An Interview With Chad Silverstein
…The rise of AI. Everyone is trying to grapple with what AI is going to do to their career paths, and that impacts coaching both on the coach side and the client side.
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 Kevin Ball.
Kevin Ball is the Vice President of Engineering at Mento. He is a software leader, entrepreneur, and coach who has co-founded and served as CTO for two startups, runs his own coaching business, and has spoken at conferences around the world. He is currently focused on exploring the intersection of AI and human coaching at Mento, helping leaders everywhere improve their performance at 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?
The light bulb moment for me was in 2017. I was running an independent consulting business, and I worked with a coach for the first time. It was transformational for me on multiple levels — professionally, in how I thought about my business, but also in my personal life. My coach helped me figure out how to be present and navigate with grace the process of managing my parents declining health at the same time as dealing with young children.
That experience was so impactful for me, I immediately started asking myself “How can I get more into this?” I started by trying to add some coaching to my existing consulting business, with pretty mixed results. I had a grand total of two clients try it, one pretty successfully and the other not so much.
Before I got too far along that journey, I ran into and got sucked into a behavioral science oriented startup, which took up all of my attention. But I continued trying to apply coaching principles, only this time applying them to managing my direct reports. I built out a growth framework that I could use to help guide career conversations, and incorporated coaching principles into it.
When that business started to implode in late 2022, I left and had to decide what to do. I was burned out on organizational chaos, but still had this nagging itch around coaching. So I incorporated KBall, LLC and enrolled in a coaching accreditation program. That was when I began shifting my identity from being an engineering leader who was interested in coaching to truly being a coach as a part of my professional identity.
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?
I think the most instrumental character trait for my success has been a fundamental curiosity about how things work. Always asking questions and trying to form mental models for how what I’m doing fits into the broader picture, how changes in one part of the business connect to the whole, and for how to better approach things.
This curiosity creates a drive for me to show up and keep learning, and is also key to successfully navigating challenging situations and relationships. As an example, in one of my previous roles as an engineering leader, I worked at a small design firm that had two executive partners. When I first joined, it was hard to navigate decision making or how to drive change — it felt like depending on the moment or which partner was making the decision, we could end up going in vastly different directions or with different priorities.
Many of my coworkers had written off the possibility of driving company-level changes, but my curiosity led me to keep digging until I started to understand what each of these leaders needed to see to make a decision. To bring one along, I needed to make the connections to process and efficiency, and really figure out how my proposed change would drive longer term effectiveness. To win over the other, I had to connect to a bigger picture and share a compelling vision of possibilities. And by addressing both of these aspects, or connecting the dots from one side to the other, we could create alignment and make coherent, business-wide progress and changes.
Another super important trait for success has been a fundamental stubbornness and willingness to take on the hard things. It’s shocking how many people will give up on something if they’re not able to figure it out quickly. Early in my career as an engineer, I built a reputation for being what one manager called a “savant-like debugger” purely by being willing to keep banging my head against problems that everyone else had given up on until I was able to break through. More recently as a leader, this stubbornness has enabled me to straighten out knotty interpersonal relationships on my team by being willing to tackle them head on and stay through the pain and discomfort of hard conversations.
A final key character trait that I will highlight is the ability to bring joy and energy to work on a regular basis. The ability to create impact is so often driven by the ability to get people out of the drudgery of their day to day, to get them excited and moving in a direction. And there is nothing more contagious than a sense of joy. My former boss called it the “Kevin whirlwind”, where by sheer application of energy and enthusiasm I could spin up a project out of nothing and get everyone moving in the same direction. There is no magic to it — if you are energized by a project, can clearly communicate your enthusiasm, and explain to someone why it matters to them and how their contribution will be important, people will move mountains.
Can you share your favorite “Life Lesson Quote”? Why does that resonate with you so much?
“You work hard so you can get lucky.” This is a quote I heard during my first startup founding experience, and it has stuck with me ever since. One of the core fundamental challenges with maintaining motivation to work hard is that true success takes both hard work and luck. When you’re working and not seeing that success, and you see someone else getting lucky, it can be easy to ask yourself ‘why am I working?’. What this quote captures is the fundamental reason for why you keep working. Yes, you will need some luck to attain what you’re aiming at, but in order to even open yourself to the possibility of that luck striking, you need to do the work.
What are some of the most interesting or exciting projects you are working on now? How do you think that might help people?
Probably the most exciting project that I’m working on right now is creating an AI coaching tool with Mento. It’s a fascinating problem — how to navigate the line between what is uniquely human and needs to be done by a human, and what is a fundamentally repeatable process that we can automate. Even more interesting to me is how we can navigate back and forth across that line, letting the AI engage directly with a coaching client for the domains that it can handle well, but also recognize which topics fundamentally require a human and hand off or recommend working with a human coach at that point.
This project has a ton of potential to help people by making coaching more available, both in price and time. I fundamentally believe everyone can benefit from coaching, but I also know that many people can’t afford it, or can’t afford more than a few sessions. Imagine if they could access an AI coach every day: working through their challenges, getting help with clarity and action planning, and keeping them moving forward towards their goals. This doesn’t remove human coaching, it amplifies it and focuses it on the most critical moments. When there is a crisis, or a big upheaval or change, the AI can connect the client to exactly the right person to help them out.
Without saying any names could you share a particularly memorable success story from your coaching career?
One of the successes that stands out most in my mind is a young woman I worked with in the tech industry. She initially came to me wanting to make a move from devops into software engineering, and to make a name and niche for herself in the industry. She was in a position that she wasn’t super happy with, and felt like she kept getting pushed to do work that didn’t feel right for her.
Early on, we talked through a number of different tactics and approaches for learning more software skills, getting more into open source projects, and speaking in public. But we ran into internal resistance, and we struggled with trying to do too many things at once.
As we dove deeper into coaching, getting deep into her goals, identifying strengths and weaknesses, and going through a process of reflection and growth, she started to realize that she had been, in her words, “Measuring herself by other people’s yardsticks”. That she could be technical without being only technical, and that she could leverage her strengths in communication and technical project management to leverage her technical skills and have more impact without having to do everything herself all the same time.
As drew to a close in our coaching engagement, this client ended up quitting her job and finding a new one, also in the tech industry. In our retrospective about the coaching experience, she told me that when we started coaching, she hadn’t expected to end up in such a different place both literally and mentally. Her statement about where we’d ended has stuck with me since. She said: “For the first time ever, I feel like maybe I’m exactly where I need to be.”
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?
The biggest evolution in my coaching over the years has been an increased appreciation for and emphasis on the importance of building out habits of action to make behavior change.
I’m a nerd. I love ideas. And I love mental breakthroughs and shifts in perception. But what I’ve seen both in myself and others is that a focus on those breakthroughs rarely creates sustainable change. It is the regular habit of reflection, self-investment, and experimentation that will over time help generate those breakthroughs. So I focus much more of my coaching energy now on helping my clients establish good habits of learning and reflection. Which isn’t to say we don’t work on blocks, identify breakthroughs, and other things like that… just that I’ve found once the foundations are laid, those breakthroughs come much more regularly.
This approach has also very much informed how I keep myself on track. I have a series of rituals I follow across three different time horizons to keep myself continuously reflecting, learning, and growing.
First, at the highest level, every year I do an annual review, looking backwards, and a plan looking forward. This is at a pretty high level — how was my year, where did I succeed and fail, and what might I want to do differently? I will then set out goals for myself, but they are typically very directional and not super concrete. “Next year, I want to do more traveling. At least 3 trips out of the country” might be a typical annual goal.
At the next layer, every month I also do a review and planning session. I look back at the previous month, assessing how I did and what I want to change. And I set myself some more concrete goals for the next month. These are more achievement oriented, but may yet be so concrete as a
SMART goal. A recent example was to orient my department around our new quarterly metrics and get everyone focused on them.
At the most concrete layer, I do a weekly retrospective and planning session on Monday mornings. At this layer, I’m doing very concrete goals, with a timeline attached, and keeping myself accountable to it.
What this layered approach does is it helps me stay on track with my development and execution, and balancing across my various priorities. I might have a week or even a month that is goes deep on a single topic, or that gets overwhelmed by an urgent incoming priority. But I have a regular cadence to check in with myself, make sure I’m not getting too far off track, and course correct as necessary.
How do you incorporate feedback into your coaching practice to continuously improve?
The most effective and consistent feedback technique I use in my coaching practice is a simple question asked at the end of every session: “What from this conversation feels most impactful for you?”
This question serves two purposes. First, it helps me understand what types of questions and shared experiences are most impactful (and by extension what isn’t having an impact). And second, it helps bring the coaching client back to the most impactful things, helping guarantee they will leave the session energized and focused on where they can make a change.
Can you discuss an innovation in coaching that you believe is currently underappreciated but has the potential to significantly impact the field?
Something I believe deeply in, which is somewhat controversial (and hence I believe also underappreciated) in the coaching world, is the value of coaching clients who are in domains that you have functional expertise. Essentially blending mentorship and coaching.
I coach youth soccer, and in the sports world one would never try to assert that someone without any skills in the sport could be just as effective in coaching as someone who had been playing their entire life. To help athletes grow, you need to be able to flow seamlessly between directive mentorship on skill development and more socratic, questioning coaching that supports them in their learning.
The same applies in the professional world — I almost exclusively coach software engineers and engineering leaders, which is a domain in which I have 20 years of in depth experience. The biggest advantage that gives me is that it allows us to much more succinctly communicate context that is unique to that experience, and move on to where the client is stuck. Instead of spending 10 minutes trying to explain and translate a particular technical situation or set of tradeoffs and why that has led to the conundrum the are facing, they can briefly describe it in the terms they are used to thinking in, and I am able to immediately move to relevant questions.
This is also the approach that Mento takes with all of our coaches. We match coaches who are subject matter experts with exactly the clients who will benefit from their expertise. Those coaches provide a blend of 80% coaching and 20% mentorship, and we hear over and over again how crucial that blend is. Coaching as an approach is incredibly impactful for helping people learn and grow, cutting through mental blocks and unlocking great progress. But sometimes, particularly when tackling something that is new for you, it’s really helpful to receive some mentorship from someone who has “been there and done that”. Combining both of those in a single person creates a powerful synergy that creates rapid and powerful change.
In what ways can coaching address the evolving mental health needs of diverse populations in a digitally connected world?
This is a bit of a tricky question. Most coaches are not therapists, and we should not pretend to be. In fact, it is extremely important for us to recognize when a client needs more clinical help, and help them to find it.
That said, there are a shocking number of skills in common between therapy and coaching, and many of the practices that we as coaches help our clients learn and adopt are useful in managing their mental health. My wife is a clinical psychologist, and we’ve sometimes joked that we teach the same skills, it is just the audience that is different.
There is a sense to which that is true. But that audience difference makes a big difference — as an example, I have no idea how to assess someone for suicidality or other extreme mental health risks, and I would be deeply uncomfortable navigating a situation that even got close to that. We do ourselves and our clients a disservice if we don’t recognize our limits and make them clear.
How do you foresee artificial intelligence and machine learning transforming the coaching industry in the next decade?
This is a question I’m spending a tremendous amount of my time and energy working on today, as at Mento we are building an AI-based coaching tool to help make coaching accessible to everyone.
This breaks into two questions for me. First, what can AI and ML do to augment coaches in supporting their clients? And second, what parts of what a coach does can be completely automated via AI and ML to provide an inexpensive, 24/7 accessible alternative to human coaching?
First, tackling the question of using AI to augment human coaches, there are many ways this is already taking place, and a number of ways it can continue. Coaches are already using AI-based notetakers to automate notes from their coaching calls and provide them to their clients. This can continue further — imagine a ride-along bot that not only took notes but summarized, captured action items, and surfaced relevant transcripts from previous conversations throughout the call.
Second, the sometimes more worrisome but also more exciting question is around what sets of things can and will be completely automated? As both a long-time engineer and a coach, I fundamentally don’t believe that we’ll be able to automate everything that a coach does. But I do believe there are a set of things that a coach does that we will be able to automate, and that in the end this will be better for both clients and coaches.
The key question is, what is the line between what can be automated and what is fundamentally human, how do you identify where that line is, and even more how do you flow smoothly back and forth across that line?
Imagine a coaching client who was able to use an AI coach to self-coach themselves through a range of normal problems, handling many of the transactional questions that come up and clog up our coaching sessions. And then, as they’re having a conversation, the AI is able to recognize, “Hey, for this topic… you really should talk to a human. And what’s more, I can recommend and connect you to three coaches that are experts on this exact situation”.
This would let us as coaches spend more of our time focusing on the places we can truly create transformational change for our clients, while the always-on and inexpensive nature of AI also makes the power of coaching available to everyone at any time of day or night.
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?
There has always been an expectation of privacy between coach and client, and most coaches I know lay out explicitly what their policies are in their opening agreement documentation. Being explicit becomes even more important as we layer on additional digital platforms.
Digital documents, AI note-taking tools, recordings of sessions — all of these provide new opportunities for a client’s information to “leak” into places and methods of use they do not expect it. And that’s not all bad! It may actually be better for a client if they’re able to search through histories of their previous call transcripts, or even have them summarized for them and referenced by an AI bot. But they need to know how their data is going to be used, and agree to it.
And as a coach — you need to understand the privacy guarantees of the platforms you use, especially as you move into the AI space. Most B2B platforms (or even the B2B products of companies that also have consumer products) have reasonably strong data and privacy guarantees. On the other hand, many consumer-oriented platforms do not, and will happily take anything you enter in as “training data”, which might result in it leaking somewhere you don’t expect.
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 . Functional expertise plays an increasingly important role.
Coaching well requires understanding the context of a client sufficiently to ask probing, powerful questions that nudge them to a new level of understanding. And when you’re coaching someone in a professional role, that context is often so deeply specific that it is incredibly helpful to have a functional background in that role or at least a similar one.
An example from my own coaching — I coach mid and late career software engineers and software engineering managers. And a good 70–80% of my coaching with them, it doesn’t really matter that I understand their area of functional expertise, because we’re coaching around classic decision making and interpersonal relationship challenges. But every few sessions a topic will come up where even if the core of what we need to work on is communication, the blocking communication challenge is in translating a deeply technical problem into something a less technical stakeholder can understand.
Having functional expertise both means we can spend much less time trying to communicate the context, and that I can coach them directly on the gap they’re perceiving — moving from technical to nontechnical communication. If they continue to be stuck, I’m also able to move seamlessly from coaching into mentorship, providing examples grounded in the same type of problem, and co-creating experiments for them to try.
2 . The rise of AI
Everyone is trying to grapple with what AI is going to do to their career paths, and that impacts coaching both on the coach side and the client side.
AI based coaching tools have the potential to make coaches much more effective. The first tools already finding use are simple things like automating note-taking from coach conversations, but I expect more and more more advanced ‘co-pilot’ style tooling that will automatically surface for a coach, live during a call, relevant information, summaries of past conversations, and suggestions for questions you might ask.
AI will also eventually be able to automate some amounts of what a coach can do, helping clients work through problems, identify action steps, and more.
This potential is seen with a lot of angst — will AI eliminate coaching as a career? This same angst is playing out across a wide range of careers right now, from photography to writing to software development. But I believe we will see the same pattern here that is showing up there and has shown up in past periods of automation: coaching will become much more widely accessible, successful coaches will need to find ways to incorporate AI into their processes, but it will also dramatically increase the impact any individual coach can have.
3 . Focus on outcomes
One trend that is already playing out in coaching and is only exacerbated by the rise of AI is the need for coaches to focus clearly on the outcomes we are able and trying to drive.
There has been a dramatic increase in the awareness of coaching as a useful tool in facilitating growth, but much less clarity on exactly what types of outcomes coaching is able to deliver. Without clear direction, coaching sessions can end up mired in helping clients solve the problem of the day, and clients can come to depend on coaches rather than using their services to grow their own capabilities.
Especially in business environments, many companies have purchased coaching for their managers and executives without a clear vision for what they want to achieve. This is a recipe for disappointment, as the motivations of companies and their employees are not perfectly aligned. Companies looking for performance improvements may instead see their employees entirely focused on wellness improvements.
Don’t get me wrong — wellness is a great outcome, if that is what you are trying to achieve. But in a world of constrained budgets and competition from AI, we need to ask ourselves the hard questions around what our clients want out of their coaches and make sure we are delivering it.
4 . Coaching for the whole organization
One of the patterns that emerges when you coach multiple people within an organization is how many of the things that people are struggling with are connected with the broader environment they are embedded in. You can help an individual learn, grow, and take action on what they have control over, but if they are embedded in a toxic environment their ability to thrive is ultimately limited.
As coaching continues to grow and innovations like AI make it more affordable to have coaching for all, I see a world in which coaches are able to surface and highlight not just individual problems but organizational and systemic issues and help them be resolved.
There is nuance here — we need to figure out how we can surface these problems without violating client confidentiality, and the tools for addressing organization change are often not in the hands of any one individual — but the potential for impact is tremendous.
5 . Integration of psychology and behavioral science
Coaching is a powerful tool on its own, but becomes even more powerful when we combine it with other disciplines that study how people learn and change.
Many coaches are already doing this, integrating knowledge around habit forming to help their clients form healthier habits, but we need to keep going further. How can we use the science of nudges to help clients keep coming back to their best selves? Use emerging knowledge about how memories form to design our workshops? Integrate cognitive behavioral techniques to help clients challenge limiting beliefs?
The future of coaching is multidisciplinary, and I couldn’t be more excited about how we incorporate these disciplines into our practices to increase our impact on our clients.
How do you envision the integration of coaching within organizational cultures changing the landscape of leadership and employee development?
Integrating coaching both as a practice and a culture is a tremendous opportunity to improve the functioning of organizations.
There is no more powerful tool for moving from stuckness to opportunity and from frustration into curiosity than working with a coach. But often the biggest barrier to an individual’s ability to thrive is their environment. And while an individual might be ready to change and work with a coach to enact it, if their leaders are creating a toxic environment, that coaching is more likely to unlock their ability to cope or leave rather than to improve their organization.
By integrating coaching within organizational culture and making it something that is normal for everyone to be receiving, we open the door to systemic change, not simply supporting individuals in coping within a toxic system.
I imagine organizations where everyone, from leadership on downward, is both being coached and approaching the world with a coaching mindset. Where every conversation can start from a place of curiosity, openness, and presence. And where we’re able to build cultures that support every individual in thriving and growing.
What do you see as the biggest challenge facing the coaching industry today, and how might we overcome it?
I think the biggest challenge facing coaching is the perceived “fuzziness” of the profession, and the related lack of credibility outside of established niches such as executive coaching. Working primarily with engineers, I run into this headlong — there is an educational process around what coaching is, why it can be helpful, and how it can drive improved performance.
To overcome this, I think we need to get much more explicit and clear about the outcomes we can drive, and hold ourselves accountable to those outcomes. Those outcomes will vary by coach and by client, but we need to be explicit about delivering results that have an impact. Are you coaching sales professionals? You had better be measuring and improving their sales results. Coaching leaders? You should be talking about, measuring, and improving the impact they’re having on their teams and organizations.
What is one long-term goal you have for your coaching practice, and how are you working towards it?
A long term goal for me in my coaching practice is to branch out beyond engineers and engineering leaders to coach high performers of all types. I’ve noticed that one of the common themes that comes up both with my clients and with other high performers I talk to is around the desire to craft their own role. To go deeper on their areas of strength and let go of some areas of frustration and weakness.
This is absolutely something that I have done, and something that I believe anyone who is a high performer should be able to do. To get there, I think there is likely to be a mix of directed and undirected coaching to help someone get clear on exactly what their ideal role looks like, how to define it and pitch it, and how to negotiate that role either within their current organization or with a new one.
But I don’t quite have a clear enough picture of what this looks like yet to focus my coaching practice on it, and so in the meantime I’m continuing to work on this when it comes up with my existing clients, and have conversations to help crystalize my thinking.
How can our readers continue to follow your work?
I write on LinkedIn and publish the Human Skills series of interviews. For the AI coaching work, I encourage you to subscribe to the Mento Blog or follow Mento on LinkedIn.
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
Kevin Ball Of Mento 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.