"This isn't 'finance' at all", reflects Diana. "It's not about investment, tax, legal, or accounting; my work concerns a client's relationship with their wealth as they move to a place of greater awareness, competence, and confidence in that regard."
Diana set up her own business in 2002 after over 15 years spent working for a range of non-profit organisations. She has the broadest of job descriptions which can, on any given day, find her addressing deeply personal questions from clients on relationships, love, and family, all through the lens of money. The kind of questions at which many traditional financial advisors or mentors would balk.
Diana has found a nice where she helps clients manage their wealth in "emotionally intelligent ways". This includes serving as a trusted confidant, one capable of providing honest and personal advice, backed by insight and experience.
In doing so, she encourages her clients to develop their Financial EQ or Emotional Intelligence—the ability to manage their emotions about money in the face of others' emotions.
"It's very customised", Diana says, "and is about our relationship with money based on our personal life experiences.
"What I do is help my clients to develop what I call 'financial emotional intelligence skills' as they understand how money changes them and their relationships, how to talk about it constructively, resolve conflicts around it, and negotiate over it.
"One significant challenge can be dating and how people with significant wealth have a trusting, generous relationship when their partner has much less financial resource than they do. It takes skill to navigate such differences in a relationship."
The results can be transformative as Diana explains. "The issues have great meaning for clients. I recently worked on a big philanthropy project over a few years with a client who was tremendously grateful that we were able to animate the project through her generosity. And she saw herself in a new light because of it. In other instances, I've helped parents share their financial plans with their children and grandchildren, couples navigate gracefully their premarital agreements, and individuals decide how best to use their wealth to reflect their values."
Her family wealth mentoring practice is a direct result of personal experience. It has been inspired in part by her studies at the University of Edinburgh, including her junior year abroad at the Wharton School of the University of Pennsylvania.
Professionally, her time at Redland PLC, where she was the first woman hired into management as a member of the strategic planning team, and her work directing three charitable organisations, have also been key influences. She knows what it takes to generate substantial wealth and, as desired, to give it away strategically.
The foundations run even deeper as Diana can speak to clients with the understanding of a third-generation member of a UK business family.
"My role as a mentor is to encourage my clients through what is new territory for many", she continues. "I act as their guide along the way. Their experience of increased understanding is so motivating to them that they want to continue because they know the benefits.
"This builds confidence. Clients feel much more comfortable with the resources at their disposal and they make increasingly conscious decisions as a result of their insights."
It is, Diana admits, an esoteric field, but one which has a deep and lasting impact on clients and their families, with whom she also works closely, to ensure they are well-prepared to manage the wealth they inherit.
I always help them to deepen their understanding, so they feel more at ease with the outcome.
Her work has inspired a book, True Wealth: Letters on Money, Life, and Love, which captures the essence of who she is and what she does.
The 2016 book takes the form of a series of letters to Diana on a variety of problems, which she then answers in a candid and personal way.
It mirrors situations she faces every day and also hints at the burden of responsibility she carries. In many ways her success cannot be measured by the bottom line and can only be truly answered by her clients.
"We have to go under the surface and distinguish the situation and role for each client. People could have arrived at apparently the same situation through very different circumstances and life experiences. It's really important to understand what drives a situation and that will determine the appropriate response.
"There are some basic principles that can be applied to every difficulty that emerges. The biggest challenge—and also the first and best line of defence around difficulties with wealth—is the ability to communicate effectively about it. Unfortunately, we are not typically taught such skills and the British are noted for their discomfort in addressing what they consider difficult conversations.
"While I might not be able to help my client to resolve fully a particular issue, I always help them to deepen their understanding, so they feel more at ease with the outcome."