Somebody that I used to know: On the weird grief of colleague departures

CNA

a day ago

This question has become part of my awkward welcome ritual for new hires: 'So ... are you a coffee person?'
Day one usually begins at the cafe downstairs with a quick hello, a commemorative libation (coffee or otherwise), then a climb up the stairs to commence our journey as co-workers.
Over the past decade of running my company, I've continued to personally onboard new workers. It's not that I can't trust someone else to do it. I just really enjoy it.
I like showing them our 'designated crying area' (our pantry space) and explaining the curious phenomenon of the office bidet geyser.
I like going through our culture deck, throwing in a few jokes to break the ice and seeing them decide how heartily they should laugh.
It's orientation, yes, but also something more – a quiet hope that if you make them feel welcome and you remember their coffee order, they might stay a little longer.
Then they leave. Sometimes after three years, sometimes three months. Sometimes on a good note, sometimes a strained one.
And in that abrupt silence that follows, between offboarding checklists and looking at handover documents, I find myself wondering if any of these efforts were worth it.
WON'T YOU STAY WITH ME?
About a decade ago, the first person that I hired when I started the company decided to make a jump to a much bigger, more prestigious agency.
It was a competitor but it paid her better and had a much more conducive structure for her career development. It made sense for her.
We parted on good terms, but it was hard to maintain the same friendship once we no longer shared the day-to-day routines.
Even seeing her career milestones pop up on social media triggered a small wave of disappointment – not at her, but at myself. It was insecurity and a bit of resentment all wrapped up in a forced double-tap of the 'like' button.
We didn't speak for a long time. Only after a good five years had passed could we both approach the situation with some perspective and humour. Thankfully, we're now friendly again.
This isn't a story about attrition rates or talent migration. It's about the emotional tax of investing in people who eventually walk away.
No one tells you, when you first become a manager, that the job requires a strange kind of short-term memory.
You pour time into someone, build a rhythm, start speaking in shared references and inside jokes – and then, poof, they're gone. Off to bigger things and better pay.
The relationship seems to end abruptly there, apart from the occasional LinkedIn sightings.
I know that's just the way the cookie crumbles. The workplace today is a revolving door of industry pivots, mental health breaks and career realignments.
Everyone's chasing something – balance, purpose, remuneration, title and so on – and it's unlikely that staying in one place can offer everything.
Still, why do I feel a small sting every time someone leaves?
SOMEBODY THAT I USED TO KNOW
I'll be honest. I still find it difficult not to take departures from the company personally.
Not in a dramatic, weeping-in-the-toilet way, but in those smaller moments.
When a photo of a past team outing pops up on social media, in a photo album or the memories in your head. Or when you retrieve an old presentation deck and you see the names tagged in the slides.
Certainly not because they're wrong to go but maybe it's because, for a brief window of time, I had imagined a future where we'd keep building something together.
This emotional dilemma isn't exclusive to managers and supervisors.
The departure I've taken the hardest happened when I was still a junior executive, in the infancy of my career.
At the time, I was part of a desk cluster with a senior who wasn't my direct boss, but who had become a de facto mentor.
Christopher was soft-spoken, serious and a little stoic, but he always humoured my terrible puns. We'd often sneak off for 'planning sessions' at the canteen that had very little to do with planning. We talked about movies, music, family – the kind of conversations that anchor you during chaotic work days.
One afternoon, Christopher told me that the following week would be his last with the company. He'd found a better opportunity elsewhere.
In the 2002 Hong Kong movie Infernal Affairs, there's a pivotal scene where Tony Leung, playing an undercover police officer, watches the only person who knows his true identity get killed. The camera lingers on his expression of shock and horror and this remains one of the strongest gut punches in cinematic history.
On that day when Christopher told me the news, my expression would've made Tony's look mild at best.
'Oh. Congrats, Chris!' I managed to say. 'Happy for you.'
Two weeks later at his cleaned-out desk, I shook his hand and said all the right things: 'Let's keep in touch. Don't be a stranger.'
What I couldn't shake was the strange sense of grief and futility. What would be the point of keeping in touch if we no longer worked together?
FRIENDS ARE FRIENDS … FOREVER?
What is 'workplace culture'?
We like to talk about it in terms of values and vision statements, but most of it comes down to the people.
It is who you sit next to, the person who replies with a meme instead of a boring thumbs-up, the one who makes the 5pm slump bearable.
So when they leave, it isn't just another email from the human resource department. It's a permanent glitch in your work day.
Conventional business wisdom dictates that investing in people is never a waste, even when they might come and go – because people are the most valuable assets of any company.
I've echoed those things. I even genuinely believe them.
But there's another truth, too: that what isn't a waste can still sometimes feel like one regardless.
It's only human of us to feel something, especially after we've poured hours into someone – coaching, giving feedback, having conversations over coffee and bubble tea – only to have them resign right when they finally started getting it.
Maybe it is not quite bitterness but certainly, there is a sense of jadedness. The kind that makes you want to pull back with the next person, just a little.
Don't get too attached. Don't ask about their weekend or their interests. Don't joke too much.
Here's the catch: If you stop investing in your people earnestly and genuinely, you will slowly become the kind of manager you swore you'd never be. Transactional. Coldly efficient. Checked out.
And ironically, that's exactly the kind of environment people want to leave.
So I will keep trying, even when the farewell Slack message reads like a LinkedIn boilerplate.
I will keep hoping that somewhere along the way, the time we spent together meant something. That, in between rushed deadlines and Monday check-ins, we managed to become more than just colleagues ticking boxes on a task list.
Maybe that's the point – to make the workplace not just somewhere people pass through, but somewhere they felt seen, where they felt real connection, even if briefly.
I love how Andy Bernard movingly puts it in the series finale of American sitcom The Office: "I wish there was a way to know you're in the good old days before you've actually left them."
The real treasure, as they say, might just be the friends we made along the way.