This is the second post in MirrorWeb’s series exploring the strategic priorities for compliance leaders in their crucial first quarter. In the first blog, they mapped out what success looks like in those initial 90 days. Now, VP of Product Jamie Hoyle discusses the landmines that can derail even the most experienced compliance professionals.
Starting as a new Chief Compliance Officer is like being handed the keys to a complex machine that’s already running at full speed—but possibly in the wrong direction. You need to understand how every part works, identify what needs fixing, and correct course, all while keeping the engine running smoothly and ensuring it passes inspection. The learning curve is steep, the pressure is immediate, and one misstep can undermine months of relationship-building.
Your first 90 days don’t just lay the foundation for your compliance program; they determine how your entire organization perceives the role of compliance. Move too fast, too rigidly, or without the right context, and you risk being seen as the “department of no” before you’ve even had a chance to prove otherwise.
Through candid conversations with seasoned CCOs across different firm types—from small advisory practices to large growth equity firms—we’ve identified five critical pitfalls that repeatedly trip up new compliance leaders. More importantly, we’ve learned how the most successful CCOs navigate around them.
Pitfall #1: Racing to Make Changes Without Understanding the Business
The temptation to hit the ground running is understandable. You’ve been brought in to strengthen compliance, so surely that means immediate action, right?
Wrong. The biggest mistake new CCOs make is launching into audits, policy overhauls, or system changes before truly understanding how the business operates. Every firm has its own communication flows, cultural nuances, and unspoken protocols. Rush in without grasping these fundamentals, and you’ll create confusion, resistance, and potentially bigger problems than what you started with.
The fix: Slow down and listen first. Use your first 30 days for deep immersion—not just in policies and procedures, but in understanding how work actually gets done, who the key stakeholders are, and what the cultural expectations around compliance currently look like.
Pitfall #2: Treating Compliance as a Solo Mission
Compliance isn’t a one-person show, yet many new CCOs act like it is. They focus intently on crafting perfect policies or implementing flawless systems while neglecting the human side of the equation —building trust with colleagues and securing champions among leadership.
This alienation leads to compliance becoming a department people tolerate rather than one they actively support. Without internal buy-in, even the most sophisticated compliance framework will fail when it matters most.
The fix: Frame compliance as a partnership, not policing. Early wins come from demonstrating that you’re there to enable the business. As one CCO put it: “It always circles back to this—taking care of our clients.” When people understand that compliance serves that shared mission, resistance melts away.
Pitfall #3: Assuming What Worked Before Will Work Again
Every firm is different, and what made you successful in your last role may not translate to your new environment. Overreliance on precedent can blind you to emerging risks, unique cultural dynamics, or industry-specific challenges that require fresh approaches.
Compliance is a function that must continuously adjust to regulatory, technological, and behavioral shifts. Bringing rigid assumptions to a dynamic scenario is a recipe for missed risks and missed opportunities.
The fix: Stay agile and question your assumptions. Yes, your experience matters, but approach each new environment with genuine curiosity about what makes this particular organization tick. The best compliance strategies are always bespoke, never copy-and-paste.
Pitfall #4: Overlooking the Technology Foundation
Here’s a painful truth: manual review and disconnected systems will overwhelm even the most capable compliance professionals. Yet, many new CCOs postpone technology evaluation, treating it as a ‘nice to have’ rather than mission-critical infrastructure.
With firms now managing a long list of communication channels, such as Slack, WhatsApp, Teams, Signal, text messages, websites, social media, and more, the volume of data requiring review has exploded. Without the right tools for automated message capture, advanced search functionality, intelligent supervision, and consolidated oversight, you’re setting yourself up for burnout and missed risks.
The fix: Make technology evaluation a Day 1 priority, as it is a time investment that could pay off exponentially. Whether it’s automated surveillance, intelligent risk detection, or unified channel monitoring, the right tools don’t just help; they transform your capacity to scale.
Pitfall #5: Swinging Too Far Toward Either Extreme
The final trap is sliding too far in either direction—either implementing overly rigid controls that stifle productivity or maintaining lax policies that create regulatory exposure. Both approaches undermine long-term compliance success.
The most effective compliance leaders recognize that oversight and usability aren’t mutually exclusive. You can maintain strong controls while preserving employee wellbeing and business efficiency. In fact, you should.
The fix: Strike a thoughtful balance from the start. Remember that compliance serves the business, not the other way around. The goal is to enable sustainable growth while managing risk, not to create a culture of fear or frustration.
The Path Forward
These pitfalls are avoidable. The CCOs who elude them share common traits: they listen before acting, build bridges instead of walls, adapt their approach to fit their environment, invest early in the right technology, and maintain perspective on what compliance should ultimately achieve.
Most importantly, they understand that compliance leadership is about cultural transformation, not just policy implementation. Your first 90 days are your opportunity to set that tone and build the foundation for everything that follows.
The compliance landscape will continue to evolve: new technologies, new regulations, new communication channels, new risks, new opportunities. But the fundamental challenge remains the same—creating a culture where compliance enhances rather than hampers business success.
Want to dive deeper into the strategic priorities that matter most for new CCOs? Our complete guide, Beyond the Checklist: Strategic Compliance Priorities in Financial Services, explores the full roadmap for your first 90 days and beyond, with insights from compliance leaders across the industry.
Jamie Hoyle is the VP, Product at MirrorWeb, where he leads product strategy. He joined MirrorWeb as Lead Software Engineer in 2017, eventually transitioning to Product and spearheading the development of their flagship communications supervision platform, MirrorWeb Insight.
In 2024, Jamie relocated to Austin, Texas, to embed himself in the heart of the U.S. compliance landscape and stay close to the customers shaping the future of digital communications oversight.
Photo courtesy Markus Winkler via pexels
