What Managing Taught Me About AI
By Nathan Waterhouse · 2026-01-27
It was late last week, and I was staring at a terminal window, stitching together outputs from three different prompts. I'd been at this for hours. My family had noticed I wasn't sleeping well — I kept going to bed with the laptop open, the blue light luring me back in for one more tweak.
Everything I'd built over the past month was consuming more and more of my time. It started to remind me of something I hadn't thought about in years: being a junior manager with too many direct reports, struggling to delegate properly.
Let me back up.
The Unblocking Phase
Before Christmas, I'd been on a journey with AI coding tools. I started with vibe coding platforms like Lovable, then moved to using Claude Code directly in the terminal. This unlocked ideas that had been sitting in a to-do list for years. I built 17 small apps, mostly things I could use in my consultancy work. It felt like a superpower.
Then reality set in. You have to maintain these things. Optimise them. Make them better. Every app I'd built created new work.
Agents seemed like the answer. If AI could work for me overnight — while I was asleep — maybe I could get ahead of the treadmill.
It didn't work out that way.
The Overnight Question
Jeremy Utley, a leading thinker on AI and innovation, asked a question in the AI community I'm part of: How could you get AI to do something for you overnight? So you wake up and the work's been done?
I started playing with that idea. My first agent built interview guides for a strategy project I'm running. I'd wake up, and there'd be a guide ready for whoever I was speaking to that day.
But instead of saving time, it created more. I'd review the output, correct it, re-prompt, refine. I was still doing all the thinking. I'd just moved the work from building to critiquing.
I felt underwhelmed. I kept thinking: isn't this just a bunch of LLM calls and prompts strung together? What actually is an agent?
What I'd built wasn't an agent. It was a cron job.
Then I watched an Anthropic video that reframed everything.
Goal-Driven, Not Task-Driven
They put it simply: real agents aren't task-driven. They're goal-driven.
"Make me an interview guide" is a task. "Ensure I'm ready for my interviews" is a goal.
The difference sounds subtle, but it changes everything. A task gets you a deliverable. A goal gets you an outcome — and leaves room for the agent to figure out how to get there.
That's when the management parallel clicked.
The Management Parallel
As a junior manager, I used to give people tasks. "Write this document." "Prepare this analysis." I'd check the work, correct it, send it back. I stayed busy because I was still doing all the thinking. I'd just outsourced the typing.
Over time, you learn that's not delegation. Real delegation is outcome-driven. You set a goal, some constraints, and let people figure out the path. You assess the outcome, not the task. That's when you stop being the bottleneck.
AI agents sit in exactly the same place. If you're task-driven, you're still the bottleneck — just at a higher level of abstraction. If you're goal-driven, you can actually let go.
Building Systems, Not Tools
This shift has changed how I approach everything I'm building now. I'm not building tools. I'm trying to build systems. Not things I prompt when I hit an obstacle, but infrastructure that runs whether I'm paying attention or not.
"Ensure I'm ready for my interviews" doesn't mean "make me a document." It means: check my calendar, pull relevant context from previous transcripts, flag if there's a gap in what we've learned so far, suggest questions worth probing — and only ping me if something genuinely needs my attention. The output might be a guide, or it might be a nudge, or it might be nothing at all. The agent decides.
I don't have this figured out. The tools may not be ready. I'm still fumbling. But the questions have changed, and that feels like progress.
How are you using AI? Has anything shifted for you recently? I'd love to hear if anyone else has had a similar reframe.