RAW Conversations: Grief, Silence and the Leadership Moments that Matter
There are some conversations at work that feel difficult before they even begin.
Not because we don’t care, but because we do.
We worry about saying the wrong thing. We don’t want to make things worse. We sense the weight of what someone is carrying and feel unsure about how, or whether, to step into that space with them.
And so, sometimes, we don’t.
Or we do – once, and then we step back.
But when it comes to grief and loss, it is often not the conversation itself that causes harm. It is when the conversation stops.
The hesitation behind the silence
In my work with leaders and teams, I often hear a version of the same concern:
“I didn’t know what to say.”
This is especially true when it comes to grief. Many managers have had little or no guidance on how to support someone through bereavement. Research from organisations such as the CIPD and Sue Ryder highlights that many managers feel underprepared and left to rely on instinct rather than guidance.
And instinct, in the absence of direct experience or guidance, often leads to caution.
Caution can look like keeping things brief. Staying practical. Focusing on workload rather than wellbeing. Or having an initial conversation and then quietly hoping that things will soon be “back to normal”.
Deeply human concerns sit underneath this: What if I make it worse? What if I say the wrong thing? What if they get upset?
But there is another question we don’t ask often enough:
What happens when we say nothing at all?
When support becomes a one-off moment
Janet had been caring for her mother for over a year.
When her mother died, returning to work after compassionate leave felt like stepping into a different life. Her manager did what many managers do: they arranged a conversation before her return and asked how she felt about coming back. Janet wanted the familiarity and routine of work.
It was a kind and well-intentioned conversation.
But it was also the only one.
In the weeks and months that followed, her manager didn’t ask how she was doing. There were no quiet check-ins. No acknowledgement that grief might still be present.
Three months later, Janet went off sick. Her sleep had been erratic. She had been experiencing recurring headaches. She felt anxious and overwhelmed at work. And yet, she had not felt able to say any of this to her manager.
Not because she didn’t need support. But because the silence around her had come to mean: this is no longer something we talk about here.
This is the often-unseen impact of a “one-and-done” conversation.
It unintentionally communicates that grief has a timeframe. That once someone has returned to work, the expectation is that they have also returned to themselves.
But grief does not work to organisational timelines.
The mismatch we rarely name
Workplaces tend to operate along linear patterns. Projects begin, follow timelines, meet deadlines, and conclude.
You take time off. You return. You reintegrate. You move forward.
Grief, however, is not linear.
It ebbs and flows. It can intensify unexpectedly. Research shows that grief can affect cognitive and emotional capacity, showing up in concentration lapses, fatigue, irritability, or a quiet sense of disconnection.
Some of its effects only become visible after someone returns to work - when the structure and distraction of work collide with the ongoing reality of loss.
Without ongoing conversation, this mismatch remains unspoken.
And people navigate it alone.
A different experience of being seen
Tom’s experience unfolded differently.
He was going through a painful divorce. He had moved out of the family home and was missing his young children. When he shared this with his department manager, he was met with empathy and understanding.
His manager recognised that Tom was struggling to focus and suggested redistributing part of his workload. Tom agreed, albeit reluctantly, concerned about how this might affect his future opportunities.
What made the difference was what happened next.
The conversation didn’t end there.
His manager continued to check in - not just in formal one-to-ones, but in small, human moments:
“How are things going this week?”
A quiet question as they walked out of a meeting. A tone that signalled openness, rather than obligation.
Tom knew the door to his manager was open. He didn’t have to perform being “okay”. And when his circumstances stabilised, he felt ready, and trusted, to take on a significant new project.
The power of ongoing, human conversation
The contrast between Janet and Tom is not about one manager caring more than another. It is about what happens when we see support as a moment or a task, versus a practice.
Difficult conversations - especially those involving grief and loss - are rarely resolved in a single exchange. They require a series of small, ongoing interactions that communicate:
You are still seen.
This is still safe to talk about.
You don’t have to carry this alone.
These do not need to be long or perfectly worded conversations. In fact, it is often the simplest language that creates the most space:
“I’ve been thinking of you - how are things at the moment?”
“No pressure to share, but I wanted to check in.”
“If things feel different week to week, that’s completely understandable.”
What matters is not getting it right every time.
It is being willing to keep showing up even when that feels uncomfortable.
Bringing a Whole Person approach
At the heart of this is a shift in how we see the people we work with. A Whole Person approach recognises that colleagues do not leave their lives at the door when they come to work. Nor do they experience change, whether personal or professional, in neatly contained ways.
Grief is perhaps the most visible example of this. But it is not the only one.
Divorce. Fertility challenges. Health diagnoses. Redundancy processes. Promotion decisions. Even positive change can carry complexity - excitement alongside uncertainty, pride alongside self-doubt.
When we adopt a Whole Person approach, we move beyond relating to colleagues purely through tasks, outputs, and performance.
We relate with both head and heart.
This does not mean overstepping boundaries or becoming a counsellor. It means creating a climate where it is safe to acknowledge that we are all human, and that our human experiences affect how we show up at work.
Importantly, it means not withdrawing from that reality when it becomes less comfortable.
From avoidance to leadership
It is easy to describe these conversations as “difficult”. Sometimes they are. But they are also something else.
They are moments that define leadership.
Because in these moments, people are paying close attention - not just to what is said, but to what is avoided. To whether their experience is acknowledged or sidestepped. To whether they are seen as a whole person, or a role that needs to be filled.
Courageous and compassionate leadership is not about having perfect words.
It’s about presence. It’s about a willingness to listen, or to sit in silence while someone expresses or processes their in-the-moment thoughts and feelings. It’s about being willing to say:
“I’m not entirely sure what the right thing to say is, but I care about how you’re doing.”
It’s about noticing when time has passed and choosing to reopen the conversation:
“We haven’t spoken about this for a while, but I wanted to check in.”
And it is about recognising that these capabilities are not “nice to have”. They are central to how people experience work.
Research consistently shows that when employees feel supported by their manager - particularly during challenging times, it strengthens trust, engagement, and long-term commitment. When they do not, the impact is equally significant, often showing up as disengagement, absence, or ultimately, a decision to leave. Some studies suggest that over half of employees would consider leaving their role if they felt unsupported during bereavement, underlining how significant these moments can be.
When the conversation continues
Returning to Janet’s experience, the outcome might have been very different if her manager had felt able to re-open the conversation.
Not to solve her grief.
But to acknowledge it.
A simple check-in a few days after her return, and again after a week or so. Another a month later. A quiet recognition that caring for her mother - and losing her - would not be something she simply moved on from.
These moments may seem small.
But they are often the difference between someone feeling alone, and someone feeling supported.
A final reflection
In conversations about grief at work, we often focus on what to say.
But perhaps a more helpful place to focus is this:
Are we willing to keep the conversation open?
To maintain presence and to listen. Because when we do, we create something far more powerful than a well-worded response.
We create trust.
We create psychological safety.
And we create workplaces where people do not have to choose between being professional and being human.
Our RAW (Resilience, Adaptability and Wellbeing) Team offer practical ways to turn awareness into lasting change - from workshops and coaching to organisation-wide wellbeing strategies. Learn more about our approach