Being Funny at Work Wasn’t Always About Being Funny

I have always been funny. At least I think I have. It is possible that people have simply been very polite for forty years.

Humor has always been a big part of how I move through the world. For a long time, I assumed it was just my personality. Looking back, I think some of it was personality and some of it was survival.

Growing up gay — particularly as a fairly obvious little gay child — you get good at reading a room. You notice when someone is uncomfortable, when a joke is coming, and when it might be safer to get there first.

If I made the joke, I had a little more control over the moment. If everyone laughed, even better.

I wasn't sitting there at nine years old developing an emotional-risk-management framework. I was naturally quick, and I learned early that making people laugh made things easier.

Years later, somewhat bizarrely, that became useful in compliance.

Compliance is serious. Compliance people do not have to be.

Financial crime is serious. Sanctions are serious. Investigations are serious. Regulators are serious.

Although regulators do laugh. I have personally made regulators laugh, which I continue to regard as one of my greatest regulatory achievements.

There is a slightly magical moment in an examination meeting when everyone has spent thirty minutes discussing governance frameworks, risk appetite and control effectiveness. Then somebody says something remotely human and the room suddenly remembers that we are all actual people.

That matters.

Difficult conversations often become harder because everyone starts performing seriousness. The room stiffens. People become defensive. A potentially useful discussion turns into eight people carefully reading sentences from PowerPoint.

Humor can break that tension. Not because the issue is funny, but because the people discussing it sometimes need permission to relax enough to talk honestly.

Compliance is largely a communication profession disguised as a technical one.

You can know the regulation inside out and still fail if nobody understands what you are saying. You can have the strongest risk argument in the room, but if you deliver it like a hostage statement, people will stop listening.

A large part of being a CCO is translation: taking something technical, complicated, or frankly incredibly boring and helping people understand why it matters.

When I speak to a board, I want them to understand the issue — not admire the number of regulatory acronyms I know. When I speak to a commercial team, I want them to understand the risk — not leave thinking, "Well, compliance has spoken."

And when I meet a regulator, I would quite like them to see that I understand the seriousness of the issue while also realizing I was not assembled in a basement underneath a bank.

These things are not mutually exclusive.

There is a less flattering truth in all of this.

For a long time, being funny was also about making sure people liked me. If the room was laughing, I knew where I stood. That was comforting.

Growing up gay, particularly before you are fully comfortable with yourself, approval can feel like safety. If people liked me, perhaps they were less likely to judge everything else.

I doubt I was consciously thinking that. The pattern is fairly obvious now.

There is a difference between making a room laugh because you enjoy connecting with people and needing to make a room laugh to earn your place in it.

I also had some help from my wardrobe.

I experimented with some truly questionable office clothes over the years. There is nothing quite like trying to project executive credibility while wearing something apparently selected by a nightclub promoter with access to a corporate expense account.

I was sometimes already halfway to being the joke. I may as well have owned it.

The lesson was not "dress better," although that would also have been valid. It was that taking yourself less seriously often makes other people more comfortable around you.

The annoying thing about becoming more senior is that your jokes stop belonging entirely to you.

Years ago, I could make a sarcastic comment in a meeting and assume everyone understood it was sarcasm. Now, if the CCO jokes about someone's project, the person responsible may spend the rest of the day wondering whether I secretly hate it.

I may have forgotten the comment before the meeting ends. They may mention it to their spouse that evening.

That is the strange thing about hierarchy: your words get heavier even when you don't feel any heavier.

Humor is instinctive for me. The joke often arrives before the responsible executive response.

Most of the time, I catch it.

Most of the time.

Every compliance organization has moments when things are not going well.

A control has failed. An examination is underway. Someone discovers something at 5:47 p.m. on a Friday that absolutely nobody wanted to discover at 5:47 p.m. on a Friday.

Those moments require seriousness. They do not require misery.

I have sat in enough of those rooms to know that the leader's emotional tone travels fast. If you panic, people panic. If you treat every problem as a disaster, people eventually stop telling you about problems.

Sometimes saying "well, this is not ideal" — when everyone in the room knows it is catastrophically not ideal — is enough to make people laugh, reset, and get back to work.

The humor does not solve the problem. It helps people stay functional while they do.

Making a regulator laugh is not a control. I have checked. It does not appear in any regulatory framework, and there is no examination rating for "pleasantly amusing."

But rapport matters.

Regulators are trying to understand whether you know your business, understand your risks, and will tell them the truth when something goes wrong. Being able to have a normal human conversation helps.

The same is true internally. People are more likely to tell you something difficult if they feel they are talking to a person rather than appearing before a tribunal.

I want someone to be able to say, "This may be nothing, but can I run something by you?" without feeling that they have accidentally initiated a federal investigation.

A little warmth goes a long way.

Not every uncomfortable moment needs to be made lighter.

Sometimes people need to sit with discomfort. Sometimes someone is upset and the right response is to listen, not entertain. Sometimes a team has received difficult news and the room simply needs to be serious for a while.

And if someone is telling you that something you did hurt them, that is definitely not the moment to try new material.

Humor can create connection, but it can also be avoidance. I know I have occasionally made a joke because I was uncomfortable, not because it helped anyone else.

Leadership sometimes means resisting the urge to change the emotional temperature and letting the room be what it is.

I have become much more comfortable making myself the joke.

There is plenty of material.

I have made bad decisions, misunderstood things, and confidently explained something only to realize five minutes later that I was completely wrong. If the professional material ever runs dry, there is an extensive archive of office outfits available as backup.

Being willing to laugh at yourself does something useful to hierarchy. It tells everyone else that perfection is not the price of entry.

It becomes easier for someone to admit they don't know something. It becomes easier to say, "Actually, I think you're wrong." And if I can make fun of my own mistake before someone else has to awkwardly point it out, everybody wins.

Humor is no less important to me now than it was when I was younger. It may be more important.

It helps me connect with people, explain difficult things, reduce defensiveness, and make serious work feel a little more human.

But the reason I use it has changed.

When I was younger, being funny helped me feel safer in the room.

Today, when I use it well, I hope it helps other people feel safer around me.

That is a much better use of it.