A strong cyber security posture begins with a thorough analysis of the basics: policies, procedures, and standards.
Has your organization defined and implemented the following policies?

Cyber Security Posture - Policies

Has your organization defined and implemented the following plans and/or procedures?

Cyber Security Posture - Plans and Procedures

Plan Testing

Assets are the backbone of any organization. Assets can be both physical and non-physical. Example Assets: Employees and their personal information Intellectual Property Documentation Computer and Network Hardware Where data is located Credentials
Do you manage your assets and ensure that they are handled appropriately?

Asset Management

Knowledge is power. Security knowledge is your advantage over the attackers.  Do you require your employees to take regular security awareness training?

Security Awareness

A small bug can turn into a serious security issue. A vulnerability assessment is designed to identify bugs and misconfigurations located in applications, systems and network devices in your corporate environment. 
Have you ever had a vulnerability assessment performed on your corporate environment?

Vulnerability Assessment

Many companies have significant issues in implementing fixes to discovered vulnerabilities in a timely manner.
How long does it usually take to get high and critical vulnerabilities resolved?

Vulnerability Management

A Penetration Test is designed to leverage the findings of a vulnerability assessment to see if an attacker could compromise your network and/or system. It is the closest thing to what an attacker would attempt to get into your environment(s).
 
Have you conducted a Penetration Test on your corporate environment? 

Penetration Testing

Do you regularly monitor and assess the risks associated with third parties and your supply chain, including Cloud Service providers?

Third Party Risk Management

What forms of monitoring do you have in place to detect an incident?