From FBI Agent to Tech Leader: Lessons in Leadership with Michael “FD” Anaya

The GTM Kickback! #37 – Michael FD Anaya

Released: September 5, 2021

What does it take to go from kicking down doors with the FBI to leading high-performing teams at Palo Alto Networks? On this episode of The GTM Kickback!, I sat down with Michael “FD” Anaya, Head of Attack Surface Analysis at Palo Alto Networks, to explore one of the most unconventional leadership journeys in tech.

Michael spent nearly 14 years as a Special Agent at the FBI before entering the private sector, first at startups and later at Palo Alto after its acquisition of Expanse. Along the way, he developed a unique philosophy on leadership—one rooted in trust, empowerment, and empathy.

Rethinking Leadership: From Reluctant Manager to Transformational Leader

When Michael first joined the FBI, leadership roles weren’t something agents aspired to. Supervisory positions were often viewed as administrative and detached from the action.

That changed when he was selected for the FBI’s Leadership Development Program. There, he was introduced to transformational leadership, a framework centered on:

• Integrity and fairness

• Setting clear goals and expectations

• Inspiring people beyond self-interest

• Encouraging growth and creativity

• Practicing empathy as a daily discipline

  
  

This shift transformed Michael’s outlook: he no longer wanted to simply manage—he wanted to lead.

Transitioning to Tech: Unlocking Team Potential

Michael’s first private sector experience was with a small startup that never scaled. But his second stop—Expanse, later acquired by Palo Alto Networks—gave him the chance to prove his leadership philosophy.

When he inherited his team, they had a history of missing targets. Within one quarter, the group exceeded expectations. The difference? Empowerment.

Instead of micromanaging, Michael gave his team the freedom to act, encouraged initiative, and built the processes to support autonomy. The results were immediate and lasting.

As he put it:

“You can’t scale by micromanagement. You scale by empowerment.”

The Hard Truth About Leadership

Michael doesn’t sugarcoat it: not everyone can be a great leader. Just like not everyone can be LeBron James, leadership requires a certain predisposition—trust, empathy, and the ability to inspire others.

That doesn’t mean people can’t improve. Anyone can become a better leader. But reaching the very top tier requires more than book knowledge—it takes innate qualities and the discipline to cultivate them.

Hiring and Building Teams: Why Autonomy Matters

One of the most striking parts of our conversation was Michael’s hiring approach. He deliberately seeks out people who want autonomy, because his leadership style thrives on empowerment.

To find those people, he uses unconventional interview techniques—questions designed to break through the “interview veneer” and reveal how candidates think. For example, asking whether someone would prefer Spam Casserole Surprise or takeout isn’t about the food—it’s about how they evaluate choices and explain their reasoning.

It’s this mix of curiosity, rapport-building, and people-reading (a skill honed in the FBI) that helps him build teams aligned with his leadership philosophy.

The Role of Empathy in Leading People

If there’s one takeaway Michael wants leaders to embrace, it’s empathy.

Empathy doesn’t mean agreeing with someone—it means understanding them. By striving to see things from another’s perspective, leaders can communicate better, adapt their approach, and create stronger trust across the team.

As Michael put it:

“The purpose is to strive to understand. That’s what I would recommend people to do.”

Final Takeaway

Michael “FD” Anaya’s story shows that leadership isn’t about titles or processes—it’s about people. From FBI squads to Palo Alto Networks, his journey proves that when you empower teams, hire for autonomy, and lead with empathy, you unlock potential that others overlook.

In today’s world of fast-scaling GTM teams and ever-changing tech, those lessons couldn’t be more relevant.