Unlocking Leadership in Cybersecurity: Lessons from Tom Scott
In today’s digital landscape, effective leadership is just as crucial as technical expertise in cybersecurity. In this exclusive interview, we sit down with Tom Scott, the founder of Cyber Sherpas and a veteran of cyber leadership. With decades of experience—from serving on advisory boards to working with the FBI’s InfraGard program—Tom has learned firsthand what it takes to lead in an industry where security and trust are paramount.
Through candid reflections, Tom reveals the key lessons that shaped his career, the power of Mentorship in leadership, and why fostering the next generation of cybersecurity professionals is vital. From navigating complex decision-making to building meaningful connections, Tom shares insights that every aspiring leader—whether in cybersecurity or beyond—can apply.
Join us as we delve into his journey, uncover the philosophies that drive his leadership, and explore the practical wisdom he’s gained over the years.
Leadership Through Mentorship: Shaping the Next Generation
One of the most profound lessons Tom Scott learned in his career came from an early mentor who told him, “I am failing you if I, as your supervisor, am not preparing you for your next job.” This perspective changed Tom’s entire approach to leadership. Rather than simply managing employees, he embraced a philosophy of Mentorship—helping his team grow beyond their current roles.
Throughout his career, Tom applied this mindset by identifying and fostering potential in those around him. Like the legendary hockey player Wayne Gretzky, who advised skating to where the puck would be, Tom believes leadership is about preparing people for the future. His approach aligns with a well-known philosophical principle: treat people as who they can be, not just who they are today.
Tom’s leadership style isn’t about maintaining control but empowering others. His success has been built on the idea that strong teams are formed when leaders invest in their people, preparing them for new opportunities rather than holding them back. By mentoring those around him, Tom has built effective teams and contributed to the broader growth of the cybersecurity industry.
Decision-Making Strategies: The Art of Prioritization
Early in his career, Tom Scott experienced a defining moment in decision-making when he asked his supervisor for a new firewall. The response was unexpected: “How big is the fine, and who goes to jail if I don’t give you one?” Initially baffled, Tom soon realized this was a crucial lesson in risk management. His supervisor wasn’t dismissing his request—he was teaching him to frame decisions based on the organization’s overall capability, not just on a need for tools.
From that moment on, Tom learned that decision-making isn’t just about reacting to immediate needs—it’s about understanding how each decision fits into a larger strategic framework. Leaders, he discovered, must approach requests based on how they align with the organization’s mission and security posture.
Moreover, Tom recognized the importance of self-awareness in decision-making. Inspired by Jeff Bezos’ practice of making critical decisions in the morning—before fatigue sets in—Tom now advises leaders to structure their decision-making processes accordingly. His experiences reinforce the idea that how decisions are framed, when they are made, and who is involved in the process can dramatically impact outcomes.
The Power of Connection: Building Meaningful Relationships
Tom’s leadership extends beyond technical expertise—he has mastered the human element of cybersecurity. One of his key strategies is building connections. Whether scanning a bookshelf for a shared interest or making lighthearted comments about a family photo, Tom understands the importance of personal engagement.
Connection is more than networking; it’s about creating genuine relationships that foster trust. Tom recalls a conversation with a colleague about a family photo featuring three daughters. He joked, “What did you do in a past life to deserve three daughters?”—a comment that broke the ice and established an immediate rapport. Moments like these demonstrate his ability to connect with people personally, making business interactions smoother and more productive.
Tom believes strong relationships are essential in leadership. He actively seeks common ground, whether in sports, education, or personal interests, to create deeper bonds with colleagues and stakeholders. In cybersecurity—where trust is paramount—the ability to connect with others has been one of his most powerful assets.
Balancing Passion and Profit: The Heart of Leadership
Tom Scott describes his approach to work as a balance between “for-profit” and “for-passion.” While his consulting business sustains him financially, his nonprofit and Mentorship efforts fuel his heart. This philosophy helps him navigate leadership purposefully, ensuring that his professional goals align with his deeper values.
His involvement in workforce development, cybersecurity events, and mentorship initiatives reflects his commitment to giving back. Recently, Tom judged high school robotics competitions, an experience that reinforced his belief in the importance of nurturing future leaders. Seeing students passionately engage in technical challenges reminded him why he invests time in educational initiatives—shaping the next generation.
Ultimately, Tom’s leadership journey is guided by his desire to balance financial stability with meaningful contributions to the cybersecurity community. He hopes that, in the coming years, he will have more opportunities to shift focus toward his passion projects, building a legacy that extends beyond corporate success.
The Future of Leadership: Expanding the Heart
Looking ahead, Tom envisions a leadership evolution centered on growth—professional and personal. He wants to create more space for Mentorship, expand initiatives that foster industry collaboration, and continuously develop his leadership skills.
His dual focus on profit and passion will shape his future. The more sustainable his business becomes, the more time he can devote to educational outreach, leadership training, and philanthropic efforts. As he puts it, “I want to have a bigger heart.” This is a reference to the transformation in The Grinch, where kindness leads to an expansion of purpose.
Tom believes that leadership is a lifelong journey. As he moves forward, he aims to refine his skills, mentor more emerging professionals, and contribute to the cybersecurity field in ways that genuinely make a difference. His goal isn’t just professional success—it’s about leaving a lasting impact.
Tom Scott’s leadership journey includes invaluable lessons—from Mentorship and decision-making to building meaningful connections and balancing passion with profit. Now, it’s your turn to apply these insights in your leadership path. Here’s how you can take action:
1. Embrace Mentorship as a Leadership Strategy: Adopt the “Prepare for Your Next Role” Philosophy – If you are in a leadership position, prioritize your team’s growth. Help them develop skills that will prepare them for future roles rather than just managing them for their current tasks. Seek Out a Mentor – Great leaders learn from those before them. Look for mentors who inspire you and can provide guidance on your professional journey. Be a Mentor to Others – Leadership is not just about individual success. Invest in people around you, offer advice, and help others navigate their careers.
2. Improve Your Decision-Making Process: Reframe Your Requests Based on Organizational Needs – Instead of asking for tools or resources, focus on the capabilities your organization must have. Present solutions that align with broader business priorities. Understand Decision Fatigue – Recognize that leaders make countless decisions daily. Prioritize critical ones when you have a fresh mind, ideally earlier in the day. Assess Whether a Decision Can Be Walked Back – If a decision is irreversible, take extra time to evaluate it carefully. If it can be adjusted later, don’t overthink—make the best call and adapt as needed.
3. Build Meaningful Connections in Leadership: Look for Common Ground in Conversations – When meeting new colleagues or clients, observe personal touches such as bookshelves, degrees, or trophies. Find shared interests to spark authentic conversations. Use Humor and Lighthearted Engagement – A well-placed joke or personal comment (like Tom’s example of referencing someone’s family photo) can instantly create rapport. Invest in Relationship-Building – Leadership isn’t just about authority—it’s about trust. Make an effort to foster strong, genuine connections with peers, employees, and stakeholders.
4. Balance Passion and Profit in Your Career: Define Your “For-Profit” and “For-Passion” Work – Just as Tom distinguishes between his consulting work and his nonprofit engagements, determine which parts of your career sustain you financially and which fulfill your mission. Carve Out Time for Your Passion Projects – Whether mentoring, volunteering, or engaging in industry events, actively set aside time to work on things that make your heart “grow bigger.” Look for Opportunities to Give Back – Can you contribute to workforce development programs? Speak at events? Mentor young professionals? Identify ways to make an impact.
5. Focus on Leadership Growth for the Future: Prioritize Continuous Learning – Stay ahead by taking courses, reading industry insights, and embracing emerging technologies like AI and cybersecurity trends. Enhance Your Leadership Awareness – Self-awareness is a critical trait for successful leaders. Regularly reflect on your leadership style and adjust to improve effectiveness. Surround Yourself with the Right People – As Tom emphasizes, choose your closest professional relationships wisely. Be intentional about whom you learn from and collaborate with. Strengthen Both Professional and Personal Leadership – Leadership extends beyond the office. Strive to grow as a mentor, parent, friend, or community member.
Tom Scott’s leadership journey is a testament to the power of Mentorship, connection, and intentional decision-making. From his early career lessons on preparing others for their next role to his commitment to fostering meaningful relationships, Tom has demonstrated that leadership is not just about managing—it’s about empowering, guiding, and inspiring.
His insights on risk management, decision-making strategies, and balancing passion with profit provide valuable lessons for emerging and experienced leaders. Through Cyber Sherpas, his advisory roles, and his dedication to workforce development, Tom has built a legacy centered on preparing the next generation and creating growth opportunities.
Looking ahead, his vision for leadership is clear: grow the heart bigger—a philosophy inspired by the transformation seen in The Grinch, where kindness expands purpose. Whether through mentoring, connecting professionals, or helping shape the future of cybersecurity, Tom continues to lead with both wisdom and heart.
As we reflect on his journey, one thing is certain: the best leaders are not those who seek power but those who use their influence to uplift others. In that regard, Tom Scott is a true trailblazer in leadership. Now, it’s your turn—how will you embrace leadership, make meaningful connections, and build a lasting impact?
Want to hear Tom Scott’s insights firsthand? Watch the full, live podcast interview [click here]
