The Two Questions Every Leader Should Answer Before Using AI (with Charley Johnson)
Part of the Kolab Connect series — free interactive sessions hosted inside Kolab, a spatial collaboration platform where you move between conversations instead of sitting in a grid.
Most organizations are approaching AI backwards. They're asking:
"What's our AI strategy?" when they should be asking "what future are we trying to create — and does AI help or hinder that?"
"What should we automate" not 'what must remain human?
This 60-minute workshop with Charley Johnson introduces the first two steps of his STEWARD framework — a systematic process for responsible tech leaders who want to use AI in ways that reflect their values and advance their strategy.
We won't cover the full framework (that's a 4-week live course), but we will work through the two things that matter most before any other AI decision gets made:
S — See the System Before you deploy anything, you need to understand what you're actually dealing with — the real inputs, hidden costs, and risks of these tools in your specific context. We'll cover what large language models actually do (it's not reasoning), the costs most organizations never examine, and a reframe that changes every AI conversation you have after this one.
T — Trace What Must Stay Human Most organizations skip straight to "what can the machine do?" This step starts on the other side — identifying what cannot be delegated, where judgment lives in responsible tech work, and the long-term capacity cost that never shows up in efficiency calculations.
You'll leave with a practical tool for redesigning work so it takes advantage of what machines do well while protecting what makes us irreplaceably human.
Who this is for: Responsible tech leaders in civil society, public interest tech, advocacy, policy, and community-facing organizations who are already navigating AI adoption and want a more grounded, values-aligned approach. You don't need technical expertise — you need to care about what your organization becomes as it uses these tools.
About Charley Johnson: Charley is the founder of Untangled, a newsletter and podcast about technology, people, and power. He was Program Director at Data & Society Research Institute, is Non-Resident Fellow at the Atlantic Council, and co-founder of The Facilitation Leadership Lab. He's spent nearly two decades helping mission-driven leaders align technology with their values — not the other way around.