An Interview With Chad Silverstein
Trust as a cornerstone: despite all of the benefits of AI, and the “group coaching” approach, these approaches can challenge the ability of a coach to earn the most important element for a successful coaching engagement: trust. Gaining the trust of a coachee has never been more important. Early on in a coaching engagement, we clearly outline what information is shared internally, externally, etc. and empower the client to define what is to remain confidential.
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 David Frost, Co-CEO and Head of Executive Coaching, fassforward.
David has led fassforward’s Executive Coaching Practice since 2018. He works with clients on how to improve their leadership, culture, productivity, and life/work balance. David coaches primarily C-Suite and EVP clients, and has driven significant growth in fassforward’s coaching practice. He is also focused on fassforward’s business development, finance and people functions. Prior to joining the fassforward team, David spent 20 years on Wall Street.
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 coaching journey began in the late 1990’s on Wall Street. No coaches at fassforward are career consultants/coaches. We’ve all had corporate leadership experience that informs our coaching. I started as an analyst at Morgan Stanley on a trading floor with 600 people. It was right out of the movie Wall Street. As the junior guy who was thrown all of the thankless work, including running to get breakfasts, lunches, and coffees, I learned an early leadership lesson: it doesn’t cost anything to be nice. My father had a great way of teaching me leadership lessons in a way that I could easily understand. One lesson that stood out was to treat the janitor in my elementary school the same way I treat the principal — with respect, humility, and gratitude. My coaching journey began by gravitating toward leaders at Morgan Stanley who treated me with kindness, appreciation, and a willingness to teach me despite my junior status. The biggest challenge I faced in those early days was that the majority of leaders on Wall Street did not have this approach!
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?
- Kindness: Every colleague you work with has a heart. They have gone through (and may be currently going through) hard times. The best leaders provide an environment in which those challenges can be shared. At times you may even be able to help them through those challenges. As Simon Sinek says “Leadership is not about being in charge, it’s about taking care of those in your charge.” Rose Fass, founder of fassforward is a gold standard for this. One of our colleagues has cats that are family members for her. She loves them as much as any mother loves their children. When her only cat at the time became sick and had to be put down, Rose and her husband drove with this colleague to the vet to put her down, and then took her out for a meal in which they grieved, shared stories and started the healing process. Rose then helped our colleague find a new cat and even adopted the kitten’s sibling!
- Gratitude: “Gratitude is not only the greatest of virtues, but the parent of all the others” -Cicero. Leadership is a privilege, but many leaders fail to see this. When I worked at Morgan Stanley I became a people leader five years in. In typical Wall Street fashion, there was no leadership training, and certainly no coaching. I took my promotion for granted, and was focused on my next promotion rather than the people I had the opportunity to lead. I focused on managing up and driving my team to produce strong numbers, but put little time into connecting with them. It was what we call “managing work instead of leading people.” After some really tough feedback, and missing the next promotion, I learned to never take leadership for granted and the importance of servant leadership.
- Desire to learn/improve: If you ever find a perfect leader, run. Perfect leaders do not exist, and the best leaders are always striving to improve and learn. Our co-founder Gavin McMahon is a perfect example of this. When AI took off a couple of years ago, he dove head first into the technology. As a leader of a company, it would have been easy to delegate tackling this revolutionary technology to a colleague, especially a younger, more tech savvy one. However, as he has consistently done since the founding of fassforward, he took the lead into learning about this new technology, and figuring out how it could benefit our business. I believe we are well ahead of the AI curve because of Gavin’s drive to learn and improve.
Can you share your favorite “Life Lesson” Quote? Why does that resonate with you so much?
“When you are finished changing, you are finished” -Benjamin Franklin. It’s probably the best quote to sum up successful executive coaching. If coaching is treated as a remedial or corrective process, it is usually set up for failure. The only way people will change is if they want to. If you are forcing executive coaching upon your employee, you should save your money. Successful executive coaching is all about change, and change is uncomfortable. Either you lean into that discomfort and recognize it will be to your benefit, or you push away from it and remain the same.
What are some of the most interesting or exciting projects you are working on now? How do you think that might help people?
Without question, it is our AI coaching offering. At fassforward, we have 3 guiding principles: 1) Be choosy 2) Touch a client everyday 3) Never compromise on a deliverable.
For our first 23 years, we were limited to coaching the highest ranking leaders in a company due to our size constraints. We are very selective in the coaches we hire, and we knew we would be compromising on our deliverable if we tried to expand our coaching services to our clients’ middle and lower tier leaders. AI has changed all of that. We are now developing our AI platform to provide coaching on a wide scale without compromising on our deliverables. This will allow first time leaders to avoid the mistakes I made at Morgan Stanley. I was not equipped with the skills and capabilities to effectively lead people, but our AI coaching will allow our clients to provide coaching to the most junior leaders as well as individual contributors.
Without saying any names could you share a particularly memorable success story from your coaching career?
I was asked to coach a leader that was just made “interim” Head of M&A and Strategy at a Fortune 500 company. The “interim” designation came from the fact that while he was a SME, and had all of the technical capabilities to handle the role, he was lacking in what we refer to as the Social and Political Spheres. The Social Sphere is about “who you know” — it’s your team and those that work most closely with you. The Political Sphere is about “who knows you” — those outside of your Social Sphere that could be advocating for you and getting you a seat at the table. To this person’s credit, he acknowledged he was not strong in these areas, but embraced the discomfort. We put a plan together to connect on a human level with his key peers, directs and skip levels in his social sphere. We then discussed techniques on how to organically get in front of key stakeholders outside of his business to win their advocacy. Three months and several leadership conversations later (that were at first uncomfortable, but became more natural for him) the “interim” designation was removed.
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?
At first, our coaching practice was like many others: very individual. Most of the coaching experience evolved around the singular relationship between the coach and the coachee. Over the years, we have increasingly embraced a team approach to coaching. I describe it below in more detail in the Top 5 trends section. In terms of personal learnings, every coaching opportunity is a chance for me to improve as a leader. Our approach to coaching is a thinking partnership. It’s a 2-way dialogue in which we talk through challenging leadership and business situations. As I tell my clients, I always learn from them. It’s not just about their subject matter expertise, but I also learn from their leadership approach, both their successes and mistakes. One important learning is about the power of listening. In the early days, I was too proactive in offering counsel and guidance. I think it was because I felt a need to prove my value. But, I recently wrote an article about “20/80 Conversations.” They are leadership conversations in which you do 20% of the talking (mostly in the form of questions) and 80% of the listening. This was a direct benefit from the work I did with clients and learning to listen.
How do you incorporate feedback into your coaching practice to continuously improve?
At fassforward, our Rapid Insight process is about getting actionable feedback. Whether it is individual coaching or a team workshop, Rapid Insights allow us to hit the ground running on any engagement. When I became Co-CEO with Gavin McMahon, he suggested we conduct Rapid Insight 360s on ourselves. It was a great call. After 6+ years of conducting Rapid Insights for clients, putting myself under the microscope was humbling and pivotal to my improvement as a leader and colleague. One important takeaway is that even though I was asking for feedback, it is hard to give a leader challenging feedback. So I was hearing about valuable developmental opportunities for the first time after leading our coaching practice for six years and asking for feedback throughout. I learned that I need to embrace the same approach we use with our clients. At fassforward, we call it “Live What We Create.” And going through our own Rapid Insight process allowed me, like my clients, to focus on 2–3 areas of development and measure my progress against them.
Can you discuss an innovation in coaching that you believe is currently under appreciated but has the potential to significantly impact the field?
Not surprisingly, it has to do with AI, and it is AI powered transcription. In “the old days” I would write a page or two of notes while conducting a coaching call. I would then manually transcribe those notes onto a Google Doc. It was a pretty laborious process. The first innovation of voice typing, which AI has improved significantly, cut down my transcription time in half (thank you Gavin for the suggestion). But now, with AI transcription, my “Coaching Notes” time is a fraction of what it used to be, and my notes are much more robust. I learned how much I was missing from taking manual notes, and it has made me a better coach.
In what ways can coaching address the evolving mental health needs of diverse populations in a digitally connected world?
With stress and burnout levels at record levels for executives, mental health has never been more important. But, nobody has the same mental health challenges and too many coaches attempt to provide counsel on this very complex subject without the appropriate expertise. At fassforward, we responded to the growing need for this specialty by bringing a mental health and wellness expert on staff. My wife Dr. Carolyn Frost has dedicated her career to this subject and consistent with the fassforward approach, provides our clients with the “how.” With her guidance they can apply specific tools and techniques to improve their mental health and wellness. In that spirit, we co-authored an article on How to Extinguish Burnout.
How do you foresee artificial intelligence and machine learning transforming the coaching industry in the next decade?
AI is a game changer for the coaching industry. It will put many coaches out of business. My favorite quote about AI is “It will not take your job, but the person who embraces AI will.” We have created our AI coaching offering to bring coaching to all levels of our clients. Previously, coaching was primarily limited to senior leaders and AI will make coaching available to all. We are also embracing AI to improve every facet of our coaching process. From the onboarding communication with a coachee, to the improved digital tools we provide, to our coaches improving their processes around coaching notes and the offboarding process, AI is a game changer. And the best part is that the ways it can help us improve increases each day.
Looking ahead, the scale of AI will significantly transform how we develop future leaders. AI will enable corporations to nurture leaders before they become leaders. Traditionally, the leadership conversation begins at the director level when companies identify high-potential individuals. By introducing coaching tools and methodologies earlier in the leadership journey, we can shape and grow future leaders in a more impactful way.
As mentioned above, we refer to our executive coaching practice as a Thinking Partnership. We help our clients navigate difficult scenarios, think through challenges, ideate on the right approaches, and draw from our tools to elevate their leadership and elevate their business. At the senior leadership level, the human element will always play a critical role. AI will improve the coaching experience, but the human touch and the wisdom that our coaches bring on demand is essential to helping our clients navigate challenging, emotional situations and develop the soft skills that are more important than ever. As advanced as AI becomes, and as effectively as you may prompt your AI coaching assistant, the human experience, wisdom and emotion remain an important aspect of effective coaching.
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 . AI: as just described above, AI is driving the future of coaching. It will make coaching accessible to all, and will make coaches and the coaching experience better. We have created a Chat GPT for each of our main coaching tools. We can prompt the GPT for each tool we are using with a client’s Coaching Plan, Rapid Insight synthesis, and other relevant background, and the insights and proposed actions that come back are more thorough and consistent than if one of our coaches were doing it on their own. However, as with most things, AI poses significant risks. As anyone who uses AI today knows, hallucinations are a big problem, and privacy of client information needs to be more guarded than ever.
2 . Team coaching: the traditional approach to executive coaching in which a coach solely works one on one with the coachee is not the future of coaching. In addition to close coordination with the sponsor (the boss) and the HRBP, we conduct Rapid Insight interviews with 8 other key stakeholders to get a full understanding of the coachee’s strengths and opportunities. While it is important that the coachee outline their own developmental goals, it is equally important that those goals incorporate the feedback from their colleagues. It also reinforces the need to not focus exclusively on the individual development for the leader, but to incorporate goals tied to the business.
3 . Defining specific outcomes/ROI on coaching: as described above, we develop 2–3 very specific opportunities that are a mix of individual and business related goals. They are not created in a vacuum by the coach and coachee but are based on coordination with the sponsor, HRBP, and other key stakeholders. These clearly defined goals/opportunities allow for a specific measure of progress and ROI. In addition to being on call for our coachee, we are on call for the sponsor and HRBP in order to get real time feedback and monitor progress. At a minimum, we will do a mid-engagement check in and an end of engagement check in to make sure we have made progress on those goals.
4 . Real time thinking partnerships: historically coaching has fallen into the trap of being “catch up sessions” in which important events are recapped with a coach every 2, 3 or 4 weeks when scheduled coaching sessions occur. We believe coaching is much more impactful when coaches are on call and as real time thinking partners. If I have a coaching call today, and tomorrow my client has a difficult performance issue to address, my ability to help is limited if we recap it on our next scheduled call in a couple of weeks. Our clients reach out to us in real time to walk through real time issues and think through different ways to address them.
5 . Trust as a cornerstone: despite all of the benefits of AI, and the “group coaching” approach, these approaches can challenge the ability of a coach to earn the most important element for a successful coaching engagement: trust. Gaining the trust of a coachee has never been more important. Early on in a coaching engagement, we clearly outline what information is shared internally, externally, etc. and empower the client to define what is to remain confidential.
How do you envision the integration of coaching within organizational cultures changing the landscape of leadership and employee development?
AI has already transformed leadership and employee development. The type of coaching that has historically been accessible to senior leaders is now becoming more accessible to all employees. AI has allowed coaching to be integrated into all levels of the organization, accelerating the trend toward asynchronous learning and development. The ability to provide coaching and learning programs to employees on their own time and specific to their role is a game changer. This trend will allow high potential talent to differentiate themselves at the earliest stages of their career.
However, as we embrace these cultural changes, it’s crucial to ensure transparency and secure employee buy-in. Leaders must actively engage with employees, fostering an environment of trust and collaboration to make these transitions successful. At fassforward, we have seen firsthand the impact of integrating coaching within organizational cultures. Our approach to transformation and cultural change goes beyond traditional methods. While our executive coaching focuses on one-to-one relationships, our training uses the same tools and methodology to coach one-to-many. With core accounts, we dive deeper and fully immerse ourselves in their organizations, applying our intellectual property and methodology from ideation to execution.
For example, our team has done incredible bespoke work with companies like Allstate, Mastercard, Commvault, and Chick-fil-A. A recent example is creating a dynamic culture map and custom culture games for Allstate. This work enhances our clients’ coaching experience and allows us to deepen our relationships, and to apply our strategic thinking and design expertise for our core accounts.
What do you see as the biggest challenge facing the coaching industry today, and how might we overcome it?
One of the most significant challenges facing the coaching industry is the proliferation of unqualified coaches and coaching firms. There are little to no barriers to advertising yourself as a coach these days. The number of coaches and coaching organizations are growing exponentially due to increased demand. This dilution of quality undermines the profession and results in an increased challenge for those seeking genuine, effective coaching. At fassforward, we believe the best coaches are those that have comparable professional experience and/or significant knowledge of the client and their business. We purposely only focus on a handful of core accounts. We have established relationships with these clients for years and have an intimate knowledge of their leadership team and their businesses. In my mind, the days of “one off” coaching within a large company in which employees are allowed to choose their own coaches from different coaching firms are limited. It has never been more important to have a trusted relationship with, and a deep understanding of, the approach and methodology of your coaching partner.
What is one long-term goal you have for your coaching practice, and how are you working towards it?
To provide coaching to any of our clients who want it regardless of seniority. As I mentioned above, we were previously limited to coaching only the most senior leaders, but AI has given us the ability to provide coaching to a much broader group of our clients. Everyone deserves a chance to better themselves and we have never been closer to the vision of “coaching for all” than we are today. There are still improvements and advances in AI that are needed to get us to where we want to go, but we are well on the way.
How can our readers continue to follow your work?
Follow me on LinkedIn and subscribe to fassforward’s HOW Newsletter. Here is the link to our site for My Articles. I also have to make a pitch for my partner Gavin McMahon. His Forward Thinking newsletter provides you with actionable and timely insights on leadership and storytelling with new content bi-weekly.
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, a seasoned entrepreneur with over two decades of experience as the Founder and CEO of multiple companies. He launched Choice Recovery, Inc., a healthcare collection agency, while going to The Ohio State University, His team earned national recognition, twice being ranked as the #1 business to work for in Central Ohio. In 2018, Chad launched [re]start, a career development platform connecting thousands of individuals in collections with meaningful employment opportunities, He sold Choice Recovery on his 25th anniversary and in 2023, sold the majority interest in [re]start so he can focus his transition to Built to Lead as an Executive Leadership Coach. Learn more at www.chadsilverstein.com
David Frost Of fassforward 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.