The Hidden Challenges of Proving Compliance (and How to Overcome Them)

For many, compliance feels like it should be a box-checking exercise. Hire the right partner, implement best practices, and you are done. The reality is far more complicated. 

The real challenge is proving you’re doing the work. Auditors, insurers, and regulators do not accept good intentions. They demand evidence. 

“The auditors aren’t just going to take your word that you’re doing something. They want to see evidence of it. So, collecting that evidence will be the biggest challenge,” explained Edward Griffin, Chief Information Security Officer at Intelligent Technical Solutions (ITS). 

Understanding these challenges is the first step to overcoming them. In this article, we will uncover the hidden pitfalls behind proving compliance and show you practical ways to overcome them, so your business can operate with confidence and build stronger trust with clients. 

Why Proving Compliance Matters 

Most businesses assume compliance is about protecting data or avoiding penalties. While that is true, proving compliance delivers broader benefits: 

• Reduces liability after a breach. Demonstrating that you followed best practices during a breach has the potential to lower penalties. 
• Secures cyber insurance coverage. Insurers increasingly demand documented proof of risk management before approving or renewing policies. 
• Builds client trust. Attestations reassure clients that you are not cutting corners. 
• Opens doors to enterprise deals. Large clients often require their vendors to show formal evidence of compliance. 

The ability to prove compliance has become a competitive advantage. Yet it is also one of the most difficult hurdles to clear. 

The Top Challenges in Proving Compliance 

Here are some of the reasons why proving compliance is easier said than done: 

1. Evidence Collection

Collecting evidence is often the hardest part. Policies and processes are not enough. Auditors want logs, screenshots, and records that show controls are in place and working. 

Griffin noted this was one of the main challenges at the beginning of ITS’s own compliance journey: “We were doing a lot of the right things. We just weren’t doing it in a manner that generates trackable evidence of it.” 

This is where many businesses stumble. They are secure, but they cannot prove it. 

2. Change Management

Change management adds complexity. Every significant change must be documented, reviewed, and approved. 

“Every change above a certain risk level has to be reviewed, approved, and scheduled. That adds a whole layer of administrative overhead that is difficult for many organizations to adopt and scale,” Griffin said.  

Change Management can feel overwhelming. Without the right systems, it slows down operations and frustrates teams. 

3.  Framework Overload

There are dozens of compliance frameworks, each with different requirements. SOC 2, HIPAA, PCI DSS, ISO 27001, NIST, and others often overlap but rarely align perfectly. 

Trying to chase them all is costly and confusing. The smarter approach is to identify the frameworks that matter most to your business model and risk profile.  

As Griffin put it, “You should apply the controls that make the most sense for you as a business according to your risk tolerance, and that are also optimal for you to provide good service to your customers.” 

4. Time and Resource Strain

Compliance is not a one-time event. It requires ongoing monitoring, audits, and reporting. Smaller businesses often underestimate the amount of staff time and budget it consumes. Without proper planning, compliance becomes reactive, rushed, and costly. 

5. Misaligned Priorities

Executives sometimes view compliance as a cost rather than an investment. As a result, it gets pushed aside until a contract, client, or regulator forces the issue. 

But waiting too long raises costs and risks. The businesses that succeed treat compliance as part of their growth strategy, not as an afterthought. 

4 Strategies to Overcome Compliance Challenges 

So how do you address these hidden challenges? Here are four strategies to make compliance both achievable and sustainable.  

1. Automate Evidence Collection

Use compliance tools that automatically generate logs, screenshots, and reports. This reduces human error and ensures you always have proof ready for auditors. 

Automation also cuts down on wasted time, freeing your staff to focus on strategic work. 

2. Build Compliance into Daily Operations

Instead of treating compliance as an annual event, make it part of your everyday processes. 

• Document changes as you make them. 
• Capture logs and approvals in real time. 
• Train teams to see compliance tasks as part of their role. 

This proactive approach avoids the scramble when audit season arrives. 

3. Focus on the Frameworks That Matter

Not every framework fits your business. Select the ones that align with your industry, risk tolerance, and client expectations. 

For example, a healthcare clinic should prioritize HIPAA. A financial services firm may benefit most from a SOC 1 report (financial controls reporting). On the other hand, service providers might benefit more from SOC 2 (service provider trust criteria). 

By focusing on the right standards, you minimize wasted effort and maximize return. 

4, Partner with Experts

Compliance is not just about passing audits. It is about building trust and resilience. Partnering with a Managed Security Service Provider (MSSP) like ITS gives you access to: 

• Expertise in multiple compliance frameworks. 
• Systems for evidence collection and reporting. 
• Guidance on selecting the right controls for your business. 

This partnership helps you meet compliance requirements without derailing your operations. 

Business Benefits of Proving Compliance 

Proving compliance may seem like a burden, but it is also an opportunity. Businesses that succeed in this area enjoy: 

• Stronger client relationships built on trust. 
• Lower cyber insurance premiums and better coverage. 
• A competitive edge in securing enterprise deals. 
• Reduced risk of fines and lawsuits after breaches. 

“Compliance attestations just help demonstrate that we are not operating arbitrarily. We are trying to operate in a manner that converges toward optimal performance,” Griffin said. 

Compliance maturity is not about perfection. It is about showing clients and regulators that you are intentional, disciplined, and trustworthy. 

Need Help Turning Compliance into a Strength? 

Proving compliance is not easy. Evidence collection, change management, and framework overload create challenges for businesses of all sizes. But with the right strategies, these obstacles can be overcome. 

The companies that succeed treat compliance as a business strategy, not just an obligation. They invest in the right frameworks, automate evidence collection, and partner with experts who can guide them through the process. 

The payoff is clear. Proving compliance builds trust, reduces risk, and creates growth opportunities. 

Our team of experts can help you simplify compliance, collect the right evidence, and turn compliance into a competitive advantage. Schedule your compliance readiness consultation with ITS. 

You can check out the following resources for more info on how MSPs can help you with compliance: 

• Can an MSP Help You with Regulatory Compliance? 
• Choosing the Best Compliance-Focused MSP (4 Insider Tips)