In this Innovator’s Hangout, we meet R. Karl Hebenstreit. A certified executive coach, organizational psychologist, award-winning author, and global speaker whose 25+ year career spans powerhouse names like Merck, AT&T, Genentech, and Kaiser Permanente. But Karl’s not just bringing wisdom to the C-suite the traditional way, he’s multiplying his impact with a digital twist. By combining live coaching, virtual delivery, and AI-powered clones of himself, Karl is democratizing access to leadership coaching and extending his reach far beyond time zones and human bandwidth. From Zoom sessions that break geographical barriers to AI clones that coach, role-play, and teach his frameworks 24/7, Karl is redefining what it means to scale human insight. His story is one of timeless people-first principles meeting cutting-edge tech and it’s exactly the future of work conversation our readers need right now.
Your AI clones deliver your voice, style, and tools to clients worldwide. When did you first realize AI could become a true extension of your coaching practice?
On August 1, 2023 (almost 2 years after I ventured out with my own executive coaching and leadership/team/organization development solopreneurship, Perform & Function, LLC) I received an email from Ali Khokhar who had just left Google and was exploring how to use AI in executive coaching. I was intrigued and immediately accepted his invitation for a conversation around what functionality I would be seeking, concerns, safeguards, from the perspective of an executive coach. One year later (2024), after seeing the capabilities and functionalities Ali and his team had created based on my and other coaches’ inputs, I signed up for Ali’s amigo.ai product and service. They created an AI clone of me, my International Coaching Federation (ICF)-centered coaching style, personality, models and frameworks I use AND an additional AI clone of me to deliver an eLearning version of my book, Explicit Expectations: The Essential Guide & Toolkit of Management Fundamentals. One more year later (2025), amigo.ai (after a change in strategic direction) transitioned my clones to a new platform provider, coachbot.ai, to continue to deliver my coaching and eLearning delivery services.
COVID normalized virtual coaching, but scaling it through AI is another leap. What challenges did you face in making the human side of coaching feel authentic through a digital clone?
Hybrid is usually the best solution to any question, challenge, or situation. No matter how much of myself could be transferred to my AI clone, true human empathy cannot (yet?) be replicated. This is why I make my coaching clones available as a supplement and complement to my human coaching services. I can still read the AI clone coaching transcripts and identify organizational themes and even address concerns personally or via group coaching Zoom calls. And my AI coaching clone AI RKarl can be there to support my executive coaching clients in between our regularly-scheduled coaching sessions and/or when I’m unavailable (a human’s got to sleep, right?).
You’re passionate about the Enneagram and human diversity. How do your AI clones preserve and communicate these deeply human insights in ways that feel personal and real?
My AI clones conform to and abide by the International Coaching Federation’s coaching and ethics principles, supporting and facilitating coaching clients to tap into the resources they already have within them, inviting them to look at the world and their situations through a diverse set of lenses and perspectives, and guiding them to come up with their own unique, actionable solutions. The AI clones have also been programmed with the models and frameworks I use in my coaching and all of my books, articles, and podcasts have been uploaded into them for their use, reference, and recommendation, as appropriate, depending on the coaching challenge presented. This includes all of the Enneagram knowledge embedded in my books (The How and Why: Taking Care of Business with the Enneagram and Nina and the Really, Really Tough Decision), articles, and podcasts, ensuring that each coaching engagement is conducted in a way that incorporates the integration of each of the nine Enneagram motivations and perspectives, along with a way to encourage AND thinking, while making it palpable for each unique coaching client. In addition, the AI coaching clones recall previous conversations held with each client (while keeping them confidential), and are able to bring them back into the current session, providing additional insights that are personal and customized, contributing to making each interaction feel uniquely personal and real.
You’ve had a long career inside major corporations. How has your corporate experience shaped your approach to innovating with AI and virtual delivery today?
Having worked as an internal employee at multiple global organizations for almost 30 years, I know the challenges and time demands created by working to accommodate multiple time zones, attendance at myriad meetings, navigating corporate politics, and competing stakeholder demands and deadlines. All of these factors contribute to the need for flexibility and customization to the changing requirements of an employee’s calendar, as well as trust and confidentiality of a coach. And you can’t (usually) forecast, predict, or schedule when something will go awry and you will need immediate coaching support. My approach to innovating with AI in general is to make sure that I have tools and services available to prepare my clients to deal and cope with the inevitabilities and demands of their corporate roles. For example, I have seen countless times the lack of resources and training provided to employees who, because of their excellent work as individual contributors, are promoted to becoming people managers (whether they’re ready, have previous successful experience doing so, aspire to, or not). Explicit Expectations: The Essential Guide & Toolkit of Management Fundamentals aims to bridge the gap between implicit and explicit expectations of each party in the equation – the new people leader, their manager, their direct reports, and even other stakeholders. It’s all about supporting the new leader in their new role by reminding them to ensure that their expectations of themselves, their direct reports, and their managers are explicit AND vice versa – that their managers’ expectations of them, their direct reports’ expectations of them, and their stakeholders’ expectations of them are clearly stated, understood, and in alignment by all parties. And that WHEN (not if) changes occur, more timely discussions are held to realign and recalibrate expectations between all parties. My AI clone is ready 24/7/365 to support and guide the new (or any tenured) manager through whatever organizational challenge they’re having or preparing for so that they can navigate them successfully and in any order. This is executed through delivery of asynchronous content as well as coaching and role plays to provide the manager with practice and experience prior to engaging with their colleagues and stakeholders. The availability and confidentiality afforded by using the AI clone ensures that the managers receive what they need in real time and without any stigma associated with asking for help for something they may think that they should already know how to do or what they think others think they should already know.
Your latest book, Explicit Expectations, now has an AI-powered eLearning companion. How does combining AI with self-paced learning change how leaders and teams engage with your work?
AI-enhanced eLearning is a gamechanger since it meets the participants where they are and where they are ready, whenever they’re ready and need assistance. It remembers previous interactions and coaching engagements with the client (and keeps them confidential and completely separate from other clients), so that it can create a more complete and robust experience for the client, recalling and integrating earlier conversations, agreed-upon actions, and themes into the current session. This results in a more comprehensive and robust coaching and support experience, enabling greater connectivity, breakthroughs, and accountability-holding. As with any eLearning, participants can access the content and material at any time that works for them. Adding AI to the mix makes it a more personalized, customized experience that brings in additional resources and context to optimize the participant’s experience and maximize the learning and “stickiness” of the content in a real, practical, and meaningful way. Furthermore, I am able to receive summaries and themes of all of the sessions, which I can then use to identify any broader factors at play in a specific organization or team, allowing me to offer additional organization development interventions to address and improve their effectiveness on a broader scale.
Some coaches might fear that AI could ‘replace’ the human element. What would you say to leaders or fellow coaches who worry about technology diluting genuine connection?
I see AI as a way to enhance and step up existing human capabilities. There is no humanly way possible to always be available to all of our clients. There is no humanly way possible to catch every single nuance in every single coaching conversation. There is no humanly way possible to capture and recall every single individual comment that may build up to a theme that is important to address in a coaching engagement.
Conversely, there is no AI way possible (yet?) to integrate additional institutional knowledge or organizational information that a coach may learn from conversations with a client’s boss, colleagues, the People & Culture department, industry news, socio-political events, etc. And true empathy is not palpably conveyed by AI, the way that it can be by humans.
Leveraging a hybrid model where AI is available for some work while human coaching is made available for a truer connection is the best way forward. And remember, some humans prefer to engage with technology more than they do with people, and vice versa. This is a way to be able to flexibly and effectively address the unique needs of all humans.
Looking ahead, what advice would you give other coaches or consultants who want to experiment with AI tools to expand their reach but don’t know where to start?
Embrace the future (actually, the present)! Search out the service providers (like coachbot.ai) who best suit your niche and can meet your needs and start experimenting! It is well worth the investment for you AND your clients. After all, as we always coach our clients (and as Velma Kelly sings in “Chicago”), you can’t do it alone. You can’t always be there for everyone (and if you try, you’ll burn yourself out and be there for no one, including yourself). AI can help prevent that so that you can be there for yourself and your clients.
Thank you, we greatly appreciate the time you spent on this.
It’s been my pleasure! Thank you for creating and providing this forum to do so!
