Professor Simon's IT and Cybersecurity Podcast

You can pull a lot of numbers out of your security tools, and the safe move feels like putting all of them in the report for leadership. A full page of charts looks thorough, but a dashboard is not a decision.
In this episode of Professor Simon's IT & Cybersecurity Podcast, I give you one question to ask about every number: what decision or action could this number change?
I use a made-up vulnerability reporting example, with no real organization behind it, to show the difference between an activity metric and a number leadership can act on. Then I cover what a number needs around it (a reference point, a trend and a stated limitation), how to present your numbers to the person reading the report, and what to do with numbers that fail the test.
I also share a simple exercise you can use on your last security report.
More free resources: https://professorsimon.com/links
▶️ Companion YouTube Video: ⁠https://youtu.be/bFcRlIiOpQc
📝 Companion Blog Post: ⁠https://professorsimon.com/blog/security-metrics-for-leadership-reports
🎧 More Podcast Episodes: ⁠⁠⁠⁠https://professorsimon.com/podcast⁠⁠⁠⁠
👉 Need help with your IT or cybersecurity career? Work with me: ⁠⁠⁠⁠https://professorsimon.com/guidance⁠⁠⁠⁠
🎯 Cybersecurity Interview Prep Pack: https://professorsimon.com/products/cybersecurity-interview-prep-pack
🔗 Resources, blog & more: ⁠⁠⁠⁠https://professorsimon.com/links⁠⁠⁠⁠
🌐 Website: ⁠⁠⁠⁠https://professorsimon.com⁠⁠⁠⁠
💼 LinkedIn: ⁠⁠⁠⁠https://www.linkedin.com/in/leonardsimon⁠⁠⁠⁠
📸 Instagram • X • TikTok: @profsimononline

Every patch carries two risks. Leave a known vulnerability unpatched, and the exposure remains. Apply a patch without proper planning, and something the business depends on could stop working.
In this episode of Professor Simon's IT & Cybersecurity Podcast, I explore how security managers balance those risks using PatchSecure Inc., a fictional teaching scenario from my book.
We'll look at what it means for a patching program to fail safely, why realistic testing matters, and how patch management connects to change management, monitoring, access controls, incident response planning and training.
I'll also share three practical questions you can use to evaluate your own patching program.
This episode is independent educational content based on my own teaching. It is not official ISC2 material, and ISC2 is not affiliated with it.

More free resources: https://professorsimon.com/links

▶️ Companion YouTube Video: https://youtu.be/L0BcUibSJ1U
📝 Companion Blog Post: https://professorsimon.com/blog/patch-management-program-security-risk-vs-stability
🎧 More Podcast Episodes: ⁠⁠⁠https://professorsimon.com/podcast⁠⁠⁠
👉 Need help with your IT or cybersecurity career? Work with me: ⁠⁠⁠https://professorsimon.com/guidance⁠⁠⁠
🎯 Cybersecurity Interview Prep Pack: ⁠https://professorsimon.com/products/cybersecurity-interview-prep-pack⁠
🔗 Resources, blog & more: ⁠⁠⁠https://professorsimon.com/links⁠⁠⁠
🌐 Website: ⁠⁠⁠https://professorsimon.com⁠⁠⁠
💼 LinkedIn: ⁠⁠⁠https://www.linkedin.com/in/leonardsimon⁠⁠⁠
📸 Instagram • X • TikTok: @profsimononline

If you found this episode helpful, please follow the podcast, leave a rating or review, and share it with someone who would benefit.

If you work in IT and want to move into cybersecurity, you have probably heard three confident answers: get the degree, get a certification, or just get experience. In this episode, Professor Simon explains why those answers contradict each other and gives you a better question to ask first: which gap are you actually trying to close? He walks through six common gaps between where you are and a specific security role, shows how a degree, a certification and experience may each help with different ones, and applies them to three made-up IT professionals. You will also get three questions to ask before you spend time or money, and a practical way to start by comparing real job postings.

▶️ Companion YouTube Video: https://youtu.be/s_w8r_Fd5Cs
📝 Companion Blog Post: https://professorsimon.com/blog/cybersecurity-degree-or-certification
🎧 More Podcast Episodes: ⁠⁠https://professorsimon.com/podcast⁠⁠
👉 Need help with your IT or cybersecurity career? Work with me: ⁠⁠⁠⁠https://professorsimon.com/guidance⁠⁠⁠⁠
🎯 Cybersecurity Interview Prep Pack: ⁠⁠https://professorsimon.com/products/cybersecurity-interview-prep-pack⁠⁠
🔗 Resources, blog & more: ⁠⁠https://professorsimon.com/links⁠⁠
🌐 Website: ⁠⁠https://professorsimon.com⁠⁠
💼 LinkedIn: ⁠⁠https://www.linkedin.com/in/leonardsimon⁠⁠
📸 Instagram • X • TikTok: @profsimononline

If you found this episode helpful, please follow the podcast, leave a rating or review, and share it with someone who would benefit.

If you have been handed a list of systems to patch without seeing the decisions behind it, this episode is for you. Professor Simon explains what a patch management program has to understand before the first patch is deployed: the inventory, risk, business and regulatory requirements, policy, tools and testing, using a fictional teaching scenario, PatchSecure, Inc. He also shares two questions to ask about any patching program. More free resources: https://professorsimon.com/links

▶️ Companion YouTube Video: https://youtu.be/GFR2sHZXrH8
📝 Companion Blog Post: https://professorsimon.com/blog/patch-management-before-you-patch
🎧 More Podcast Episodes: ⁠https://professorsimon.com/podcast⁠
👉 Need help with your IT or cybersecurity career? Work with me: ⁠https://professorsimon.com/guidance⁠
🔗 Resources, blog & more: ⁠https://professorsimon.com/links⁠
🌐 Website: ⁠https://professorsimon.com⁠
💼 LinkedIn: ⁠https://www.linkedin.com/in/leonardsimon⁠
📸 Instagram • X • TikTok: @profsimononline

If you found this episode helpful, please follow the podcast, leave a rating or review, and share it with someone who would benefit.

Sooner or later, someone who is thinking about hiring you is going to say, "Okay, I believe you know cybersecurity. Show me what you can do." A lot of capable people have a certification, a course certificate or a home lab, but nothing that lets the other person see how they work. In this episode, Professor Simon explains what actually counts as evidence of cybersecurity skill: a piece of work that shows your reasoning, so another person can evaluate it.
He compares naming a tool with documenting your work in a hypothetical example, covers five things a piece of work should show, and explains how work you already do in IT can count, what to leave out before you share it and where to share it. He also covers how to write it up for technical and non-technical readers and how to practice explaining it out loud. It is for people trying to move into cybersecurity or already working in IT. He is also clear that evidence does not guarantee an interview or an offer.
In this episode you'll learn:
- Why certifications matter, but knowing something and being able to do it are different
- The progression from knowledge to application to evidence to explanation
- Five things a piece of work should show: the problem, what you looked at, what you found, your decision and why, and what you would do differently
- How work you already do in IT can count, and what to remove before you share it
- Other forms of evidence beyond a home lab, and where to share them so a stranger can open them
- How to write for technical and non-technical readers and practice explaining your work

▶️ Companion YouTube Video: https://youtu.be/SJLnl_1tzhk
📝 Companion Blog Post: https://professorsimon.com/blog/evidence-of-cybersecurity-skill
🎧 More Podcast Episodes: https://professorsimon.com/podcast
👉 Need help with your IT or cybersecurity career? Work with me: ⁠⁠⁠⁠https://professorsimon.com/guidance⁠⁠⁠⁠
🎯 Cybersecurity Interview Prep Pack: ⁠⁠https://professorsimon.com/products/cybersecurity-interview-prep-pack⁠⁠
🔗 Resources, blog & more: https://professorsimon.com/links
🌐 Website: https://professorsimon.com
💼 LinkedIn: https://www.linkedin.com/in/leonardsimon
📸 Instagram • X • TikTok: @profsimononline

If you found this episode helpful, please follow the podcast, leave a rating or review, and share it with someone who would benefit.