Leading with AI Requires You to Be Human
Before I took the Lead with AI course for Fractionals, my relationship with AI was mostly driven by worry. It was a creeping worry that if I didn’t get on board, I’d be left behind. Didn’t help that I’d heard on a podcast that professionals who don’t embrace AI now could be obsolete in two to three years. I couldn’t shake that off but didn’t know how to move forward.
Like many others, I started by following AI thought leaders on Instagram, subscribing to newsletters, and trying to keep up. But without a clear structure or framework, everything felt fragmented—like I was picking up random pieces of a puzzle without knowing what the final picture should look like.
Then came a recommendation from Elena Chow, whom I consider my big sister in the professional world. She told me about Lead with AI, a course designed for business leaders. The investment gave me pause, but when a collaboration with Portfolios in Asia became available, I decided to give it a shot. If people pay me for my expertise, why not I accelerate my learning with expert guidance too?
To my surprise, the course was well-designed, engaging, and—most importantly—human-centric. It wasn’t fear-mongering, overly inspirational, or painfully technical. Instead, it was a thoughtful blend of leadership strategy, practical AI application, and a strong learning community.
Three Key Shifts in How I Think about AI (In Light of Humanity)
1. AI Is Fallible—And That’s Okay
One of the first things I learned was that AI, for all its prowess, is inherently imperfect. We often expect computers to be flawless—faster, more efficient, and free from errors. But the reality is, AI is not human. It predicts words and responses based on tokens, probabilities, and context, not understanding.
From the course I learnt the basics like what is a Large Language Model (engine behind Modern AI), what are tokens (building blocks of AI language), what is a context window (AI’s short-term memory) which helped me understand why AI can be both powerful and flawed (hallucinations anyone?).
Once I embraced this paradox—that AI can be both powerful and flawed—I found it much easier to work with. Instead of being frustrated by its limitations, I started seeing how AI was like a human - it required guidance, refinement, and, sometimes, a healthy dose of patience.
2. Treat AI Like a Team Member
Before this course, I viewed AI as just another tool to make tasks more efficient. But one of the biggest mindset shifts I experienced was treating AI as a team member—sometimes a junior team member, sometimes as a senior thought partner.
For example, when I struggled to create a custom GPT, Daan (course instructor and host) suggested I give it a brief like I would to a junior team member. That changed everything. Instead of just typing vague prompts, I wrote structured, detailed instructions—just like I would in an email to a team member. The results were far better than I expected.
On the other end of the spectrum, I started using ChatGPT’s voice mode for higher-level brainstorming, treating it like a senior colleague. I’d challenge it to counter my ideas, help me refine my strategy, or point out gaps in my thinking. This was a game-changer. Where were you ChatGPT when I co-founded My Working Title?
3. Mastering AI Is a Hands-On + Trial & Error Process
From not knowing where to start or how to experiment smartly, I went on to learn how to communicate with AI via prompt engineering and how to build my AI team.
It was not without what Min Chia in our podcast interview calls a “productive struggle”. I tried. I failed. I got stuck. I questioned. I fumbled. I tested. I found ways to move forward. Thankfully, there was Daan and the learning community to share learnings as we experiment.
One of the most practical takeaways from the course was learning how to engineer powerful prompts. Understanding concepts like chain of thought reasoning and super prompts allowed me to get far more targeted and strategic results from AI tools.
For instance, I learned that when working with ChatGPT O3 models, where you can shape its reasoning patterns to get more sophisticated outputs. This is especially useful when writing, editing, and brainstorming for strategy —making AI an effectiveness multiplier rather than just a shortcut.
I also discovered practical AI applications that directly impacted my work:
✔ Building custom GPTs for clients—so that when I transition out from being a fractional CMO, they still have an AI knowledge base tailored to their needs.
✔ Tapping into global expertise—using AI to simulate advice from industry leaders such as Adam Grant (for organisation psychology), Marshall Goldsmith (for executive coaching) etc. I experimented with starting my super prompt with “Imagine you’re a StoryBrand consultant from Donald Miller’s team and you’re creating a tagline for this website…”, and received surprisingly insightful website header ideas.
✔ Using AI to write and edit faster—especially with features like Canvas, which allows for targeted refinements without regenerating an entire article.
The Power of a Learning Community - Learning AI with Fellow Humans
Beyond the technical and strategic takeaways, one of the most valuable aspects of the course was the community. Learning AI alone can be overwhelming, but having a WhatsApp group to share struggles, ask questions, and celebrate wins made all the difference.
AI isn’t a “set and forget” tool—it’s an evolving space that requires continuous learning. In just three weeks, I’ve felt like so much has happened.
But now, instead of feeling lost when someone mentions terms context windows or token limits, I feel confident and informed. If I’m curious or don’t understand anything, I know I can always reach out to the community. This shift—from worry to confidence—has been priceless (ok, not exactly, it did come with a price tag)
The Existential Question: What Makes Us Valuable as a Human in an AI World?
Beyond practical applications, the rise of AI has also pushed us to confront fundamental questions about work, identity, and value as a human being.
If AI can automate admin-heavy tasks and even some aspects of strategic thinking, what remains uniquely human? If AI eliminates the need for certain kinds of labour, what pushes us to be valuable in our existence, in the market?
One of the key discussions in the course revolved around the idea that “human is the new luxury”. In a world where AI can generate content, analyse data, and execute tasks at lightning speed, what cannot be replicated?
This is where career design becomes critical. AI can’t replace human qualities like:
✔ Facilitating complex discussions—navigating conversations where multiple perspectives need to be heard and reconciled.
✔ Iterating in real time—responding to unpredictable situations with emotional intelligence and nuance.
✔ Bringing warmth and trust—people don’t just want efficiency; they want connection.
Instead of fearing AI, we should be asking: How can we use AI to free up space for what truly matters? How can we leverage AI to design careers that allow us to be more human, not less?
The Future: AI as a Career Design Partner
As someone deeply involved in career design and organisational development, I see AI as an incredible ally in shaping work that is both meaningful and scalable.
✔ AI can help us explore career possibilities—by analysing job market trends and personal skills to suggest paths we may not have considered.
✔ AI can accelerate skill-building—by providing real-time coaching, personalised learning pathways, and access to expert knowledge.
✔ AI can assist in decision-making—by synthesising vast amounts of information to help us make informed career moves.
However, AI does not replace the deep, personal work of understanding who we are and what we want — that is the human inner “work” we need to do.
Leading with AI Means Staying Human
The biggest lesson from Lead with AI? AI is only as good as the human guiding it.
Yes, AI is powerful. Yes, it can save time, generate ideas, and improve efficiency. But at the end of the day, leadership, creativity, and judgment remain human strengths. The most effective way to work with AI is not to fear it, but to understand, shape, and integrate it into our workflows in a way that aligns with our goals.
The future of work isn’t just about AI—it’s about how we, as humans, lead with it.
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Reference: https://www.flexos.work/leadwithai/ai-basics-every-executive-should-know
Written by: Jael Chng