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Why AI Conversations Feel Fake (And How To Fix That)

The Digital Project Manager

Chapters
0:00
Cold Open On AI Perception
1:53
Why Conversation Design Builds Trust
4:35
Will Conversation Replace Website Navigation
10:42
Where Voice AI Shows Real ROI
16:12
Cloning A Brand Voice With Guardrails
17:56
Social Presence And Why Phones Persist
26:06
Turn-Taking Problems That Break Voice UX
31:51
Backchanneling And Getting Inputs Right
35:00
Pragmatics And The Danger Of Overexplaining
39:35
How To Disclose AI Without Ruining Tone
43:06
Why Language Is Hard For AI
47:27
Mindset Shifts For Visual Design Teams
51:51
Agents Talking To Agents In The Future
54:56
Do We Really Need AI Hardware
56:49
Where To Find Oliver And Final CTA
The Digital Project Manager
Why AI Conversations Feel Fake (And How To Fix That)
May 26, 2026
Galen Low

What happens when AI stops being a tool you type into and starts becoming something you talk to? In this episode, Galen Low sits down with Oliver Shoulson, Agent Design and Engineering Lead at PolyAI, to unpack the surprisingly human problem at the heart of conversational AI: most AI conversations still feel weird.

From clunky chatbot scripts to overly polite “LLM voice” personas that sound like they were trained by a committee of HR robots, Oliver explains why good conversational design is less about mimicking humans perfectly and more about removing friction. The conversation explores the psychology of trust, the mechanics of social presence, and why the future of AI interfaces may depend less on visual design and more on understanding how people naturally speak, interrupt, hesitate, clarify, and collaborate.

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