An Interview With Chad Silverstein
Coaching will be ubiquitous, always-on, and available to everybody.
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 James Cross.
I’m the co-founder of Tenor, AI for leadership development, with a mission to make every people leader more effective using AI. I’ve dedicated my career to unlocking human potential with technology. Before starting Tenor, I was the vice president of Workforce Products at Workday. I’ve also worked with the White House on skills and technologies for American workers.
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?
I’ve had an interesting career journey, that’s taken me from being a high school teacher in northern England, to being an AI company founder in San Francisco. The theme of my career has been unlocking human potential with technology — especially when new waves of innovation happen, and new ways of learning suddenly become possible.
I became a teacher in 2005, around the time that YouTube and streaming video were really taking off. I saw that this technology was going to change learning forever. After seeing its impact in my own classroom, I wanted to bring video learning to every institution — and became part of the founding team at MediaCore, a cloud video platform for learning. We went on to power video learning at some of the world’s best institutions — like Yale, Columbia, and Stanford.
In 2015, we were approached by Workday, who wanted to bring this technology to their customer base as part of a brand new LMS. Workday acquired MediaCore in August of that year, and I became the product strategy lead for what would become Workday Learning — which is now one of the largest learning platforms by market share. I loved being at Workday, launched a lot more products during my tenure, and got to learn from world-class leaders and mentors.
Towards the end of my eight-year tenure at Workday, I saw that the technology paradigm shift was happening again, with AI being poised to reshape how we all work and learn. My longtime colleague and friend Charlie had been exploring voice AI for leadership development, and it was clear to both of us that we could have a big impact with this approach. I joined Charlie as a co-founder, and today we’re building Tenor — the AI platform for leadership development.
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?
Getting folks rallied around a compelling vision for the future is one of the most important traits in a leader — to employees, investors, and customers. Developing a clear narrative that captures the vision is important — but I think that leaders can only be truly effective in doing this if they’re genuinely passionate, to their core, about the possibilities.
Another trait I love, is what Tom Hanks describes as “equipoise.” In Hank’s words: “equipoise means that you have to have this perfect balance between relaxation and concentration. You’ve got to be able to move in whatever direction is required at the moment. When that phone call comes in and says, ‘We have a disaster on our hands,’ you have to say very calmly and quietly, ‘Let me see what I can do, I’ll take care of this, don’t worry.’ Then you put it down and then you go off and take care of whatever it is.” Leaders need to have a balance of patience and impatience, flexibility and rigidity, strategy and execution, and need to be able to fluidly traverse all of this as the moment requires.
Can you share your favorite “Life Lesson Quote”? Why does that resonate with you so much?
“Nothing is ever as good or bad as it seems.” Whenever something unexpected happens — good or bad — it’s a reminder to take a breath, be present, and put things into perspective before responding.
What are some of the most interesting or exciting projects you are working on now? How do you think that might help people?
Right now, I’m working on a company called Tenor, with my co-founder and longtime friend Charlie. We’re building the AI platform for leadership development — a platform that will be a force multiplier for every leadership development team that wants to grow and enable their managers. We use voice AI, to help managers practice important conversations with simulated employees, and get feedback on their approach. And we’re also building an AI coach, that will bring in-the-flow-of-work support and learning to people leaders. We’re just getting started, and we’re so excited: building with AI is unlike any other technology we’ve experienced, and the possibilities are so great.
Without saying any names could you share a particularly memorable success story from your coaching career?
I’m so proud that Tenor is already supporting managers with AI, in a way that wasn’t technically possible even a year ago. One area that we’re helping with is getting managers more comfortable giving effective feedback and coaching to their directs, in the moment. We all know that feedback should be given early, and that letting performance concerns linger is a recipe for disaster. But that doesn’t make it any easier when you’re in the moment with a direct report, delivering that feedback. Until now, the only way to help managers here were conversation guides, frameworks, and the occasional roleplay. With Tenor’s voice AI, we’re able to drop that manager into a realistic voice conversation with a simulated employee — who exhibits the same emotion, questions, reactions, and voice inflection, as a real one. It’s a game changer, and we’re hearing that it’s really helping managers get comfortable after this practice.
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 haven’t ever been a formal coach — but I’ve coached and mentored people as a leader throughout my career.
Can you discuss an innovation in coaching that you believe is currently underappreciated but has the potential to significantly impact the field?
I’m going to mention AI again. Things are moving so quickly — and I often think of Amara’s law — that “we tend to overestimate the effect of a technology in the short run and underestimate the effect in the long run.” That’s definitely true here (and there are parallels with Gartner’s hype cycle!). And across the AI stack, I personally think that most people are underestimating the impact that voice AI specifically will have. Voice interfaces are getting so mind-blowingly good, and it’s already hard to fully appreciate that you’re speaking to a computer. Voice will be the primary interface for AI, and everybody should be thinking about what that looks like — because it’s just so fundamentally different to a text-based interface.
In what ways can coaching address the evolving mental health needs of diverse populations in a digitally connected world?
We know that the best way to work through problems — both emotional and tactical — is to talk them out. “A problem shared is a problem halved” is an idiom we’ve all experienced and live by.
Voice AI will give every one of us an emotive, caring, supportive guide. One that’s always on. One that knows your history, and all of the context in your life. And one that listens without judgment. All at a cost that makes it accessible to every human on earth. I think that this is going to be the single biggest leap in emotional wellbeing that we’ve ever seen.
And we’ll see this in the workplace too. When managers encounter stressful or new situations, they’ll be able to instantly talk them out and work through solutions with a hyper-realistic voice agent.
How do you foresee artificial intelligence and machine learning transforming the coaching industry in the next decade?
Whenever we see a new technology paradigm come along, we first see it replace what’s already happening today, and then later, we see completely new possibilities emerge.
There are so many growth interventions that we know work really well — like roleplaying, coaching, and highly personalized, contextual learning. The challenge today is that these approaches just don’t scale — and as a field, we’ve been trying to find ways to solve this problem for decades. AI, almost overnight, has changed everything.
From AI coaches to realistic voice roleplaying, to learning in the flow of work, we’ll first see AI helping bring. But what comes after that is the most
As an example here, I often think back to the best Human Resources Business Partner I ever worked with. He was a true partner to me: he knew me as a leader, my growth journey, and he also knew my team, and the broader business. He was able to use this to help coach and guide me as a leader, in a really practical and contextual way.
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?
As AI coaching becomes widespread, we’ll need to face, and be incredibly thoughtful about, the ethics and privacy concerns that surround them. AI coaching needs to be psychologically safe and must not do any harm. Its interactions with people, the things it remembers, and the context it’s tapped into, all need to be secure and private. Things are moving so fast, and we need to be thinking about this right now.
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 . Coaching will be ubiquitous, always-on, and available to everybody.
2 . AI will help leadership development teams scale their impact, at a fraction of the cost of today’s interventions, for all managers across their business.
3 . Learning in the flow of work will finally arrive — through proactive nudges and interventions, delivered by an AI coach that has a deep understanding of every employee’s skills, growth, and work,
4 . The role of human coaches will be elevated to high-impact interventions that really move the needle for leaders and companies.
5 . Managers will use AI coaches to work through their day-to-day ‘blocking and tackling’ challenges — and human coaches for truly transformational experiences at inflection points in their lives and careers.
How do you envision the integration of coaching within organizational cultures changing the landscape of leadership and employee development?
Back in 2002, David Bowie said that “music itself is going to become like running water or electricity”. He predicted the streaming age, where every song ever recorded was available instantly, to us all, at the same cost per month as a single physical album.
The same is going to happen for coaching in the coming years. It’s going to flow like water from a tap to every person in an organization, just like Spotify.
The music industry went through a lot of sudden shifts and had to adapt to a new model. Many artists today get less revenue from streaming than they did from traditional records — and have shifted to live experiences, concerts, and partnerships, to adapt to the new landscape. And music consumers are better off for it.
There’s a parallel here with coaching. What’s the coaching equivalent of a live concert? Seeing an artist live can be a transformational, inspiring experience. What’s the coaching equivalent of this? I think this is where coaching should be heading.
How can our readers continue to follow your work?
You can try a voice AI simulation for yourself on our website, at Tenorhq.com. I’m also active on LinkedIn and am always happy to connect and share.
Thank you so much for sharing all of these insights. We wish you continued success and good health!
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
James Cross Of Tenor 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.