The Four People You’re Actually Leading

Here’s something that surprised me early in my career: the people I was responsible for “leading” were often not my employees.

Let me set the background story. As a junior compliance officer, I had to explain to a veteran stockbroker they were offside on a margin call and had to pay up, and it was no small sum. I approached the sales assistant first and her reaction was to wish me all the best rookie, patted me on the back and sent me into the brokers office and closed the door behind me. It worked out well because I explained, listed and had a conversation about what will resolve the margin call.  

And that was a pivotal moment for me as a compliance officer.

In financial services, many advisors are independent contractors. They run their own businesses, have their own clients, and have real options to walk to a competing firm. You can’t simply tell them what to do. You have to earn it.

Over 25 years, I’ve found that the people in any regulated organization tend to fall into four groups when it comes to their relationship with compliance:

The True Believer — genuinely understands why the rules exist. Self-reports. Asks questions before acting. Risk: they burn out if they feel like the only one who cares.

The Pragmatist — follows the rules because it’s good business. Not passionate, not resistant. Respond to logic and evidence, and they often become strong allies.

The Skeptic — not sure the rules make sense, and says so. A lot. Dismiss them and they become resistors. Engage them seriously and they often become pragmatists.

The Resistor — actively pushes back. Your highest-risk group, and also the one that most needs leadership rather than enforcement. The question is never “how do I make them comply.” It’s “what’s actually driving the resistance.”

Most organizations have all four types sitting in the same room. The job isn’t turning everyone into a True Believer overnight. It’s knowing which approach works with which person — and moving each one a single step in the right direction. Build the trust in the relationship incrementally over time.

Which one is hardest for you to lead?

Why Post

The idea behind postings on this platform is to ask questions. Also, hopefully provide ideas, concepts or thoughts that highlight the challenges facing risk and compliance managers in the corporate governance structure. These postings are based on my personal experience, the experiences of others, and developing my understanding of the many leadership challenges, through publications and literature.

It’s my desire to help close the perceived negative gaps between corporate governance and risk/compliance management. There are ways and means to enhance the relationship, which I’ve focused on for several years. Direct message me for additional information on how to create a collaborative governance environment.