SXSW 2027 · Workplace Track
What Leaders Won't Admit About AI
And Why Rollouts Fail
A proposed session by Jennifer Simmons · The Human Side of AI by Jenn × JSAI Consulting
So I did a thing. I submitted a session to SXSW 2027. It's the most honest version of the conversation I keep having behind closed doors. The people running AI are quietly overwhelmed. They Google the basics at midnight. They ask for help one-on-one so nobody sees them learning. And that quiet, not the tech, is what sinks the whole thing. This is the room I actually live in, so bringing it to a stage like SXSW would mean a lot.
The Problem
What nobody says out loud
Midnight Googling
They look up the basics at midnight, because asking in a meeting feels like admitting they shouldn't be in charge.
The quiet 1:1
They skip group training and ask for private help, so their teams never see them learning.
The brave face
They project a confidence they don't actually feel.
"That silence, not the technology, is where rollouts die."
Why This Seat Is Empty
One person sits where these two worlds meet
19 years, federal scale
Led large-scale programs across DHS, HHS, VA, and USPS. Walked into complex, stalled environments and built structure where none existed.
A living culture platform
The Human Side of AI by Jenn. AI explored through food, wine, music, and real life. Trust built in public, not a theory read about.
The intersection nobody else occupies. A category of one.
What The Room Walks Away With
Three things every leader leaves with
Spot the silence
How common leadership confusion really is, and how it turns into public rollout failure when no one catches it early.
Fear is not resistance
Why leader fear and team resistance are different problems, and why most rollout plans only fix the second.
The three moves
Make it safe to not know. Build honest checkpoints into the rollout. Separate leader fear from team resistance.
Do the humans in charge feel equipped to lead it?
SXSW is the right room, because the people in that audience are the ones being asked to lead.
Vote for this session
Community voting is open now through August 23.
Two quick steps: create your free SXSW account, then cast your vote. It takes about two minutes.
Interested in bringing this work into your organization? Visit JSAI Consulting.