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Commentary: Maybe bosses shouldn’t try to be funny and make jokes at the office

Should bosses be funny? And when should they quit joking around? Lily Cheng and Peter Cheng discuss how to navigate humour in the workplace.

SINGAPORE: How many of us have had bosses with no sense of humour? Working under them can leave us feeling bored and unmotivated. 

On the other hand, if they joke too much, it can be hard to take them (or the job) seriously. 

COVID-19 has changed the face of our work life as we know it. We’re telecommuting, safe distancing, and trying to connect in our virtual teams - yet not enjoying ourselves very much.

According to a COVID-19 mental health survey run by the National University Health System’s Mind Science Centre published on Thursday (Aug 19), 61 per cent of respondents who work from home reported feeling stressed. 

It’s sensible that bosses therefore try harder to lighten the mood and make their teams laugh.

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We already know humour in the workplace can be a powerful force. Laughter is associated with higher productivity, better morale and greater rapport at work and has numerous proven health benefits, including alleviating stress, studies have shown. 

You might think these findings do not apply to Singaporeans who seem like serious people who want to get down to business. 

Yet Singaporeans ranked both “happiness” and “humour/fun” in their top 10 personal values as words that best described themselves and their notion of the ideal Singapore society, according to the 2018 National Values Assessment survey.

But here’s the thing about humour: “It’s hard to do well and easy to do badly,” astutely noted by time management guru and author of What The Most Successful People Do At Work, Laura Vanderkam.

We all remember the painful, conspicuous silence of a joke falling flat on its face. Or the obligation to laugh at a bad joke. In other instances, some jokes are just downright inappropriate. 

So how do leaders strike that balance and know when to quit joking around?


Telecommuting is forcing us to take a good hard look at our existing relationships with our coworkers. 

(Photo: Mimi Thian/ Unsplash)

We are devoid of physical connection, feeling the loss of opportunities to connect socially, whether over coffee or a chance meeting at the pantry, and eager to find some level of camaraderie.

We would argue humour isn’t the only way to foster a positive team culture that can withstand COVID-19.

After all, a Work Happy 2019 study by recruitment agency Michael Page showed 97 per cent of Singaporeans feel being on good terms with colleagues and bosses can improve productivity at work. 

This suggests that the answer lies less in humour, but in the intentional strengthening of existing workplace relationships, through having genuine conversations or through team-building exercises.

Rather than crack jokes - which can be tricky because different employees might have different sensibilities and sensitivities regarding humour - we would counsel managers and workers instead to focus on finding ”moments of levity” to bring the team together.

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Efforts could be at the organisational level - in celebrating a birthday or playing games - or taking personal moments - for instance, being able to laugh at yourself when you make mistakes - which all contribute towards creating a relaxed environment where people feel safe, supported and heard. 

Even when running our Zoom workshops with clients, we encourage check-ins and check-outs to encourage listening and team-bonding separate from work-related matters. 


We often advise executives we coach to visualise the goal at the end of the day as one that “builds a strong container” for the team.

Coined by the founder of consulting firm Dialogos and author of The Power of Collective Thinking, William Isaacs, a container is “the sum of the assumptions, shared intentions, and beliefs of a group … (which) creates a collective atmosphere or climate".

(Photo: Unsplash/Austin Diestel)

Strong containers can withstand the winds of change in the workplace, while weak containers break when external pressures are exerted on the team.

A strong container can be built through talking and thinking through projects, challenges and issues together as a team, which establishes understanding even if workers have diverse perspectives, priorities or roles. 

Doing this requires leaders to suspend judgment and listen to concerns and ideas, which can be challenging when managers are used to a directive leadership style and often lead from the front. 

Those who are competitive and set high standards can be intimidating to staff, but in our experience, this is when such moments of team discussions where managers demonstrate they care about their teams and see their team-mates as more than number-crunching digits are most appreciated.

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At the end of the day, humour can be a valuable asset if channelled constructively to ease tensions at critical, peak periods, set the tone for the organisation and make leaders more human and relatable.

When considering humour through the lens of strengthening the container, it helps to be mindful of three key guidelines: Personalities, authenticity, and no-go zones.

First, be mindful that workers have different personalities in the office. Not all employees enjoy laughing and joking with their bosses. 

Some may prefer to maintain a strictly professional relationship with their leaders. This boundary should be respected.

Second, don’t use humour if it feels contrived or even forced. When many people are looking to you for direction, it’s better to remain authentic to ourselves and develop a healthy sense of self at work. 

A leader with a healthy sense of self might say, “I know I don’t naturally crack jokes, but I know other ways to foster engagement with the team.”

Finally, keep in mind the no-go zones and red lines in the sand that should never be crossed. Remember that racist, sexist, immoral, and dirty humour have no place in the office or any other spaces. 

2020 has been a whirlwind of a year. Now, more than ever, we need strong business communities anchored by solid ties and good communication. 

Bosses don’t need to joke to create strong interpersonal relationships in the workplace. They just need to find fresh ways to bring teams together in a world of remote working.

Dr Lily Cheng and Dr Peter Cheng are the co-founders of PACE OD Consulting, an organisational development consulting firm. They have coached leaders and guided teams throughout Asia, Europe and the United States.


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