We caught up with the brilliant and insightful Damon D’Amore a few weeks ago and have shared our conversation below.

Damon, thanks for taking the time to share your stories with us today We’d love to hear about the best advice you’ve ever given to a client?

A client was starting a new job as CEO of a large public company. This was her first position in the C-Suite and the company, due to the nature of it’s business in a highly-regulated industry had a deeply political corporate culture with most senior executives having been employed there for many years. There was a deep skepticism and reluctance to support a new CEO from outside of the organization.

I advised the client that while there would be a number of leadership challenges she will need to address and skill sets to develop, the most important resource for her to possess was a crystal clear narrative of why she was the right leader for this company at this time in their history and, more importantly, how the executive teams and other internal stakeholders would measurably benefit by supporting her efforts and plans.

By the end of her first quarter as CEO not only were the majority of executives and team members supportive of her actions and the various changes she was implementing but she received unsolicited feedback from team members, employees and the board of directors of her acceptance as part of the culture. This provided her with confidence and positive emotional relief allowing her to focus on executing her core strategies rather then spending time and energy on consensus building. And, to her surprise, the most reluctant and skeptical members of the executive team engaged and advocated for her initiatives as they clearly understood how they would personally and professionally benefit from her success as key stakeholders.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

I advise C-Suite clients, the majority of whom are women, in the areas of personal and professional performance, developing personalized systems to perform at their highest levels while maintaining a healthy psychological and emotional self, storytelling for key stakeholders to build advocacy and engagement to support their efforts in achieving what matters most, and leading in crisis and navigating ambiguity.

Clients participate in a structured curriculum, working one-on-one over six or twelve month programs. One of the unique aspects of Legacy Mentor proprietary programs is that clients are able to dive deep into all aspects of their performance: psychological, emotional, communication, and execution – bridging the gaps between these pillars of performance and measure progress and success at any step in the process.

I am most proud of the moments where clients felt empowered, understood and valued by their stakeholders. The emotional benefit from not only realizing success in their business but seeing a direct correlation between success and their ability to manifest lasting legacy goals, to positively affect the lives of those most important to them for years or even decades to come.

What’s worked well for you in terms of a source for new clients?

Referrals have hands-down been the best source for new clients in my business. A lot of the work clients do in our programs is deeply personal and confidential as it relates to their business model, strategy, execution and practices. When these leaders are able to share their success stories with close peers in mastermind groups, their board members or personal stakeholders, they are able to convey the true value of making the time and resource commitment to a structured curriculum over six to twelve months as opposed to casual coaching which aims to get a client “better” but without clear, specific or measurable goals.

Also, the female leaders I work with experience benefits they convey to the other women in their network at a level that transcends general testimonials or references.

Are there any books, videos or other content that you feel have meaningfully impacted your thinking?

There are five books that I consider to be highly impactful on my personal and professional development that I recommend to clients, mentees and students I work with. https://legacymentor.co/five-favorite-personal-development-books-time/

(in no particular order)

1. Turning Pro by Steven Pressfield:

“Ambition is the most primal and sacred fundament of our being. Not to act upon that ambition is to turn our backs on ourselves and on the reason for our existence.” The premise of the book is that the world is divided into two camps of people: Amateurs and Professionals. Amateurs make up the bulk of society. They bow to resistance at every turn when confronted with challenges on the journey to finding their bliss in life, true meaning and most productive offerings to others. They are fearful, seek external validation from the crowd and do not believe they are deserving of great accomplishments.

Professionals are willing to do the hard work – internally and externally – in committing to fight any and resistance daily. They create and sustain habits, they self-validate and see themselves as a hero in the story of their lives. They know that resistance can never be completely overcome but instead a battle each and every day of life, and the professional re-commits to that battle daily.

2. Essentialism by Greg McKeown:

“If you do not prioritize your life, someone else will. What are you going to do with your one wild and precious life?” This book is not only a great read for increasing productivity on a tactical level but also in crafting a philosophy for life in all areas regarding choice, control and perspective to the end of living a life of meaning and contentment – your “Essential Intent.”

We all have problems regardless of the degrees of success that are attained. The real question is: What problems do we WANT to have? A core principle of Essentialism is saying ‘no’ but not for the sake of saying no – instead creating filters so you are saying ‘yes’ to the right things – those which can clearly lead to accomplishing your life goals. This means making trade-offs – another core component of this mindset and the one that most folks have problems committing to.

“If you take one thing away from this book, I hope you will remember this: whatever decision or challenge or crossroads you face in your life, simply ask yourself, ‘What is essential?’ Eliminate everything else.“

3. Nobody Wants To Read Your Sh*t by Steven Pressfield:

“There are only two fundamental principles: 1. Nobody wants to read your sh*t; 2. If you want to write and be recognized, you have to do it yourself.” This is my favorite book ON writing – the actual process, not just the necessary mindset for success. Filled with tons of examples from both Steven’s life and fictional case studies it represents everything most important when sitting down to begin writing. Some core principles:

Streamline your message. Focus it and pare it down to its simplest, clearest, easiest-to-understand form.

Make its expression fun. Or sexy, or interesting or scary or informative. Make it so compelling that a person would have to be crazy NOT to read it.

Apply that to all forms of writing or art or commerce. When you begin to understand that nobody wants to read your sh*t you begin to understand that writing/reading is, above all, a transaction. Readers donate time and attention, and the writer must give the reader something worthy of his gift.

4. Zen Mind Beginner’s Mind by Shunryu Suzuki:

“Zazen (meditation) practice is a direct expression of our true nature.”
I am definitely not super foofy or new age, but I am spiritual and believe that lessons learned about our core emotional and mental selves only serve to empower us in all areas of life including business and legacy.

This is a very accessible book for beginners in meditation and also considered a classic among experts who continue to mine its lessons for decades. And I love the core principle:

“There is no need to have a deep understanding of Zen. You should never say “I know what Zen is,” or “I am enlightened” – that is ridiculous and also the secret of the arts: always be a beginner.“

5. Letters To A Young Poet by Rainer Maria Rilke

“Perhaps all the dragons in our lives are princesses who are only waiting to see us act, just once, with beauty and courage. Perhaps everything that frightens us is, in its deepest essence, something helpless that wants our love. Have patience with everything that remains unsolved in your heart….live in the question.”
Over a period of five years the great poet Rilke wrote a series of remarkable responses in letters to a young would-be poet who wrote to him of his problems and hopes. Rilke’s responses provide lessons far beyond writing poetry into areas of life, love, work and surviving as a “sensitive observer in a harsh world.”

I gift this book to all of the students I teach and mentor upon their graduations – MBA, undergraduate and high school. It’s a short book but one that can be read many times and provide valuable guidance on any and all journeys.

Contact Info:

• Website: https://legacymentor.co/
• Instagram: https://www.instagram.com/legacymentorofficial/
• Linkedin: https://www.linkedin.com/in/damondamore/