RiskMasters · 2026-06-20 · 5 min
Key moments - from our scoring
Substance score
40 / 100
Five dimensions, 20 points each
The chief compliance officer role demands far more than technical expertise alone. Jennifer Gehry and Natalie McManus challenge the conventional view that regulatory knowledge and procedural mastery define CCO effectiveness, arguing instead that three critical capabilities will distinguish high-performing compliance leaders over the next three to five years: data and AI literacy, curiosity, and empathy. Gehry emphasizes the importance of "flair" - the ability to interpret rules creatively, embed compliance into organizational culture, and bring policy to life - while McManus stresses that technical brilliance, though necessary, remains insufficient without genuine curiosity to ask the right questions and empathy to build relationships and influence outcomes. The conversation reveals that compliance leadership is fundamentally multidimensional and human-centered, requiring leaders to navigate complex interpersonal dynamics, read room sentiment, and influence stakeholders who may prioritize compliance far less than CCOs do. This episode is essential for current and aspiring chief compliance officers, general counsels, risk leaders, and organizational executives seeking to understand how compliance leadership is evolving beyond rigid rule-application toward strategic influence and organizational stewardship.
Data and AI capability, curiosity, and empathy. Data and AI proficiency enables better compliance execution; curiosity ensures leaders ask the right questions; and empathy allows them to build relationships and influence stakeholders effectively - with technical brilliance being necessary but insufficient alone.
Technical brilliance must be paired with curiosity and empathy to be effective. Without curiosity, leaders don't ask the right questions; without empathy, they fail to build relationships and influence outcomes. Being right technically isn't enough to drive compliance outcomes organizationally.
Leaders underestimate the nuance, humanity, and emotional labor required. CCOs must balance humility and firmness, mask frustration when meetings are deprioritized, and influence stakeholders without appearing duplicitous - a multidimensional pressure that can take a lifetime to navigate well.
Flair refers to the ability to interpret rules creatively, embed compliance meaningfully into organizational culture, and bring policy to life - moving beyond mechanical rule-application to strategic, contextual leadership that resonates with stakeholders.
Compliance officers face significant wearing pressure because they must often mask frustration and emotional responses to be effective, particularly when stakeholders deprioritize compliance meetings that CCOs have extensively prepared for, requiring emotional regulation and influence skill rather than just technical knowledge.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode surfaces a handful of genuinely useful ideas - 'flair' as a compliance capability, the 'going native' risk, and the emotional wearing of influence work - but in five minutes much of the runtime is throat-clearing and vague leadership generalities like data/AI being important. The ratio of novel claims to filler is mediocre.
flair, you know, you can apply flair to how you interpret rules, to how you embed things in an organization
sometimes compliance officers think being right is enough, and it's not. You have to read the room
'Flair' applied to compliance and the 'going native' concept are genuinely unexpected framings, but the data/AI point is completely predictable, and the curiosity/empathy framing is recycled generic leadership advice found everywhere.
The answer you may not expect from me and the word that I had in my mind as I heard Natalie explain the CCO role and the way that she does was flair
Without curiosity, don't ask the right question. And without empathy, you don't build the right relationships
Natalie McManus speaks from evident personal practitioner experience as an active CCO, grounding her answers in lived frustration rather than theory; however, the episode also has a clear book-promotion angle and the guests' seniority and organisational context are never established in the transcript.
it is wearing when you are the least important meeting of someone's week
you've prepped for two weeks to influence someone and they've literally taken your meeting agenda. So from like 10 minutes down to 30 seconds
There are almost no named companies, metrics, or concrete case studies; the only specific detail is the anecdote about a meeting agenda being cut from ten minutes to thirty seconds, which is illustrative but not evidence of anything at scale.
they've literally taken your meeting agenda. So from like 10 minutes down to 30 seconds
having the capability to understand, map, think about data and apply the best of the nascent capability that we have
The host's reverse question ('what do leaders consistently underestimate?') is a smart structural move, but there are no genuine follow-ups, no pushback on vague claims like 'flair,' and the format is too brief for real dialogue; the episode reads more like a lightly moderated excerpt than a crafted conversation.
what is the one capability leaders consistently underestimate in compliance? What is the thing they don't get right? So almost a reverse question
Two, three max. Just for the sake of time
Computed from the transcript - who did the talking, and the words that came up most.
The Chief Compliance Officer role is often defined through technical expertise, regulatory knowledge, and control frameworks. In practice, the effectiveness of compliance leadership depends on something broader. In this RiskMasters extract, Jennifer Geary and Natalie McManus explore how the capabilities required for high-performing Chief Compliance Officers are evolving in response to increasing complexity, data availability, and organisational pressure. The discussion highlights how compliance is no longer limited to interpreting rules or maintaining frameworks. It is increasingly defined by how leaders apply judgement, influence decisions, and integrate compliance into business operations. A central theme is the distinction between technical capability and leadership effectiveness. While data and AI are reshaping compliance functions and enabling new forms of monitoring and insight, they do not determine how compliance performs in practice.
Transcribed and scored by The B2B Podcast Index.
Julien Haye: M the chief compliance officer role is often defined by technical expertise. General Gary and Natalie McManus take a different view. They explain that technical knowledge is necessary, but it does not determine how effective a compliance leader will be in practice. That distinction reshapes how leaders think about compliance leadership, decision making and the future of the chief compliance officer role. Welcome back. You're listening to a download where I share bite size insights from our latest interview. This highlight comes from a conversation with Jennifer Gehry and Natalie McManus where we explore one of the closing ideas from the episode. Uh, we break down what capabilities will define high performing chief compliance officers and why compliance leadership is evolving beyond technical expertise toward data, AI and human judgment. Here is Jennifer and Natalie and before we get to a close, I'd like to ask one last question around the cco. Uh, what capabilities will define a high performing compliance leaders over the next three to five years? Two, three max. Just for the sake of time.
Jennifer Gehry: Um, so, uh, I'm going to say two things. Um, the one that you would expect me to say is data and AI, right? So having the capability to understand, map, think about data and apply the best of the nascent capability that we have, I think, let's face it, is going to be the thing, uh, that changes and improves how we run compliance. The answer you may not expect from me and the word that I had in my mind as I heard Natalie explain the CCO role and the way that she does was flair. And it's not a word that you would ever think of applying to comply. Sorry Natalie, no, no offense intended, but flair, you know, you can apply flair to how you interpret rules, to how you embed things in an organization, to how you bring things to life. And I think that for me was the huge learning about this book.
Natalie McManus: Nathalie, one, two, more curiosity, uh, empathy and technical brilliance. Um, too often I think technical brilliance is considered necessary. Uh, but it is not sufficient. Without curiosity, don't ask the right question. And without empathy, you don't build the right relationships and nudge things in the right way.
Julien Haye: And with that I'd like to take the discussion to a close and ask a few again, running around the edges of the cco, um, what is the one capability leaders consistently underestimate in compliance? What is the thing they don't get right? So almost a reverse question that what I just asked you.
Jennifer Gehry: Oh, I'm going to slightly repeat myself I think and kind of say, you know, I came into this project thinking that this was quite, quite a black and white role to Take and actually how much nuance and humanity that there is in this role. I think for me that was the surprise. And in terms of these books, all of the C suite books are about helping people to be more able and more capable and so on. And this book does, uh, inform you as to what the role entails. But what it brought to life for me was how multidimensional and complex and interconnected the role really is.
Natalie McManus: And I think for me it's, uh, a blend of humility and rigidity. So sometimes compliance officers think being right is enough, and it's not. You have to read the room and you have to work really, really hard to influence it. And that is wearing. It is wearing when you are the least important meeting of someone's week. Um, and it's your most important meeting and you've prepped for two weeks to influence someone and they've literally taken your meeting agenda. So from like 10 minutes down to 30 seconds, you're like, I'm not going to swear, but I want to swear. And it happens to me time and time again and you cannot wear it on your face. And I am a very emotive thinker and speaker, so when I am angry or annoyed, I wear it. And having to mask that in a room, because it's all about everybody else, it's about them, not about you. That, that is, that is very, very hard to do. And I think people who go into the CCO role sometimes underestimate just how wearing that Is. Especially because CCOs are by their very nature very law abiding, very frank, honest people. And so to be faced with a room where you have to be in their mind, sometimes a little bit duplicitous to get them a better outcome and just feel like the wrong thing today, um, um, and sometimes it's polished, but sometimes it goes too far. And so when you try and overcompensate, then sometimes you do, as I say, go native. And that creates really bad compliance outcomes. So being in the middle lane of those pressures is really, really hard. Um, and it can take a lifetime to get right. But, and this is the shameless plug. Hopefully if you read the book, it will give you some guidance as to how you navigate that really tricky path.
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