15 Cybersecurity Questions Every Leader Should Ask

As a business leader, you’re used to taking charge, making decisions and guiding actions. Asking the right cybersecurity questions is hard when the issues are so complex, technical and ever changing. Don’t let that stop you from taking steps to protect your business. The right IT managed service provider (MSP) can take a lot of that anxiety off your plate. 

Whether you are using an MSP or an in-house team, here are 15 cybersecurity questions you can ask to make sure you are getting the coverage you need.


  • Do you have the latest firewalls, operating systems, malware? 
  • Are your remote workers using a VPN? 
  • Are the computers and mobile devices your employees use owned and serviced by your company?
  • Are FTP servers closed unless needed?
  • Are end users blocked from local admin rights?
  • Do you run penetration support tests to find weaknesses to shore up?
  • Do you have guest wireless access to keep your main access protected?


  • Are you using multi-factor authentication (MFA)?
  • Are you requiring strong passwords that are changed every 30-90 days? 
  • Do you have a password bank for storage (or at the very least an encrypted file)? 
  • Are you training staff about phishing and how to avoid falling for scams?
  • Are you encouraging a culture of “Ask before you click or buy” so your team doesn’t feel pressured into immediate action?


  • How are you staying up to date about the latest cybersecurity technology?
  • Are you monitoring whether your passwords or personal data appear on the dark web
  • Are you running phishing tests to train/educate staff? If so, what tests were done, how many people fell for it and were they trained how to avoid getting caught?

Remember, security is a balance. (You can have a network that’s too secure and nobody uses it).  Better security will require you to step outside your comfort zone and learn some new tools. I promise, it will be far less painful than dealing with the aftermath of a breach. 

If you missed it, check out Part 1 of our Cybersecurity Guide for Business Leaders. Don’t forget, you can contact us or book an appointment anytime you need some help.

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