The Messy Reality of AI Transformation

Allison McMillan Jul 17, 2026 Share Last month, we talked about designing frameworks that accommodate human reality. This month, the conversation shifts from theory to the messy, high-stakes reality of execution. We are officially past the phase of merely ‘experimenting’ with AI, and we’ve landed squarely in the era of restructuring. It’s forcing us to ask hard, practical questions: How do you interview and hire an AI-native engineer today? Why does consensus-driven decision-making fall apart in this fast-paced environment? How do you move experimentation and implementation from silo’ed to cohesive?

Moving past the playground phase of technology into true AI transformation is tough, but it’s exactly where the real work happens (and happens to be the space I love helping leaders navigate). And as we rewrite these professional playbooks, the ripples are hitting home, too—fundamentally altering how our kids grow up while working parents face an uphill battle for their time. Let’s dive into what execution looks like on the ground right now, with a few comforting recipes and creative distractions thrown in to keep us grounded.

Legend:🎙️ podcast | 🏡 parenting hack | 📰 article or blog post | 🪩 conference | 📕 book | 📺 tv show | 🎬 movie | 🔍 random product

A random assortment of products, groups, hacks, tips, podcasts and more that I’ve discovered recently

🔍 Pipsticks - The cutest stickers for literally anything! (They were a hit at our Fractional Women’s Summit in May!)

📰 What to Cook When You Don’t Feel Like Cooking - One stop shop for quick meals that use as few dishes/tools as possible because let’s be real, you won’t find me in the kitchen cooking for 2 hours every night.

🎙️ What AI Could Be Doing to Our Kids - Even as an AI trainer/facilitator I’m acutely aware of its downfalls, and when it comes to my kids I’m mindful about how technology might be affecting their young minds.

Things I’ve read recently that are interesting or noteworthy in some way

📰 How we hire AI-native engineers now: our criteria - Augment is restructuring their hiring process to focus on the skills engineers need now that AI is doing most of the coding.

📰 Decision-Making by Consensus Doesn’t Work in the AI Era - Algorithms and data aren’t the markers for success they used to be — “organizational agility” is what determines if a company sinks or swims.

📰 To Succeed with AI, You’ve Got to Nail the Basics - Successful AI adoption isn’t about how fast you can start using the tools, it’s taking the effort to set them up well for the long term.

📰 Employees Are Relying on AI for Personal Support. That’s Risky. - Increased personal AI use in the workplace is notably decreasing human connection, collaboration, trust and socials skills.

📰 How to Move from AI Experimentation to AI Transformation ← I can help with this!

📰 Which popular beliefs about GenAI and software engineering hold up to research? - What you’ve been hearing may not be what’s actually happening for real teams.

📰 AI enthusiasts are in a race against time, AI skeptics are in a race against entropy - On closing the gap between the AI “enthusiasts” and the AI “skeptics.”

🏡 AI is here. And growing up looks different now. - Such a helpful tool for parents to learn more about how AI is affecting our kids and how to use it safely in our families.

📰 The Gap Nobody Measures in AI Adoption - Nobody’s questioning whether AI tools work anymore, we’re just stuck in the building-infrastructure-around-AI stage.

📰 Working Parents Say They’re in a Losing Battle Over Their Time - As a working mom, I get this. I love my job and my family, but making the time to do all that and take care of myself is…hard.

📰 Does Your AI Have a Personality Problem? - AI is still being evaluated like data, but measuring how it talks to your staff is just as important.

📰 How does deepening AI fluency change what it means to be a software developer? - Developers want to spend less time on reactive work and for many AI hasn’t freed up the time it promised—it’s time for AI tools to meet developers where they want them.