder of Culture Kings—who now devotes his time to supporting other entrepreneurs. Despite achieving financial freedom, Baird continues his work because, as he describes it, it’s both his job and his hobby. Kylee resonates with this sentiment, explaining that having the freedom to choose when and how to work gives her the flexibility to design her business around what matters most to her—especially her family.
This freedom and intentional design, she explains, is what makes her practice so valuable. Whether it’s going “all in” on a workday or stepping back when needed, her business gives her autonomy that traditional roles never could. That sense of fulfilment—choosing what she does and loving it—is what sustains her momentum and joy.
Responding to the question many people ask—how she manages it all—Kylee dispels the myth that she has a secret trick, like a time machine, although one client jokingly insists she must. She credits her ability to juggle family, clients, and creative projects to a strong routine and disciplined structure, not magical time-warping powers. Drawing on lessons from thought leaders like James Clear (Atomic Habits), she emphasises the liberating nature of structure. Contrary to the common belief that routine is restrictive, she insists that structure actually creates freedom.
Kylee describes herself as an early riser—up at 4:00 AM—with a strong morning routine that includes personal care, reading, writing, and sometimes connecting with international clients. Her days are deliberately designed, with certain types of work scheduled on specific days to avoid task-switching fatigue. She admits that the first years of her business were marked by “organised chaos” and constant code-switching between different types of work. While she was successful, it wasn’t sustainable.
Now, with systems and structure in place, her business feels more spacious and effective. That intentional design has created more room for creativity, family, and joy—an evolution that has taken time, experimentation, and self-awareness, but which now serves as a model for building a fulfilling, values-aligned practice.