AI leadership
AI leadership means deciding where AI belongs in the work, who owns the outcome, and how people will use it. These conversations connect executive priorities with everyday adoption, management and human judgment.
How should our executive team prioritize AI adoption initiatives?
Start with a specific business problem, make the workflow and its rules clear, and choose an outcome you can measure. Identify the person who owns the process, the expert who can judge the output, and the budget needed to continue if the pilot works. This combines Eddie Irvin's emphasis on process clarity with Ronnie Coleman's advice on expert involvement, funding and an expansion path.
From these conversations:
What should leaders do before adding AI to a shared workflow?
Map the handoffs, permissions, shared information and quality standards first. Justin Watt recommends starting with one important workflow or a department's work so the team can establish a shared way of operating. Giving everyone a chatbot account does not, by itself, fix how work moves between people.
From these conversations:
How can leaders preserve human judgment in AI-assisted decisions?
Make decision ownership explicit and give people a chance to form a view before consulting AI. Rana Gujral describes writing down the decision, an initial instinct and the evidence that could change it, then asking AI to challenge that thinking. Decisions that are harder to reverse need a clearer trail of the reasoning and human responsibility.
From these conversations:
How do leaders build AI adoption beyond a small group of enthusiasts?
Combine executive support with employee-led experiments, practical enablement and conversations about concerns. Denis Romanovskiy discusses internal champions and small experiments. Jason Hill's school-district experience shows why access, understandable use policies and community trust also need attention. These are examples to adapt to your organization, rather than a universal rollout formula.
From these conversations:
How should leaders measure the value of an AI pilot?
Choose a business outcome and record the starting point before the pilot. Ronnie Coleman distinguishes producing more work from reducing risk, improving growth or changing operating costs. Ask how the result will be demonstrated, who will evaluate it, and what happens after the pilot if it succeeds.
From these conversations:
Explore the conversations
- How to Make Enterprise AI Adoption Successful: Inside the Chief AI Officer Role with Denis Romanovskiy
Denis Romanovskiy, Chief AI Officer at SOFTSWISS, describes enterprise AI adoption as work that spans technology, operations, security, and employee enablement. The conversation focuses on turning practical experiments into business results rather than launching one enormous AI project.
- How to Use AI Without Losing Human Judgment: AI Decision-Making and the Future of work | Rana Gujral
Rana Gujral, CEO of Behavioral Signals and author of The AI Instinct, explores how AI can make teams faster while weakening the judgment they still need. Chris and Rana distinguish making a decision from simply approving a model's recommendation.
- How AI Is Changing Management at Work: From AI Assistant to AI Chief of Staff with Erkang Zheng
Erkang “Ken” Zheng, founder and CEO of Ariso, explains why automating execution makes management and judgment more important. Chris and Ken discuss the AI chief of staff as a way to support coordination, prioritization, and accountability.
- How to Use AI to Hire Better: AI Recruitment, Screening & the Future of Hiring | James Terry
James Terry, Head of US Revenue at Indeed Flex, discusses the growing volume and complexity of recruiting. Chris and James explore AI screening and interviews, human review, and evaluating candidate skills at greater scale.
- How to Build an AI Strategy That Delivers Real Business Results | Eddie Irvin
Eddie Irvin, founder of Nashville AI Advisory, explains why a useful AI strategy starts with process clarity and prioritization. Chris and Eddie discuss communication between business owners and technical builders before focusing on tool selection.
- How to Implement AI in Your Business: From AI Use Cases to Real ROI | Dr. Markus Schmidberger
Dr. Markus Schmidberger, founder and CTO of JuntoAI, challenges the idea that every company needs a Chief AI Officer. Chris and Markus discuss adoption as cultural enablement, with distributed ownership and coordination across governance and HR.
- 113: Using AI Agents for Business: From Chatbots to Autonomous Workflows with Bryan McAnulty
Bryan McAnulty describes moving from asking a chatbot questions to assigning an AI agent ongoing work.
- 112: AI-Driven Leadership: Using the CRIT Framework Make Faster, Smarter Decisions with Geoff Woods
Geoff Woods argues that executive AI adoption should support consequential business decisions, not stop at minor tasks.
- 111: Using AI in the Workplace for Smarter Hiring and Pay Decisions with Cary Sparrow
Cary Sparrow explains how timely labor-market intelligence can inform hiring, compensation and workforce planning.
- 110: AI in Education: Building Trust While Preparing Students for the Future with Jason Hill
Jason Hill, Deputy Superintendent and CBO at Redlands Unified School District, describes enabling AI for staff before the district had completed its policies. The rollout created momentum, but community resistance made him pause and bring parent, student and staff feedback into the next stage.
- 108: Using AI Detection Tools to Fight AI Slop and Preserve Authenticity Online with Max Spero
Max Spero, co-founder and CEO of Pangram Labs, discusses recognizing generated text in an internet increasingly filled with synthetic content. Chris and Max examine how fake reviews, posts and engagement can distort the information leaders use to make decisions.
- 107: Using Generative Engine Optimization (GEO) to Win the AI Search Race with Cole Casperson
Cole Casperson explores how AI retrieval is changing search, e-commerce and customer discovery.
- 106: Using AI Assessment Tools to Reveal Hidden Automation Opportunities with Corey Ganim
Corey Ganim explains how assessments can uncover manual work that small businesses could automate.
- 105: Using Voice AI for Customer Service, Sales, and Enterprise Growth with Shawn Zhang
Shawn Zhang discusses voice AI as a communication layer rather than only a call-automation tool.
- 103: Using AI in Manufacturing: Generative vs. Predictive and Autonomous AI with Bryan DeBois
Bryan DeBois distinguishes generative AI from predictive and autonomous systems used in manufacturing.
- 102: The AI-Native Company: What Comes After the Org Chart with Melissa Reeve
Melissa Reeve explores organizational structures that can keep AI initiatives from delivering value.
- 101: How to Audit Your Dev Partner in the Age of AI with Matt Strippelhoff
Matt Strippelhoff discusses software development models that give mid-market businesses greater financial predictability.
- 99: Using AI Automation to Build Smarter Workflows Across Your Organization with Marc Boscher
Marc Boscher explains how fragmented systems and missing context limit AI across an organization.
- 98: How to Build AI Agents That Automate Workflows Without Coding with Etan Polinger
Etan Polinger explains agent design for non-technical professionals through process clarity and fundamentals.
- 94: Using AI vs Human Intelligence: When Should Leaders Trust Machines with Vasant Dhar
Vasant Dhar offers a framework for judging when to trust machine intelligence.
- 93: Using Generative AI to Develop a Winning Strategy for Business Leaders with Justin Trombold
Justin Trombold explains why generative AI strategy is a transformation question, not simply an IT rollout.
- 91: Using AI in Sales to Automate Go-to-Market Execution with Jason Eubanks
Jason Eubanks examines AI-native go-to-market operations rather than adding isolated features to legacy sales work.
- 89: Using AI at Work to Lead Through Change Without Losing Trust with Bill Gallagher
Bill Gallagher explores introducing AI without creating unnecessary fear and confusion.
- 88: Using AI at Work to Rethink People Strategy and Leadership with Kate Bravery
Kate Bravery discusses AI in talent planning, skills intelligence and workforce design.
- 87: The AI Tool Stack Every Executive Needs
Chris Daigle discusses an executive AI tool stack without chasing every new release.
- 86: Using AI at Work to Rethink How We Learn and Build Expertise
Panos Siozos distinguishes easy access to information from developing genuine understanding.
- 85: Using AI at Work to Reduce Tool Overload and Drive Real Productivity with Tim Cakir
Tim Cakir explains why collecting more AI tools does not necessarily create workplace productivity.
- 83: Using AI to Scale Marketing and Revenue Teams with Patrick Leung
Patrick Leung shares examples of AI supporting go-to-market execution and internal knowledge sharing.
- 80: Using AI at Work to Evolve Content Strategy and Audience Growth with Michael Stelzner
Michael Stelzner describes bringing AI into a business already working in Google's ecosystem. The conversation explores Gemini, connected company information, reusable Gems and training built around tasks employees actually complete.
- 79: Using AI at Work to Reimagine Marketing and Customer Experience with Etan Polinger
Etan Polinger discusses marketing systems that improve customer journeys without displacing human insight.
- 77: Using AI at Work to Fix Business Bottlenecks with Chris Duffy
Chris Duffy explains why practical AI adoption starts with listening for business bottlenecks.
- 76: Using AI at Work to Build Creative Strategy with Allen Martinez
Allen Martinez explores turning business data into creative insight and stronger audience alignment.
- 75: Using AI at Work to Activate Humans in the Workplace with Kristin Ginn
Kristin Ginn examines why individual AI productivity gains may not become organizational results.
- 73: Using AI at Work for Small Business Adoption and Team Alignment with Maria Elena Duron
Maria Elena Duron describes AI adoption for smaller businesses without overwhelming their teams.
- 69: Using AI at Work with Peter Swimm: From SaaS to Conversational Workflows
Peter Swimm recounts a week-long experiment running his business through conversational AI.
- 67: Using AI and Automation to Scale Lead Generation with Jay Feldman
Jay Feldman describes AI-assisted lead generation across cold email and omnichannel outreach.
- 65: Using AI at Work to Transform Learning and Leadership with David Martelli
David Martelli discusses AI-powered learning environments for students, executives and business leaders.
- 64: Using AI for Building Internal AI Teams with Diane Hammons
Diane Hammons describes WG Content's volunteer AI Pathfinders council.
- 63: Using AI for Content, Analytics, and SEO with Debra Andrews
Debra Andrews describes Marketri's progression from AI-assisted content into analytics and client communications.
- 61: Using AI for Seamless Workplace Booking with Khurram Sheikh
Khurram Sheikh discusses natural-language workplace booking for hybrid teams.
- 60: Using AI to Drive Organizational Change with Sara Flowers
Sara Flowers shares applications of AI across customer service and internal operations.
- 58: Using AI for Building Multi-Agent Systems with Jake George
Jake George discusses AI agents in sales and business operations beyond the surrounding hype.
- 55: Using AI for Upscaling Your Career Trajectory with Chris Daigle
Chris Daigle takes the guest seat to discuss AI skills, productivity and career progression.
- 49: Using AI for Improved Prompting Strategies with Segovia Smith
Segovia Smith discusses managing prompts so business teams can use AI more consistently.
- 46: Using AI for Business Consulting Strategies with Karl Yeh
Karl Yeh discusses tailored AI consulting for medium-sized businesses and traditional industries.
- 44: Using AI for Data-Driven Decision Making with Avi Perez
Avi Perez explains natural-language business intelligence and generative AI's role in working with company data.
- 43: Using AI for Innovating Global Enterprises with Sanjay Cherian
Sanjay Cherian shares enterprise AI lessons informed by his technology-strategy work at Nike.
- 38: Using AI for Better Leadership Outcomes with Geoff Woods
Geoff Woods discusses AI as support for executive decisions and business growth.
- 9: Using AI for Business Coaching & Consulting with Jodie Cook
Jodie Cook explains building AI coaches informed by a creator's style and content.
- 5: Using AI for Events and Email Marketing with David Gonzalez
David Gonzalez discusses using language models in event planning and team work.
- 3: Using AI for Email Newsletter Campaigns with Joe Stolte
Joe Stolte discusses automated newsletters and broader AI use across business work.