One Conversation at a Time: The Power of Human Connection in Security Leadership

By Mark Dorsi

The most transformative moments in my career haven't happened in boardrooms or conference halls. They've happened in conversations,sometimes over coffee, sometimes on a Zoom call, sometimes in the hallway after a meeting,where someone shared a real challenge and we explored solutions together.

In an industry obsessed with technology, frameworks, and automation, we often forget the most powerful tool we have: human connection.

The Acquisition That Started with a Coffee Chat

A few years ago, a startup founder reached out for advice on preparing their security program for acquisition. Instead of sending them a checklist or pointing them to a vendor, we sat down for what was supposed to be a 30-minute coffee meeting.

Three hours later, we'd mapped out not just their security needs, but their entire approach to demonstrating trustworthiness to potential acquirers. We talked about compliance not as a box-checking exercise, but as a way to tell their story of maturity and reliability.

That conversation led to a complete transformation of their security program. More importantly, it led to a successful acquisition eight months later. The acquirer specifically mentioned their "mature security posture" as a key factor in the decision.

No PowerPoint presentation could have achieved what that conversation did.

Beyond the Technical: What People Really Need

Here's what I've learned from hundreds of these conversations: people rarely need more technical information. They need:

• Context: How does this relate to what I'm actually trying to achieve?
• Confidence: Am I making the right decisions for my specific situation?
• Connection: Am I alone in facing these challenges?
• Clarity: What should I do next, and in what order?

You can't deliver these through a webinar or white paper. They emerge from dialogue, from listening to someone's specific situation and helping them think through their options.

The Art of the Meaningful Question

Great conversations aren't about having all the answers,they're about asking the right questions.

Instead of: "Do you have multi-factor authentication?"
Try: "What would happen to your business if someone gained access to your core systems?"

Instead of: "You need to implement zero trust."
Try: "Help me understand how your team currently thinks about access control."

Instead of: "That's not compliant."
Try: "What's the business outcome you're trying to achieve here?"

The first set of questions positions you as an interrogator. The second set positions you as a collaborator.

Tabletop Exercises: Conversation as Learning

Some of my most impactful work has been running tabletop exercises,scenario-based discussions that help teams think through how they'd respond to various incidents.

I've run exercises on fraud and abuse scenarios for fintech companies, ledger inconsistency incidents for financial platforms, and supply chain compromises for SaaS providers.

The magic isn't in the scenarios themselves,it's in the conversations they generate. When people talk through "what if" situations together, they discover gaps in their thinking, alignment issues in their priorities, and opportunities for improvement that no consultant could have identified from the outside.

Mentoring: Conversations That Change Careers

I've been fortunate to mentor dozens of emerging security leaders over the years. In every case, the breakthrough moments came through conversation, not instruction.

There was the engineer who discovered they were passionate about risk communication after we talked about translating technical vulnerabilities into business language.

The compliance manager who realized they wanted to be a CISO after we explored how security strategy connects to business outcomes.

The startup founder who completely restructured their security approach after we discussed what "security" means to different stakeholders.

These weren't training sessions,they were dialogues about challenges, aspirations, and possibilities.

Investment Conversations: Due Diligence as Dialogue

Through my work with SVCI, I've learned that the best investment due diligence happens through conversation, not spreadsheets.

Yes, we need to understand the technical details,what frameworks they're using, how they handle data, what their incident response process looks like. But the real insights come from understanding how the founders think about security, how they balance risk and growth, and how they communicate with their team about these issues.

A 30-minute conversation with a CEO often tells me more about their security maturity than a 50-page assessment report.

The Ripple Effect

The beautiful thing about conversation-driven leadership is that it scales beyond what you might expect. When you help someone solve a problem through dialogue, they often take that approach to their own teams and relationships.

I've seen CISOs who learned to ask better questions become more effective at board communication. I've seen startup founders who experienced supportive security conversations create more collaborative relationships with their own security teams.

One meaningful conversation doesn't just solve one problem,it changes how people approach problems.

Making Space for Real Dialogue

In our world of back-to-back Zoom meetings and constant Slack notifications, creating space for meaningful conversation requires intentionality.

Some practices that have worked for me:

• Start with listening: Ask about their goals before talking about solutions
• Get specific: Move from general principles to concrete situations
• Stay curious: When someone says something unexpected, explore it rather than correcting it
• Share stories: Abstract concepts become real when illustrated with specific examples
• Follow up: Check back in a few weeks to see how things are going

The Technology Paradox

Here's the paradox: as our industry becomes more technical, more automated, and more AI-driven, human conversation becomes more valuable, not less.

Anyone can Google "NIST Cybersecurity Framework" or "SOC 2 requirements." What they can't Google is how to apply these frameworks to their specific situation, their specific constraints, their specific goals.

That wisdom emerges from conversation with someone who's been there before, who can ask the right questions and help them think through the implications.

An Invitation

If you're reading this and facing security challenges,whether as a CISO, a founder, an engineer, or anyone who cares about building secure systems,I want to extend an invitation.

Let's have a conversation.

Not a sales pitch, not a formal consulting engagement, not a networking event small talk. A real conversation about what you're trying to achieve and how security can help you get there.

Because in a world full of tools, platforms, and frameworks, sometimes the most powerful solution is still the simplest: two people talking through a problem together.

That's how we make the world a better place,one conversation at a time.

Ready to start a conversation? I'd love to hear what challenges you're working on.