The Number That Actually Measures AI Transformation
Most leaders can tell me what AI added. Almost none of them can tell me what disappeared.
Most leaders I talk to can tell me exactly what AI has added to their business.
A faster proposal. A cleaner summary. An email that used to take 45 minutes now takes 10. They’ve got a list. They’re proud of the list. And honestly, they should be. Starting is hard, and they did it.
But here’s the question that stops most of them cold: What has disappeared?
Not slowed down. Not improved. Disappeared. Meetings that no longer happen. Approval steps that no longer exist. Workflows that were on the calendar every Tuesday for four years and are now just... gone.
That’s the question a CAIO at Logitech I’ve been studying uses to measure real AI transformation in his organization, not what got added, but what got deleted. And when I started applying that lens to the businesses we work with, it changed how we see everything. We had been identifying these areas but not naming them directly.
Here’s why it matters. Adding AI to an existing workflow is like adding a faster engine to a car that’s stuck in traffic. You’ve got more horsepower, but you’re still in the same lanes, hitting the same lights, following the same route. Real transformation asks a different question: does this road still need to exist at all?
Most businesses are at the “faster engine” stage. That’s not a criticism, it’s a starting point. But there’s a ceiling to how much value you can extract from accelerating the same processes. At some point, the real work is structural. Which workflows need to change shape? Which decisions should move closer to the people doing the work? Which dependencies between people, teams, and systems only existed because you didn’t have better tools?
Transformation doesn’t mean blowing everything up. It means being willing to ask what needs to stay and what needs to go and being honest about which answer is a values decision and which one is just fear of change dressed up as caution.
The businesses we see making real progress aren’t the ones with the most AI tools. They’re the ones where leadership has started asking structural questions. Where the shape of work is changing, not just the speed of it. Where someone in the room can point to something that used to take four people and a two-week timeline and say, that’s gone now, and here’s what we built instead. (not that the people are gone, but the heavy lift is no longer required)
What this means for you
Pull up your calendar and your recurring workflow list. Look at the last 6-12 months. Count what’s disappeared: meetings, reports, approval steps, handoffs between people. If the number is zero or close to it, that’s useful information. It doesn’t mean you’re failing at AI. It means you’re in the “adding” phase, and the next phase is waiting.
The question isn’t whether you’re using AI. It’s whether AI is changing the architecture of how your business works or just making the existing architecture a little more comfortable.
One thing to try this week
Pick one recurring meeting or recurring report that exists in your business right now. Ask yourself: if we were building this company from scratch today, with the tools we have, would this exist? If the answer is no, or even maybe not, that’s your starting point.
This framework came out of a tool we’ve been building called Workflow Intelligence — a diagnostic for leaders who want to know if they’re genuinely transforming or just running the same playbook faster. If you want to be one of the first to try it, reply to this email and I’ll send it your way.
Until next week, keep asking the uncomfortable questions. That’s where the real work lives.
— Kendra
*This post was inspired by Jason Hauser and sharing the story of how Logitech CAIO, Eric Porres, started focusing on the measurement of deleted workflows.
Resources
For the last three years, leaders have asked me for the assessments, templates, and planning guides we use in our AI sessions. So I pulled together the most requested resources and made them super affordable for small businesses and nonprofits because everyone deserves access to practical, approachable AI.
Inside you’ll find:
AI planning playbook for 2026, 11 pages
Policy templates (2 templates)
Adoption assessment reviewing 16 categories
AI leadership insights (lessons from 160+ sessions, 12 pages, including an Assessment)
ChatGPT modes, connectors and shortcuts
Claude Cowork 101- 8 page non technical guide. NEW
Or a bundle to get them all for only $99, a $250 value.
If you’ve been wanting a simple starting point or something to help your team move faster, this is for you.
Take a look: https://payhip.com/AISimplified
Would love your feedback on what to add next. Thank you all for your kind feedback. It makes me happy that you are finding them to be so helpful.
2026 AI Adventures
We also just announced our private digital community of CincyAI Champions:
For $25/month or $250/year ($50 off!), access our paid member portal with: BIG thank you to the 100 members that have signed up already!
• 6 CincyAI Human Huddle virtual interest groups: AI for beginners, AI for intermediates, AI for advanced, AI for Women, AI for Arts and Creative, and new AI for nonprofits.
• Limited time only: “CincyAI Founding Champion” Badge
• CincyAI Champions Member Directory
• Monthly Office Hours with Helen & Kendra — Bring your AI questions each month.
• Cincinnati Area AI Job Board
• CincyAI & Community Partners Events Calendar
• CincyAI Champion Matchups
And more!
Limited time only: 30 days free trial as we’re seeding the community — join now to get your Founding CincyAI Champion member badge!!
https://app.heartbeat.chat/cincyai/invitation?code=D73D97#choose We are loving our digital community.
June 17 Greater Harrison Chamber luncheon. Love giving back to my local community. https://www.greaterharrisoncc.com/calendar/#!event/2026/6/17/business-leadership-lunch
June 24 Interact for Health from 1-3 Georgetown, OH hands-on AI Simplified for nonprofit session. Free to attend. https://lp.constantcontactpages.com/ev/reg/z7kctmn/lp/8f0ebe68-7308-4c5e-ad9b-7ce4ebdf8542
I love answering your AI questions. Feel free to message me.
Where AI and inspiration collide!
Kendra Ramirez
KendraRamirez.com
We provide AI Enablement (AI Speaking and Training, AI Readiness, AI Strategy, Workflow Automation, and Implementation). Our clients love that we sit side by side with them in our human centered approach to AI.
**For those new to my work, I have been in tech my whole career. Over 15 years of running my digital agency (website, social media, and lead generation) and 7 years of helping businesses navigate AI. Over the three years and, I’ve had the privilege of leading over 250 AI sessions and speaking sessions (over 20,000 people), empowering businesses to embrace the transformative potential of AI. My passion lies in simplifying complex technologies to help organizations grow, innovate, and thrive.
I am so excited that you are on this journey with me! Thank you! 🤗
I have been writing weekly about AI here for almost three years. You can search all of my enewsletters here if you are looking to brush up on a certain topic. kendratech.substack.com