As a founder, your calendar is packed. Investors, customers, product, hiring — security often slips to the bottom of the list. But here’s the truth: ignoring security is not saving time; it’s borrowing risk.
You don’t need to be a cybersecurity expert to stay on top of it. You just need to ask the right questions — consistently. Here are five questions every founder should ask their team every week.
1. What new assets went online this week?
- New domains, servers, or SaaS tools often appear faster than policies can catch them.
- Forgotten or unmonitored assets are one of the top ways attackers get in.
👉 Ask: “Do we know every new system that went live?”
2. Did we patch the most critical vulnerabilities?
- Software updates aren’t just features — they often close security holes.
- Attackers automate scanning for outdated versions within hours of release.
👉 Ask: “Are we fully patched where it matters most?”
3. Have any credentials leaked?
- Employee or customer logins sometimes appear in breaches without you knowing.
- One leaked password can open the door to your entire business.
👉 Ask: “Do we monitor for stolen credentials?”
4. Who has access they no longer need?
- Former employees, contractors, or role changes often leave “orphan” accounts behind.
- Every extra account is a risk waiting to be exploited.
👉 Ask: “Has anyone’s access been removed or reduced this week?”
5. Did we test our response readiness?
- Incidents aren’t “if” but “when.”
- A 30-minute simulation today can save days of chaos tomorrow.
👉 Ask: “If something happened right now, do we know who does what?”
Final thought
Security isn’t about building a fortress overnight. It’s about building habits. By asking these five questions weekly, you create rhythm, accountability, and visibility.
As a founder, you don’t have to solve every problem yourself.
But you do have to keep asking.
