Di first began working with Ann Paul when she stepped into her first Chief Executive role at a national healthcare charity, Doctors in Distress. While she brought strong capability and commitment to the role, the transition into executive leadership brought the same challenges faced by many first-time CEOs: balancing strategic leadership with operational realities, managing stakeholder expectations and developing confidence in her own leadership style.
Several years later, the relationship continued through a very different chapter as she navigated a complex departure from the organisation and prepared for her next leadership role. Today, she serves as CEO of a creative social enterprise, Pluto Productions, applying many of the lessons and leadership approaches developed throughout that journey.
Challenge
Leadership challenges rarely arrive in isolation. The early conversations focused on defining what effective leadership looked like in a first CEO role, creating space to think strategically while managing the day-to-day pressures of running a growing organisation.
Later, the focus shifted towards navigating uncertainty, making difficult decisions and managing a leadership transition at a time when the path forward was not always clear. Throughout both periods, there was a need for trusted support, honest challenge and an experienced perspective that could help separate immediate pressures from long-term priorities.
Approach
Di acted as both mentor and strategic sounding board, creating a confidential space for discussion, reflection and decision-making.
Drawing on her own leadership experience, she provided practical challenge, strategic perspective and what her client describes as "straight talk" when it was needed most. Together, they worked through organisational challenges, leadership decisions, stakeholder dynamics and broader questions around career direction and personal leadership development.
An important aspect of the relationship was knowing when additional perspectives could add value. Rather than making introductions for the sake of it, Di carefully connected her mentee with individuals whose experience or expertise could genuinely help inform key decisions, ensuring every conversation had a clear purpose and practical value.
Over time, the relationship evolved from supporting a first-time CEO to acting as a trusted adviser through some of the most significant decisions of her leadership career.
Outcome
The mentoring relationship helped build confidence, clarity and resilience across multiple phases of executive leadership.
The client successfully navigated both the opportunities and challenges of her first CEO role before moving into a new leadership position with a clearer sense of direction and stronger decision-making confidence.
In her current role, she has gone on to strengthen governance structures, develop a more commercially aware organisational culture and build stronger partnerships, particularly within the NHS, helping create a more sustainable platform for future growth and impact.
Testimonial
“Di has been my rock through at least two separate challenges. When I took on my first Chief Executive role, Di was my sounding board, not only in developing my own role but also in listening to and advising on the charity's strategic direction.
Some years later, Di helped me navigate some very tricky times as I worked toward the exit of that role and my next one. Having Di as my mentor on both occasions has meant I have a critical friend, sharing her years of experience and some very straight talk. Without this, my decisions might have been very different.
Di would be top of my list of recommendations for mentoring.”