An Interview With Chad Silverstein
…My coaching approach has shifted from a solutions-focused methodology to one that prioritizes self-awareness and empowerment. I’ve learned that lasting change happens when clients uncover their own insights and take ownership of their growth. Personally, I continue to challenge myself with ongoing education and feedback, ensuring that I remain adaptive to my clients’ needs…
The world of coaching is undergoing a seismic shift, with emerging trends set to redefine its boundaries and possibilities. From digital transformation and the integration of artificial intelligence to the growing emphasis on mental health and the global rise of coaching cultures within organizations, these developments are reshaping the landscape of personal and professional growth. As we navigate through these changes, understanding the forces that drive the future of coaching becomes paramount. I had the pleasure of interviewing John Little of The Winners Edge Coaching.
The Winners Edge Coaching was established by John Little, who has over 25 years of experience as a business leader, entrepreneur, and consultant. John has developed and coached hundreds of talented people who have since advanced to Executive Directors, Vice Presidents, Senior Managing Directors, Managing Directors, Senior Business Leaders, and Individual Business Owners.
Strategically, John helps leaders identify priorities, assess and address challenging situations, develop short and long-term goals and establish a plan of action to achieve successful outcomes. His expertise lies in helping leaders identify and overcome imposter syndrome.
John holds certifications in DISC, Myers Briggs Type Indicator (MBTI), and Fundamental Interpersonal Relationship Orientation (FIRO-B), as well as a certificate from Cornell University for Diversity and Inclusion for HR Professionals. With extensive experience in corporate Equity, Inclusion, Belonging, and Engagement strategies, John combines his vast leadership knowledge and coaching skills to help elevate seasoned and emerging leaders. John’s lifelong passion for people is evident in his work as a developer of talented individuals, from those starting their careers, all the way into the C-Suite.
Thank you for joining us. To start, could you share your “origin story” with our readers? How did you begin your coaching journey, and what challenges did you face in the early days?
My career as a leader and my coaching journey began over 25 years ago. I describe my job history as a jungle gym rather than a ladder, but at every stop, I was in some level of a leadership role. Freshly out of college working in television network production, I was positioned to recruit and supervise interns. As a supervisor of a group of editors and freelancers I was simultaneously teaching, coaching, leading and partnering with my team on a daily basis. When I transitioned into corporate roles, I was leading teams both locally and remotely.
I noticed a recurring theme: many talented individuals were held back by limiting beliefs, imposter syndrome, and a lack of emotional intelligence. These obstacles prevented them from reaching their full potential. Inspired by this, I transitioned into coaching to help others overcome these barriers.
The early days were challenging. Establishing credibility in new fields and roles required me to lean into my own vulnerabilities while learning to articulate the value of coaching. I also didn’t have the type of leadership role modeling early in my career that served me well, thus I struggled greatly ‘finding myself’ as a leader when I was in my first few roles. Balancing the need for growth with maintaining authenticity as a coach was a delicate act. Fortunately, I met some tremendous mentors and realized that each challenge became an opportunity to model the behaviors and resilience I now teach my clients.
You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?
- Empathy: As a leader, I realized early on that understanding others’ perspectives is key to fostering trust and collaboration. For example, during a high-pressure moment of departmental change, I took time to listen to my team’s frustrations and aspirations. I recognized that if my team didn’t have my ear and I wasn’t responding in the way that they needed me to in those moments, the transition would be much more challenging. That empathy helped me guide them to success while improving trust and morale.
- Resilience: Setbacks are inevitable, but how you respond defines your growth. Early in my career, I faced a significant professional setback that could have derailed me. I was moved from a leadership role into one of being an individual contributor. It was public and embarrassing, and I wanted to give up and quit. Instead, I reframed it as an opportunity to learn and pivot, which ultimately led to greater opportunities and most importantly, lessons that have served me greatly since that time.
- Personal Leadership Brand: When I’ve struggled the most as a leader have been the times that I was trying to be someone other than my genuine self. My genuine leadership brand is kind, consistent, loyal and solution oriented. When I’ve stepped too far outside of that, it makes it harder to build trust. It makes it more difficult for others to connect with me and for me to be effective. What I’ve found is my brand of kind, consistent, loyal and solution-oriented makes it easier for me to hold people accountable, give direct feedback, create space for innovation and have necessary conversations. This brand has regularly strengthened relationships with stakeholders and fostered trust with my team.
Can you share your favorite “Life Lesson Quote”? Why does that resonate with you so much?
One of my favorite quotes is: “Between stimulus and response, there is a space. In that space is our power to choose our response. In our response lies our growth and our freedom.” — Viktor Frankl. This resonates deeply because it underscores the importance of self-awareness and choice. It reminds me — and the leaders I coach — that while we cannot control every circumstance, we can control how we respond and grow from it.
What are some of the most interesting or exciting projects you are working on now? How do you think that might help people?
I’ve recognized that the #1 people/talent-oriented challenge that organizations face is imposter syndrome. While the common assumption is that imposter syndrome is an individual issue, the reality is that most, if not all, areas that organizations are faced with — high turnover, low engagement, reduced productivity, increased legal risk — are a direct or indirect result of leaders struggling with imposter syndrome.
That leads to challenges in building trust within teams, cultures that don’t support innovation, low psychological safety/security, micromanagement, self-preserving behaviors and disconnected leaders.
One project I’m particularly excited about to help navigate and overcome those issues is my Leadership Accelerator Bootcamp, which is based on the EMBRACE framework (Empathy, Mindset, Brand, Resilience, Authority, Capabilities, Effectiveness) that I developed. This program empowers leaders to build their emotional intelligence, enhance their leadership brand, and unlock their influence and authority.
It has already radically and rapidly transformed how my clients engage with their teams and approach challenges, creating a ripple effect of positive impact within their organizations.
Without saying any names could you share a particularly memorable success story from your coaching career?
One client came to me feeling overwhelmed and stuck in a mid-level leadership role. Through coaching, we worked on dismantling their imposter syndrome, redefining their personal leadership brand, and improving their communication strategies. Within a year, and with just 4 key models around trust, communication, change and leading in the moment, they were promoted to a senior leadership role (and a $60k pay increase) and became a trusted advisor within their organization. Watching their transformation and how much their confidence has skyrocketed has been amazing to see.
Ok, thank you for that. Let’s now jump to the primary focus of our interview about coaching. How has your approach to coaching evolved over the years, and what personal learnings have you applied to your own development?
My coaching approach has shifted from a solutions-focused methodology to one that prioritizes self-awareness and empowerment. I’ve learned that lasting change happens when clients uncover their own insights and take ownership of their growth. Personally, I continue to challenge myself with ongoing education and feedback, ensuring that I remain adaptive to my clients’ needs.
How do you incorporate feedback into your coaching practice to continuously improve?
Feedback is invaluable and I believe that genuine feedback is the ultimate form of kindness. What better way to show that you’re invested and care than to give your honest perspective?
After a series of sessions, I often ask clients what resonated and what could be improved. This iterative process not only strengthens my effectiveness as a coach but also models the importance of feedback for the leaders I work with.
Can you discuss an innovation in coaching that you believe is currently underappreciated but has the potential to significantly impact the field?
The use of data-driven insights in coaching is underappreciated. Tools like psychometric assessments and behavioral analytics can provide deeper, actionable insights for clients, leading to tailored strategies that accelerate growth.
Also creating measurable alignment of KPIs that are related to coaching goals brings an added layer of tangible components of the direction and impact of coaching. For example:
Patience — Maintain professional composure in challenging situations by documenting and responding to at least 90% of issues without escalation. Solicit feedback from colleagues quarterly, achieving a satisfaction score of 80% or higher regarding handling frustrations constructively.
Teamwork — Participate in or lead at least three cross-departmental projects per quarter, with at least one project requiring collaboration with a department outside Marketing. Ensure 90% of team members involved rate the collaboration as productive in follow-up surveys.
Adaptability — Successfully implement or contribute to solutions for at least three unforeseen challenges or new initiatives per quarter, achieving a minimum success rate of 80% based on project objectives or outcomes.
In what ways can coaching address the evolving mental health needs of diverse populations in a digitally connected world?
All of my coaching is done virtually from my home base just outside of Ft. Lauderdale, FL. By being able to utilize technology to connect with anyone across the globe, it not only allows me to be a resource but more importantly, it gives me the chance to be a student and learn about the various challenges that people are facing. This provides perspective and a vast array of potential solutions as things continue to rapidly change.
How do you foresee artificial intelligence and machine learning transforming the coaching industry in the next decade?
What I think we will see…and I am brainstorming on now…is coaches who will be able to train AI on their coaching pillars, models and goals that will create a ‘Coach in Your Pocket’ type of experience.
Think of this scenario — You have a tough meeting coming up with the CEO and you want to do a ‘dry run’ of your conversation. Using the coach’s pillars and models, along with some info about the topic and the individual, you can practice the conversation with a LLM (large language model) to build confidence and smooth rough edges of your preparation.
What role do you believe ethical considerations and privacy concerns will play in the future of coaching, especially with the increased use of digital platforms?
Coaches must establish transparent practices for data use, ensure confidentiality, and remain vigilant against biases introduced by technology. Simply having a confidentiality or non-disclosure statement aren’t really going to be satisfactory going forward. Coaches will need to be intentional about privacy.
Could you list and briefly explain “Top 5 Trends Shaping the Future of Coaching” based on your experiences and insights? If you can, please share a story or example for each.
- Hybrid/Group Coaching Models: Combining in-person and virtual coaching for accessibility.
- Emotional Intelligence as a Cornerstone: EQ is becoming increasingly critical for leadership development. It has been for a long time but there’s a need to continue to emphasize the basics, especially for newer leaders.
- AI Integration: Using AI tools for personalized client insights and progress tracking.
- Focus on Holistic Health: Coaching that addresses both professional and personal well-being while also being mindful of other areas of life (financial, spiritual, etc.) that may be relevant.
- Community-based Coaching: Fostering peer support and shared growth through group coaching environments.
How do you envision the integration of coaching within organizational cultures changing the landscape of leadership and employee development?
Coaching remains integral to strong leadership pipelines. Training is the entry point, but the reality is that most organizations don’t have the capacity to do training AND coaching…which are two different things.
Organizations that embrace coaching as part of their culture will see improved employee engagement, retention, and innovation, as leaders are empowered to mentor and inspire their teams effectively.
What do you see as the biggest challenge facing the coaching industry today, and how might we overcome it?
Saturation and homogeneousness. You can’t log onto LinkedIn without stumbling into seventeen coaches.
Being able to find specifically what you need is paramount to mutual success. If I were merely a ‘leadership coach’, I would starve. But being an Executive Performance Coach who focuses on helping people find ways to live inspired, influential lives by overcoming imposter syndrome so they can become confident, authentic leaders in their homes and careers allows me to serve a specific role for a specific profile.
What is one long-term goal you have for your coaching practice, and how are you working towards it?
My long-term goal is to build an online leadership community as part of my Leadership Accelerator Bootcamp that provides continuous learning, peer support, and resources for emerging and established leaders. I am working toward this by developing a digital coaching platform and seeking feedback from my clients to ensure it continuously meets their needs.
How can our readers continue to follow your work?
https://www.linkedin.com/in/bigjohnlittle/
https://thewinnersedgecoaching.com/
https://www.linkedin.com/company/thewinnersedgecoaching/
Thank you for offering such valuable insights into the future of coaching. We look forward to seeing your work continue to reach new heights, and we wish you continued success.
About the Interviewer: Chad Silverstein is a seasoned entrepreneur and Thought Leader with over 25 years of business experience. He has founded, operated, and exited multiple companies and now builds into a handful of high impact CEOs. Chad has launched multiple online communities, including a recent leadership development platform, and also serves as a strategic advisor for Authority Magazine’s thought-leader incubator program. To learn more and connect with Chad visit: chadsilverstein.io
John Little of The Winners Edge Coaching on The Top 5 Trends Shaping the Future of Coaching was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.