Last summer, I was walking my dog Reuben around the neighborhood. I had some things on my mind from work, and when that happens, I would often dictate my thoughts in a voice memo to listen to later or transcribe and review some of the highlights. Somewhere in my ramblings, I typically find - well, a few gold nuggets - that I want to employ or implement in my life. This time, though, I decided to try the relatively new two-way conversation mode with ChatGPT.
What I discovered was both thrilling and a bit unnerving. This wasn’t like conversing with Google or Siri. It was an 'open mic' where ChatGPT listened and then responded. Suddenly, I found myself in a deep dialogue with an AI.
It wasn't about asking it to summarize an article or create a checklist. It was about sharing, reflecting, and thinking out loud about my day and my week. It's strange to say, but it felt like a form of therapy. Or a stroll with a remarkably wise friend who wasn’t in a hurry to reply. Just curious. Just present. Every time I paused, it posed another open-ended question. Nothing showy. Nothing generic. Just... thoughtful. After a full hour of this, I felt a breakthrough and a newfound clarity.
That conversation really stuck with me. Not just because of what I uncovered about myself, but because of a question ChatGPT asked, and because of what it modeled and why I’m talking about it with all of you.
What if leaders asked better questions?
What if we gave better instructions?
What if we showed up the way we wish others would?
Turns out, GenAI has quietly been teaching me how to do both. Or rather, I made space for the opportunity to find a teachable moment in this to make me a better human. And neither of those lessons is about technology at all. In fact, they're about how we lead.
1. How GenAI Taught Me to Ask Better Questions
If you’ve used ChatGPT more than a few times, you know this: it rarely takes your prompt at face value. It asks for context. It seeks clarity. It follows up. Even after it gives you your answer, it still follows up with questions. It is always asking how it can continue to be helpful even after the deliverable has been made.
That may not sound profound, but it is because most people don’t do that, especially not in leadership.
As the Greek Stoic philosopher Epicetus once said, we have two ears and one mouth for a reason - so we can listen twice as much as we speak. But yet, we rush to respond. We offer advice before understanding. We assume instead of asking. We often fail at active listening.
But great questions are a leadership superpower. Not just the kind that probe, but the kind that reveal. Great questions show authentic, raw, and real curiosity. They show that the person asking the questions truly cares to understand. And when that goes right, that person wins by building a connection and trust.
Because in my world, law firms, corporate counsel, and consulting, asking good questions should be table stakes. Yet we often default to assumptions. We miss the real issue. We miss the person.
If you’re in sales, it is no different. If you don’t ask the right questions, you never get to the right answer. You offer solutions to problems that were never there. And the opportunity evaporates.
As a friend, as a partner, as a professor - if you don’t stop, actively listen, and are mindful of the words the other person is saying, you miss a life opportunity. And the reality is, the person on the other end feels it; they feel as if they are not heard.
And, in all of those situations, you’re just wasting everyone’s time.
In that walk around the neighborhood, GenAI reminded me that curiosity is the bud that blossoms into the brilliant flower of influence.
2. How GenAI Taught Me to Give Better Instructions
Too many people look at GenAI as just another Google search engine, which is unfortunate. The way that so many input a prompt into that search box often falls short of leveraging the true, amazing, and sometimes incredibly scary power of GenAI. When I became more curious about the art and science of prompting, it forced me to develop a structure I didn’t even realize I needed.
I use a framework now that’s built on the best practices of prompt engineering—but it turns out, it works even better for human leadership. It's called:
G.O.L.D.™: Goal, Objective, Language, Deliverable
Goal – What’s the big-picture outcome? Why are we doing this?
Objective – What are the key steps or targets to hit?
Language – How should this be communicated? Who’s the audience, and what tone or context do they need?
Deliverable – What is the final output? What does success look like?
Where this structure comes from: frameworks like C.A.R.E. (Context, Ask, Rules, Examples), C.O.R.E. (Context, Objective, Role, Example), and G.C.T. (Goal, Context, Task) all emerged from the AI world as a way to get clearer, more helpful responses. No single person invented them—they evolved through iteration, trial and error, and collective learning. I’ve adapted these ideas into a structure that works for how I think, lead, and delegate. And I use it now with people just as much as I do with AI.
Here’s the leadership punchline: What if we did this with people?
How many times do managers give vague direction, unclear expectations, or half-formed ideas—and then blame their team when the output disappoints?
The truth? Garbage in, garbage out.
Whether it’s AI or your junior associate, you are the input. Your clarity determines the outcome.
If we want people to grow and thrive, then we need to teach through precision. Not micromanagement. But real instruction. Real context. Real coaching.
Don’t just expect excellence. Enable it.
3. Why Leadership Is Still a Human Game
AI didn’t teach me to code. And, I have no idea how to code either.
But it did teach me to slow down. To listen more carefully. To think more clearly. To communicate more intentionally and mindfully.
It taught me to lead the way I want to be led—with curiosity, context, and care.
If you’re a partner in a firm, a VP in a business unit, or a team leader managing deadlines and deliverables, this is your opportunity. Every prompt you write can become practice. Every interaction with AI is a mirror that reflects your ability to lead:
Are you clear?
Are you curious?
Are you kind?
AI can teach us all a lesson, if we’re open and willing to receive it, to make us more human and more emotionally intelligent.
And strangely… that’s exactly what it’s been doing for me.
Three Takeaways for Gold Standard Leaders
Lead with G.O.L.D.™. The G.O.L.D.™ Framework (Goal, Objective, Language, Deliverable) isn't just for AI—it’s how great leaders communicate with real people. It creates clarity, empowers action, and minimizes rework.
Ask before you answer. Questions unlock context, clarity, and connection. Don’t assume—engage.
Tech is a teacher. Every prompt you write is a leadership exercise. Use it to build better habits, not just faster answers.
Want a free one-page PDF of the G.O.L.D.™ framework? Click [here] to download and keep it as a leadership cheat sheet.
The future of leadership isn’t artificial. It’s intentional.
And it starts with how you prompt.
