The CLIMB to People-First Leadership: Building Future Leaders to Innovate, and Serve with Derik Calhoun

Season #5

Episode 43: The CLIMB to People-First Leadership: Building Future Leaders to Innovate, and Serve with Derik Calhoun 

"Systems move organizations, people move systems.” ~Derik Calhoun 

Episode Summary 

What happens when the kid from Richmond grows up to run train operations for the very system that serves his hometown? In this episode, I sit down with Derik Calhoun, Chief Transportation Officer at BART, for a conversation about leadership that starts in the mirror and ends on the frontline. This conversation will change how you think about your own leadership. Derik shares how to step into a complex system in your first 90 days, why “building a tree” of legacy matters more than building a resume, and what shifts when you finally understand who you actually work for as a leader. The son of two union presidents, he makes the case that trust with your frontline is earned through honesty and presence, and that psychological safety in high-stakes work means raising honesty, never lowering standards. If you lead people at any level, you'll walk away with the CLIMB framework in your pocket and a challenge you won't be able to shake, which is to develop your people with the same intensity you develop your operations. 

Key Takeaways 

  • Lead from the mirror first asking yourself daily, “What could I have done better today?” 
  • Your first 90 days as a new leader are for listening, not launching. 
  • Middle management is where culture lives or dies, so cultivate it. 
  • Unions are partners in workforce development, so build relationships that matter and last. 
  • Psychological safety means increasing honesty, not compromising standards. 
  • Adopt AI to elevate people, make room for the next generation of leaders, but not as a tool to replace critical thinking. 

About Derik Calhoun 

Derik Calhoun is currently the Chief Transportation Officer for BART (Bay Area Rapid Transit) he joined BART in February of 2025. He manages and oversees, through subordinate managers and supervisors, all operations and activities of the Transportation Department, including movement and control of revenue railed vehicles throughout the system within the Operations Control Center (OCC). 

 

Before joining BART, Calhoun was Chief Operating Officer at Santa Clara Valley Transportation Authority (VTA), managed a budget of $350 million and provided executive-level operational oversight and direction for VTA's bus and light rail operations, maintenance, Accessible Services, and Facilities Maintenance. Also helped to reinforce VTA’s workforce development program (Highroad partnership) with ATU. 

 

Before VTA, Calhoun served as the Director of Transportation for 6.5 years at AC Transit, in Alameda County, California. In that role he managed the delivery of transportation services for all operating divisions, opened the new TEMPO BRT along the international corridor in Oakland during the Pandemic, managed a budget of $238 million, opened a new Operations Control Center, and helped open and manage the Sales Force Transit Center. Calhoun also spent over 20 plus years in the private sector as a General Manager and Regional Vice President. He was able to see over 100 contracts, and was involved and chaired several union negotiations with ATU, Teamsters, IBEW, SEIU, and AFSCME. 

 

Resources & Links 

 

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