AI Frontier Ledger · CYOG Podcast / AI Mastermind AfterShow · Recorded 10/06/26
By Joe Moore · Hosted by Joe Moore and Katrena Drake · Guest: Jesse Pudles

Your team hears “we’re rolling out AI.” You hear possibility. Someone else hears a countdown.

That gap was at the center of Tuesday’s conversation with Jesse Pudles. With Katrena Drake leading the interview, we explored what happens to trust, identity, and ownership when AI enters the workplace—and what leaders can do before uncertainty hardens into resistance.

The question running through the room: How do we make AI adoption an invitation people can participate in?

What you’ll discover

1. Fear arrives before the workflow

Jesse described job security as the first concern many employees bring to an AI rollout. Next comes trust in the people leading it. Changes to familiar tasks, responsibilities, and ownership add another layer.

A tool can be technically ready while the team using it feels unprepared. People may hesitate because they cannot see their place in the new workflow. Buying software does not resolve that uncertainty.

Explore the replay library on Territory →

2. Tell the truth before asking for commitment

Jesse’s advice was to bring people into the conversation when a possible rollout becomes an actual decision. Be clear whether leadership is seeking input or announcing a change already on the way. Those are different conversations.

Ask what people are nervous about, what remains unclear, and what support they need. Give them time to answer before asking them to commit to a new way of working.

He also drew a firm boundary around reassurance: if cuts are planned, leaders should not tell employees their jobs are safe. Clarity begins with leadership agreeing on what is known, what remains undecided, and who needs to be included.

3. Make room for growth and accountable oversight

When AI takes over part of a job, Jesse encouraged leaders to ask what the person could grow into. What interests them? Where does the business need human contribution? What training would help them move forward?

He distinguished moving someone into a different role without a conversation from developing skills with their participation. Both cross-training and upskilling can have value when people understand the purpose and have a voice in the process.

Oversight needs the same clarity. Calling someone the human in the loop is not a complete plan. Jesse emphasized multiple people providing oversight and a chain of command for situations where AI behaves differently from what the organization expects.

Continue exploring the conversations on Territory →

4. Measure the change you actually intended

Jesse described an engagement that begins with an AI culture survey: which teams feel confident, which need support, and where trust is low. From there, the work can include workshops, leadership communication, and connecting enthusiastic champions with people who are uncertain.

He said engagements typically last about four months. That was a description of his approach, rather than a guaranteed timeline for every company.

To evaluate progress, he discussed before-and-after culture surveys and the STAR method: situation, task, action, result. Start with a specific team and a specific issue, identify the intervention, and measure the relevant change.

Katrena pressed on the relationship between those measures and productivity. Jesse’s distinction mattered: smoother meetings, greater trust, faster adoption, and reduced busywork can all be goals. Decide which outcome you are trying to improve before declaring success.

5. Storytelling can change the room

Jesse’s background in theater shapes how he works with teams. He described theater and storytelling as a pattern break: activities people do not expect from a conventional business workshop can interrupt familiar resistance.

As participants become more comfortable, the exercises invite them to share experiences, explore how they have handled change before, and practice new responses. His account offers a different way into a difficult conversation: create an experience in which people can discover something about themselves and each other.

For consultants, founders, and agency owners, this is a useful question to carry forward: what kind of experience would help your team participate more openly?

6. Start with one tool and an honest check-in

Jesse closed with a practical exercise. Avoid asking employees how they feel about AI as a whole. Pick one tool the organization uses or plans to introduce.

The following questions paraphrase his check-in approach:

Jesse cautioned that commitment may take more than one conversation when trust is low. The first step is a commitment people can describe and own, followed by continued support.

Visit the Territory replay library →

The direction to carry forward

AI can change how work gets done. Leaders still shape whether people understand that change, believe what they are told, and see a future inside it.

Before the next rollout, choose one tool. Ask one honest question. Listen long enough to hear the answer. Then build the next commitment together.

Related Frontier Signal: AI Workplace Trust—Can Your Team Tell the Truth? →

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Source: the October 6, 2026 Riverside recording, “Jesse & Joe — Take 02.” Quotations were checked against its transcript. This article focuses on Jesse’s practices and perspective; numerical labor-market claims mentioned in the discussion are omitted.