Bridging People and Possibility: Leadership Lessons in an AI Era

How We Met

I had the pleasure of working with Kyle in the same organization at Cisco, where I saw firsthand his rare ability to lead governance operations with both accountability and humor. Our partnership was grounded in mutual trust, a shared commitment to finding smarter ways of working, and yes—plenty of humor to keep things moving forward.

Kyle Strickland, PMP, CSM

Q & A

On Supportive Spaces

Q: Kyle, can you share a pivotal moment when someone created space for you during a professional transition or period of uncertainty—and how that experience shaped your career path?

A: At Cisco, I had the good fortune to work under Cindra Ford, who was then the Director of Strategy, Planning, and Operations for Global Partner Programs. During a particularly challenging stretch in my career, she truly created space for me—offering trust, support, and room to grow when I needed it most.

The project I was placed on wasn’t a perfect match for my skill set—not initially. The scope was fuzzy, and let’s be honest, governance isn’t exactly known for being “fun.” But Cindra trusted me to shape the role as I went. That trust made all the difference—it gave me the space and confidence to grow into the work and make it my own.

“Trust made all the difference—it gave me space to grow and make the work my own.”

I quickly realized that if I wanted to engage others in governance work, I’d need to bring personality to the process. So, I used humor. Lightening the mood helped shift people from resistance to participation. But I also knew when humor needed to take a backseat to strategy—especially when I began working across audits, management plans, and governance steering committees.

Cindra’s phrase—“It’s not an obstacle, it’s an opportunity”—still grounds me. Her leadership created the space I needed to step into accountability—not just for myself, but for cross-functional stakeholders. It’s a philosophy I now model for others.

On Reciprocating Safety

Q: How do you now create psychological safety for colleagues adapting to AI?

A: I lead with influence and empathy—values I learned from leaders like Cindra. I try to model what the best leaders did for me: help people feel capable, even in the midst of uncertainty.

My approach is simple: “Strong people lift up others.” I often open calls with that phrase as a reminder that we’re in this together. Especially in the world of AI, where many feel unsure, the goal is to empower—not overwhelm. We’re all experimenting.

“Psychological safety looks like learning out loud—together.”

Psychological safety looks like creating shared space to learn, make mistakes, and ask, “How are you using this?” Because no two people use AI the same way, learning together becomes the most valuable tool we have.

On Meaningful AI Experience

Q: What has surprised you most about using AI tools?

A: At Palo Alto Networks, I had the opportunity to collect internal use cases for AI. I expected to see the usual—email writing, KPI summarizing, report automation. What surprised me were the people using AI to learn beyond their roles.

“Curiosity, not obligation, drove people to stretch—and then teach.”

Support and sales professionals were using AI to deepen technical skills—not because they had to, but because they wanted to. Even more impressive, they started hosting internal webinars to teach others. That peer-led learning was a powerful reminder: when people feel curious and supported, they raise the bar for everyone.

On Collaboration and AI

Q: What human dynamics stood out to you in AI adoption?

A: People crave direction—and with AI, there’s no clear playbook. That’s both the obstacle and the opportunity.

Collaboration becomes the bridge. Whether through webinars or informal share-outs, people gain confidence when they learn together.

The collective process gives us structure. It’s less about “mastering AI” and more about staying curious and connected as we explore it.

On Self-Discovery through AI

Q: What skill did AI help you rediscover?

A: Precision. I tend to be a bit of an over-sharer (as you’ve probably noticed). But working with AI sharpened my focus. It’s helped me be more concise, especially when translating ideas quickly.

I also completed the PMI’s “Generative AI for Project Managers” course, which opened my eyes to the bigger picture. There’s still so much to learn—but I’m excited for what’s ahead.

On the Year Ahead

Q: Kyle, how do you plan to apply your AI skills meaningfully?

A: For me, the throughline is people. Whether I’m forecasting budgets or managing strategic plans, I want AI to give me more time to focus on collaboration—not less.

It’s about helping others use the tools available to them. When teams have the same foundational capabilities—but different specialties—that’s a force multiplier.

“Twelve months from now, I want AI so integrated into our workflows we hardly notice it—just better outcomes.”

I want to use AI to enhance decision-making and reduce friction so people can do their best work. As the saying goes: “AI won’t replace you—but someone using it effectively might.”

On Resistance and Adaptation

Q: What was your biggest resistance point with AI, and how did you work through it?

A: One of the biggest hurdles—especially in B2B settings—is a reluctance to trust AI-generated outputs. Some customers don’t want executive summaries or reports touched by AI. And I get it.

“It’s not about giving up control—it’s about efficiency without compromising integrity.”

Trust and transparency are key. I worked through this by understanding the “why” behind the hesitation and reinforcing that human review is still a core part of the process. It’s not about giving up control—it’s about creating efficiencies without compromising integrity.

On Unexpected Outcomes

Q: What’s the most unexpected positive outcome from your AI exploration?

A: Hands down: increased collaboration. At Palo Alto Networks, I was blown away by internal AI submissions. People weren’t just using tools—they were sharing breakthroughs, building resources, and teaching others.

“What surprised me most? The generosity—people building, sharing, and teaching each other.”

It became less about the technology and more about community. That spirit of generosity and experimentation was something I didn’t expect—but deeply value.

On Human-AI Partnerships

Q: Where do you see the most valuable intersection between human and AI skills?

A: Coaching, training, and mentoring—those will always be human strengths.

“In project management, nuance is everything—and that’s still human work.”

I’ve learned so much from project managers and change leaders who shaped how I present ideas, structure slides, and guide teams through ambiguity. AI can assist with templates and suggestions, but human experience brings nuance. And in project management, nuance is everything.

On Ethical Considerations

Q: What ethical concerns stand out most to you in using AI?

A: Having worked in governance at Cisco, accountability is always top of mind. AI can suggest—but if you’re using it, you’re responsible for the outcome.

That means understanding how a recommendation was generated. “AI told me so” isn’t an excuse. Ethical use includes explaining your process and ensuring decisions are grounded in human judgment.

“AI can suggest—but you’re still accountable. ‘It told me so’ doesn’t fly.”

We also need to stay vigilant about privacy, surveillance, and bias—AI systems can inherit and amplify harmful assumptions. At both Cisco and Palo Alto Networks, part of my role was to hold teams accountable. That doesn't change just because a machine is involved.

On Identity Shifts

Q: Has AI changed how you see your professional identity?

A: Yes and no. I work in an environment where AI is encouraged—but not fully integrated. Tools are evolving, especially for project management.

But the conversation has changed. I think more strategically now about how AI supports—not replaces—the human elements of my work. It’s not just about outputs; it’s about outcomes and relationships.

On Career Navigation

Q: What advice would you give someone exploring AI and career impact?

A: Ask questions. I’ve built a reputation for being curious but focused.

Start with the areas that excite you and align your AI learning with that purpose. It’s easy to get distracted by shiny tools—stay grounded in what matters to you. And be kind to yourself. It’s a learning curve, not a competition.

“Stay grounded in what excites you—and be kind to yourself. It’s a learning curve, not a race.”

On the Learning Journey

Q: What learning approach helped you develop AI literacy?

A: Honestly? Just starting. The best part is, AI can help you learn AI.

That recursive loop helped me break through the intimidation factor. I’ve also learned to mix it up: courses, conversations, trial and error. No one learns the same way—so stay curious and flexible.

On Unexpected Mentors

Q: Who’s been an unexpected guide during this AI transition?

A: Following AI creators, prompt engineers, different AI models, and everyday users has been surprisingly educational.

Social media is not traditional mentorship—but it’s a window into how people are using these tools creatively. And that creativity is contagious.

On Personal Boundaries

Q: Where do you draw the line with AI use?

A: Anything personal—absolutely not. I won’t feed it my Social Security number, driver's license, or birthday. We’re not there yet on data protection.

“AI is an assistant, not a vault. Some decisions—and all personal data—stay human.”

Professionally, I also won’t allow AI—or people using AI—to make decisions within governance or compliance frameworks. Those interpretations require human oversight.

On Connecting Roles: Cisco → Palo Alto Networks

Q: Kyle, how did your Cisco experience prepare you for your current role?

A: My time in Cisco’s Global Partner org was foundational. I learned how to lead with diplomacy and empathy—skills I now apply in my Chief of Staff and Program Manager role at Palo Alto Networks.

“Governance taught me how to influence without authority—those lessons show up in every project I lead.”

Governance may not sound glamorous, but it taught me how to influence without authority and drive accountability across teams. Those lessons show up in every project I lead today.

On Career Resilience and Education

Q: How did you leverage a layoff into new opportunities?

A: After transitioning from governance into compliance, I was laid off from Cisco. It was tough—but it also gave me the time and space to invest in myself.

I’d always wanted to earn my PMP, but global meetings made it difficult. After the layoff, I earned both my PMP and Certified Scrum Master credentials. That investment was key to landing my role at Palo Alto Networks.

“The layoff gave me space to invest in myself—and write the next chapter on my own terms.”

The leadership I experienced at Cisco gave me the foundation. The next chapter? That was mine to write.

You can connect with Kyle on LinkedIn.