The Power of a Lollipop is one of the best and most original leadership books I’ve come across in years. It’s a delightful blend of solid theory, practical advice, and sheer fun. Authored by Feena May, CEO of The Inspiring Company and former Chief Learning Officer at the International Committee of the Red Cross—not to mention her stint as a clown—this book is a treasure trove of insights. Disclaimer: This review is more of a love letter than a critique because I agree with nearly everything May writes.
The research question that May started out with was simple yet profound: Can we model leadership that stakeholders experience as inherently good and apply it across cultures and contexts? She was frustrated that both Hitler and Churchill could be labeled as leaders, regardless of the pain or the optimism related to their impact. Her mission became to reclaim the word “leader” so it implies a positive impact. As she puts it, “I wanted leadership to inherently imply a positive outcome, a positive difference – that people, teams, organizations, and communities were better because leadership had been exercised. The more I read and reflected, the more I wondered why so much literature, research, and the billion-dollar industry that is leadership development had not led to better experiences of leadership at any level. My heart bled for every leadership story I heard that featured pain, poor outcomes, burnout, demotivated staff, bad experiences in the workplace, and – in the worst cases – serious mental and physical harm. The trouble with the traditional definitions is that they ignore the quality of the journey, the quality of the leadership space for the people involved and the impact created.” So she gets rid of the neutral approach towards leadership, defining good leadership as “the ability to mobilize people and resources towards a clear, collective goal and inspire a positive impact for people and context at all levels.”
Her leadership model is called the Lollipop model because she travelled the world for the Red Cross with a large bag of lollipops, handing them out at the office or to soldiers at roadblocks. “Two hundred adults with multicoloured lollipops in their mouths changes a lot of things.”
The Lollipop model has five stages. The first is presence. Presence is in this book about being self-aware and showing up, actively making the choice to step in and take the space. To be truly present, you have to be truly you, she writes. Self-awareness is important to leadership but presence is bigger than the self. “I can be the most self-aware person on the planet – but if I sit in my corner, it doesn’t benefit anyone.” It is the act of stepping in that starts a leadership process. “It is a leadership skill to be able to notice and understand how the quality of our presence is impacting the nature of the space.” Being present allows leaders to be in the moment, available to the potential of what is.
The second stage of the Lollipop model is relating. “It is only by being present that we can take on the the challenge of relating – the capability to understand the impact that you have, to build a relationship with people, place and context. Being present allows a leader to listen because the act of leadership always takes place within a relationship. When we truly relate to others, we create connections, and these connections become the pathways for information to travel.” This allows leaders to gather the information that is vital to the act of leadership, to get as close as possible to an unbiased view of reality. Which is not easy because information is filtered in many layers before it finally gets to the top dogs.
The third stage is sensemaking, envisioning the future and the potential for action. “It is creating the vision for a desired positive impact and sharing it in a way that enables everyone to understand the same thing.” Sensemaking starts from the gap between what is and what needs to be. “The leadership power at the core of sensemaking is that leaders have the ability to open space for the best outcomes on the journey ahead, inviting others to co-create the future.” Leaders mobilize others more than doing things themselves. From there an organization can move from a singular to a shared vision of a positive impact that can be implemented, resulting in the same story being told by all involved.
Action is the fourth stage. This is about “the ability of a leader to take a decision and to put a system into movement to get things done”. Making a decision unleasheses energy. Not deciding is also a decision: it creates the energy of resistance and being stuck or losing time. In May’s view decision-making is more about moving the energy of the system than about the quality of individual decisions. “A leader doesn’t need to do everything, control everything, or be everything (for some, this a blow to the ego). A good leader just needs to embody the right amount of energy to start a system vibrating.” She adds that complex systems are beyond the knowledge scope of expertise of any one person. Facilitating good decision-making depends on the leader’s ability to hold a space for collective intelligence to operate.
The fifth and final element is service, which is greater than purpose. “People respond to a leader’s sense of service. It changes the foundation of what makes leadership have impact. The lack of focus on service, more than anything else, contributes to a poor experience of leadership.” Leadership service is “the commitment of an individual to make their unique, positive and sustainable difference in the world”.
Service starts with service to the self: the ongoing journey of discovering and living our uniqueness, May writes. The self end ensures that we support ourselves to be able to act well in the leadership space. May considers it necessary that leaders self-reflect so that they can show up in alignment with who they are and explicitly understand the difference they want to make in the world. In her view more time to reflect is necessary when less time is available. Based on the service to the self comes the service to the world. “Service embodies a generosity of spirit that inspires people to become something more than they were before.” One might even call this love. “Not the mushy kind, but the real caring for the self and others, caring for what was, what is, and what possibilities the future holds.”
Feena May concludes: “Leaders willing to make the Lollipop journey leave in their wake people who have grown and organizations that are better places. It takes a good heart, a bit of skill, and a genuine desire to make a difference.” I like that: a good heart, a few capabilities, and the courage to step in and act. This book is the perfect guide for those ready to take that journey. So, grab a lollipop and get ready to lead with a smile.
Feena May. The Power of a Lollipop. A model for inspiring leadership. GFB, 2025