Prompt and Circumstance

Most CEOs face the challenge of wanting to leverage AI for business growth but struggle with where to start and how to implement effectively. The common misconception is that AI implementation should be straightforward like ERP integration, but the reality requires a strategic, phased approach. This episode reveals how fractional AI teams can help businesses scale without linear headcount growth, focusing on three key areas: revenue operations automation, document analysis, and customer service transformation.

The conversation covers essential frameworks including the importance of AI strategy alignment across leadership teams, the "buy vs. build" analysis for AI solutions, and the critical role of process mapping before implementation. The discussion emphasizes that successful AI adoption starts with culture shift from the top, where leaders must become AI champions and model "AI-first thinking" to drive organizational change.

Highlights
  • Identify scaling bottlenecks by asking: "What hires would you need if your business grew 50-100%?"
  • Start with AI strategy alignment before any tool implementation to ensure leadership consensus
  • Focus on automating existing manual processes before pursuing predictive analytics
  • Use visual process mapping to uncover workflow inefficiencies and redesign for AI optimization
  • Implement fractional AI teams rather than hiring single "director of AI" roles
  • Target low-hanging fruit in revenue operations, document analysis, and customer service
  • Develop "AI-first thinking" by asking "How can AI help me?" for every business challenge
  • Experiment with different AI models (Claude, OpenAI, Gemini) to understand their strengths

Important Concepts and Frameworks

Tools & Resources Mentioned
Claude (Anthropic) — Advanced AI model competing with OpenAI, known for strong reasoning capabilities
OpenAI/ChatGPT — Leading AI platform for general-purpose AI assistance and automation
Google Gemini — Google's AI model integrated across Google Workspace and cloud services
Lovable — AI-powered presentation and visualization tool for creating interactive content
Whisper Flow — Voice-to-AI tool for dictation and conversational AI interaction
Super Whisper — Mac-specific voice-to-AI tool with customizable prompts and workflows
AWS Trainium 3 — Amazon's custom AI chip for training large language models
Cadre AI — Fractional AI teams providing strategy and implementation services

Calls to Action
  1. Conduct a leadership alignment session to define your company's AI strategy and ensure all executives share the same vision.
  2. Map three key business processes using visual process mapping to identify automation opportunities and workflow inefficiencies.
  3. Experiment with at least one new AI tool you haven't tried before (Claude, Gemini, or specialized tools like Lovable).
  4. Ask the scaling question: "If our business grew 50-100% in the next year, what hires would we need?" to identify AI automation priorities.
  5. Start using voice-to-AI tools for daily tasks to increase personal productivity and model AI adoption for your team.
  6. Conduct a "buy vs build" analysis for your top three AI use cases before committing to implementation.
  7. Schedule regular AI demo sessions where team members share practical applications they've discovered.

Key Quotes
  • "It's not about the agent, it's about the workflow" — Riley Stricklin
  • "Everybody wants to chat with their company data like they chat with ChatGPT" — Riley Stricklin
  • "I am 60-80% more efficient every week, essentially twice as productive" — Riley Stricklin
  • "The only way we've seen true culture shift happen is starting at the top" — Riley Stricklin
  • "What hires would you need if the business grew 50-100%?" — Riley Stricklin

Chapters
00:00 — Introduction to AI Strategy and Fractional Teams
02:47 — Time Magazine's AI Architects and Industry Recognition
04:00 — AWS Infrastructure and the AI Hardware Race
06:57 — Model Selection Challenges in the Enterprise Space
09:21 — From Consumer Electronics to AI Entrepreneurship
13:00 — Building Fractional AI Teams for Business Transformation
17:29 — Common CEO Misconceptions About AI Implementation
20:16 — Strategic Patterns in AI Adoption Conversations
23:33 — Identifying Scaling Bottlenecks Through Hiring Analysis
26:48 — Process Mapping and Workflow Redesign Fundamentals
29:20 — Visual Process Mapping to Reveal Inefficiencies
34:47 — Low-Hanging Fruit: Revenue Ops and Document Analysis
37:44 — Buy vs Build Analysis for AI Solutions
39:55 — Personal Productivity Gains Through AI Adoption
42:20 — Building AI Culture from Leadership Down
47:01 — Essential AI Tools for Daily Business Operations
50:19 — Actionable Steps to Begin Your AI Journey

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This Episode's Guest: Riley Stricklin
LinkedIn: https://www.linkedin.com/in/rileystricklin/

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Meet the Crew

Mike Richardson – Agility, Peer Power & Collective Intelligence
Website: https://mikerichardson.live/
LinkedIn: https://www.linkedin.com/in/agilityexpertmikerichardson/

Ryan Niemann – Software CEO & Board Operator
Website: https://bob3.pro/
LinkedIn: https://www.linkedin.com/in/ryanniemann/

Mark Redgrave – Agility, People and Performance
Website: https://www.shift-transform.com/
LinkedIn: https://www.linkedin.com/in/mredgrave/

Tom Adams – Executive Coach, Advisor & Trail Blazer
Website: https://tomadams.com/
LinkedIn: https://www.linkedin.com/in/tomadamscoach/





Creators and Guests

Host
Mark Redgrave
Agility, People and Performance
Host
Mike Richardson
Agility, Peer Power & Collective Intelligence
Host
Ryan Niemann
Software CEO & Board Operator
Host
Tom Adams
Executive Coach, Strategic Advisor & Thought Partner

What is Prompt and Circumstance?

It’s human-friendly banter about code, culture, and CEO reality checks—served up by Mike Richardson, Ryan Niemann, Mark Redgrave, and Tom Adams. No jargon. No hype. Just real talk from four guys who’ve seen it all, and aren’t afraid to say what everyone’s thinking.