AI and Work

Are you building a smarter workflow, or just generating AI-assisted process debt? In Episode 98, HubSpot expert Chris Carolan reveals how to abandon rigid industrial-age models and build AI-native systems that prioritize human connection and eliminate waste in knowledge work.

The individuals closest to the technology are moving into increasingly speculative territory. What we have right now is a lot of individuals running faster — but not necessarily in the same direction, on the same track. AI is making individuals dramatically more productive. The question nobody has answered yet is: so what?

The best AI integrations do one small thing reliably and get out of your way. The worst find twelve new ways to interrupt you before you've had your morning coffee. But there's a third category worth paying attention to: AI that lets a well-meaning person — a team lead, a business analyst, even a CEO — execute plain-English commands directly against your live production data. No developer. No IT ticket. No sandbox. That's process debt in a new form. And it moves faster than t

There's a difference between a rollout and a seep. A rollout has a project plan, a go-live date, and a post-mortem where everyone agrees it went better than expected while privately knowing it didn't. AI didn't do any of that. It just showed up — in your search engine, in your SaaS platforms, in your teammates' emails — while you were handling something else. That's what makes this adoption moment genuinely strange. And why the usual change management playbook doesn't quite

Middle managers are the 'glue people'—the vital translators between executive vision and frontline reality. As companies look to AI to trim the fat, are they accidentally cutting the air cover that keeps teams productive? We explore why the 'middle' is the primary target for automation and why history proves these roles are harder to delete than they look.

Lately, when people talk about AI, I think they believe they are buying Rosie. But we are not building Rosie. Not yet. And chasing Rosie too early is how you quietly pile up a whole new layer of process debt. AI is not doing your dishes In the real world, the direction of AI right now is information, not activity. It can summarize meetings, draft emails, write status updates, brainstorm project plans. It can churn through data at a scale that used to require an army of analys

AI can generate anything, but it can’t deliver the one thing computers depend on: predictable abstraction. Unlike ones and zeros, LLMs guess — which means humans still end up in the middle, fixing the gaps and cleaning up the process debt that follows.

The AI boom feels a lot like the telecom bubble of the early 2000s — a race to build infrastructure faster than anyone can figure out how to monetize it. Investors like Michael Burry and industry insiders aren’t betting against AI itself; they’re betting against the unsustainable hype cycle surrounding it. Just like fiber-optic cable once outpaced demand, today’s AI valuations are outpacing real business value. The tech is real, the promise is real, but the process behind it

AI can scaffold apps in minutes, but without software-style guardrails (branches, small commits, unit tests), “vibe coding” turns into vibe chaos. Steal developers’ rigor for business change: pilot locally, commit small, add checks, then merge. Small commits beat big vibes every time.

AI made input cheap and expectations sky-high, but our human throughput hasn’t changed. Without clear “done” definitions and a verify step, we ship polished artifacts that miss the mark and burn out in the process. Slow down, cap WIP, and build tiny rituals that prove the work actually worked.

We love “military-grade” tools until they slow us to a crawl. Build rituals that contain their own proof, design for shedding, and make unblocking your management job description, or your shell becomes your shackle.

Generative AI is fluent and fast, but if we over-delegate our thinking, we’ll ship more and understand less. This piece shows how to keep humans “generative” by staying close to customers, designing rituals with embedded proof, and using AI between us and our repositories, not between us and our relationships. Accelerate good process, not polished waste.