Professor Simon's IT and Cybersecurity Podcast

Professor Simon
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Welcome to The Professor Simon IT & Cybersecurity Podcast, where we go beyond the textbook with real-world career advice, practical guidance, and lessons from the field. Whether you're breaking into IT or cybersecurity, building your skills, transitioning careers, or planning your next move, you'll gain practical insights to help you make better career decisions and understand what the work actually looks like. Topics include careers, certifications, IT fundamentals, SOC, GRC, leadership, AI, cloud security, and more. Cyber & IT Beyond the Textbook.

  1. 7h ago

    Before You Reimage That Laptop, What Should You Check?

    A laptop might be compromised, the user needs it back by tomorrow, and somebody on your team says, "Just reimage it." Reimaging may be the right fix, but it also erases the machine's current state, which may be the only record of what happened. In this episode of Professor Simon's IT & Cybersecurity Podcast, I walk through four questions to ask before you change the machine. I use one clearly made-up laptop and alert. I cover whether your organization has a process, who has the authority to decide, what you would lose by wiping the laptop, and what you can safely do within your own role. I also cover keeping a time-stamped note that separates what you saw from what you think happened, talking to the user without blame, handing the matter to the responsible team, telling a manager why the laptop is being held, and what to do under pressure to move fast, or when the laptop is just slow. This episode is for people in IT support, systems administration or early security roles. It does not teach forensic collection and makes no legal claims; follow your organization's process. ▶️ Companion YouTube Video: https://youtu.be/pvCj_6L8InA 📝 Companion Blog Post: https://professorsimon.com/blog/before-you-reimage-a-laptop-questions-to-ask 🎧 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

  2. 1d ago

    The Job Title Says Security Analyst. What Will You Actually Be Doing?

    The job title says security analyst, but you can't tell from the title whether you'd be watching alerts all day or doing something quite different. In this episode of Professor Simon's IT & Cybersecurity Podcast, I walk through four things to look for in any posting so you can read the work behind the title. I use two made-up postings that share a title and describe very different weeks, then a third, messier one. I cover the verbs, the technologies, the deliverables and the people in a posting, a test I like: finish the sentence, "On a normal Tuesday, I would...", why a posting is a clue and not a promise, how to turn missing information into interview questions, and how to describe your own IT work in honest, plain verbs. This episode is for people in IT, such as help desk, systems administration or networking, who are looking at security jobs and deciding which postings to apply for. No real employer is described, and I don't recommend any product. ▶️ Companion YouTube Video: https://youtu.be/hnYc-DbLWQQ 📝 Companion Blog Post: https://professorsimon.com/blog/how-to-read-a-security-analyst-job-posting 🎧 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

  3. 2d ago

    The App Team Says It's the Firewall. How Do You Find Out?

    A ticket says the firewall is blocking an application and asks you to open a port. Before you change anything, how do you find out whether the firewall is really the problem? In this episode of Professor Simon's IT & Cybersecurity Podcast, I walk through a practical order of checks for testing that theory. I use one made-up example: a new database server that an application cannot connect to. The server, the error message and the old address are invented for illustration. I cover why opening the port to see what happens is a poor test, what to ask the app team first, the five things that have to be true for one machine to reach another, how to check the service, the name and the port, and where to run the test from. I explain what connection refused and a timeout each tell you, what a failed ping does and does not prove, what to do if the port test still times out, and how to hand a firewall team evidence they can use. This episode is for help desk staff, sysadmins and early-career security people who get firewall change requests for systems they are responsible for, inside their own change process. If your team's process says something different, your team's process wins. I don't recommend any product. ▶️ Companion YouTube Video: https://youtu.be/QdKpCMKCXhI 📝 Companion Blog Post: https://professorsimon.com/blog/is-it-the-firewall-how-to-find-out 🎧 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

  4. 5d ago

    Vulnerability Scan Results: Where Do You Start?

    A vulnerability scan finishes overnight, the report is sorted by severity, and your manager asks, "Where should we start?" In this episode of Professor Simon's IT & Cybersecurity Podcast, I show a practical way to turn a long vulnerability scan report into a short, reasoned starting list. I use one made-up scan: 400 findings, 60 laptops missing the same update, and roughly 70 distinct issues once the duplicates are grouped. The scan, the systems and all of the numbers are invented for illustration. They are not real scan results. I cover how to check what a scan actually covered and which findings might not be real, how to group duplicate findings, why severity is only a starting point, how exposure, known exploitation, system importance and existing protections change the order, and a worked comparison of why a medium severity finding can come before a high severity one. I also cover how to hand system owners a short starting order with a reason for each item. Fixing the findings belongs to the people who own the systems, through whatever change process your organization uses. This episode is for IT professionals moving into security and early-career analysts who are handed scan results for systems they do not own. I don't recommend any product. ▶️ Companion YouTube Video: https://youtu.be/sPmU6OuTB2g 📝 Companion Blog Post: https://professorsimon.com/blog/vulnerability-scan-results-where-to-start 🎧 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

  5. 6d ago

    "But So What?" How to Turn a Finding Into a Risk Statement

    You found something real, wrote it up in one line, "No MFA on the VPN," and two weeks later someone asks, "Okay, but so what?" In this episode of Professor Simon's IT & Cybersecurity Podcast, I show how to turn a security finding into a risk statement, so the person reading it can make a decision. I use one made-up example, about 40 accounts in an older group that were never moved to a multi-factor authentication policy, and build the statement one part at a time, from the weak one-line version to a stronger one. The details and numbers are invented for illustration. I cover the difference between a finding and a risk statement, and the six parts of a useful one: the condition, the event it could allow, what is affected, what already reduces the risk, what you don't know, and the decision you are asking for. I also cover how to describe an existing control without overstating it and how to write for the system owner and for a busy manager. I also cover two mistakes to avoid, inflating everything and inventing numbers. If your team has a risk statement template, use it. I don't claim any framework requires this structure. This episode is for IT professionals moving into security or GRC and for early-career analysts who have been asked to write up an issue for someone else to decide on. I don't recommend any product. ▶️ Companion YouTube Video: https://youtu.be/lAHaqRikgmA 📝 Companion Blog Post: https://professorsimon.com/blog/how-to-write-a-risk-statement-from-a-finding 🎧 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

  6. Oct 28

    Is This Data Sensitive? What to Ask Before You Share It

    Someone asks you to set up a shared folder, and one of the spreadsheets has employee home addresses and personal phone numbers in it. Before you click share, how do you decide whether the data is sensitive, and whose call is it? In this episode of Professor Simon's IT & Cybersecurity Podcast, I walk through how to recognize the issue, find the right person to decide, and find a safer way to help. I use one made-up example, a colleague who wants a shared folder and a link anyone can open, to cover what to look at in the data, whose information it is, who gets to decide, what your own organization's rules may say, and how to share less. I also cover how to ask without making it awkward, what to do if the owner isn't answering, and what to write down afterward. I don't cover what any law or regulation requires; that is a question for your privacy or legal team. This episode is for IT professionals and early-career security practitioners who get routine data requests, and I don't recommend any product. Your own organization's process and the data owner's approval come first. ▶️ Companion YouTube Video: https://youtu.be/6gcLIJeJfxU 📝 Companion Blog Post: https://professorsimon.com/blog/is-this-data-sensitive-checks-before-sharing 🎧 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

  7. Oct 27

    Cybersecurity Interview Questions: How to Answer "Walk Me Through What You'd Do"

    An interviewer says an account signed in from one city and, twenty minutes later, from a city on the other side of the country, then asks you to walk them through what you'd do. In this episode of Professor Simon's IT & Cybersecurity Podcast, I explain how to answer a scenario question like that out loud, even if you have never worked that exact alert. I use one made-up question and two made-up answers. First, an honest answer that lists tools and still doesn't land, because it tells the interviewer where you'd go and nothing about what you'd look for or why. Then a stronger answer built step by step: repeat the situation back and ask a clarifying question, say what you'd look at first and why, rule out the boring explanations such as a VPN, say what would change your mind, say plainly what you don't know and how you'd find out, and finish with who you'd tell and what you'd say. I also cover how to connect your answer to real help desk or IT experience without stretching it, how to handle follow-up questions, what to do when your mind goes blank, and how to practice out loud before the interview. This episode is for IT professionals going for a first security analyst role and early-career analysts interviewing for the next one. I can't tell you how any company scores interviews, and they don't all do it the same way. The question and both answers are made up for illustration, and I don't recommend any tool or product. ▶️ Companion YouTube Video: https://youtu.be/C2g8PMJjUvs 📝 Companion Blog Post: https://professorsimon.com/blog/cybersecurity-interview-questions-scenario-answers 🎧 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

  8. Oct 26

    Your Backups Succeeded. Could You Actually Recover?

    Every morning the backup report says success. But if the file server died tonight, how long would it take before people had their files back? In this episode of Professor Simon's IT & Cybersecurity Podcast, I explain what a backup success message does and doesn't tell you, and how a small, approved restore test answers the question that security actually cares about: could we recover? I use one made-up example, a file server whose nightly job has reported success for months, to show what a restore test can reveal: a folder that was quietly excluded and a restore that takes far longer than anyone assumed (the numbers are invented). I cover why restoring files isn't the same as getting people working again, why attackers go after backups and why a separated copy matters, and how to propose a restore test and write down the result even when you don't own the backup system. This episode is for IT professionals moving into cybersecurity, especially people who already run or watch backup jobs. I don't recommend any product, and your own organization's process and the backup owner's approval come first. ▶️ Companion YouTube Video: https://youtu.be/32lIQ8V00ac 📝 Companion Blog Post: https://professorsimon.com/blog/backup-restore-test-could-you-actually-recover 🎧 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

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Welcome to The Professor Simon IT & Cybersecurity Podcast, where we go beyond the textbook with real-world career advice, practical guidance, and lessons from the field. Whether you're breaking into IT or cybersecurity, building your skills, transitioning careers, or planning your next move, you'll gain practical insights to help you make better career decisions and understand what the work actually looks like. Topics include careers, certifications, IT fundamentals, SOC, GRC, leadership, AI, cloud security, and more. Cyber & IT Beyond the Textbook.

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