The #1 Newsletter for Owner-Led Teams Navigating the Shift to AI
For founders and small teams ready to trade bottlenecks for breathing room.
Welcome to Human in the Loop: Because Tools Don’t Run Teams.
This newsletter explores how owner-led, service-based businesses adapt to an AI-shaped world — not by chasing tools, but by reworking how they lead, decide, and operate.
I’m Karen Sergeant, and I believe growing pains are part of the business growth process — but you don’t have to get stuck there. I help founders and small teams move from load-bearing leadership to Upstream Leadership: running a business with systems that are transparent, repeatable, and not dependent on heroics.
Growing pains are part of the growth process — but you don’t have to get stuck there.
Here you’ll find grounded, field-tested insight on:
Building systems that let you delegate judgment itself so decisions stop bottlenecking at your desk
Strengthening decision hygiene and day-to-day leadership habits
Turning AI from shiny distraction into real leverage
Running human teams that stay calm even during crunch time
I don’t write about hype, hacks, or “10 tools you need.” I write about the invisible systems that make AI adoption—and leadership itself—actually work.
If that’s the kind of clarity you’re looking for, you’re in the right place.
How to Get the Most from Human in the Loop
Start with these essays — they’ll give you the foundation for how I think about leadership, systems and AI adoption. New essays build on those foundations with real-world examples (and the occasional rant).
Faster If I Do It: The Business Model No One Means to Build (But Everyone Does)
TL;DR: The “How the $^&# did we get here?” installment of my Owner Dependence series: How the habits that made you successful harden into bottlenecks later (aka How bad habits happen to good businesses. Like yours.)
Other People’s Use-Cases Won't Solve Your Bottlenecks
TL;DR: Use-case inspiration is useful — but only if you know what you're looking for. If you don’t have a clear picture of your own friction points, use-case roundups just become a list of other people’s problems dressed up as opportunities.
If you’re tired of the breathless AI shiny-tool noise, stay awhile. This is where we talk about what actually works—how to lead, decide, and build in ways that hold up when things get weird.
Subscribe, dig in, and make your business run a little cleaner (and your head a little clearer).
Work With Me
There are a few ways to move from reading about Upstream Leadership to building it inside your business.
1. The AI Upside Audit 🤖
A strategy session for solos + small teams who want AI adoption to be clean, targeted, zero-waste and focused on what moves your business forward.
Most AI advice highlights cool tools (or random use-cases that don’t really apply to your business). In this Audit we start with your business challenges: what’s slowing you down or holding you back, and then map AI onto those points.
Praise for The AI Upside Audit
“I didn’t need someone to train me on AI adoption. I needed someone who could connect the 45 disparate thoughts I had and make it make sense.
That’s exactly what she did.
Karen is just so intelligent and deep thinking and prepared and organized
— it’s such a rarity in the online space. ”
— Kim Wensel, Copywriter & Founder of The Bench
2. The Bottleneck Audit 💥
A diagnostic deep dive to identify the operational habits, approvals, and workflows keeping your team dependent on you. You’ll get a structured plan for where to simplify, delegate, and design for scale.
3. Pocket COO Retainer 👩🏼💻
For owners who want an ongoing strategic operator in their corner. I help you translate plans into repeatable systems, keep decisions clean, and lead through growth without reverting to heroics.
Not sure where to start?
Book a quick Discovery Call — a short conversation to identify where your current bottleneck is and which path makes the most sense.
Happy to be in YOUR loop,
Karen