In my years of consulting, across almost every client of every size and industry, some challenges remain frustratingly persistent. Despite significant investments in technology and talent, five core pain points continue to plague security leaders worldwide, creating vulnerabilities that adversaries are all too eager to exploit. Understanding these common struggles and the resources available to address them is crucial for any organization serious about maturing their cybersecurity program.

1. Identity and Access Management

Of course we begin here: Identity and Access Management (IAM) consistently ranks as one of the most challenging aspects of a robust cybersecurity program. The explosion of cloud services, remote work, and digital transformation has created an identity sprawl that many organizations struggle to control. Users accumulate access rights over time, former employees retain system access, and privileged accounts often lack proper oversight. To make matters even worse, there are poorly designed implementations of RBAC, ABAC, and MFA that may create havoc for legacy systems.

The core challenge lies in balancing security with usability. Organizations need seamless access for legitimate users while preventing unauthorized access attempts. This becomes exponentially complex in hybrid environments where identities must work across on-premises systems, multiple cloud platforms, and third-party applications.

NIST recognizes that "Identity and Access Management is a fundamental and critical cybersecurity" function, offering comprehensive guidance through their Digital Identity Guidelines (SP 800-63-4). The NIST framework emphasizes risk-based authentication, where access controls align with the sensitivity of resources being protected.

Modern IAM implementations require organizations to move beyond traditional perimeter-based security models toward zero-trust architectures, where every access request is verified regardless of source location or previous authentication status.

2. Asset Inventory

Perhaps the most fundamental cybersecurity challenge is maintaining accurate visibility into organizational assets. Recent studies show that the "identify" function continues to have the lowest coverage in cybersecurity implementations, highlighting a persistent gap in asset management practices and yet one dollar spent in identifying assets can save you hundreds of dollars in response & recovery.

The challenge extends beyond simply cataloging hardware and software. Modern asset inventory must account for cloud resources, mobile devices, OT/IoT systems, data flows, and business processes. Unauthorized technology deployments (aka Shadow IT) further complicate visibility efforts, as security teams discover assets they never knew existed which usually will happen during an incident.

Effective asset management requires real-time discovery capabilities, automated inventory updates, and integration with configuration management processes. Organizations struggle with asset lifecycle management, often losing track of systems during provisioning, changes, or decommissioning phases.

NIST Special Publication 1800-5 provides detailed guidance on IT Asset Management, offering practical approaches for implementing comprehensive asset discovery and management programs. The publication emphasizes the importance of automated tools and integration with existing IT service management processes.

3. Data Governance

Data governance represents one of the most complex cybersecurity challenges facing modern organizations. The sheer volume of data creation, combined with diverse storage locations and varying regulatory requirements, creates a perfect storm of complexity.

Organizations struggle with data classification, often lacking clear policies for identifying sensitive information and applying appropriate protection measures. Data sprawl across cloud services, employee devices, and third-party systems makes comprehensive governance nearly impossible without automated tools and processes.

The challenge intensifies with regulatory compliance requirements. Different jurisdictions impose varying data protection standards, creating complex compliance matrices for multinational organizations. Privacy regulations like GDPR, CCPA, and other emerging legislation require organizations to understand not just what data they have, but how it's collected, processed, stored, and shared.

Data governance requires cross-functional collaboration between legal, compliance, IT, and business teams. Many organizations lack the organizational structures and processes necessary to implement effective data governance programs that align with business objectives while meeting regulatory requirements.

4. Cloud Security

Cloud adoption continues accelerating, but security considerations often lag behind deployment speed. Organizations struggle with the shared responsibility model, unclear about which security aspects they control versus those managed by cloud providers.

The complexity multiplies in multi-cloud environments where organizations use services from multiple providers, each with different security models, management interfaces, and compliance capabilities. Configuration management becomes challenging when infrastructure changes constantly through automated provisioning and scaling.

Cloud security requires fundamentally different approaches than traditional on-premises security. Organizations must adapt security processes for ephemeral infrastructure, API-driven management, and service-oriented architectures. Many organizations struggle with visibility and control in cloud environments, lacking tools and processes designed for dynamic, distributed systems.

Identity and access management becomes particularly challenging in cloud environments, where federated authentication, attribute or role-based access controls, and cross-service permissions create complex security matrices. Organizations often discover they have more cloud resources and services than they realized, creating shadow IT challenges in cloud environments.

5. Third-Party Risk Management

Modern organizations operate in interconnected ecosystems where third-party relationships create extended attack surfaces. Third-party risk continues to be a major weak point for organizations across industries, as supply chain attacks have become increasingly sophisticated.

The challenge lies in assessing and monitoring the security posture of vendors, partners, and service providers without direct control over their environments. Organizations must balance due diligence requirements with business relationship management, often lacking visibility into their vendors' cybersecurity practices.

Third-party risk extends beyond direct relationships to include fourth-party risks creating complex risk cascades that are difficult to assess, understand, and manage. Organizations struggle with standardizing risk assessment processes, monitoring ongoing vendor compliance, and responding to incidents involving third parties.

Contractual security requirements often lack enforcement mechanisms or regular review processes. Many organizations discover they have limited leverage over critical vendors, creating situations containing business dependencies that conflict with their security requirements.

Finding Solutions

Addressing these persistent pain points requires structured approaches and professional guidance either from respected cybersecurity bodies or from highly skilled consultants.

Organizations like SANS, ISACA, and NIST provide many resources, guides, and frameworks to assist CISOs on addressing these concerns. From my experience, these pain points are usually discovered during an incident thus preventing the CISO and security team the ability to learn, socialize, and implement the guidance effectively.

On the other hand, hiring skilled consultants with a proven track record of designing and implementing effective programs to address these pain points can prove well worth the expense.

These five pain points represent persistent challenges rather than unsolvable problems. Organizations that acknowledge these challenges and invest in systematic approaches by leveraging professional resources and proven frameworks, position themselves for long-term success. The key lies in recognizing that these challenges require ongoing attention and continuous improvement rather than one-time solutions.

Success comes from building organizational capabilities that align with business, not just deploying technology.