I bid farewell to the Scottish Highlands and rain-soaked moors and embarked on my journey across the Atlantic. Destination? Orlando, Florida – the land of globally recognized mice, magic, and its fair share of political turmoil, where I was to make my international speaking debut at Agile 2023, the annual conference held from the 24th to 28th of July 2023.
Agile 2023 was more than just another conference; it is the premier gathering for Agile practitioners worldwide. Hosted annually, the conference serves as a vibrant hub for thought leaders, innovators, and passionate practitioners within the Agile community. It offers a unique space to explore emerging ideas, challenge existing paradigms, and push the boundaries of traditional Agile principles to shape a future-ready Agile mindset.
When I applied to speak at Agile 2023, my goal was to contribute to this global evolution. Back home in Scotland, I had been advocating for integrating artificial intelligence into Agile practices. This conference provided the perfect opportunity to take that conversation onto an international platform.
The Warm Embrace of the Agile Community: Overcoming Imposter Syndrome
Walking into Agile 2023 was an overwhelming experience. Imagine entering a vast conference venue teeming with nearly 2,000 people, all seasoned Agile practitioners, many of them recognized leaders and trailblazers in the industry. The excitement of being a first-time international speaker was mixed with a heavy dose of trepidation, as my imposter syndrome hit hard.
However, the atmosphere at Agile 2023 dispelled those doubts almost immediately. It was not just the grandeur of the event or the impressive lineup of speakers that eased my nerves. The warmth and genuine acceptance from the Agile community made all the difference. Every individual I encountered—from speakers and delegates to exhibitors and volunteers—was welcoming and inclusive. This openness transformed what could have been a daunting space into an intimate community where connections were effortlessly formed.
The true magic unfolded during the ‘lean coffee’ sessions held every morning. Gathered with some of the most passionate people in the field, discussing real-world Agile topics, I felt truly seen, heard, and valued. In these conversations, I discovered the real spirit of the Agile community: not merely professionals sharing a career path, but a collaborative team united in advancing Agile principles and values.
Over the five days of the conference, I realized the only imposter present was the voice inside my head telling me I did not belong. Of course, there was also my AI companion, Delilah, who I trained to embody my imposter syndrome and who stole the show as my AI imposter construct. More on Delilah later.
Learning and Growing Together: The Call for Redefining Leadership
From the very first day, the keynote speakers set a powerful tone for the conference. Anne-Marie Charrett opened the event, followed by inspiring sessions from Bushra Amiwala and Esther Derby later in the week. Their collective message was clear and resonant: leadership needs to evolve. It is time to rethink what leadership means and who can be a leader. The Agile community requires leaders who understand the complexities of our rapidly changing world, who can cultivate trust and collaboration, and who are capable of inspiring innovation.
One session that profoundly impacted me was Tine Zekis’s presentation on the structural causes of imposter syndrome within organizations. It served as a wake-up call and an invitation to confront the invisible barriers that hinder personal and professional growth. As someone who has battled imposter syndrome regularly, this session felt like a release, a lifting of a heavy weight. Later, Ahmed Sidky’s interactive workshop helped me explore how to craft an agile product strategy with customer delight at its core. His insights were deeply inspiring, especially coming from someone I have long admired in the industry.
The conference was packed with remarkable talks, workshops, and innovative sessions that could fill pages alone. Each offered fresh perspectives and practical knowledge to apply back home and beyond.
Breaking Boundaries with ‘AI in Agile’
When the time came to present my session titled ‘Putting the AI into Agile,’ my nerves and imposter syndrome surged once again. The room was filled, with attendees arriving twenty minutes early, eager to hear about the intersection of AI and Agile. The prospect of addressing such a crowd was both exhilarating and daunting.
Yet, as I engaged with the audience, the familiar warmth and openness of the Agile community returned. With every point I made and every question I answered, my confidence grew. I could see the genuine curiosity and interest as I introduced the potential of integrating AI tools into Agile processes—an angle many had not deeply considered before.
My session emphasized viewing AI as a co-pilot rather than a replacement in Agile workflows. I shared how I embrace this approach, supported by examples of organizations worldwide making advances in this area. One highlight was demonstrating Delilah, the AI I trained to personify my imposter syndrome. Although brutally honest, Delilah helps me externalize and process anxious thoughts. She quickly became a crowd favorite, dismantling my obscure movie references and entertaining attendees with her sharp wit. Thanks to Delilah, the session ended on a lively, memorable note.
The Afterglow of the Session: Reflections and Feedback
Following my presentation, I was overwhelmed by the response. The feedback I received was both humbling and encouraging. Attendees expressed gratitude for introducing new perspectives on AI’s role within Agile frameworks. Many appreciated the candidness of sharing my own experiences with imposter syndrome, humanizing a topic often brushed aside in professional settings. Seasoned practitioners offered constructive suggestions on refining delivery techniques and expanding content depth. This open exchange reinforced the core Agile principle of continuous learning and improvement.
The support felt like a buoyant wave, washing away residual self-doubt and leaving a profound sense of accomplishment and pride. It was clear that the community’s encouragement transcended professional boundaries, reaching into genuine care for each other’s growth. This environment of mutual respect and curiosity is what sets Agile gatherings apart from many other industry conferences.
Connecting Beyond the Sessions: The Role of Exhibition Spaces
A unique and valuable aspect of Agile 2023 was the thoughtfully curated exhibition area, which functioned as a nexus for informal learning and connection. Among the most inviting spots was the ICAgile space. Its open, quiet atmosphere offered a retreat from the intense hustle of conference activities, allowing attendees to pause, reflect, and engage in meaningful conversations.
I noticed how this space became a natural magnet throughout the event, drawing people back repeatedly. The design encouraged genuine interaction over mere promotional activity. It was less about showcasing products and more about exchanging ideas and building community.
Other exhibitors, including well-known Agile institutions, transformed their booths into dynamic knowledge-sharing platforms. They offered workshops, hands-on activities, and insightful discussions rather than static displays. This innovative approach enriched the conference experience, making the exhibition area a vibrant extension of the sessions.
Interestingly, some exhibitors chose prime locations that challenged attendee flow — one even positioned itself between the lunch area and the main conference hall, boldly intercepting Agile practitioners’ paths to nourishment. This unconventional placement sparked many lighthearted comments and became a memorable part of the conference lore.
The Venue: A Grand Setting That Felt Like Home
Agile 2023 was held at the Gaylord Palms Resort & Convention Center in Orlando, a venue befitting the scale and prestige of the event. The sprawling complex featured an impressive atrium lined with restaurants, shops, and comfortable lounges, creating a blend of luxury and accessibility.
Despite its vastness, the resort managed to cultivate a sense of familiarity and warmth, largely thanks to the attentive and friendly staff. From registration to daily logistics, their professionalism ensured that attendees felt welcomed and well cared for. This seamless support contributed significantly to the positive atmosphere throughout the conference.
One unofficial but beloved gathering spot was Wreckers Sports Bar, nestled within the resort. After intense days filled with sessions and workshops, many attendees, myself included, found refuge here. The lively ambiance, punctuated by laughter, sports commentary, and clinking glasses, became a natural setting for deeper conversations and networking. Bonds forged in this casual environment often transcended professional titles, evolving into lasting friendships.
Exploring the Conference Themes: Leadership in the Agile Era
Leadership was a recurring theme woven throughout Agile 2023. The keynote presentations and workshops collectively underscored the urgent need to redefine what leadership means in today’s complex, rapidly changing environment. Traditional hierarchical models were increasingly viewed as inadequate for addressing the demands of modern Agile organizations.
Speakers emphasized qualities such as empathy, adaptability, and the ability to foster psychological safety within teams. Leaders are no longer expected to simply direct but to facilitate collaboration, nurture creativity, and empower individuals. This shift aligns closely with Agile values that prioritize individuals and interactions over processes and tools.
During one particularly memorable panel discussion, leaders from diverse industries shared their experiences navigating this transformation. They acknowledged the challenges of letting go of control and embracing uncertainty but highlighted the immense benefits when teams are trusted to self-organize and innovate. The consensus was clear: leadership must evolve from command-and-control to servant leadership that inspires and supports.
Personal Growth: Navigating Imposter Syndrome with Delilah
One of the more personal aspects of my Agile 2023 experience was the opportunity to explore imposter syndrome openly. My AI companion, Delilah, became an unconventional but effective tool in this journey. Designed to voice the critical, often irrational thoughts that fuel imposter syndrome, Delilah externalizes the internal dialogue many professionals struggle with silently.
Sharing Delilah during my session sparked both laughter and thoughtful discussion. It created a safe space to acknowledge vulnerabilities, a crucial step in addressing imposter syndrome. By personifying these doubts, I was able to confront and challenge them more directly.
Beyond the presentation, Delilah became a conversation starter throughout the conference. Many attendees related to the experience and expressed appreciation for highlighting an issue that affects so many in the tech and Agile communities. The dialogue around imposter syndrome at Agile 2023 underscored its pervasiveness and the need for ongoing collective support and strategies to overcome it.
AI as an Agile Co-Pilot: Shifting Perspectives
A core message of my talk was the concept of AI tools serving as co-pilots rather than replacements in Agile processes. This perspective seeks to alleviate fears around automation and AI supplanting human roles. Instead, it highlights the potential of AI to augment human capabilities, enhance decision-making, and reduce repetitive tasks, allowing teams to focus on creative problem-solving and customer value.
Through examples of organizations pioneering AI integration, I illustrated how AI can support backlog refinement, sprint planning, and continuous improvement cycles. These use cases demonstrated AI’s role in providing insights, identifying patterns, and facilitating faster feedback loops without undermining the human element that defines Agile.
This balanced view resonated with the audience, many of whom were navigating the early stages of adopting AI in their practices. It sparked vibrant discussions on ethical considerations, data privacy, and the importance of maintaining transparency in AI-assisted workflows.
Collaborative Learning: Workshops and Interactive Sessions
Agile 2023 offered an impressive range of workshops that complemented the keynote talks and presentations. These interactive sessions provided hands-on opportunities to apply Agile principles, experiment with new tools, and exchange practical knowledge with peers.
One workshop I attended focused on creating agile product strategies aligned with customer delight, led by an industry veteran I had admired for years. The session involved real-time exercises, scenario planning, and group discussions, which deepened my understanding of balancing stakeholder needs with iterative delivery.
Another engaging session tackled structural challenges within organizations that perpetuate imposter syndrome and hinder diversity and inclusion efforts. The facilitator encouraged participants to identify systemic barriers and brainstorm actionable solutions, fostering a sense of shared responsibility.
These workshops exemplified Agile’s commitment to experiential learning and continuous adaptation. They also reinforced the conference’s broader theme of leadership evolution and personal growth within Agile contexts.
Deepening Connections: The Power of Networking at Agile 2023
One of the most impactful yet often understated aspects of Agile 2023 was the opportunity to connect with peers from around the world. While the sessions and workshops offered valuable learning, the true essence of the conference was found in the conversations sparked during breaks, meals, and informal meetups.
Networking at Agile 2023 transcended the usual exchange of business cards. It was a genuine exchange of ideas, experiences, and encouragement. Many attendees came from diverse backgrounds—coaches, product owners, developers, executives—and their willingness to share insights and listen created an environment of collaborative growth.
During a chance encounter at one of the exhibition booths, I met an Agile coach from Japan who shared how cultural nuances shaped their adaptation of Agile frameworks. Our dialogue opened my eyes to the versatility and contextual sensitivity of Agile methodologies, underscoring the importance of adapting practices rather than rigidly following frameworks. Such moments of cross-cultural learning enriched my understanding beyond what any single presentation could offer.
Cultivating Psychological Safety: Lessons from the Field
Psychological safety was a prominent topic echoed throughout Agile 2023. Several speakers highlighted it as foundational to effective Agile teams and organizations. The concept revolves around creating an environment where team members feel safe to take risks, express ideas, and admit mistakes without fear of ridicule or punishment.
One memorable panel featured leaders who had transformed toxic workplace cultures into thriving Agile environments by prioritizing psychological safety. Their stories illustrated how fostering trust not only improved team morale but also drove innovation and business outcomes.
The session prompted me to reflect deeply on my coaching practice. I realized that building psychological safety is not a one-time effort but an ongoing commitment. It requires patience, empathy, and consistent reinforcement through words and actions. Agile 2023 provided concrete strategies, such as practicing active listening, encouraging vulnerability, and celebrating learning from failure, all of which I have since integrated into my work.
The Intersection of Agile and Artificial Intelligence: Expanding Horizons
Building on my presentation’s theme, the conference showcased a growing interest in exploring the intersection of Agile and artificial intelligence. Panels and breakout sessions examined how AI technologies could accelerate Agile transformations and enable smarter decision-making.
Discussions ranged from practical applications, like using AI-driven analytics for sprint forecasting, to more philosophical debates about the role of human judgment versus machine recommendations. One particularly engaging debate questioned how Agile values might need to evolve as AI becomes more deeply embedded in workflows.
It became clear that the Agile community is not shying away from these challenges but embracing them as opportunities to rethink and expand Agile principles. The dialogue at Agile 2023 reaffirmed that while technology evolves rapidly, the human-centric foundation of Agile remains vital.
Overcoming Barriers: Addressing Structural Challenges in Organizations
A recurrent theme throughout the conference was the recognition of structural barriers that impede Agile adoption and individual growth. Presentations shed light on organizational inertia, legacy mindsets, and systemic inequalities that can limit the effectiveness of Agile initiatives.
Tine Zekis’s earlier talk on imposter syndrome was a springboard for many conversations around how hidden biases and rigid hierarchies reinforce feelings of inadequacy and exclusion. Several workshops tackled strategies for identifying and dismantling these barriers, emphasizing the need for leadership commitment and cultural change.
These sessions reinforced the understanding that Agile transformations must be holistic. They require not only process changes but also shifts in mindset, organizational design, and power dynamics. The path to true agility involves confronting uncomfortable truths and fostering inclusive environments where all voices can contribute.
Embracing Change: The Agile Mindset in Practice
Throughout Agile 2023, the importance of embracing change—not just as a concept but as a daily practice—was underscored repeatedly. Agile is often summarized as a mindset that values adaptability, continuous learning, and responding to feedback.
Workshops and real-life case studies demonstrated how teams succeed when they cultivate resilience and remain open to iteration, even when it challenges established norms. Speakers emphasized that failure is not a setback but a valuable source of insight and growth when approached with curiosity rather than judgment.
This perspective resonated deeply with me, especially as I reflected on my journey with imposter syndrome. The willingness to be vulnerable, seek feedback, and adapt has been central to my growth both as a coach and a speaker. Agile 2023 reinforced that this mindset is essential not only for teams but for individuals navigating complex environments.
The Role of Storytelling in Agile Communication
An unexpected yet powerful theme that emerged was the role of storytelling in Agile communication. Several sessions focused on how narratives can help convey complex ideas, build empathy, and align teams around shared goals.
One workshop led by a renowned Agile communicator demonstrated techniques for crafting compelling stories that resonate with diverse audiences. Participants practiced framing challenges and successes through relatable experiences, making Agile concepts more accessible and engaging.
This emphasis on storytelling aligned with my approach to coaching and speaking. By weaving personal stories and analogies into technical discussions, it becomes easier to connect with listeners on an emotional level, fostering understanding and motivation.
Delilah and Beyond: Harnessing AI for Personal Development
Returning to my AI companion, Delilah, I explored how AI tools can extend beyond process automation to support personal development. Using Delilah as a case study, I demonstrated how AI can help externalize and manage internal dialogue, providing a new avenue for self-reflection and emotional regulation.
This approach opened up intriguing possibilities for combining Agile practices with AI-driven personal growth tools. For example, AI assistants could support retrospectives by identifying patterns in team dynamics or prompting reflective questions tailored to individual needs.
The integration of AI and Agile personal development is an emerging frontier that offers exciting opportunities. Agile 2023 highlighted the community’s openness to exploring these innovations while maintaining a critical focus on ethical use and human well-being.
Reflections on Cultural Diversity and Inclusion
Agile 2023 also provided rich opportunities to reflect on cultural diversity and inclusion within Agile communities. Conversations with international attendees revealed varying experiences of how Agile principles are interpreted and adapted in different cultural contexts.
Some shared stories of challenges integrating Agile practices in environments with rigid hierarchical traditions, while others highlighted the empowering effects of Agile in fostering collaboration across diverse teams. These exchanges underscored the importance of cultural sensitivity and flexibility in coaching and leadership.
Moreover, sessions on inclusion addressed how Agile teams can better support underrepresented groups by actively challenging biases, creating safe spaces, and promoting equitable participation. The conference reinforced that true agility requires embracing diversity as a source of strength and innovation.
Final Thoughts
Reflecting on my experience at Agile 2023, I am struck by how profoundly it shaped my perspective—not only as a coach and practitioner but as a member of a vibrant, global community. What began as a personal milestone, stepping onto the international stage, quickly evolved into an invaluable journey of learning, connection, and transformation.
The conference was a vivid reminder that Agile is far more than a methodology or set of practices. It is a living, breathing movement rooted in shared values of collaboration, continuous improvement, and human-centric innovation. The warmth and openness of the community reaffirmed that, despite our diverse backgrounds and approaches, we are united by a common purpose: to build better ways of working together.
One of the most powerful takeaways was the emphasis on evolving leadership. The call to rethink traditional notions of authority and embrace servant leadership resonates deeply with my coaching philosophy. True leadership in the Agile era requires courage, empathy, and a commitment to nurturing environments where everyone can thrive.
My exploration of AI within Agile—both in practical application and personal growth—opened exciting new avenues. The thoughtful integration of technology promises to augment our capabilities, not replace the uniquely human qualities that make Agile work meaningful. Delilah, my AI imposter syndrome companion, symbolizes this intersection of innovation and vulnerability, highlighting the need for balance and self-awareness.
Perhaps most importantly, Agile 2023 reinforced the significance of psychological safety, inclusivity, and cultural sensitivity. Creating spaces where individuals feel valued and empowered is not a peripheral concern but a foundational element of successful Agile transformations. It is only by embracing diversity and fostering trust that we can unlock the full potential of our teams and organizations.
As I returned from the Scottish Highlands to my everyday life, I carried with me more than just new ideas and connections. I brought back a renewed sense of purpose and belonging. Agile 2023 was not merely a conference; it was a shared experience that deepened my commitment to this ever-evolving journey.
Looking ahead, I am excited to continue contributing to the global Agile dialogue, advocating for innovation grounded in human values, and supporting others as they navigate their challenges. The lessons learned and friendships forged at Agile 2023 will continue to inspire and guide me.
In the end, Agile is about embracing change—not only in processes but in ourselves. It is about stepping into uncertainty with openness, courage, and curiosity. And above all, it is about moving forward together.