Transforming technical leaders into business enablers

In partnership with:

Members of The CISO Society gain access to an exclusive, tailored training seminars designed to assist CISOs in equipping themselves with the skills to become true business enablers.

This uniquely tailored course, developed following feedback from our members, equips participants with the tools and knowledge to make a significant impact on the business, providing a valuable step in the journey into the boardroom.

We are honored to bring these courses to our members and help them progress in their ever-evolving careers.

2025 Seminar Schedule

Avoiding Shadow AI --Used by Employees in the Enterprise

March 29

AI is the fastest-moving technology innovation ever seen, and technical innovation is a constant both negative and positive risk for any business. AI can offer any sized organization incredible improvements in productivity, efficiency, and effectiveness.  Emerging use cases are already in use and becoming better understood.  However, many organizations, especially those who are more risk averse, may be either stopping or at least slowing, AI adoption for fear of the many negative risks associated with these emerging technologies.   

However, what is the risk in that approach in itself?  The answer is “Shadow AI” – the use of these tools by employees without the consent, knowledge of, or permission of their employers.  Without a sound strategy for technology leaders to help with the ethical and responsible deployment of these new AI tools into the business, the unknown and escalating risk of Shadow AI is real.  Technology leaders must get ahead of this issue and drive controlled innovation and early piloting of emergent use cases to ensure they remain contemporary, competitive, and compelling as a product or service provider.  In this seminar, we will explore:

  • Explore ways to educate employees on the risks of shadow AI and how to ensure that the enterprise gets ahead of this risk curve immediately while working simultaneously on starting to deploy AI tools across the enterprise more rapidly.

  • A model for the ethical and responsible use of AI-based on principles that can be applied to all use and business cases being considered by the enterprise.

  • Develop internal messaging appropriate to boards, executive teams, and executive peers that temper early AI adoption until appropriate policies and risk mitigation practices are understood and implemented organization-wide.

AI, Analytics, and Automation “AAA”

April 25

Technology leaders need to blend a contemporary understanding of how the fields of AI, data science and technology innovation are rapidly merging to create seismic shifts in the way organizations are going to structure, perform and analyze their workflows. The future of work requires deep tech innovation accomplished quickly.  This trend – while it may depend on technology progress– transcends the technology itself and goes straight to the heart of our political, economic and social systems in which all organizations ultimately operate.  There are significant legal, compliance, data and privacy concerns to be raised and dealt with. First-movers may face more risk than reward initially and which is already causing needless polemical debate and unproductive conflict between technology and the business. Expand your understanding of: 

  • High-value AI use cases and the opportunities and threats these technologies present.

  • Connect the rapid evolution to the impact of improved analysis and automation to its implications for workflows, jobs, and new economic realities for business productivity.

  • Consider how to manage innovation when technologies present unknown risks

  • Learn to manage expectations and to temper enthusiasm for early adoption except where first-mover advantage is a mission-critical strategic/competitive imperative

Rhetorical Communication and Advocating for your Ideas

May 30

We often communicate with one goal in mind: to influence behavior and outcomes. So being able to speak to business peers and clients – either internally, as a consultant or as an industry influencer -  is a critical skill that few people get a chance to learn and practice before they enter a room where success matters. The outcomes of gaining support for your ideas define your ability to make a difference, and achieving this goal requires a deep understanding of how to be an effective rhetorical communicator and storyteller! Do you speak the language of strategy? What is strategy? Learn methods that help you advocate for your ideas and gain resource support to execute them effectively. In this session, you will:

  • Understand and reflect back on the ‘Business Mandate’ that truly matters for the success of advocating for your ideas, projects and technology initiatives.

  • Develop opportunities to influence others through skilled and persuasive presentations.

  • Cultivate specific language and impactful thought approaches that are adaptive to various audiences, purposes and fluid or dynamic situations like the boardroom.

  • Practice how to pre-influence and prepare for handling objections to build effective joint sessions with business peers that can elevate your business success.

  • Learn a proven strategy to develop nimble decision-making capabilities throughout the business while making actual decisions.

Mastering Executive Leadership

June 25

Leadership is a way of being; leaders today are required to think critically and lead strategically under pressure, all while engaging with softer people skills. Whether you are already in the C-Suite, or aspiring to get there, learn practical insights and tools from experienced corporate leaders that will resonate in today’s increasingly complex world. To be successful requires the ‘softer skills’ of self-awareness, empathy, a positive attitude, conscious communication, deep listening, emotional intelligence, vulnerability, an executive presence, and an expression of confidence. In this session, through guided reflection you will learn how to:

  • Shift towards a leadership mindset and away from a manager mindset

  • Cultivate a more executive presence using body language and active listening

  • Find your confident self and a sense that you belong at the executive level

  • Master constructively engaging in conflict, and choosing when to prompt good conflict

  • Manage egos and authority bias, especially in the board room

Finance is Your Friend

August 27

One of the most foundational skills for any IT leader is to have a well-informed knowledge of the financial processes that drive projects. As an emerging tech leader, can you speak the language with your financial counterparts? Can you secure sponsorship of your projects? Success in today’s organizations require leaders who understand the financial pressures and processes of the business and how to navigate those. In this session, you will:

  • Assess your understanding of the key financial terms’ technology leaders must know

  • Recognize what key financial measures are important to compete for project capital

  • Assess financial elements of project risk learning to minimize financial exposure

  • Explore financial expectations from a business outcome perspective to improve IT

Emerging Tech and Global Information Warfare

September 25

The information battlefield is now a global geopolitical war, and particularly as the interests of various nation states like the US and China come into direct conflict, there is a need for technology leaders to enhance their understanding of the geopolitical drivers of technology innovation and management to avoid putting their organizations in harm’s way.  During this provocative and thought-provoking session, learners will be able to:

  • Identify nation state motives and their participation in information warfare activity

  • Link technology trends and emerging technologies to emerging security risks

  • Consider how technology innovation may be influenced by geopolitical motives

  • Determine the impact of these forces on large enterprise security posture leader

Leading with Design Thinking

October 29

Too often, technology leaders jump to delivering outcomes only technical outcomes without thinking through business design choices or anticipating potential pitfalls in advance. This can lead to disastrous business outcomes that ruin careers.  In this provocative, example-laden session, enhance your strategic executive effectiveness by expanding your thinking repertoire, brainstorming tool kit and asking better “What if?” questions. Learn how to design solutions for business outcomes instead of technology advances, expanding your thinking about driving strategic change and your leadership posture. The art and science of design thinking helps leaders to eliminate biases and consider possibilities, ensuring that leaders effectively guide the design of solutions to maximize both short and long-term goals of the business by delivering measurable gains. In this session, participants will:

  • Learn to frame and re-frame conflict to achieve consensus on alternatives.

  • Embrace the art of both the possible and the impossible in designing initiatives.

  • Focus on advancing strategic business solutions not technology implementations

  • Understand and apply a practical design thinking toolkit to a real business problem

Dr. James L. Norrie, DPM, LL.M.

Course Leaders

James is the Founder and CEO of cyberconIQ, a firm committed to changing the global cybersecurity conversation from fear to hope. Internationally known, his areas of research interest delve into the intersection of society and technology and the clash this can create. The author of six books and multiple journal articles, James is a sought-after expert, frequent media commentator and national newspaper op-ed guest writer.  He conducts, presents and publishes industry-related research and consults globally to prominent companies concerning cybersecurity, information privacy and security, and economic crime detection and prevention methods

Eugene Roman, MBA, CMA, ICD

Eugene started his career in telecommunications and has worked for Nortel Networks Corporation, Bell Canada Enterprises Inc., and Open Text Corporation. In progressively senior technology and business roles in Canada, the U.S. and the U.K., Eugene was responsible for integrating critical technology and business processes to better deliver innovative programs and led efforts to deliver current and ‘next generation’ services. An award-winning CIO, he now advises senior leaders in digital technology/transformation via Design Ai Ltd, a tech advisory company. Eugene is a frequent speaker on “The Future of Digital”, is a faculty advisor in AI/Analytics/Tech at the Schulich Business School, York University, and a board member at Epam Ltd, Community Trust Co Ltd, Lakeland Holdings and York University.

Dr. Tamara Schwartz, DBA

The mastermind behind the Cyber-Based View of the firm, conducting advanced cyber strategy research. Tamara is an independent consultant, an Assistant Professor of Business Administration & Cybersecurity at the York College of Pennsylvania, and a recognized Cyber Thought Leader with over 20 years of experience serving large complex government organizations in international policy and planning, security assistance, and technology strategy. A skilled information operations professional, she is comfortable with ambiguity and the complexity of today’s information driven environments, enabling her to work with organizations ranging from high-tech startups to advanced research institutions.

Cindy Seibel

Cindy is an award-winning CIO whose experience spans the public, not-for-profit and private sectors. Her unique combination of expertise in information technology, human resources, leadership and learning has led to a track record of high-performing multi-disciplinary teams. She has served as a program director for successful multi-million-dollar technology implementations. Her work in developing strategic technology plans for organizations has been led both as a CIO, and as an external consultant. Cindy is a lifelong learner who loves to share her passion for leadership and technology in the 21st century.