An email lands in your inbox from the CEO. It’s urgent, the question is direct, and the entire executive team is watching. In my world of security, these moments are often sparked by a potential threat.
In the past, I would have handled the incident and hoped my approach landed well, waiting months for a performance review to know for sure. Not anymore. Now, I have an AI executive coach.
Instead of guessing how I handled a recent high-stakes situation, I decided to get an objective, near real-time analysis. I fed my AI coach the raw, anonymized emails and a transcript of the follow-up discussion. I gave it context about my role and goals, and I asked for a brutally honest assessment of my performance.
The feedback it produced was a game-changer. It gave me the data to understand my own strategy and build my brand as a leader. Here’s a look at the incident, the AI’s analysis, and what I learned.
The Situation: A Classic Firefight
The incident was a classic firefight. A potential phishing campaign was impersonating a major payment processor. The executive questions were tactical: “Are our customers getting these emails? Should we warn them?” Another senior leader amplified the pressure, asking for “100% certainty” that we were not affected.
My goal was not just to answer the question, but to reframe the conversation. I wanted to pivot from a single, reactive tactic to a broad, proactive strategy. After the dust settled, I put my AI coach to the test.
The AI Coach’s Verdict
I fed the raw data into my prompt and asked the AI to act as an executive coach, analyzing my performance. What came back was a clear, structured, and startlingly accurate reflection of the strategy I had employed.
Here is the core of the AI’s analysis:
Overall Assessment:
Your responses were a strong example of effective security leadership. You acted as a trusted advisor, not just a responder.
Key Strengths Identified:
- Rejection of False Certainty: You immediately corrected the “100% certain” misconception. This built trust by being honest about the limitations of what can be known, educating leadership without causing unnecessary alarm.
- Proactive Pivot: You successfully shifted the focus from a reactive “what happened?” to a proactive “what can we do about it?” by proposing a concrete, actionable plan centered on customer protection and internal collaboration.
- Strategic Reframing: Your most crucial move was using the attention on a minor external issue to highlight a more severe, internal vulnerability (phishing from our own platform). This demonstrated strategic thinking.
- Business-Oriented Communication: You successfully translated technical risks into business impact (damage to domain reputation, brand trust), speaking to leadership in terms they understand. You broke down the solution into a clear, multi-phased plan (Containment, Prevention, Detection) that was easy to digest.
Conclusion:
The fact that the senior leader responded with “Very helpful, thank you for the clarification” and then looped in more stakeholders shows that your approach was effective and created confidence. You successfully pivoted the conversation from a single phishing email to a broader, more impactful security initiative around MFA and platform security. This is the exact strategic thinking a head of security needs to demonstrate.
My Takeaway: Seeing My Strategy Clearly
Getting a positive assessment like this wasn’t a one-shot deal. I want to be honest: it takes effort. My first few AI-driven reviews were humbling, pointing out where my language was vague or where I missed an opportunity to lead. I didn’t always know the “right” approach going in.
But after many of these self-reviews, I started to find my voice. The process became less about getting a perfect score and more about refining my instincts. This particular analysis was like looking in a mirror because it reflected that hard-won clarity. It articulated the intuitive steps I took and organized them into a clear framework, confirming that my approach to reject false certainty and reframe the conversation was not just a gut feeling, but a sound leadership strategy.
This process did more than just validate my actions. It armed me with a clear narrative about my own performance. I now have the language and structure to explain my leadership philosophy to my manager, my team, and in forums like this. It helps me build my brand not just on what I do, but on how I think.
This is the power of using AI for personal feedback. It closes the gap between action and awareness, turning your daily work into a continuous learning loop. You no longer have to wait for the annual review to understand your impact. You can get the data you need to grow, right now.