In this episode of RC’s Best of Success Podcast Show, Jill Bloom, group publisher of Roofing Contractor, spoke with Trent Cotney, partner at Adams and Reese, about essential legal and business strategies for contractors. The conversation covered three major areas that contractors should focus on: software selection, business acquisitions, and managing backlogs in a shifting market.

Smart Software Decisions

Contractors should prioritize carefully evaluating software agreements, preparing for the operational and emotional impacts of business acquisitions, and strengthening fundamentals like cash flow and accounts receivable to navigate a shifting market. Trent Cotney emphasizes that proactive planning, realistic expectations, and strategic decision-making are essential for long-term stability and success in today’s contracting environment.

Cotney emphasized the importance of understanding software agreements before making purchases. Contractors often invest in expensive platforms without fully evaluating how the software will integrate with existing systems or whether it will meet their data needs. “The biggest issue is lack of access to data or inability to retrieve it cost-effectively,” Cotney explained. He advised treating software agreements with the same care as customer contracts, negotiating terms carefully, and anticipating potential issues.

He highlighted three main pitfalls contractors face with new software. First, systems often fail to communicate with other platforms, which can lead to inefficiencies. Second, adoption failure is common; without proper training and enforcement, employees may continue using old methods, rendering the investment ineffective. Third, rapid technological changes—especially the rise of AI—can render software outdated in a short period. Cotney recommends testing software in real-world conditions whenever possible, establishing phased rollouts, and setting measurable milestones to ensure smooth integration and value from the investment.

The discussion then shifted to business acquisitions, a topic fraught with emotional and financial complexities. Cotney warned that many business owners are unprepared for how their company may change post-sale.

“Owners often get surprised or upset about what happens after acquisition because the business may dramatically change—or even disappear—due to additional acquisitions or restructuring,” he said. Cotney stressed the importance of understanding the future role of leadership in transition periods, managing expectations, and preparing emotionally for changes in ownership.

Finally, the conversation turned to managing backlogs and operational challenges amid slowing demand. Cotney described the current market as a “course correction” following the artificial demand spikes during the COVID-19 pandemic. His advice was straightforward: focus on business fundamentals. Contractors should monitor accounts receivable closely, maintain strong cash flow, and eliminate inefficiencies wherever possible. “Cash is king,” he noted, emphasizing that contractors with sound business practices will weather market adjustments successfully.

Throughout the conversation, Cotney underscored that proactive planning, attention to detail, and realistic expectations are critical to long-term contractor success. Contractors seeking further guidance can reach Cotney via email at Trent.Cotney@ARLaw.com or connect on social media, while industry news and resources are available at roofingcontractor.com and wconline.com.

By addressing software integration, acquisitions, and market fundamentals, Cotney’s insights provide contractors with practical strategies to safeguard their businesses, maximize investment, and navigate change with confidence.