Dear Penny: The hangover you didn’t expect

Dear Penny: The hangover you didn’t expect

I was chatting with the COO of a company not so long ago about culture fit and their hiring process. They mentioned how thorough they needed to be during the interviews when considering people who had previously worked at a specific organisation. People from this organisation either flew or completely flopped and there didn't seem to be much in between. The COO recognised how well trained these people were and their level of expertise, but also recognised the culture they were coming from was vastly different to the one they would potentially be going into. They had a process in place to try to identify those who would fly but it wasn’t foolproof. 

It was an interesting conversation that got me thinking about culture transition and how we manage this in organisations. When we start a new job there's always a period at the start when we’re getting to know everyone, learning how everything works and figuring out the social ins and outs of the place. It’s usually a nerve-racking but exciting time. Lots of highs, lots of lows and everything in between. What we may not see or recognise during this time is that we’re also unlearning the old workplace culture. So not only are we learning, we’re unlearning too. 

You see, workplaces play quite a significant role in who we are. It’s a little bit like the saying ‘you are who you hang around’. Because we spend so much time at work it naturally influences who we are, shaping our behaviours, thinking patterns and how we show up in the world. And naturally, the longer we’re in a workplace, the more it affects who we are because patterns and behaviours become so deeply engrained. This can make transitioning into new work cultures a little more complex than what we realise. I’ll give you an example. One of my past roles required an exceptional amount of resilience. Whilst the organisation had a control and command leadership style, they weren't particularly good at giving clear directions or instructions. It was quite common practice for me to complete work and then be reprimanded because it wasn't right. Regardless, I kept turning up and showing up and completing the work to the best of my abilities. I became very resilient, but I also learnt not to entirely trust leadership. 

This brings me to the term ‘workplace hangovers’. When I left this role and started a new job I experienced a ‘workplace hangover’. The skills and behaviours I’d learnt to survive and thrive in my old role were now creating negative after-effects. The new workplace operated on a high-trust model where leaders did what they said and trusted employees to complete work how they saw fit. As you can imagine, my distrust and wariness of leadership became rather unhelpful in this new role. I was always on guard, I questioned what they said and had little confidence when delivering work. I liked the new environment and culture and chose the job because of it, but due to the after-effects of my ‘workplace hangover’ it was difficult to transition into. Thankfully I became aware of this early on and was able to manage and intentionally shift my behaviours and patterns. I should note though, a serious silver lining of this ‘workplace hangover’ was just how resilient I was. The new culture operated with endless ambiguity so my ability to continuously ‘show up’ was exceptionally helpful and led to me thriving within this space. I’m curious to know though, has anyone else ever experienced a ‘workplace hangover’? If so, what after-effects were you left with? Were they helpful or more of a hindrance?

Since I first experienced this I’ve transitioned in and out of organisations and roles a few times and each time I think to myself, I wish I could sit down with my new leader and talk to them about this. The impact these ‘workplace hangovers’ have on my wellbeing and ability to quickly and efficiently transition is quite significant. Should we be offering new employees wellbeing meetings early on in the onboarding process to discuss things like this? I can’t help but think that if we did, organisations and leaders would be able to better support employees, make their transition easier and actually possibly shorten their transition period. 

Alongside this, I also wonder how many highly talented people organisations are missing out on because they rule people out due to the culture of their current workplace. At times I’ve purposefully sought out workplaces with opposite or vastly different cultures to the one I was in because I was aware of how it was negatively impacting me. I knew that by shifting to a different culture I could rebalance myself, strengthen certain skills or behaviours and overall, level-up. 

We don’t always think about it, but culture transition is a real part of starting a new job. And for organisations, it’s a missed opportunity if it’s not acknowledged. Supporting someone through that transition isn’t just a nice-to-have, it can directly improve engagement, shorten the time it takes for someone to find their rhythm, and help unlock their full potential.

People who actively seek out a different culture often do so with intention. They know something’s not working, they want to grow, and they’re brave enough to make a change. That level of self-awareness is something to value, not be wary of. With the right support, those individuals can bring fresh energy, adaptability, and hard-won clarity about how they want to work and lead.

For individuals, it’s a reminder to go gently. Transitions take time, especially when you’re unlearning as much as you’re learning. Keep choosing what feels right for you. That’s not weakness, that’s wisdom.

When we start seeing culture transition as something to support, not survive, everyone benefits. The people. The teams. And the organisation.