In this episode I want to discuss failed delegation, and how leaders can leverage AI to fix it.
Welcome to Lead Prompt // executing leadership from the root. I’m your host, John Collins.
We need to have an uncomfortable conversation about failed delegation. Specifically, why it happens, the hidden costs it incurs, and how the explosive rise of Artificial Intelligence is giving leaders an entirely new, and sometimes controversial, way to fix it.
Recently, I had a fascinating, and frankly eye-opening, conversation with a Senior Vice President at a major tech firm. He shared something with me that felt like a quiet confession: he has been using AI to generate code himself.
Now, my very first thought was a sense of genuine admiration. I was impressed that an executive at his level was still technical enough, and hands-on enough, to fire up an LLM and get into the weeds of code generation. But almost immediately, that admiration was replaced by a deep concern. As an SVP, he sits at the top of a massive organizational chart. Shouldn’t he be able to delegate this to literally anyone on his huge team? Why is an executive spending his highly compensated time doing the work of an individual contributor?
When I raised that concern with him, his answer was incredibly telling. He explained to me that he was generating the code himself to, in his exact words, "stop the engineers from BS-ing him" about their project estimates. He had grown so intensely frustrated with the friction, the pushback, and the padded timelines, that he decided it was simply easier to bypass his own management chain and do it himself.
That conversation stuck with me. It reminded me of the core mechanics of delegation, why it breaks down, and how AI is fundamentally changing the way leaders think about getting things done. AI opens up possibilities that simply never existed before.
For example, I've started telling the managers on my own team that they now have two distinct paths forward. Option one: They can get work done via managing people. Option two: They can get work done via managing AI.
Now, of course, I am being deliberately provocative when I say that. In the real world, it’s not a strict binary choice; it should be a strategic blend of the two. But making the statement forces a necessary shift in perspective.
The cold, hard truth of leadership is this: when the mental and operational overhead of managing a person becomes greater than the overhead of managing an AI to do the exact same task, the person in question is in serious trouble.
You only have to look at the recent news. The media is flooded with headlines about massive layoffs across the tech industry, and AI is frequently being quoted by executives as the primary reason making these headcount reductions possible. "We are restructuring to focus on AI," they say, or "AI efficiencies allow us to operate leaner."
My personal take? It’s a bit more nuanced. I believe that many of these companies, having bloated their headcounts during the zero-interest-rate phenomenon of the past few years, wanted to make these reductions anyway. AI is acting as a very convenient, forward-looking excuse to trim their organizations without spooking their investors. However, while AI might be the cover story for the cuts today, it is absolutely the enabler that will prevent those companies from ever hiring those roles back tomorrow.
Let’s get back to the root of the issue: why does delegation fail in the first place?
Historically, it fails because the manager in question no longer trusts the employee to get the job done. That lack of trust might be about competence, but more often, it’s about alignment, urgency, or attitude.
It also fails because the manager believes, sometimes correctly or sometimes through ego, that they can get the job done faster and with better quality themselves. In the past, doing it yourself meant sacrificing your weekend.
But today, we have a third, increasingly common reason. Delegation fails because the manager realizes it will be radically cheaper, significantly easier, and often more accurate to just get an AI to do the work instead. There is no on-boarding. There is no negotiating over story points. There is just a prompt and a result.
This is not a passing fad; it is a trend that will define the future of corporate execution.
Think about the ultimate employee profile from a purely robotic, capitalist perspective: An AI never complains. It never calls in sick. It never quits on you for a better offer, it never undermines your authority in a meeting, and it never loses motivation on a Friday afternoon.
As humans, we have to get real. We have to wake up and realize that this is our baseline competition now. If your primary value to your company is churning out boilerplate code, writing generic marketing copy, or synthesizing meeting notes, you are competing against an entity that does it instantly and for fractions of a penny.
I have spoken on this podcast before about the reality of our current era. We have a choice: we either embrace AI, mastering it to leverage a massive productivity boost in our own careers, or we fight against it, cling to the old ways of working, and get left behind. For the ones who get left behind, finding it difficult to build a long-term career in tech will be an understatement. I genuinely think it will become impossible for them.
AI is here to stay. Delegating discrete tasks, and eventually full, complex projects to AI agents, will become standard operating procedure. Yes, right now, keeping a human in the loop for oversight, security, and validation is mandated by compliance rules and common sense. But even that will gradually diminish. As our trust in the technology grows, as the quality of AI output skyrockets, and as AI hallucinations become a quaint memory of the past, the "human in the loop" will transition to "human at the helm."
In this near future, the most valuable skill a leader can possess is discernment. A true leader must master the new matrix of delegation: choosing exactly what tasks require the empathy, strategy, and complex problem-solving of human colleagues; what tasks are pure execution that go straight to AI; and what tasks require a combined approach of powerful AI tools guided by expert human operators.
The SVP I spoke with wasn't wrong to use AI, but he was using it to mask a cultural failure on his team. True leadership isn't about using AI to avoid your team; it's about using AI to elevate them, so no one ever feels the need to BS anyone ever again.
Thanks for tuning in. Keep executing from the root.
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File details: 9.9 MB MP3, 7 mins 35 secs duration.
Title music is "Apparent Solution" by Brendon Moeller, licensed via www.epidemicsound.com
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