What Leaders Get Wrong About Grief (And What It Costs Them)
How avoidance, platitudes, and silence are eroding trust, culture, and performance, one missed opportunity at a time.
Table of Contents
Most leaders get grief wrong. Not because they’re bad people. Not because they don’t care. But because no one taught them what it really is or how to handle it at work. Instead, they fall into avoidance, overcompensation, or well-meaning platitudes. And while those responses may feel safe in the moment, they often do more harm than good.
And here’s the truth no one likes to admit: Many leaders aren’t protecting the grieving person. They’re protecting themselves. They don’t want to feel awkward. They don’t want to say the wrong thing. They don’t want to confront something they can’t control or fix. And they want things to return to normal as quickly as possible.
The fear of making things worse than they already are is real. But that emotional self-protection comes at a cost: trust, loyalty, safety, and performance.
Let’s take a look at the common traps and what you’re leaving on the table when you fall into them.
Mistake #1: Saying Nothing
“I figured they’d let me know if they wanted to talk.”
“I didn’t want to upset them.”
What’s really happening: You’re telling yourself silence is respectful. In reality, you’re avoiding discomfort—yours, not theirs. And the silence doesn’t feel neutral. It feels like absence.
The cost: They feel alone, forgotten and unseen. And the rest of the team sees the silence and thinks, “This isn’t a place where you can be human.”
What you missed: A chance to build unshakable trust with someone who will remember your response—for better or worse—for the rest of their career.
Mistake #2: Rushing the Return to Normal
“She’s back—let’s get her up to speed.” “He seems okay. Probably ready to dive in.”
What’s really happening: You’re equating presence with readiness. But showing up doesn’t mean they’re whole. Grief doesn’t clock out when the laptop opens.
The cost: They burn out trying to prove they’re okay. They pull away rather than ask for help. And when performance slips, leaders get frustrated instead of curious.
What you missed: A chance to lead with patience and steadiness, proving that support and high standards don’t have to compete.
Mistake #3: Trying to Fix the Unfixable
“At least you had time to say goodbye.” “They’re in a better place.” “Everything happens for a reason.”
What’s really happening: You’re trying to soothe your own discomfort by tidying up their pain. These aren’t words of comfort—they’re escape hatches from emotional complexity.
The cost: You invalidate their experience. They stop sharing. And others on the team learn: “Grief doesn’t belong here.”
What you missed: A moment to stay steady in someone else’s pain and to become the kind of leader people trust and turn to when things are hard.
Mistake #4: Assuming Grief Looks One Way
“She’s not crying—she must be doing fine.” “He’s angry all the time. That can’t still be grief.”
What’s really happening: You’re using your own emotional template to read theirs. But grief isn’t a feeling—it’s a state of disorientation. It shows up as silence, sarcasm, rage, detachment, or workaholism.
The cost: You misread the signs. You make the wrong call. And over time, your team learns to hide what’s real to be seen as “okay.”
What you missed: A chance to lead with humility and curiosity and practice empathy that meets people where they are, not where you, or they, think they should be.
Mistake #5: Vague Support with No Follow-Through
“Take all the time you need.”
“Let me know if there’s anything I can do.” “We’re here for you.”
What’s really happening: It’s Not About Getting It Perfect. It’s About Showing Up.
You're not expected to have all the right words. That's an impossible expectation for anyone to achieve. So please, let it go right now.
What to Say and What to Ask
You don’t need perfect words. You need the courage to say something—and the character to follow through. Most leaders go silent around grief—not because they don’t care, but because they’re afraid to say the wrong thing. That silence can feel safer in the moment, but it often leaves the grieving person feeling unseen, unsupported, and unsure if it’s okay to be fully human here.
You don’t need to fix grief. (you can't anyway)
You don’t need to deliver a flawless speech.
But you do need to show up, and speak with intention.
No-oriented questions – to offer control and safety
Compassionate questions – to deepen trust and connection
Grounded recognition – to honour their strength and humanity
No-Oriented Questions: Offer Control When Everything Feels Unstable
What They Are
No-oriented questions are a communication tool designed to make it emotionally easy for someone to decline or set a boundary—without guilt, explanation, or fear of disappointing you. These questions are structured so the most comfortable, low-effort response is “no,” which helps the person protect their time, energy, and emotional space.
Why They Work
When someone is grieving, their inner world is often chaotic and unpredictable. Their energy is low, their decision-making feels cloudy, and even simple interactions can feel like too much. In that state, well-intended offers can feel like pressure:
Protect autonomy by giving the grieving person control in a moment where so much feels uncontrollable.
Reduce emotional labor by offering a low-effort way to respond—“no” is quick, clear, and safe.
Signal respect by showing you’re not trying to push, fix, or intrude—you’re offering support, not demanding engagement.
Foster trust because the other person doesn’t have to wonder what’s expected or fear saying the wrong thing.
At their best, no-oriented questions open a door without requiring someone to walk through it. And when someone’s capacity is limited, that might be the most compassionate thing you can offer.
A Quick Example: Yes-Oriented vs. No-Oriented
Yes-Oriented Question:
Examples:
“Would it feel intrusive if I asked what kind of support feels most helpful right now?”
“Would it be crossing a line to ask how you’re holding up?”
“Would it be inappropriate if I offered to take something off your plate this week?"
“Would it be too much if I checked in again tomorrow or a few days?”
“Would it make you feel worse if I suggested we pause or reschedule that meeting?”
No-oriented questions don’t avoid the hard stuff—they make it easier for the other person to set boundaries without having to explain themselves.
Compassionate Questions: Invite Reflection Without Pressure
What They Are
Compassionate questions are gentle, open-ended invitations for a grieving person to explore and express what’s true for them—without assumption, intrusion, or expectation. They aren’t about “getting someone to talk.” They’re about
Don’t require emotional labor to answer
Let the other person lead the depth of the conversation
Normalize grief without making it heavy
Invite—but never demand—disclosure
These are relational tools, not emotional crowbars. They’re built on presence, patience, and deep respect for the other person’s boundaries.
Why They Work
Grief often creates an internal shutdown. People feel numb, disconnected, or overwhelmed. They may be unsure of what they feel, or feel too much at once. In that disoriented state, people tend to withdraw—not because they don’t want support, but because they don’t know how to ask for it.
They reduce pressure by making it okay to say as little or as much as the person wants.
They restore agency by letting the person steer the conversation.
They normalize grief by creating space for hard, honest, and even joyful parts of the experience.
They build trust because they say, “I care about your reality—not just what’s convenient or comfortable for me.”
These are not starter questions. You don’t open a one-on-one by diving into someone’s pain. You offer presence first. You show you’re trustworthy in small moments. You listen without trying to fix. Only when psychological safety has been established should you begin to ask these kinds of questions.
Examples:
Opening the Door Without Pushing It Open
"If it feels right today, I’d love to hear something you love about them. How would that feel to you?
"What memories of them have been showing up for you these days?"
Keeping It Conversational
“What's reminded you of them in meaningful or unexpected way?”
“What’s a memory of them that still makes you laugh?”
Letting Them Feel Without Pressure
“How are other people’s expectations of your grief affecting you?”
“In what ways has your grief surprised you?”
“What’s something you’re carrying that you wish you didn’t have to carry alone?”
“What’s something you’ve been holding back from saying but feel like you need to?”
Making Space for the Hard Parts
“What kinds of moments make you feel like you need more space from others?”
“What’s been frustrating you the most about how people react to your grief?”
“What’s been the most exhausting part of all this?”
“How do you feel when people try to tell you how you ‘should’ be grieving?”
Helping Them Feel Less Alone
“What’s something people say with good intentions that doesn’t sit right with you?”
“Who has been there for you in a way that’s really mattered?”
“How do you handle the pressure to act ‘okay’ around others?”
Before you ask, ask yourself whether you truly want to understand them better or, are you asking to feel better about yourself?
“What happened?”
“Was it expected?”
“Do you have closure yet?”
These questions are about your curiosity, not their healing. Stay focused on what serves them.
Grounded Recognition: Honour Their Strength Without Putting It on a Pedestal
What It Is
Grounded recognition is the practice of naming what someone is carrying—and how they’re carrying it—with clarity, respect, and steadiness. It’s not about cheerleading, praising, or trying to make them feel better. It’s about
Why It Works
When someone is grieving, they’re often navigating an invisible, exhausting internal world. On the surface, they may look composed—or angry, distracted, quiet, fine. But inside, they’re carrying something immense. And too often, no one names it.
You see their effort to keep showing up in the middle of pain
You accept them as they are, without trying to fix or change them
You’re not afraid of their grief or uncomfortable with their truth
You’re here, not because of obligation—but because you care
Where silence leaves people feeling invisible, grounded recognition offers something rare and powerful: the experience of being fully seen, without being put on display.
What It Sounds Like
Sometimes, the most meaningful thing you can do is name what’s true:
“You’re carrying something heavy, and I see the strength it takes to keep showing up.”
“You don’t need to explain or be any other way than how you truly are. This space is here for you.”
“I won’t pretend to know what it’s like—but I respect the way you’re walking through this.”
“There’s no expectation to be okay. You’re doing this in the way that’s right for you.”
“You don’t have to hide your grief to be supported here.”
These statements don’t fix anything. They don’t need to. Their power lies in their steadiness, their sincerity, and their refusal to look away from what is hard.
Leadership Isn’t Just What You Say. It’s What You Do Next.
Words matter. But follow-through matters more.
If you say, “I’m here,” be there next week, not just today.
If you say, “Take your time,” don’t rush them with passive-aggressive deadlines.
If you say, “Let me know if you need anything,” follow up with something specific.
Make your care measurable.
Offer something real:
“I’ll block your calendar for that recurring meeting for now.”
“Let’s check in next Friday and adjust things as needed.”
“I’ll take that client call this week so you can focus on breathing room.”
“I’ve set a reminder for the anniversary date—we’ll plan for a lighter load that week.”
You’re Not Failing - You’re Learning What No One Taught You
If you’ve made some of these mistakes, you’re not alone. Most leaders were never shown how to support grief at work. But the fact that you’re reading this now—that you’re willing to look closer, to lead differently—already sets you apart.
You don’t need to be flawless. You need to be present. And you need the language that helps people feel seen, not silenced.
In the next chapter, we’ll go deeper into that language: How to validate someone’s emotions in a way that respects their experience, honors their strength, and doesn’t overstep.
Because the moment you’re willing to hold space for grief is the moment you begin to strengthen trust, one human interaction at a time.
I wish this was part of all leadership training with annual refreshers. Not tick the box, I completed this type of a refresher. Instead a refresher where real conversations are had and real hearts heard.
Thankyou for such an excellent article.