Subscribe Share Full episode and show notes Leadership , Incident Response , Security Staff Acquisition & Development Optimize Legal Operations as the CISO Role Changes to Address Skills Gaps and AI – Walter Scott Wilkens – BSW #447 Legal departments are under continual pressure to solve problems effectively and integrate innovative technology all while reducing costs and complexity. Enter cybersecurity, a complex and potentially costly risk. How should legal departments prepare? Walter Wilkens, Head of Delivery, North America at DWF Legal Operations, joins Business Security Weekly to discuss how legal operations can help optimize your legal department by eliminating bottlenecks, identifying and fixinginefficiencies and developing processes tailored to enhance your team’s performance. Walter will discuss how you can move from a lack of coordination to a structured legal operations to address cyber incidents before an... May 13, 2026 Full Segment Notes Legal departments are under continual pressure to solve problems effectively and integrate innovative technology all while reducing costs and complexity. Enter cybersecurity, a complex and potentially costly risk. How should legal departments prepare? Walter Wilkens, Head of Delivery, North America at DWF Legal Operations, joins Business Security Weekly to discuss how legal operations can help optimize your legal department by eliminating bottlenecks, identifying and fixinginefficiencies and developing processes tailored to enhance your team's performance. Walter will discuss how you can move from a lack of coordination to a structured legal operations to address cyber incidents before and after the event. In the leadership and communications segment, The Art of Security: It Is Time to Rethink the CISO’s Role, The Best Leaders Embrace the Role of Supporting Character, Empathetic Leadership Can Make or Break AI Adoption, and more! Guest Walter Scott Wilkens Head of Delivery, North America, Chicago, DWF Legal Operations at DWF Legal Operations Walter is Head of Delivery for North America, overseeing client engagements across DWF service lines including litigation, contracts, regulatory compliance, technology implementation support, financial services, legal analytics, horizon scanning and global tax developments. Hosts Matt Alderman Ben Carr Jason Albuquerque List of Articles Matt Alderman CISO shortage may reflect unrealistic job expectations A new report warns of a CISO shortage, but interviews suggest the reality is more complex. The gap may reflect unrealistic job expectations rather than a true talent shortage. The Art of Security: It Is Time to Rethink the CISO’s Role Traditionally, executives placed the Chief Information Security Officer (CISO) within the IT department, where they focused primarily on managing cybersecurity threats with technical measures — a vulnerability in itself. To know thyself is to know that this approach is inadequate and treats cybersecurity as a series of isolated skirmishes rather than an all-out war that demands a comprehensive strategy. Skills Gap Top CISO Concern, Says New SANS Survey Concerns about the skills and capabilities of cybersecurity teams have for the first time overtaken worries about headcount and unfilled vacancies among chief information security officers, according to a new survey. CISOs step up to the security workforce challenge A robust cybersecurity program needs a range of skilled people, yet many CISOs continue to face an ongoing skills shortage — and the squeeze may only get worse as AI gains traction. The Best Leaders Embrace the Role of Supporting Character The rise of “founder mode” and “main-character energy” as approaches to leadership has pushed many executives toward self-centered, top-down styles that research shows are deeply counterproductive—eroding trust, stifling performance, and ultimately leaving leaders themselves less engaged and fulfilled. The antidote is what might be called “supporting-character energy”: a humble, curious leadership style focused on understanding and advancing other people’s stories rather than one’s own. Leaders can cultivate it by practicing intellectual humility, asking better questions, and helping employees connect their work to their own values—a process shown to boost satisfaction, performance, and loyalty. As AI takes over information and technical skills, this deeply human capacity to inspire and connect will increasingly define what leadership is actually for. The New Leadership Skill Nobody Is Developing Knowing how to use AI is a tool skill. Knowing how to design environments where using AI makes your people better is a leadership skill. Almost nobody is building it. Empathetic Leadership Can Make or Break AI Adoption Research shows a wide gap between how executives perceive AI adoption and how employees actually experience it—most workers feel anxious and far less enthusiastic than their bosses assume. Without psychological safety, employees are less likely to experiment with new tools, more likely to produce shallow AI-generated work, and in some cases actively sabotage company AI initiatives. Empathetic leadership directly addresses these problems: employees with caring managers are significantly more likely to innovate and embrace new technologies. Leaders should involve employees in shaping AI strategies rather than simply announcing them, invest in training frontline managers, and look for ways to use AI to deepen human connection rather than replace it. Show More Stay in the Know, No Smoke and Mirrors – Join Our Newsletter Get expert insights and technical breakdowns straight to your inbox. Join Now Related Segments Leadership Teach to Sell and Two Interviews from RSAC 2026 from Dropzone AI and Microsoft – Dan Rochon, Edward Wu, Arunesh Chandra – BSW #446 Leadership A Founder’s Journey: From Microsoft Active Directory MVP to Co-Founder and CTO – Guy Teverovsky – FS #14 Leadership Not All CISO Gigs Are Created Equal and RSAC Interviews from ESET and Mimecast – Joanna Chen, Tony Anscombe, Rob Juncker – BSW #443 Related Content Security Operations State cybersecurity leaders discuss prioritizing security upgrades Government security Trump’s CISA director nominee exits consideration for leadership role Security Operations China emerges as ‘peer competitor in cyberspace,’ UK NCSC head warns You can skip this ad in 5 seconds