Caspar Craven
Most organisations know the goals they want to achieve. Fewer have the thinking required to pursue them when conditions deteriorate or complexity compounds. Leaders default to what worked before. Teams fragment when pressure peaks rather than cohere when it matters most. The gap between strategic ambition and actual execution is rarely a skills problem, it is a mindset and behaviour problem that standard leadership development does not address.
Why organisations work with Caspar Craven
His Big Bold Mindset® and Big Bold Circle give leadership teams a named, structured framework for changing how they think and act under pressure, not a set of borrowed principles, but a system built and tested through his own experience of pursuing extreme goals in commercial and offshore environments.
His background as a KPMG Associate Director and CFO, including a technology business exit to a listed company, grounds the material in commercial and financial reality, making it credible with boards, finance teams and senior executive audiences, not only culture or L&D audiences.
The argument he makes is unusual: that the behaviours required to hold a team together on a two-year ocean voyage are the same behaviours that determine whether a leadership team delivers or stalls, and he can evidence that claim from both sides of the equation.
The Big Bold Circle’s 20 principles connect individual mindset to team behaviour to organisational execution, giving buyers a framework that extends beyond the event into coaching, offsites and leadership programmes.
Organisations including Johnson & Johnson, GSK, Boston Consulting Group and Burberry rebook him, evidence that the material holds up under repeated use with commercially sophisticated audiences.
Biography highlights
Author of three Bloomsbury-published books: Where the Magic Happens, Be More Human: Rethinking the Rules of High-Performance Teamwork, and The Big Bold Mindset: Re-thinking the Rules of Leadership
Former Associate Director at KPMG; former CFO in the technology sector, including a business sold to Private Equity
Built, scaled and sold a technology business to a stock market listed company
Team leader on trophy-winning yacht in the BT Global Challenge (2000/01)
Captain of family circumnavigation (2014/16), leading a crew that included three children under ten
Speaker for global organisations including Johnson & Johnson, GSK, Boston Consulting Group, Burberry, Standard Life and BAE Systems
Biography
Most leadership teams do not lack ambition. They lack the thinking that holds when ambition meets sustained pressure. Caspar Craven has spent three decades studying that gap, in FTSE-boardroom pressure, in the execution risk of building and selling a technology business, and in the conditions of offshore sailing, and building the frameworks that close it.
His commercial background is foundational. As an Associate Director at KPMG and then CFO of a technology business sold to Private Equity, Craven worked inside the financial and strategic pressures that boards and senior leadership teams actually face. He then built and exited his own technology company, selling it to a listed firm for a seven-figure sum. That sequence – corporate discipline, then ownership, then entrepreneurial risk – is the basis of his credibility with finance, commercial and executive audiences.
The two round-the-world sailing voyages are not adventure narrative. The first, as a team leader on a trophy-winning yacht in the BT Global Challenge (2000/01), tested leadership under competitive pressure and physical exhaustion. The second (2014/16), as captain of a family crew including three young children, tested something harder: sustaining shared values, clear roles and collaborative decision-making over two years in an environment where the cost of poor leadership is immediate and real. Both voyages provided the evidence base for the frameworks he now teaches.
That evidence base is formalised in the Big Bold Mindset® and the Big Bold Circle, 20 principles connecting individual mindset to team behaviour to organisational execution, published across three Bloomsbury books. The framework has been applied with leadership teams at Johnson & Johnson, GSK, Boston Consulting Group, Burberry and Standard Life, among others. The core argument is practical: that the gap between ambitious goals and actual delivery is a thinking and behaviour problem, and that it can be addressed systematically.
Key speaking topics
Leadership mindset and behavioural change
High-performance team dynamics
Goal-setting and execution under pressure
Decision-making in uncertainty
Resilience and organisational adaptability
Entrepreneurship and business growth
Culture change and human-centred leadership
Ideal for
Senior leadership teams and executive committees setting ambitious growth or transformation targets
CHROs and L&D leaders designing leadership development programmes, particularly for high-potential talent or senior cohorts
Commercial and sales organisations at annual kick-offs or strategic resets
Boards and C-suite audiences navigating significant change, M&A, or sustained performance pressure
Audience outcomes
A named, structured framework (The Big Bold Mindset® and Big Bold Circle) applicable immediately to their own goals, team dynamics and leadership behaviours
Clearer understanding of why leadership teams stall under pressure, and what specifically needs to change in how they think and make decisions
Practical approaches to aligning teams around ambitious goals, reducing execution friction and sustaining momentum through setbacks
A shared vocabulary for discussing leadership mindset and team behaviour that moves beyond generic or abstract concepts
Renewed confidence in pursuing bold goals, grounded in evidence and principle rather than motivation alone