Coaching AI Transformation

Lynn Wolf-Hill • July 9, 2023

Be Ready for the Disruption: You Don't Have To Go It Alone

Introduction

We are on the cusp of yet another technological revolution, which inevitably has an impact on business communities. Artificial Intelligence (AI) is currently and more so in the future, a business disruptor, whether one chooses to see this as an extension of digital transformation, the advent of intelligent automation, or something entirely different. 


So, yes! The AI Revolution is here! The release of ChatGPT made AI real to millions of people possibly blissfully unaware before. The inevitability of this has helped companies understand that they need an AI Transformation to stay competitive. At the same time, AI has created an uptick in people’s fear that they and their jobs will be replaced. Blame too many science fiction movies; people fear what they don't understand.


Like other organizational change initiatives, companies may expect resistance and ,or a high failure rate at a time when failure to quickly adapt will put many them out of business or seriously lagging behind. Coaching plays a crucial role in less bumpy and cooperative (aka successful) transformation; now more so than ever. 


AI longevity and Impact

While Artificial Intelligence isn’t new, it has been a fairly abstract concept to most people until now. The term was coined back in 1955 by an Assistant Professor of Mathematics at Dartmouth College. At the time, the term AI was largely inspirational, but the ideas generated at that time led to the development of rule-based systems over fifty years ago.


Breakthroughs in neural networks and natural language processing, combined with massive amounts of data in the early 2000s, enabled a shift from rules-based processing to machine learning. The adoption of machine learning fueled cloud computing and lowered the barrier to entry for most companies. These advances, in tandem with  the internet, made way for the need of organizations to develop Digital Literacy (the ability to use digital tools) and then Digital Fluency (the ability to create something new with digital tools.)


Coaching and AI Transformation

Some ways that coaching can have a profound impact on an organization’s view of AI may be relatively easy to implement and can have a positive impact on how a company’s people view an AI Transformation.

  • Culture and Mindset: Coaching promotes curiosity and a willingness to experiment. Coaches can help people view AI as a tool rather than an adversary. When nurtured by an organization, this creates an environment where teams and individuals embrace change, adapt quickly, and continuously test, learn, and implement innovations.
  • Enhanced Collaboration and Communication: Coaching encourages collaboration, knowledge-sharing, and cross-team communication. Paired with AI-powered communication tools and platforms, seamless collaboration and streamlined decision-making is possible
  • Adaptive Strategy Development: Coaching helps people identify the data they need to effectively leverage real-time market insights and predictive analytics, allowing for rapid adaptation of strategies and encouraging leaders to integrate AI thinking into their strategic planning in a rapidly evolving market.
  • Continuous Learning and Improvement: Coaching supports personal development and organizational learning. Coaches can facilitate the integration of AI-powered learning into the coaching process, promoting continuous learning and improvement at both individual and organizational levels.


Conclusion

The transformative power of coaching amplifies organizational agility and prepares people for the Age of AI. Through coaching, individuals and teams develop the mindset, skills, and behaviors necessary to embrace change, innovate, and thrive through an AI Transformation.


AI can enhance decision-making, problem-solving, by leveraging data-driven insights and automation. It will change every company on earth: some will make it through this age and some will not, By leveraging the power of coaching, organizations can create a culture of agility, leverage data for informed decision-making, enhance collaboration, and continuously adapt to the evolving business landscape. Embracing a synergy between coaching and AI will position organizations for success in the age of agility and technological advancement.


If you’d like to discuss the power of coaching and your company’s AI Transformation, please reach out.



Resources

By Lynn Wolf-Hill July 24, 2025
 A couple of years ago a friend shared an article on how a man made art using artificial intelligence and had an online store. I think his real money came from charging people to learn how to do it. She said,” You could do that!” I wasn’t really sold on the idea but did check out the app she sent my way. It was fun to play with it. I could tweak the prompts and refine how it showed up, long before I knew what a “prompt” was. It had a free trial, and then a monthly price, but as it was in beta, if I gave it a lump sum I could have it for life. And so I did… I used to create images with it every day, but I can’t remember the last time I used it. I can now do the same thing in ChatGPT if I really work hard on the prompts, super specific. I initially paid for the pro version, and now I am using the “plus” option. This allows you to use it as much as you like, and you have access to early releases of functionality. I can think of similar evolution of online tools. There was a race between My Space and Facebook. Before some of the widely used browsers like Google and Safari, there were SO MANY browsers. I like Infoseek and Peoplefinder. Their titles alluded to their differentiation from the competition. And now…? Workplaces got all policy-happy with use of internet at work, and now it’s free out-of-the-box software included with your laptop. So why pay for AI? I very often see these AI-generated advertisements letting me know that old people only use AI like they would Google, and then the ad will go on to list all the AI tools and apps you need to train yourself daily. “Wait, am I being bullied into doing homework? Initially, just as companies have self-contained large learning models, I believed if I paid for my AI, my “projects “or “agents,” were protected. I was writing The A3 Framework: Staying Ahead of the Curve by Combining Agile, AI, and Audit. Related to that activity, I was researching a great deal around international protections in place. (They changed more than once in a short timeframe. I was concerned that things I wrote and submitted could be searched for and found by anybody, making my book obsolete before it was ever published. I really really wish I had searched on the public version for contrast. I did compare different AI tools to contrast what came back. Some were better than others. And now, many organizations are asking employees to use internal AI tools to “teach” the LLM. Several people I have been coaching have provided some feedback on this. Their insight includes frustration with teaching the internal tool when they already had trained their own LLM, and the AI gave them worthless return on their prompts. There’s concern that their ideas can be “stolen,” or what they looked for can be somehow weaponized by HR. So what is your favorite AI platform? I miss my “Ask Jeeves” browser… are we going to continue paying for AI, and are we sure the very things we think need protecting ARE? A couple of years ago, a friend sent me an article about a guy who used artificial intelligence to make art and sell it online. She said, “You could do that!” I wasn’t totally sold on the idea, but I tried out the app she recommended. It was fun—tweaking the inputs and refining what showed up, even before I knew what a “prompt” was. The app had a free trial and a monthly fee, but since it was still in beta, I could pay a lump sum for lifetime access. So I did. I used to generate images every day. Now? I can’t remember the last time I opened it. These things evolve fast. I can now create similar images in ChatGPT—if I get really specific with the prompts. I’ve gone from using the “pro” version to “plus,” which gives me unlimited access and early releases of new tools. It feels like I’m always upgrading, always shifting, but never really arriving. I’ve seen this before. Remember My Space vs. Facebook? Or before Google and Safari took over—there were tons of browsers: I liked Infoseek and PeopleFinder. Their names hinted at their unique flavor. And now? Browsers are just baked into your laptop, part of the default software package. No big deal. So, why pay for AI? Lately I keep seeing ads that say only “old people” use AI like Google. Then the ad flips and starts listing the 12 AI tools I’m apparently supposed to train myself on daily. Wait—am I being bullied into doing homework? When I first started using AI tools to help write The A3 Framework: Staying Ahead of the Curve by Combining Agile, AI, and Audit, I assumed that paying for them meant my data was protected. I believed that my “projects” or “agents” were somehow mine. I was researching a lot of international privacy protocols at the time (which changed more than once during the writing process), and I was genuinely worried that drafts I submitted could be scraped and show up in someone else’s search results before my book was even published. I really wish I had searched on the public version too—just for contrast. I did compare responses across different AI tools. Some were better than others. But I didn’t expect the rapid pace of change to outpace the very protections I was researching. And now, many companies are encouraging employees to “teach” internal AI tools—to help train their organization’s LLMs. Several of the people I’ve coached have shared frustrations with this. Some of them had already spent time training their own personal LLMs to get decent results. Now they’re being asked to start over—often for worse outcomes. There’s also this quiet anxiety around ideas being harvested, someone tracing their searches, will this be used by HR in ways I didn’t agree to? The discomfort is real. We pay for AI tools hoping for privacy, productivity, maybe even a competitive edge—but are we getting that? Or are we just onboarding ourselves into systems we don’t fully understand? So what IS your favorite AI platform? I miss my Ask Jeeves browser. Maybe we’re not just paying for AI—we’re paying for a false sense of control.
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