Tom Preston Of The Preston Associates On The Top 5 Trends Shaping the Future of Coaching
  • Chad Silverstein
  • March 28, 2025
  • 6:11 pm
  • 0 comments

An Interview With Chad Silverstein

Our priority is to partner with our clients to help them enhance business performance through the development of better leaders. Through this, we are able to help the greatest number of people in the most meaningful way. We work towards this goal every day and in everything we do.

In today’s tech-driven world, artificial intelligence has become a key enabler of business success. But the question remains — how can businesses effectively harness AI to address their unique challenges while staying true to ethical principles? To explore this topic further, we are interviewing Tom Preston

Tom Preston, co-author of COACHING POWER, is the founder of The Preston Associates, one of the world’s premier executive coaching firms. With decades of experience coaching leaders across industries and geographies, he has helped organizations achieve extraordinary outcomes. A former private equity executive and bestselling author of Coach Yourself to Success, he brings deep insights and practical wisdom to his work.

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 parents were both in the medical profession so I guess the seeds of being in service to others were sown early. My career started as a commodity trader working in Africa and the Middle East where I really cut my commercial teeth. I was then charged with running a Private Equity fund based out of Hong Kong and it was then that my coaching career started to form. I sat on the boards of several companies at any given time and I quickly realized that I was far more interested in helping the CEOs and their management teams to think through strategy, engaging their people and how to define and deliver on a shared definition of collective success than I was in discounted cash flows. In other words, I started to coach senior executives. At the point that I realized that coaching was “a thing”, I did a post-grad in Executive Coaching and the rest is history including the formation of The Preston Associates.

Twenty-two years ago, the biggest challenge was persuading organizations of the value of coaching and that the best people to offer it to were not remedial cases but their top talent. Thankfully, today, that is not what we need to discuss with 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?

In my personal experience, these are the traits that have helped me to build The Preston Associates successfully over many years.

  1. Optimism. When I started Executive Coaching, few believed in its longevity. I had experienced firsthand the power of it so I just knew that if I stuck with it long enough it would work — no matter how many people told me to think otherwise.
  2. The will to engage people in a vision of collective success. People need to know where they are headed. They need a vision to guide them and they need to believe that it is possible to get there. As I have had to do this over many years in my own organization and with many clients, we developed a leadership mantra to help people: “The perfect leader absorbs pressure, transmits clarity and builds the confidence in others that they need to succeed.” If leaders do those three things, more often than not, they are successful.
  3. Determination. In the early days of The Preston Associates, like many leaders late at night, I questioned my abilities. My imposter syndrome would come out to roam and the psychological ghosts that haunt many leaders played havoc with my brain. But every morning I would wake up after my dance with my ghosts and remember something that a wise woman had once said to me: “How do you walk a thousand miles? Put one foot in front of the other, and don’t stop.”

Can you share your favorite “Life Lesson Quote”? Why does that resonate with you so much?

It is a Tibetan saying: “You never know when you are being lucky”. And it is important because all business people are buffeted about by change. Sometimes things happen that seem bad but are actually for the best because they lead us to think differently or to problem solve differently. This approach keeps me solution oriented no matter what is going on.

What are some of the most interesting or exciting projects you are working on now? How do you think that might help people?

The opportunities to help clients are almost infinite right now. Some of the key areas we are focused on: coaching of executive teams to become high performing; helping businesses to understand and harness neurodivergent talent; ensuring that the leaders we coach are becoming better coaches themselves through the process of being coached which is the subject of my new book COACHING POWER written with my colleague Luciana Nunez; and helping ultra-high net worth families cohesively plan succession and intergenerational success.

Without saying any names could you share a particularly memorable success story from your coaching career?

It was working with the leadership team of a fast-moving consumer goods company that manufactured food products in a North African country. When we started the coaching journey sales were falling, people in the company were dispirited, and profitability was evaporating. I guess the overriding describer would be “depressing.”

Working with the leadership team we developed, on a single sheet of paper, a strategy — three key business drivers and four behaviors which would rekindle the company’s success. We then launched this internal recovery “brand” to drive empowerment, accountability, and responsibility using screen savers, posters, conferences, celebrations of success and storytelling to engage the 1,000 employees. Slowly the ship started to turn around and after eighteen months sales were growing at 26%. The best part of a challenge like that is that, while it is hard work, it is also incredibly rewarding and also fun! Did I mention that it all started with a meeting with the leadership team in an oasis in the Sahara Desert?

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?

I think that the fundamentals of coaching have stayed fairly constant. What has changed is the different interventions that have evolved from those strong foundations. Today, coaching is not just about working one-to-one with a leader. It is about team coaching, group coaching, and on-boarding talent into senior roles to ensure that they are best set-up for success. It is about working with groups of people in the same organization to optimize cross-functional collaboration and trust to lubricate success. And it is about really listening to all levels of organizations to understand what is working as much as what is not working yet.

At The Preston Associates, we really apply to ourselves, both individually and collectively, what we preach to our clients. This results in continuous learning and development, which we take very seriously.

Personally, I have the fortune to spend a lot of time with my colleague Luciana Nunez, who is one of the most talented coaches out there so I am continuously learning from her.

How do you incorporate feedback into your coaching practice to continuously improve?

As you might imagine, we are big into feedback. We encourage our clients to both give us feedback on their experience of working with us and also to seek feedback on how their work with us is being experienced by others. This two pronged feedback approach allows both us and our clients to understand what has changed and what is still a work in progress. We spend significant amounts of time understanding what our clients’ needs are and then we create internal pods to build and innovate on what we know works and how to make that consistently better and relevant to our clients in a changing world. We also have a culture of generous learning where we share our individual learnings with the collective so that we are all constantly learning from each other.

Can you discuss an innovation in coaching that you believe is currently underappreciated but has the potential to significantly impact the field?

We believe that traditional management consulting will need to embrace a combination of their expertise coupled with the coaching approach and skills of coaching experts. We recently did some very interesting work where a client hired one of the very well-known consultancies for their expert technical knowledge, and us to help deploy the mindset change, engage their leaders to adopt and apply the change and to cascade the required changes in ways-of-working.

In what ways can coaching address the evolving mental health needs of diverse populations in a digitally connected world?

Today, good coaches are focused on the full spectrum of a client’s being. As my colleague and contributor to Coaching Power, Julie Stokes describes it — the constellation of Person, Role and System. Having an external, objective and trusted thinking partner aware of all three of those lenses goes a long way to helping people maintain their mental health or becoming aware at an early stage if something is slipping. And where possible, we encourage a combination of in-person and virtual meetings in an attempt to avoid digital isolation.

How do you foresee artificial intelligence and machine learning transforming the coaching industry in the next decade?

It will undoubtedly have a tremendous impact, not least because of the impact it will have and is having on the clients we work with. So we need to stay totally current on both AI and machine learning and the opportunities and challenges they bring.

We think that in many instances, both will help us to become more efficient, use data better, and deliver many of the benefits that apply to all businesses.

It will also facilitate more commoditization or democratization of coaching such that it becomes more accessible to more people at reasonable cost through digital platforms.

However, at the senior level where we operate, for the foreseeable future, we see technology as an enhancer and enabler of our work rather than a replacement of the human coach. In fact, demand is likely to increase because leaders will be faced with the new leadership challenge of humanizing the adoption of technology.

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?

We think that these will be critical, and not just in the context of coaching. It is perhaps even more relevant in the context of coaching because one of the fundamentals of coaching is confidentiality.

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.

1 It’s here to stay. The vast majority of medium and large companies and organizations now know that coaching is effective both as a talent enhancer, retainer and a critical development tool.

When I first started coaching and did a Google search of the phrase Executive Coaching, there were about 1.6 million entries. Today there are over 200 million.

2 . Flexibility. As more talent professionals understand all the various ways in which coaching can be used, it will grow both in uptake and adoption to address multiple talent support and growth goals.

An example of this was our recent work with a major bank helping to on-board a new CFO. The engagement involved speaking to all his stakeholders to get clarity on expectations, helping the new CFO understand the culture of the hiring organization and providing coaching to help the CFO land well and feel embraced early on in his tenure.

3 . Bifurcation. There is a clear bifurcation in the coaching market. At the top end, servicing the top 10 percent of executives, it requires high touch, deep business understanding and leadership experience from the coach. The level of sophistication required for the coach to act as a true thinking partner to senior people has never been higher or more needed as the complexity of navigating the commercial jungles grow. Below that top 10 percent, companies are likely to take a more commoditized approach using primarily coaching platforms, purely virtual sessions and increasingly the use of AI to provide a minimum level of coaching support to more members of their organization at affordable cost.

4 . Leading with coaching. Leaders will increasingly be expected to lead with a coaching style and have advanced coaching skills. This is because their leadership audience is more diversified than ever before in terms of age, now covering five generations all with different leadership expectations, cultures, change adoption skills and experience of transformation.

We consistently see in our work that leaders who can embrace and apply coaching as part of their leadership outperform those with more monochromatic styles.

5 . Emotional intelligence focus. As the demands of leadership become ever more complex the need to understand, firstly self and secondly others, becomes ever more important. In order to develop the ability to empathize, to create optimal social awareness and to manage relationships effectively, there is an acknowledgement that the first step is born from self-awareness. Once the awareness of one’s own emotions, strengths and weaknesses, motivators and energy drainers can be identified and articulated then self-regulation can be achieved. This combination of self-awareness and self-management, unleashes the emotional intelligence required to better lead others.

Many of our clients are truly changed once they understand how their beliefs and life stories have resulted in both helpful and unhelpful unconscious impacts on how they lead both themselves and others.

How do you envision the integration of coaching within organizational cultures changing the landscape of leadership and employee development?

Organizations know that embedding a coaching culture has become a must have, especially for the younger generations who throughout their education have grown used to having coaches both in the form of tutors and sports coaches. Ignore this need at your peril.

What do you see as the biggest challenge facing the coaching industry today, and how might we overcome it?

Quality. Everyday hundreds and perhaps thousands of people become coaches. How are they trained, what commercial, leadership, strategy and sector experience do they have to support the term executive or business coach? How well does the platform they work from know them, how deeply have they done their due diligence on the coaches they proffer? How does their continued professional development and supervision work? The best users of coaching today really understand how to select the best coaches. After all, putting your best talent in good hands with a coach is the priority.

What is one long-term goal you have for your coaching practice, and how are you working towards it?

Our priority is to partner with our clients to help them enhance business performance through the development of better leaders. Through this, we are able to help the greatest number of people in the most meaningful way. We work towards this goal every day and in everything we do.

How can our readers continue to follow your work?

About the Interviewer: Chad Silverstein is a seasoned entrepreneur with 25+ years of experience as a Founder and CEO. While attending Ohio State University, he launched his first company, Choice Recovery, Inc., a nationally recognized healthcare collection agency — twice ranked the #1 workplace in Ohio. In 2013, he founded [re]start, helping thousands of people find meaningful career opportunities. After selling both companies, Chad shifted his focus to his true passion — leadership. Today, he coaches founders and CEOs at Built to Lead, advises Authority Magazine’s Thought Leader Incubator.

Tom Preston Of The Preston Associates 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.