Being Funny at Work Wasn’t Always About Being Funny

I have always been funny. At least I think I have. Other people may simply have been being polite for forty years.

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

Growing up gay, particularly when you are a fairly obvious little gay child, you get good at reading the room. You notice when someone is about to make a joke, when someone is uncomfortable, when someone is trying to figure you out, and when it might be useful to get there first. If I made the joke first, I had a little more control over the moment. If everyone laughed, even better.

That probably sounds more strategic than it actually was. I was not sitting there at nine years old developing an emotional-risk-management framework. I was just naturally quick, and I learned pretty early that making people laugh made things easier.

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

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

Compliance has a reputation for being very serious, and to be fair, much of the subject matter is serious. Financial crime is serious. Sanctions are serious. Investigations are serious. Regulators are serious.

Although, for the record, regulators also laugh. I have personally made regulators laugh. I consider this one of my greatest regulatory achievements.

There is always a slightly magical moment when you are sitting in an exam meeting, everyone has spent the first thirty minutes using words like “governance framework,” “risk appetite” and “control effectiveness,” and then somebody says something remotely human and the entire room suddenly remembers that we are all actual people.

That matters more than it sounds. A lot of difficult conversations become harder than they need to be because everyone starts performing seriousness. The room gets stiff, people become defensive, and suddenly something that could have been a productive discussion turns into eight people carefully reading sentences from PowerPoint.

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

Being correct is only half the job

One of the things I have learned over time is that compliance is largely a communication profession disguised as a technical one. You can know the regulation inside out and still fail completely 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 stop listening.

A huge part of being a CCO is translation: taking something technical, complicated or frankly incredibly boring and helping people understand why it matters. If I am explaining something complicated to a board, I want them to understand the issue, not admire how many regulatory acronyms I know. If I am talking to a commercial team, I want them to understand the risk and what we can do about it, not leave thinking, “Well, compliance has spoken.”

And if I am meeting a regulator, I would quite like them to believe that I understand the seriousness of the issue while also realizing I am not a robot who was assembled in a basement underneath a bank. These are not mutually exclusive concepts.

I probably used humor to make people like me

There is a less flattering truth in all of this. For a long time, I think being funny was also a way of making sure people liked me. If the room was laughing, I knew where I stood, and that was comforting.

Growing up gay, especially before you are fully comfortable with yourself, approval can feel like safety. If people liked me, then perhaps they were less likely to judge me for everything else. I do not think I was consciously thinking that, but looking back, the pattern is fairly obvious.

There is a difference between making a room laugh because you enjoy connecting with people and feeling like you need to make a room laugh so that you have earned your place in it.

There was also the fashion. I have experimented with some truly questionable office clothes over the years, which probably gave people plenty of material without me having to work particularly hard. There is nothing quite like trying to project executive credibility while wearing something that, in hindsight, looked like it had been selected by a nightclub promoter with access to a corporate expense account.

I suspect part of the reason humor came so naturally was that I was often already halfway to being the joke. If you are going to walk into the office dressed in something objectively ridiculous, you may as well own it.

The useful lesson was not “dress better,” although that would also have been valid. It was that taking yourself less seriously can make other people more comfortable around you. I have never wanted people to confuse seniority with solemnity, and occasionally my wardrobe made sure they didn’t.

Seniority makes jokes more dangerous

The other 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 that I was being sarcastic. Now I have to remember that if the CCO makes a joke about somebody’s project, the person who owns that project 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 if you do not feel any heavier.

A joke that would be completely harmless between peers can land very differently when it comes from somebody with a title. This has been something I have had to learn because humor is instinctive for me. Often the joke arrives in my brain before the responsible executive response does. Most of the time I manage to catch it. Not always.

Humor is useful when things are going badly

Every compliance organization has moments when things are not going particularly well. There is a regulatory exam. A control has failed. A remediation program is taking longer than expected. Somebody has found something at 5:47 p.m. on a Friday that absolutely nobody wanted to find at 5:47 p.m. on a Friday.

Those moments require seriousness, but they do not require misery. Teams often perform better when leaders can reduce the emotional temperature without minimizing the problem. Sometimes saying, “Well, this is not ideal,” when everyone in the room already knows it is catastrophically not ideal is enough to make people laugh and reset. Then you get back to work.

The humor does not solve the issue. It helps people stay functional while they solve it. Leaders underestimate how much their emotional tone travels through an organization. If you panic, everyone panics. If you behave as if every problem is a disaster, people eventually stop telling you about problems. If you can acknowledge that something is difficult, occasionally laugh at the absurdity of it, and then calmly work through it, people tend to do the same.

Making a regulator laugh is not a control

I should probably make this very clear. Making a regulator laugh is not a control. I have checked. It is not in any regulatory framework. There is no examination rating for “pleasantly amusing.”

But the ability to build 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 applies internally. People are much more likely to tell you something difficult if they feel like 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 like they have accidentally initiated a federal investigation. A little warmth goes a long way.

There are times when funny is exactly the wrong thing to be

Not every uncomfortable moment needs to be made lighter. Sometimes people need to sit with discomfort. Sometimes somebody is upset and the correct 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 somebody is telling you that something you did hurt them, that is definitely not the moment to try out 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 instinct to fix the emotional temperature of the room and simply letting the room be what it is.

The funniest thing is usually me

One thing I have become much more comfortable with over time is 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. I have made enough bad calls professionally to provide plenty of material, and if those ever run dry, there is an extensive archive of office outfits available as backup evidence.

Being willing to laugh at yourself does something useful to hierarchy. It tells everyone else that perfection is not the price of entry. It makes it easier for somebody to admit they do not know something or to say, “Actually, I think you are wrong.” And if I can make fun of one of my own mistakes before someone else has to awkwardly point it out, everybody wins.

The reason changed

I do not think humor is any less important to me now than it was when I was younger. It is probably more important. It helps me connect with people, explain difficult things, reduce defensiveness and make very serious work feel a little more human.

But the reason I use it has changed. When I was younger, being funny often 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.

And if I can get a regulator to laugh along the way, I will continue to consider that a bonus.