The Leadership Enigma

This episode was filmed in front of a live studio audience at Vorboss in central London. Kevin O'Leary spent 30 years as a police officer with the Metropolitan Police retiring as a Chief Superintendent. Kevin was also, now famously, episode No.1 of The Leadership Enigma which started during the pandemic. This episode is a fascinating insight into the world of crime and punishment including undercover policing, hostage negotiation, stolen vehicles, riots, serial killers and more. Kevin decided to become a police officer after he was robbed at knife point at 14 years old and the police solved the crime and actually recovered his bicycle. As a very young probationary police officer Kevin found himself policing the miner's strike in the 1980's during the time Margaret Thatcher was Prime Minister and also the Broadwater Farm riots which involved the murder of PC Keith Blakelock, all providing Kevin with a baptism of fire into the world of policing. Kevin's time with the Stolen Vehicle Squad was his initiation in the Criminal Investigations Department (CID) and learning how to carry a case load of allocated reactive investigations. In 1999 Kevin became involved in the Admiral Duncan Pub bombing. He was around the corner on an unrelated surveillance operation when the bomb was detonated. At the scene, Kevin was faced with chaos and destruction. As one of the first on scene his ability to make quick decisions and prioritise were tested to the max. As a police officer and leader, picking up on 'weak signals' is a must in a world of constant change. Kevin tells the story of dealing with a High Risk missing person which turned into uncovering the actions of an international serial killer, John Sweeney, who is currently serving life in prison and will be the focus of a recent television documentary. Kevin as a senior officer held the role of Head of Undercover Policing for the Metropolitan Police and explains the iconic investigation he was involved in that was headlined in the newspapers as 'The Hip Hop Cop Shop.' Kevin had to make a series of difficult and at times unpopular decisions for the ranks and file officers in order to help protect them from the rigours and stresses of undercover operations. One of Kevin's final roles in his career was as Bronze Commander during the London 2012 Olympics with a funny story of the cycle protest group 'Critical Mass' that had been infiltrated and decided to see if they could intercept the Queen! Kevin is also the 'referee' for the award winning TV show 'Hunted' which is on our screens each year. www.kevinoleary123.com

Tom Monahan took on the role of CEO of Heidrick & Struggles in 2024. He came to Heidrick & Struggles with a decades-long career of building and leading innovative technology, data, and services companies and as a long-time Heidrick & Struggles client.Most recently, Tom was president and CEO of DeVry University, where he led the university to digital innovation, sustained growth, outstanding student success metrics, and financial strength as a newly independent institution.Tom is passionate about people and the role that leadership has to create a world better led. Tom explains to me that the right people, in the right role leading in the right way is the single most important driver for high performing organisations. Tom's decision to take up the CEO role of Heidrick & Struggles was based on the ability of H&S to really make a difference for organisations in finding the right leaders and to co-create great performance on an individual and collective basis. Tom describes leaders are Magpies, building their nests out of anything they can find within themselves and in their surroundings based on insatiable curiosity and a beginners mindset.I ask Tom about his parents and family background as I search for clues into his focus and success. His answer will surprise you.Tom tells me that in his role as CEO he is the steward of the business and the people are the only thing that won't be worth less from the day they begin working in the organisation. Each and every day a person grows, learns and experiences in a way that builds the sum of the parts. It is the human capital that is the most precious resource of any business.One of Tom's primary strengths is his ability to frame a problem or issue in order to create focus as opposed to always having an answer. 'Fast Starts matter' Tom explains, so getting quick insight is paramount for any leader and organisation in gathering the collective intelligence to focus on the issue or problem and resolve it.Leading experts has always been a leadership challenge and Tom tells me that he is expert in the way we used to do things and not how we should do things so he has to get out of the way of his people and allow them to operate in a way that they know is best.As CEO Tom is focused on creating an environment where the best people come to do their best work. Tom also understands that any new CEO must be 'courageously humble' as he tries to understand the business that he is taking over, the people that he leads and the culture that he initially inherits. The most dangerous thing a CEO can do, is be a focus group of one.Tom is an introvert by nature so the very social and public facing element of the role is a constant challenge for him and he fondly remembers the advice from an inebriated aunt that if something is worth doing, it is worth overdoing.www,hedrick.com

Stevie Ward is the former captain of the Leeds Rhinos Super League Rugby team, winner of the Super League and Challenge Cup and he was also one of the youngest captains aged only 26. Stevie had 10 operations during his playing career and had to retire early due to a brain injury. This is a powerful episode of humility, vulnerability and resilience. Stevie was lucky enough to play for Leeds during the 'Golden Generation' playing with a number of England Internationals including the late Rob Burrows. He made his debut at 18 years old sharing his formative years doing battle on the professional rugby field. I explore Stevie's background to try and understand what allowed him to find the the strength to enter professional rugby at such a young age with maximum intensity and dedication to being the best he could be. Stevie was named captain at just 26 years old and this official leadership role meant he felt the enormous pressure to perform and succeed which initially led to a feel of overwhelm and essentially sub optimal performance. Stevie remembers the toughest times when the team lost their unique identify and didn't know who they were which translated into poor performances on the pitch. The team needed to overcome fear and reflect on how they could leverage their unique differences and personalities to create something special, authentic and compelling as a team. How could they create their own high performing culture? There is so much uncertainty in a Rugby League team amongst a group of warriors who needed to create a high level of psychological safety for all the players to all feel able to bring their best without fear of failure and or criticism.A brain injury (multiple concussions) forced Stevie to step away from professional rugby whilst he was in his prime. To this day he still feels the effects of the injuries he suffered on the pitch and he has had to completely reassess who he is and what he is passionate about.Stevie filmed a Sky Sports documentary 6-8 months after stepping away from the game and he initially hoped that he would actually be able to return to the game but even attending the stadium as a spectator for the documentary, Stevie found was a sensory overload and he had to leave at half time. Stevie also emotionally remembers his friendship and playing time with Rob Burrows who fought very publicly against motor neurone disease but unfortunately passed away in June 2024. Stevie hosts 'Mantality' and works with individuals and organisations focused on the importance of mental health, psychological safety, courage, humility and masculine vulnerability, all potentially a paradox with the brutal and competitive world of professional rugby. Don't miss this episode. www.stevieward.co.uk

Loree Draude (call sign 'Rowdy') was one of the first female combat pilots in the US Navy with over 300 aircraft carrier landings and two deployments to the Persian Gulf. Loree who is based in Boston is currently an author, executive coach and keynote speaker with a passion for focusing on the human being and not just the human doing. Leadership and service are part of Loree's personal values and she leverages her military experiences to help teams across the world. Loree grew up in a Marine Corps family and after college she went on a field trip that changed her life after visiting a number of naval stations and seeing a variety of aviation options. At that time women were not allowed to fly most aircraft, they were either trainers or crew. She went for her first flight with a friend and suddenly she knew the way forward, especially when the first Top Gun movie came out! As part of her flight training she was in awe of all the people who made military flying possible and then about one and half years after she earned her wings, the ban on women flying combat aircraft was lifted. in 1991 military officers were alleged to have sexually assaulted or engaged in improper and indecent behaviour with up to 83 women and 7 men at the Las vegas Hilton at the 35th annual Tailhook Association which became known as the Tailhook Scandal of 91. This was a major catalyst for the evolution of change and Loree had her opportunity. She became part of the first wave of female combat pilots for the US Navy and was flying the F18 Hornet and S3B Viking anti submarine warfare jet. Loree vividly remembers her first landing on an aircraft carrier and the feelings of terror and thrill combining. Once she deployed to her fleet squadron she then flew night time carrier landings which was a very different challenge.As a combat pilot, I ask Loree about her role and mindset required to potentially have to take the life of another. Loree explains that this is a very real part of her role, fortunate to never have to, but the expectation was constant and heavy. She also recognises the distance between her and the enemy as compared to the infantry, was also a factor in how she processed her role. As she tested her own limits she speaks of the need and requirement for high levels of trust with her leaders to determine life and death decisions. Finally Loree chats about her one woman show that was delivered just off Broadway which was part of her inner journey that also became part of the Edinburgh Fringe Festival. Check out: www.loreedraude.com

Edwin Brenninkmeyer is the CEO of Oriens Aviation and this episode was filmed on a Pilatus PC24 jet at Biggin Hill. The Pilatus PC24 can carry 8 passengers and 2 pilots although it can be flown by a single pilot. Edwin started the company back in 2015 as he is passionate about aviation having qualified as a pilot at 17 years old. Edwin comes from a family of 6 generations celebrated within the fashion and retail industry as the original founders of C&A and now their business interests reach across multiple horizons.His upbringing provided him a strong belief in doing business ethically and this is at the foundation of his leadership. He studied an executive MBA at Oxford where he describes the benefits of studying with such a diverse group of people from all over the world.Oriens Aviation started working with a Swiss manufacturer Pilatus and is now a one stop shop for those flying privately creating a high customer service and cost effective model. Edwin's philosophy is entrepreneurial in spirit as he is always looking to scale and be intentional about standards and customer centricity. He is passionate about doing business with a strong purpose, sharing what he has learned in the aviation industry with a wider community. The private aviation industry can be an easy target for those who believe the industry as elitist and unsustainable in a world full of excess. Edwin explains that pre pandemic, 90% of people who could afford to fly privately chose not to, yet the pandemic pushed many of those people into using private services which increased usage and commitment. The vast majority of those flying privately (especially in the US) are middle management and not top executives as businesses understand the importance of time saving and increased productivity.Private aviation is heavily regulated and Edwin is passionate in trying to help the world understand the realities of the industry and myth bust. For example, emissions are minuscule. Aviation is 2% of global emissions and private aviation is 2% of that. The industry continues to strive to become even more sustainable. Electric aviation is underway and predictions are that by 2035 we will start to see the technology make a real impact on the industry.Customer centricity is a particular focus for Edwin, especially within the high net worth community. His belief is that the purpose of business is to create a community of value and good rooted in 'unreasonable hospitality' whilst also providing a positive experience for the body mind and spirit of those working within the business. Edwin as CEO is focused on creating a culture where 'to work is to create and to create is being human.' A key focus in on being the favourite supplier as opposed to just being the best supplier.Safety is paramount for Edwin and the industry so trust is at the heart of all his customer relationships. 'It's a people business' as Edwin explains and congruence between what is said and done is critical.As CEO Edwin is learning everyday and explains his role as culture creator and visionary to explore where the business can go next. His management team are all entrepreneurs and value creators in their own right.Edwin is a humble and value driven leader who hopes he can help shape and define the aviation industry for a better future.

Sir Max Hill KC is the former Director of Public Prosecutions (DPP) for the Crown Prosecution Service in the United Kingdom. Max was called to the Bar in 1987, appointed a Recorder 2004, Queen's Counsel 2008 and knighted by The King in the 2024 New Years Honours list.The role of DPP is the highest non political appointment as the most senior prosecutor in the country, acknowledged by the Prime Minister but politically independent. As Head of the Crown Prosecution Service, Max was responsible for the the most high profile criminal cases, leader of over 8,000 staff nationally and ensuring consistency of approach in the courts across the country.This episode is a fascinating and rare 'peek behind the curtain' of the criminal justice system.Max studied law as a student, attending Oxford University before arriving at The Inns of Court School of Law to qualify as a barrister and specialise in court advocacy and criminal law. Max has both prosecuted and defended during his career which he explains assisted his ability to empathise and understand the independence and importance of both roles.Max explains to younger lawyers, 'be careful not to take too much credit for the cases you win unless you are ready to take full responsibility for the cases you may lose.' Max had to transition for independent practitioner to leading almost 8,000 people nationally. He used his experiences of running large and complex cases with multiple stakeholders as a basis for his personal approach to leadership.Max was part of the prosecution team (with Victor Temple QC) for the trial into the Preddie brothers aged 12 and 13 years old accused of the murder of 10 year old Damilola Taylor, tragically killed in November 2000, stabbed with a broken bottle and died on his own in a stairwell in Peckham. This was a tragic and horrific case that caught the attention of the national press and conscience.One of the greatest challenges for an advocate is an ability to communicate with an eclectic audience, from High Court judge, to victim and from witness to jury members. His advice is having a core understanding that your way of doing things is better than trying to inauthentically replicate someone else.Max was first introduced into the world of terrorism during the Real IRA activity in London and Birmingham in 2001. This led to him being involved with the trials post the events of 7/7 where 52 Londoners lost their lives during a series of 4 explosions, followed by 21/7 where London was again the target of four suicide bombers all of which failed as only the primary fired within the devices without the main charge detonating.Max was instructed as part of a three strong barrister team tasked to prosecute all the suspects from 21/7 and also prosecute those who assisted them. Max was also asked to represent the Metropolitan Police at the Inquest into the deaths of the 52 Londoners from the 7/7 bombings.Many of Max's roles have required significant senior stakeholder engagement with multiple agencies, navigating politics, bureaucracy and intense media and public scrutiny.The leader is always a role model for the organisation and Max tells the compelling story of how he decided to connect with thousands of people within the Crown Prosecution Service which turned into the ultimate listening exercise.Enjoy this incredible episode.

Lisa Bodell is the CEO of Future Think, award wining author and one of the world's Top 50 Keynote speakers on issues such as creating simplicity and killing complexity. This episode was filmed in New York City during the 'Future of Everything' Festival. Lisa always thought of herself as a helper and was naturally creative from an early age. She grew up in Michigan, studied business and wanted to go into marketing and advertising. However, she wanted to find a path where her ideas would be heard and mattered. At this point, the entrepreneur emerged and Lisa decided to do her own thing, start her own business and create a platform for ideas and collaboration. Lisa's books became a global calling card for her thought leadership and ability to help others learn and master new skills and capabilities. Time is a non renewable resource that we never get back and this became the catalyst for Lisa's focus on simplification. In a society fixated with more, Lisa is intent we also see the value in less. This requires focus and an ability to get rid of things. What will you stop doing is a wonderfully powerful question for all leaders although fear is something that holds all of us back. Stopping and saying 'no' is a critical ingredient for innovation. Simplicity is not about being more productive, its the front end of innovation and gives people the space to do what matters. It's also not about getting rid of everything, it's about getting rid of unnecessary complexity, the invisible waste, the work without the benefits. This is all about getting to the work that matters and not being more productive. As a leader, are you defining what meaningful work is? Grooves and ruts look and feel the same. Grooves are productive, ruts are a waste of time. Lisa speaks all over the world and I asked her in this episode what she wanted to talk about that she doesn't usually talk about in order to make this episode truly memorable. She decided to connect simplicity to wellbeing so we can feel that we are doing what we were born to do.Lisa explains that much of our daily workload is based around meetings and emails, therefore within our control to change, yet most will not. As Lisa says during her keynotes, many of us 'survive another meeting that should have been an email.'Technology has amplified the issue of complexity and the ease to create meeting after meeting. If you could kill off any 2 rules at work, what would they be? Many of the answers she hears are not even rules, they are just historical methods of working.Lisa's top tips include (1) for leaders to mandate the right for people to get rid of things that they feel are unnecessary, and (2) model the behaviour.All businesses fear becoming irrelevant, especially during great technological change. To be relevant we must change, we must innovate and people need time to think. People want to leave a legacy, not shareholder value. Simplicity is not a productivity exercise it's a about helping people to get to the work that they were hired to do in the first place and be their best self. Simplicity is also a foundation for a high performing culture. In an age of Generative AI, time is something to harness and allow people to think more. As Lisa explains. 'thinking is a daring act'. Perhaps now, we have more time to be human which is actually the basis of our leadership capability. www.futurethink.com

Giuseppe Stigliano is the global CEO of Spring Studios in New York which was the venue for the Wall Street Journal 'Future of Everything' Festival. We filmed this episode on the rooftop of the studio overlooking The Hudson river and surrounding area.Giuseppe is Italian and moved to Milan to study marketing working in multiple businesses with early experiences of leadership.He now travels between London and New York in his role as CEO for Spring Studios. He has an entrepreneurial spirit so the NYC location is a multiple use site including an event space, studio business, private members club and more making it a unique agency with a core business focused on luxury, fashion and lifestyle.Giuseppe is an entrepreneur by background, an author with Philip Kotler (the grandfather of marketing) adjunct professor and keynote speaker who also holds a Phd in marketing and economics. Giuseppe believes that the more you curiously explore opportunities and relationships the more life has to offer.He is currently redefining retail in a landscape of significant digital transformation and specialises in helping people navigate the 4P's of marketing (product , price, place & promotion) with a mindset shifting from making people want things to making things people want.Is the High Street dead? Giuseppe says no, if you can make it absolutely compelling for people to leave their sofas and online lives. Some of the biggest shifts for a retail business is the role of 'Figital', a three dimensional world of the physical, digital and the virtual. The plethora of data allows business to target the right message to the right person at the right time. Gen AI is changing the landscape again as it can create new ways of using what we already have available to us. However, Giuseppe also reminds us that AI will give us back time and can never compete with the truly human centred capabilities such as curiosity, empathy and creativity, simply more time for us to be human.Marketing is key for every business. This is also changing. Supply exceeds demand so the competition is high. Marketing has historically been focused on making people want things but now the sheer amount of data available allows people to consider what do we need to create for the people based on the insights we have. Gen AI can now help the smallest of businesses to master the data analytics.Giuseppe is always learning as a leader. He is a believer that the next generation of employees require servant leaders but also recognises that no one size fits all. Leadership has to flex to the context of the businesses growth and maturity. Giuseppe understands the importance of allowing smart people who are more expert that the CEO to be allowed and fully empowered to operate as they see fit. A leader must know when to get out of the way.www.linkedin.com/in/giuseppestigliano/