The Room Where V2 Happens

I ran the same internal AI workshop twice in one week. Same content, same agenda, same Zoom link, just offered at multiple times to cover different schedules. By the second session, half of my material was wrong.

Between the two scheduled sessions, something had changed. In the first session we couldn't use the skills feature in Claude. By the second, we could. Nothing dramatic happened. The feature had simply cleared our internal approval process in the four days between sessions, and the part of my demo where I was going to talk about our current system limitations was wrong before I'd even opened my laptop.

I hadn't made a mistake. The subject matter had refused to hold still for a few days.

My instinct, after years in L&D, is to come prepared with materials that are polished. That instinct doesn't hold up here, there's not a week where AI sits still long enough for me to get everything exactly right.

I had to stop treating the content for these workshops as something that would reach a final state. I open my notes before each session assuming something will need to change, and I'm rarely wrong. We Start Simple and Iterate has always been one of my favorite Teleport behaviors, and this is just the latest place I've felt it. Redoing my content for the third time in one week was my opportunity to live out that behavior.

One person iterating is good, but the AI landscape is moving faster than any one person can track. The good news is that I am not alone.

The room has my back

There's a well worn idea when a group is stuck on a hard problem, the expertise to solve it is usually already sitting in the room. It's just that nobody has connected the dots yet.

That's shown up in all of these sessions, and it's my favorite part every time.

Someone describes something they're stuck on: an automation they've been meaning to build, a call review that eats an afternoon every week, a workflow that's technically possible but nobody's wired together yet. Before I can offer anything, someone from a completely different function jumps in with a prompt they'd already built for something adjacent, or a workaround for a limit the first person hadn't hit yet.

We record for people who can't make a session and plenty of people watch them later, but there is a kind of magic that happens live. Someone raises a problem, and two or three people jump in with pieces of the answer before I have the chance to say a word. It’s the kind of exchange that can happen when people share the same space (even if it’s a virtual space).

It’s an unscripted bonus that these workshops build cross-departmental networks that keep iterating on their own between sessions. People are trading fixes across teams faster than any one of us could accomplish alone. Finance solves something Sales hasn't hit yet. Someone on the People team already built a workaround someone in Legal needed last week. The room does the same thing that Start Simple and Iterate asks of each of us, just faster. That's social learning at work. One person's rough first attempt meets the part someone else already has, and it becomes a v2 before anyone officially asks for help.

Back to that room

I'll run more workshops soon and it’s likely that half of the content will be different by the time I do. I've learned to stop worrying so much about that. What I was feeling anxious about was just me holding onto the idea that somewhere, after enough preparation, I’d reach a final version.

Now I focus on the current version and build from what I know today. It'll probably be wrong again in a few weeks, and I've made a kind of peace with that. The reality is that the technology is not going to hold still long enough for one person, or one room, to get ahead of it for good. The real advantage is having enough people iterating together that we can keep up.

Every session, I join ready to teach. Every session, I log off having learned something new, a solution for something I hadn't thought to ask about yet.

It's good to be in the room where v2 happens.

Kathleen Sikora

Kathleen Sikora is Senior Manager, Learning & Development at Teleport, where she designs the learning, performance, and development systems that help employees grow alongside the company's mission of building Infrastructure Identity for humans, machines, and AI agents. Sikora brings over 15 years of experience in talent development, having built learning strategies, engagement programs, and people-development practices at organizations including Code42 and Apple. Her work spans instructional design, program evaluation, and organizational development, with a focus on creating systems that drive clarity, growth, and measurable impact for the teams she supports.