AI Live Chats: The Prompt Doctor

Weekly AI News Recap

Kelsey talks with CIT President and CEO Kyle Etter about recent AI releases like GPT 5.4’s native computer control, Gemini 3.1 updates, and the shift from chatbots to agentic AI that can navigate business systems and complete real work. They discuss why IT infrastructure must now include AI governance, identity, logging, permissions, and emerging liability and insurance considerations for “digital teammates,” noting early examples like insured voice agents. Kyle advises deploying narrow, task-specific agents with strong guardrails, human-in-the-loop checks, and layered QA/security agents to reduce risk. They also cover preventing shadow AI by providing authorized business licenses, training staff to manage agents, and why ROI is increasingly driven by integrating agents into existing software and data workflows, including analysis and data cleanup. 00:00 Welcome and AI Shift 00:50 GPT 5.4 Computer Control 03:16 Governance and Liability 06:31 Designing Digital Workers 12:05 Risks and Guardrails 18:35 Jobs and Agent Managers 23:34 Stopping Shadow AI 26:04 Training and First Use Cases 28:51 AI Licensing ROI 29:35 Software Over Hardware 30:26 Agents Deliver Value 33:57 Data Cleanup With AI 36:58 Conversational Analytics 40:34 Automations Built Faster 43:34 Governance And Guardrails 44:27 Capture Ideas With Tools 48:29 AI To Do Assistant 52:03 Wrap Up And Resources

AI Live Chats: Show Me the ROI

In this third LinkedIn Live AI chat, Kelsey and Todd discuss how to define and prove AI ROI, arguing many AI projects fail due to poorly defined returns beyond simple time-savings. They distinguish AI activity from AI value, stressing goal-driven, iterative adoption and measurable milestones executives and CFOs can trust—typically cost savings (growth without headcount) or revenue impact (more leads, faster launches, higher win rates). They walk through ROI approaches for practical scenarios including SOP creation and searchable copilots, marketing email HTML generation, new-hire self-serve process help, AI-assisted RFP drafting, job descriptions and onboarding templates, automated revenue-report narratives, customer success call recaps, contract review prep, and meeting-to-action-item pipelines, emphasizing reduced rework, fewer dropped tasks, better decisions, improved customer satisfaction and retention, and lowered legal and operational costs. 00:00 Live Chat Kickoff 00:14 Defining AI ROI 01:39 Activity Versus Value 02:33 Proving ROI to CFOs 04:19 Measuring After the Fact 06:04 ROI Scenario Challenge 06:42 SOPs and Process Consistency 09:36 Marketing Email Automation 10:49 Onboarding and New Hire Support 12:53 Sales RFP Drafting 13:58 HR Docs and Consistency 15:44 Finance Reporting Summaries 18:55 Customer Success Recaps 20:27 Legal Contract Review 22:06 Meeting Actions and Accountability 24:00 Todd’s ROI Tips 26:02 Wrap Up and Next Episode

AI Live Chats: The Prompt Doctor

In this LinkedIn Live episode, host Kelsey and Todd discuss how to improve AI workflow results by moving beyond vague prompts like “write me a marketing email” and using an iterative approach. Todd shares the CRIT framework (Context, Role, Interview, Task), recommends prompting AI to ask clarifying questions one at a time, and stresses specifying desired outputs such as a Word document, table, or executive summary. They demo a prompt-building tool called Prompt Cowboy and discuss using screenshots or PDFs to extract, simplify, or reformat information, including translating legal documents into plain English. The conversation highlights governance concerns such as AI memory, paid vs. unpaid tools, and avoiding sensitive data like PII, employee information, financials, and health details. Todd also mentions agents for specialized compliance use cases and a voice tool called Whisper Flow for capturing ideas while away from a keyboard. 00:00 Welcome and Setup 00:55 Why Prompts Fail 01:49 CRIT Prompt Framework 04:10 Handling Complex Requests 05:50 Prompt Cowboy Demo 07:58 Iterative Prompting Tips 10:32 Screenshots and Privacy 16:23 Everyday Business Use Cases 19:04 Saved Prompts Debate 26:44 Agents and Compliance 27:53 Wrap Up and Voice Tools 30:05 Outro and Next Episode

Tech insights from GENIANS

Kyle (CEO & President at CIT) and Brett (VP of Technical Sales at Genians) join us to discuss recurring and emerging security challenges, including protecting the inside of the network, visibility into who and what is connected, and meeting audit requirements in regulated industries like credit unions and manufacturing. They discuss how VPN zero-days and compromises render perimeter-only defenses insufficient, emphasizing network access control (NAC), device trust policies, alerts, segmentation, and zero-trust principles such as least privilege. They note many organizations lack accurate asset inventories and are surprised by the number of connected devices, including rogue or unmanaged equipment. For prioritization, they recommend starting with core best practices (firewalls, EDR, MFA) and moving toward NAC and ZTNA-style remote access as VPN risk increases. They also cover budget and complexity barriers, product overlap, analysis paralysis, and practical AI adoption examples like Slack AI and Microsoft Copilot for search. Learn more about Genians: https://www.citsolutions.net/about-computer-integration-technologies/partners/genians/ [https://www.citsolutions.net/about-computer-integration-technologies/partners/genians/] 00:00 Security Challenges Today 01:18 Inside Network Threats 03:14 VPN Zero Days Defense 04:13 Why Problems Persist 08:40 Prioritizing Security Steps 10:50 Budget and Complexity Barriers 13:34 Hidden Devices Discovery 18:05 Common Missteps and Overlap 19:48 Practical AI Use Cases 24:08 Action Steps and Wrap Up

AI Live Chats: Enhancing Business Operations

In the first AI Live chat on LinkedIn, Kelsey interviews CIT President and CEO Kyle about how he uses Claude Code as an agent-based executive assistant running locally on his MacBook. Kyle describes building MCP connectors into business systems like Halo (ticketing/PSA), NetSuite (financials), email, and team chats, plus using “skills” that load only when needed to save tokens and cost. He explains how he prompts in plain language while the AI helps build the setup, and shares examples like generating daily “morning” and end-of-day recaps, creating customer health summaries, and quickly producing spreadsheets to identify inactive customers by correlating invoicing and support data. They discuss rapid shifts in AI-assisted coding, data quality checks, ROI, and how AI may transform roles more than replace them. 00:00 Welcome And Setup 00:47 CEO Nighttime AI Habits 01:45 Building A Local Agent 03:44 Daily Workflow With Claude 05:11 Plain Language Development 07:37 Claude For Everyone 08:54 Skills And MCP Explained 14:19 AI Writing Software Shift 16:59 Productivity ROI Examples 19:56 Quick Hit Use Cases 20:55 Voice Notes to Tasks 21:19 Instant Customer Checkins 23:14 Reengaging Stale Accounts 26:21 Access Permissions and Data Quality 28:07 Validating AI Outputs 29:28 Cost Value and Key Users 31:44 Daily Recap Replacing Dashboards 33:37 Agents and the Future of Work 36:05 Replacing vs Transforming Roles 41:35 Adoption Advice and Wrap Up