Bret Henning started college as a music major and entered technology through a trade school and a computer operator job. He handled backups, printers, support, and disk drives before moving into programming and application work. Building systems for accounting, payroll, inventory, and manufacturing gave him an education in how a business runs.

Bret traces the shift from computers as an after-the-fact record to computers as the place where work happens. He recalls how Y2K made technology’s place in the business harder to ignore and describes an early web sales interface that turned month-end reports into current information people could act on during the month.

The conversation then turns to shadow AI. Bret explains why an immediate no can drive employees around IT instead of changing their behavior. His approach starts with questions, listening, and a clear explanation of risk. IT still has to offer an option that meets the employee’s need. He also shares why he hires teachable people with customer service experience, how empathy affects vendor and employee relationships, and why trust starts before a difficult business conversation.

Brian Laird's career has taken him through tech support, networking, security, software development, enterprise architecture, consulting, and the CIO seat. In this conversation with Doug Camin, he looks back on the week his former company sent thousands of employees home during COVID. Some customer service agents had no internet at home, so staff lined up at Verizon stores to buy hotspots three or five at a time. Early planning gave the company something to work from when the situation changed fast.

Today, Brian is CIO at Bahler Group, a group of construction companies with manufacturing, supply chain, and field operations. His team is replacing a twenty-year-old Excel sales tool, connecting data across operating companies, and building systems that can support more revenue without adding staff at the old rate. He explains how family ownership changes the pace of decisions, why leaders need to understand the rhythm of the business, and how clear decision criteria help teams act with confidence.

Brian also walks through Bahler Group's AI strategy. AI-assisted development helps the team build faster. Department copilots make operational data easier to query. Purpose-built copilots check estimates, contracts, and material takeoffs for details that may have been missed. Brian keeps people in the decision loop while the team learns where the AI can be trusted. He closes with four rules for team decisions and a direct challenge to rising IT leaders: learn how the business works and prove the value your work creates.

Demetrios Xarhoulakos began his career producing CAD drawings and became the person colleagues called when technology stopped cooperating. That curiosity eventually led him into application support, global team management, cloud migration, and technology leadership for an international engineering business.

In this conversation with host Mike Kelley, Demetrios explains why solving every problem personally limits a leader's reach. He shares how he trained support teams to handle specialized tickets, connected technical groups that had been operating in silos, and aligned IT priorities with organic growth and acquisitions.

The discussion also covers follow-the-sun licensing, vendor scorecards, unused contract value, role fit on lean teams, and the difficult decisions that come with people leadership. Demetrios closes with a practical look at governed AI adoption, the support burden behind employee-built applications, and a future where IT spends less time reacting to tickets and more time enabling the business.

Andrew Schutsky took a circuitous path to the CIO seat. Co-ops and help desk work led to management consulting, aerospace and defense, medical devices, supply chain, R&D, procurement, and manufacturing transformation. Each stop gave him another view of how the business experiences technology and measures results.

In this conversation with Doug Camin, Andrew explains why IT leaders should study their industry's competitive levers and build real relationships with organizational leaders. He shares the 180 concept for seeing a proposal through the audience's eyes, a direct method for keeping executive presentations relevant, and a mentoring process that turns career goals into accountable action.

Andrew also describes how his teams use accessible generative AI tools to prove value in pricing, cost, supplier, freight, and market analysis. He looks ahead to AI-supported customer experiences where faster quotes and warranty responses can create competitive advantage. Throughout the episode, his message stays practical: learn what matters, make the value clear, keep the ask concise, and find peers who will help you follow through.

Farhan Zakir's path into technology started far from a server room. After leaving medical school in Pakistan, he returned to Orlando, worked across hospitality roles, moved into accounting, and found his opening through ERP implementation for the club industry.

In this conversation with Phil Howard, Farhan explains how that operating background became an advantage in IT leadership. He shares practical ways to translate technology into business language, make support interactions feel safe, teach cybersecurity through personal relevance, protect historical data during software migrations, and communicate value to executives.

Farhan also explores the service cost of automation, the responsibility to keep learning as AI evolves, and the three-part framework he gives emerging IT professionals: listen, understand, execute.

In Episode 441 of You've Been Heard, Michael Moore speaks with Matt Thomas, Director of IT and Marketing at Crabapple Roofing, about the communication skills that turn technical expertise into business leadership.

Matt traces a career spanning small MSPs, music, recording, photography, video production, and internal IT leadership. He explains why technology becomes easier to support when leaders tell clear stories, respect the people asking for help, and connect cost to time saved and business outcomes.

The conversation also covers practical AI adoption, documentation and SOP libraries, the danger of leadership losing touch with frontline work, the value of solving problems every day, and the governance needed to keep AI automations useful, secure, and maintainable.

In Episode 439 of You've Been Heard, Phil Howard speaks with James Dunlap about turning technology and security work into language executives understand.

James draws on leadership experience across healthcare, banking, fintech, and legal services to explain why projects, ticket counts, and technical jargon rarely tell the full story at the board level. He shows how to lead with risk reduced, value created, revenue impact, competitive advantage, and reputational consequences.

The conversation follows his path from fine art photography and medical imaging into CIO leadership, including his decision to step down from a healthcare CIO role to learn directly under a banking CISO. James also recounts leading a seven-location medical practice from paper charts to electronic records, examines the security challenge of legacy healthcare equipment, and warns that governance and accountability for AI agents are not keeping pace with capability.

He closes by reframing imposter syndrome as part of growth and explaining why credibility comes from quiet, consistent follow-through.

Bill Garcia explains why IT leaders lose credibility when they speak technology but cannot translate it into business outcomes. Drawing on a career in process redesign, ERP transformation, COO roles, and global leadership, he shows how governance can increase speed, why AI needs clean and trusted knowledge, and why communication remains the skill that separates strategic leaders from service providers.

In Episode 435 of You've Been Heard, Doug Camin speaks with Stephen Hightower about a career that spans aerospace and defense, information security, quality engineering, private equity consulting, YETI Coolers, and technology leadership at Harmar.

Stephen explains why cycle time, service quality, and unit cost are the three metrics he uses to understand whether a business process is working. The conversation moves through private equity speed, order-to-cash thinking, Lean Six Sigma, master data, ERP and CRM discipline, AI decision quality, proactive monitoring, and the need for IT leaders to earn trust through transparency.

Stephen's through line is clear: technology should not be treated as a cost center when it can remove waste, improve customer experience, and help the business make better decisions.

In Episode 434 of You've Been Heard, Phil Howard speaks with Tim McCrosson about a career that moved from dot-com era web development into federal IT leadership, policy, cybersecurity, and large-scale operations.

Tim explains how an early leadership correction changed him from a command-and-control project manager into a more sustainable coach and collaborator, while also showing why leaders still need the right style for the moment.

The conversation moves through CIO authority in the federal government, laptop refresh policy, the use-or-lose budget problem, enterprise depot operations, pandemic-era network consolidation, SASE risk reduction, AI in acquisition, and the danger of chasing AI without a clear business case.

Tim's through line is simple: technology can be powerful, but it works best when leaders manage up, manage down, build trust, and keep people at the center.