5 cringe-worthy moments from ‘The Office’ we’ve all witnessed in real life

The viral popularity of the television ‘mockumentary’, The Office, is due in part to its relatable comedy: anyone who has worked in an office setting knows some of the situations (and people) portrayed are far too real…
The Office may be early noughties TV, but it’s still painfully true! So we’ve re-watched some of our favourite episodes (both the British and American versions) to find five of its most cringe-worthy moments, highlighting what we can learn from their horrific – and hilarious – mistakes.


Every office has one. Sometimes he’s funny, sometimes he’s likeable – but when he’s the boss, it’s usually just awkward.

…Like the time the UK Office boss, David Brent, told administrative assistant Dawn Tinsley she was being let go…as a prank to try ‘make friends’ with a new employee.

The lesson

As a leader, never try ingratiate yourself with your team by trying to be ‘friend first, boss second’. It will backfire spectacularly!


While a ‘hands-on’ approach can in fact be the best way to learn, the US Office’s ‘Assistant to the Regional Manager’, Dwight Schrute, shows us what can happen when we take a teachable moment way too far:

The lesson

Some lessons require us to perform, experience and practice a task repeatedly to master it. Other times, researchers say we can actually hinder our ability to learn by overthinking it – aka ‘paralysis by analysis’, as coined by tennis player, Arthur Ashe.

So how can we encourage our teams to unlock their potential without overthinking it? Try our Insights Discovery questionnaire for personal and team growth.


It can be frustrating and inefficient to find yourself on a team that doesn’t recognise its shared purpose and goals from the outset – like this USA Office first aid seminar that veers dangerously off course:

The lesson

Keeping your team on the same page can be ‘life or death’ when it comes to achieving company benchmarks. This article outlines five ways you can create and implement shared team values to hit your targets, along with some helpful workshops to try at your office.


Who among us has not sat through a meeting with an inexperienced manager that’s gone horribly wrong? …Like when UK Office boss David tried to be a motivational speaker and somehow ended up with no shirt?!

The lesson

Moving into your first management position can require a change in behaviour and attitude, both personally and professionally.

At CONTRACT, we’ve developed Leadership Development training that will help you build self-awareness, focus on your strengths, develop positive communication and motivate others – without the song and dance!


Employers can come up with well intentioned – but misguided – incentives programmes to inspire hard work or improved results. But as newbie US Office manager Andy Bernard soon finds out, not all rewards systems are created equal:

The lesson

Are you trying to get employees to perform better with systems that don’t really work? Switch to an ‘Appreciative Inquiry’ (AI) model, which helps leaders tap into their team’s strengths.

By focusing on the positive and potential opportunities, employees will gain confidence and see their ‘gold’. They’ll have more reasons to grow and contribute in the workplace – which will have an overflow effect on the entire office.

On the flip side, misapplied rewards can have disastrous consequences for intrinsic motivation, according to this study.

Find out more about how you can implement an AI model at work by clicking here.