Work

Perspectives

About

Work

Perspectives

About

Work

Perspectives

About

Perspectives

Perspectives

Sharing my outlook on building successful products and teams.

  • Intentionally designing processes

    Frameworks like agile provide a strong foundation, but often fail. High-pressure situations arise and teams to revert to old habits. Process decks are created but not adopted. To be effective, a process must be pragmatic, tailored to the company’s current product maturity, business practices, and designed to scale as the organization grows.

  • Conversational integrity over "human-like" mimicry

    Frameworks like agile provide a strong foundation, but often fail. High-pressure situations arise and teams to revert to old habits. Process decks are created but not adopted. To be effective, a process must be pragmatic, tailored to the company’s current product maturity, business practices, and designed to scale as the organization grows.

  • Intentionally designing processes

    Frameworks like agile provide a strong foundation, but often fail. High-pressure situations arise and teams to revert to old habits. Process decks are created but not adopted. To be effective, a process must be pragmatic, tailored to the company’s current product maturity, business practices, and designed to scale as the organization grows.

  • UX starts at the API, not the UI

    As UX evolves from static pages to dynamic data delivery, its critical to deeply understand how your LLM and database process information. If the backend can't provide, for instance, a reason as to why your bill increased this month, no amount of clever copy or UI can save the experience. I spend most of my time in the data documentation, not the Figma file, because that is where the experience is won or lost.

Users should never see your org chart

Product-agnostic intent handling

Most enterprise AI feels disjointed because the "Internet Bot" doesn't talk to the "Mobile Bot." Orchestration must be product-agnostic. The customer doesn't care that billing and technical support are different departments, or that one bot answered versus another. I advocate for a "Single-Brain" architecture that dissolves internal silos to provide one cohesive answer.

Conversational Integrity Over "Human-like" Mimicry

Product-agnostic intent handling

Most enterprise AI feels disjointed because the "Internet Bot" doesn't talk to the "Mobile Bot." Orchestration must be product-agnostic. The customer doesn't care that billing and technical support are different departments, or that one bot answered versus another. I advocate for a "Single-Brain" architecture that dissolves internal silos to provide one cohesive answer.

Leadership as an incubator

Protecting team growth

I absorb the contradictory demands, shifting priorities, and political friction of the broader organization. By managing the stakeholders upward, I create a "quiet zone" where my team has room to fail, iterate, and eventually become the subject matter experts that the business actually listens to.

Lindsay Bolger © 2026. All rights reserved.