Prompt Playbook: Big Questions in AI PART 1

Every time I go an give workshops or talks about AI the same 4-5 questions from the audience pop up again and again. Again.

The first time they come up I have to think on my feet and hope for the best. But after answer the same question 10 times? Easy.

If you are venturing into the world of AI building or becoming an authority in your industry on the use of AI you will get these kind of questions. Whether its from clients or audiences doesn’t really matter- you need to have answers at your fingertips.

This is what separates the casual AI enthusiast from the genuine AI expert. When you position yourself as an authority on AI in your field, these big, thorny questions will come your way—often in public, high-pressure settings where your response can make or break your credibility.

In this Playbook we're tackling the five most common "curveball" questions you'll face as an AI expert.

Having fielded these questions countless times on stage, in workshops, and during consulting engagements, I'm sharing my approach to each—along with alternative perspectives you might consider.

I am not the be all and end all of this! Far from it! I’m probably very wrong ha!

BUT I want to i) surface the questions that get asked ii) give you my answers and iii) help you start to formulate your own.

So that when the question is asked (and it will be!) you’ll be ready to wow the asker.

Let’s get started

The Inevitable Question

"Will AI take our jobs?" isn't just a common question—it's practically inevitable. In my experience, if this doesn't come up during a formal Q&A, it will emerge during breaks, in private conversations, or in follow-up emails. And it makes perfect sense: people's livelihoods and professional identities are at stake.

It won’t necessarily be asked in such a blunt way. Often there are layers - people will ask about automation, hiring practices or job progression. But the underlying root cause is the same: is my job safe??

Let's look at three distinct positions you might take

Position 1: "AI Will Create More Jobs Than It Eliminates"

The optimistic view holds that, like previous technological revolutions, AI will ultimately create more opportunities than it displaces. Proponents point to history: the industrial revolution, computerisation, and the internet all sparked initial fear but ultimately expanded the job market.

In this view, while certain roles will disappear, entirely new categories of jobs will emerge—AI trainers, AI ethics specialists, prompt engineers, and countless roles we can't yet imagine. The key is adaptation and re-skilling.

I personally don’t believe in this. AI is different because whereas other technologies augmented human skill and intelligence AI can (potentially) wholesale replace it. It can also self improve which no other technology is human history has been able to do.

It’s new territory so applying existing historical paradigms is…risky!

Position 2: "The AI Job Apocalypse Is Coming"

The flip side alarmist perspective suggests we're facing something fundamentally different from previous technological shifts. Because AI can potentially automate both physical AND cognitive tasks, it threatens a much broader swath of employment—even knowledge work that previously seemed immune to automation.

This view suggests massive displacement across industries, with only a small fraction of new AI-related jobs created to replace those lost. The result: widespread unemployment and profound economic disruption.

I think that this is closer to the long-term truth. We’ll need to find different ways to organise our economies. Remember that modern capitalism is only actually 400-500 years old. Seems like a long time absolutely but it’s a small blip in terms of human history and even in terms of civilisation.

In the West we assume it’s the primary way to organise societies economically (and indeed not all humans agree with this!) but this doesn’t preclude other forms. Something will have to shift - it’s just very difficult to predict what!

Position 3: "AI Will Erode Job Creation and Transform Organisational Structures"

My position takes a more nuanced middle path. I’m focusing on the short and medium term where we can predict with a (little!) more accuracy. Trying to prognosticate out too far is a fool’s errand so instead let’s keep it focused.

I believe the primary impact won't be sudden job displacement but a gradual erosion of job creation, particularly at entry levels, which will ultimately transform organisational structures.

Less utopian, less apocalyptic. Let me outline my basic argument.

How AI Will Transform Employment: The Erosion Theory

I used to repeat the common refrain: "AI won't take your job, but someone using AI will take your job." I've come to believe this is overly simplistic. That was 2024 - old school!

The reality is (I think!) more subtle and, in many ways, more concerning. Rather than directly eliminating existing positions, AI is more likely to slow or stop the creation of new jobs—particularly at the entry-level. This has profound implications for organisational structures and career pathways.

Consider fields like law, accounting, or business analytics. The most algorithmic, routine work tends to happen at the early career stages. It’s how new hires cut their teeth. They aren’t given responsibility right out of the gate but instead go through the basic grunt work first.

These roles—law clerks doing document review, junior accountants processing transactions, analysts creating standard reports—are precisely where AI excels. Ruh roh shaggy.

As these tools become more sophisticated, organisations will need fewer entry-level staff. We're already seeing the beginnings of this with hiring freezes and reduced head-counts in sectors with robust AI adoption.

If you're currently established in your career, especially at mid or senior levels, you're likely relatively safe in the short term. You’ve put in your years and secured your position. Your role probably involves complex judgment, interpersonal skills, and institutional knowledge that AI can't easily replicate. Yet.

But here's where the secondary effects become important—and these are harder for many to grasp.

Most organisations are structured like pyramids, with more people at the bottom than the top. If we reduce the base of that pyramid through AI automation, there are downstream consequences for the entire structure. With fewer junior staff to manage, organisations need fewer managers. With fewer managers, they need fewer directors and executives. You get the picture.

This is similar to what happens with an aging population in countries like Japan. You are probably more familiar with this particular Jenga tower:

I think we’ll see something similar with AI’s effects on work. Over time—we're talking years or even decades—the combination of fewer entry-level positions and improved AI capabilities will likely transform many traditional career ladders and organisational structures entirely.

Who Will Be Affected and When?

The timeline and impact vary significantly depending on your career stage

If you're established in your career: The immediate effects will likely be minimal. Organisations and regulatory frameworks move slowly, and skills like judgment, creativity, and interpersonal dynamics remain challenging for AI to replicate. Is your industry unionised? Likely effects will be even slower. Your job may evolve to incorporate AI tools, but wholesale replacement is unlikely in the near term. If retirement is within sight, you can likely navigate to the finish line. Congrats you, dodging bullets like Neo.

If you aren’t entering the workforce for another ~10 years: If you are still at school then you are equally lucky. The world has time to adapt to this new technology. You'll be stepping into a transformed landscape. The advantage is that you'll enter knowing the new rules of the game, without having to unlearn old patterns.

If you're in the "messy middle" (finishing up university / early career): You are in your early 20s and (sorry!) facing the most challenging transition. You may graduate into an environment where traditional entry-level positions have significantly diminished. At the same time new roles haven’t yet opened up because older institutions are working out how to deal with this whole “AI thing”. This group will need to be particularly adaptive and entrepreneurial - you can’t wait for the world to sort itself out for you. You need to get on with taking control yourself.

For everyone, regardless of career stage, I believe developing alternative income streams and entrepreneurial skills is increasingly essential. This isn't just about financial safety nets—it's about developing the adaptability and self-direction that will be increasingly valuable in whatever economic reality we find ourselves in.

The Entrepreneurial Opportunity

One of the most profound ironies of the AI revolution is that while it may reduce traditional employment opportunities, it simultaneously makes entrepreneurship more accessible than ever.

When I launched my first business, I had to handle everything myself: building products, writing marketing copy, designing websites, providing customer service—the full spectrum. While it was educational, it was extraordinarily difficult to build a sustainable income this way. It took a decade plus realistically to start making good money. That’s too long and I wouldn’t recommend it to my worst enemy!

That’s changing now.

asks that once required teams of specialists—coding, design, content creation, marketing, customer support—can now be accomplished or augmented through AI tools by individuals or small teams. The barriers to entry for starting a business have never been lower.

I’m writing this in a Vietnamese coffee shop right now whilst in another window Cursor chugs away building an SEO optimised website for me. As someone who started building businesses in the “before times” believe me : this is special.

Today's entrepreneurs (read: you) can leverage AI to handle or augment many startup tasks. In fact, this is precisely why I've focused my work on AI entrepreneurship—to help people harness these tools to create sustainable, independent income streams regardless of what happens to traditional employment models.

Argument Summary

OK so here’s a quick roundup of the basic thrust. So that when asked a question about job security you have a framework to answer with:

• If AI excels at automating routine, algorithmic tasks concentrated at entry-level positions,

• Then job creation at these levels will gradually erode rather than existing jobs suddenly disappearing.

• If entry-level positions diminish over time,

• Then organisational structures will transform from the bottom up, like removing lower blocks from a tower.

• If organisational structures fundamentally change,

• Then the impact varies by career stage: minimal for established careers, challenging for early careers, transformative for new entrants.

• However the same AI making traditional employment uncertain also makes entrepreneurship more accessible than ever.

Remember, this is just one perspective! And I’m not particularly smart!

With AI's rapid development, no one can predict the future with certainty. Anyone who says they can is B.S.ing. The purpose of this argument is to give you a nudge to prepare your own answer to this question.

In fact - if you have an answer shoot a video, post it to TikTok and tag me in and I’ll see it.

What's Next?

Next we’ll tackle a philosophical curveball: "Is AI really intelligent, or just mimicry?" This question tests your understanding of both technical capabilities and the nature of intelligence itself. It’s a doozy.

Keep Prompting,

Kyle