The FUN-damentals of Leadership

Ryan Cullen
6 min readMay 24, 2021

I want you to close your eyes and picture the best day you’ve had at work. It’s likely that you’re surrounded by a team of people you get on with, you’ve achieved something pretty remarkable and, critically everyone is smiling or laughing. It’s no surprise and logically it makes perfect sense that the moment of success is tied to enjoying what you do. So why is it when times get tough that the fun is one of the first things to evaporate?

Consider the type of fun you’re trying to foster

I make the case that a critical part of leadership is about enabling others to have fun at work. I think it’s also important to acknowledge that there is Type A fun (you’re having a laugh along the way and enjoying every moment) and Type B fun (it’s hard and challenging, at times it’s frustrating, but you enjoy it after the event on reflection due to what you’ve achieved). But in either instance part of the role of the leader is to ensure that there is time to savour and enjoy the good times, making it fun along the way.

Much like psychological safety, fun isn’t going to be a game-changer without high standards (else you run the risk of a ‘country club’ mentality, where everyone is comfortable, content but not really pushed, motivated or driven). But it’s an important tool in the toolkit for leaders. That’s not to say they have to be the life and soul (go easy on the terrible jokes that create an audible groan from your team), but it does mean you have to understand what makes each of the members of your team ‘tick’ and what they’re going to have fun doing.

Why care about fun?

I believe that intuitively we all know that having fun at work is a good thing. The vast majority of the work that many of us will undertake is not completed in a vacuum, unsurprisingly 94% of workers suggested that collaboration was either important or critically important to their role. Enjoying each other's company is only going to help this and lead to greater creativity and engagement. Equally, it’ll do wonders for your employer brands as I know very few people who wouldn’t want to work in an environment in which they have fun. Finally, there have been a few studies that have shown that laughter improves both health markers as well as increasing the ability to absorb information and learn.

Researching this article took me down several different tangents. The difference between ‘fun’ and ‘pleasure’ is a difficult one to draw a line between, however, the concepts of ‘flow’ (being in the zone doing something that you enjoy) are deeply and well researched (Csikszentmihalyi is a good place to start).

I think we’ve all felt like this at a virtual ‘forced fun’ session.

You’ve then got the ‘organised fun’ which delights some and makes others recoil in horror. The issue that I personally have with large-group organised fun is that if it is forced on everyone, it’s likely to have the adverse effect of what was intended. If attendance is self-selected then it’s more likely to be successful. Broadly speaking though, a zoom quiz is unlikely to create that lingering feeling of fun and attachment to either the team or the organisation.

See each of your team as the individual that they are

I am a strong believer in the concept of individualism when curating Employee Experience. The changing nature of the future of work means that to be successful in achieving our knowledge work ambitions we have to create smaller, more agile functions which can lend themselves well to catering to the sense of individualism within the teams, whilst operating in broader guide rails of a larger organisation. What do I mean by this? Well, I mean that if you have the right size team (the two pizza rule holds relatively true), you have the opportunity to shape the concept of ‘fun’ within that team based on the individual needs and preferences of its members. To truly understand what these desires and needs are, you need to create environments in which people can bring their whole self to work and therefore feel ‘safe’ to be themselves.

How to do it

Building on this concept, Matt Weinstein sets out a great framework for having fun at work:

  1. Think about the specific people involved (as per above);
  2. Lead by example. If you as a leader demonstrate that it’s okay to have fun and enjoy yourself at work, then your team will model the same behaviours;
  3. If you’re not getting personal satisfaction from what you’re doing then it’s not worth doing;
  4. Change takes time. Be patient but consistent.

Point 3 is really interesting and goes back to the principles of flow, meaningful work, and a sense of purpose.

Fun, engagement, and motivation are a closely wedded trio and it’s important to hold all these things in balance when considering what fun means to your team. Reading Dan Pink’s Drive will give you some insights as to how to improve engagement and motivation through meaningful work created by delivering autonomy, mastery, and purpose (he also further considers the concept of flow).

I would argue to bring a true sense of ‘fun’ in work you need to be able to inject BOTH Type A and Type B fun. Only when you create meaning in your work whilst also creating fun day-to-day for the team based on their individual preferences is likely to be the only way to truly harness the power of fun. The Type A fun can be by injecting fun into team meetings, team buildings, going to lunch, ensuring that you create enough space in settings to be able to talk about things beyond work.

What I would say is that a scheduled time for fun is unlikely to be the solution, but more commonly building it into all of your team activities so it is part and parcel of what you do, rather than a bolt-on, is likely to have a more sustained impact. For example, when I used to run our monthly retrospective, we would frequently change the topics and have ‘pictures’ that everyone would have to draw for each category to loosen everyone up before the main session. It was a small thing, but it was a signal that it’s okay to have fun and it’s a safe space to laugh, even when work is tough.

In contrast, Type B fun is going to be by stretching your team and giving them projects and work that excite them and provide them with a sense of achievement. Without Type A fun, the work is going to feel impersonal and you run the risk of feeling detached from it, without Type B fun it’s going to feel superficial and unfulfilling.

Watch Out for these

Some key caveats and things to watch out for here is that unless you take the time to lay the foundations of creating safety, trust, and an understanding of the person, it comes with some risks. Jokes can miss the mark, some of the ‘fun’ you try to inject might miss the mark and you might find the whole thing misfiring. Therefore ensure that you have the foundations right and you’ve built the right relationships from the outset. Hertzberg’s Two Factor theory still rings true here also and if the basic hygiene factors are not met then it is unlikely that any of these value-added motivational activities are likely to have an impact.

One final note, as a leader it’s also important that you are getting the same. Your team and colleagues will draw from your energy and if you are not having fun, there’s very little chance you’ll be able to encourage fun in others.

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