Last night I had the privilege of joining Kyle Coleman and a remarkable group of leaders for a ClickUp networking dinner, my third in the past year, and each one keeps getting better.
It started with everyone taking ClickUp's AI Maturity Assessment, which maps organizations across two dimensions, AI maturity and context maturity, into four quadrants:
- Disconnected, Manual Work — fragmented tools, manual processes, one-off AI use cases
- Siloed Automation — automation exists, but only within isolated teams or apps
- Unified, Manual Work — work is centralized and visible, but still largely manual
- Ambient AI — AI is deeply embedded in a unified workspace, proactively optimizing how work gets done
Then came the real conversation: how accurate did we each think the results were about our organizations, and why?
The answers were honest, sometimes surprising, and often humbling.
Over dinner, tables of six, strangers becoming collaborators, we traded personal stories about our AI journeys. Not the polished LinkedIn version. The real one. The fumbling. The experiments that didn't land. The moments where we got it right by accident. The tension between moving fast with AI and making sure we're still showing up as human beings in how we lead, communicate, and connect.
I'll be honest about my own experience, because it captures the irony perfectly.
At Functionize, we've built an AI-Native SaaS solution directly on Google's Gemini Enterprise Agent Platform. And yet, when I took the assessment, I concluded that as an organization we fall squarely in the Unified, Manual Work quadrant. We have a unified workspace, solid visibility, good collaboration. But we have enormous opportunity to better leverage AI to improve our own internal business processes and the productivity of our people. Building AI for others doesn't automatically mean you've figured it out for yourself.
Then I shared part of my personal AI journey over the past two months. I've been using Claude to build and begin executing a full partner ecosystem strategy for Functionize, from scratch. I then mapped that strategy against my 6,600 LinkedIn connections to identify warm paths and create targeted execution plans. From there, I mapped it all to the sponsors at Google Next and built my battle plan for the event. At Google Next, I captured notes on the fly in Claude and revised my to dos. By the time I was boarding my flight home after three days on the ground, I had a 15-page event report ready to share with my leadership.
That's not a small thing. I could have never built that on my own.
A few things stayed with me from last night's dinner:
- Most of us are further along than we think in some areas, and further behind than we'd like in others. The assessment has a way of making that uncomfortably visible.
- "Keeping it human" isn't a soft idea. It's becoming a genuine strategic discipline as AI takes on more of the work around us.
- The people in that room weren't waiting for permission or a playbook. They were learning by doing, sharing what worked, and generous enough to share what didn't.
That's the kind of evening that makes you want to go back to your team the next morning with new energy and a few new questions.
Thank you to Kyle and the ClickUp team for creating the space. And to everyone at the table. I'm already engaged in several follow-on discussions.