
Let’s be honest: the modern workplace is often built for productivity, not for people. We’ve all been there, trying to maintain a professional “game face” while dealing with the messy reality of being human. Yet, when a colleague or employee experiences a profound loss, that professional mask doesn’t just slip; it shatters.
In my work at Arik Housley Speaking, I’ve seen firsthand how communication often breaks down the moment grief enters the room. We want to be supportive, yet we are so terrified of saying the wrong thing that we often end up saying nothing at all, or worse, we say exactly the wrong thing.
If we want to build resilient, connected teams, we have to stop treating grief like a HR problem and start treating it like a human experience. Here are the biggest communication pitfalls to avoid and how you can actually show up for your people.
Pitfall #1: The “I’m Sorry for Your Loss” Wall
We’ve all done it. We hear the news, we walk up to the person’s desk (or send a Slack message), and we deliver the standard: “I’m so sorry for your loss.” Then, we check that box and never mention it again.
It’s safe. It’s polite. Yet, it’s also a wall or even a tick-box. By never bringing it up again, we might signal to the grieving person that their loss is a one-time event that we’ve already moved past. It can make them feel like they have to hide their ongoing pain to keep the office vibe “normal.”
The Fix: The Authentic Follow-Up
Instead of the one-and-done approach, try saying, “I’m thinking of you.” It’s simple, it’s low pressure, and it doesn’t require a script. The magic is in the follow-up. Check in a few days or a week later. Check in a month later. A quick, “Hey, I’ve been thinking about you today, I brought you a coffee” lets them know they don’t have to carry the weight in total isolation and the coffee (even if not their preferred order) shows presence of mind.

Pitfall #2: The Comparison Trap (The “Dead Dog” Paradox)
This is the one that makes everyone cringe after the fact. In an attempt to empathize, we try to relate our own experiences to theirs. “I totally know how you feel; when my dog passed away last summer, I was a wreck for a week.”
Stop right there. While your grief for your pet (or your grandmother, or your childhood home) is valid, comparing it to someone else’s current tragedy is a fast track to making them feel unheard. Grief isn’t a competition, and “I know how you feel” is never true.
I have used frequently, “I know how it feels, yet I have no idea how you are feeling.” Shit, I didn’t know how my wife felt in losing Alaina, unless she told me and we suffered the same tragedy.
The Fix: Admit You’re Speechless
You don’t need to be a philosopher. You just need to be a person. Use a simple acknowledgment like: “I don’t have the right words, but I’m here.” It’s honest. It’s vulnerable. It lets them know that their loss is significant enough that words actually fail to cover it. That is far more comforting than a forced comparison.
Ironically, my pet peeve for some reason was the “I have no words” comment. I would think…Then don’t say anything, yet I knew it was an intention of kindness and compassion. It works, it’s simple.
Pitfall #3: Toxic Positivity
“Look on the bright side, at least they aren’t suffering anymore.” Or my personal favorite: “Everything happens for a reason.”
In a workplace setting, toxic positivity is often a defense mechanism. We want to “fix” the person so they can get back to their 100% productivity levels. We try to find the silver lining because sitting in the dark with someone is uncomfortable. Yet, silver linings are for clouds, not for humans whose hearts are breaking.
The Fix: Holding the Heavy Moments
Real support means giving space for the “heavy moments” without trying to fix them. If an employee is having a rough Tuesday because a song reminded them of their person, don’t try to cheer them up with a Starbucks run and a pep talk. Don’t try to cheer them up at all. Just acknowledge it. “It’s okay that today is heavy. We’ve got the workload covered; take the space you need.” We are humans and know we are here. In fact, be prepared to sit with them even in silence. If they want to talk about their loved one lost, ask for a fond story. Just be present.

Why This Matters for Your Business
When we avoid these pitfalls, we create a culture of psychological safety. People don’t leave jobs because they experienced a tragedy; they leave jobs because they felt unsupported or invisible during that tragedy.
Communication around grief doesn’t have to be perfect. It just has to be present. You don’t need a fancy policy to tell someone you’re in their corner. You just need to show up, stay present, and realize that “professionalism” shouldn’t come at the cost of our humanity.
If you’re looking to transform how your leadership team handles these tough conversations and builds real resilience, let’s talk. You can find more resources and ways to connect at arikhousley.com.

Final Thought
The next time you’re about to use a cliché or stay silent because you’re uncomfortable, remember: your colleague isn’t looking for a solution. They are looking for a witness. Be the person who isn’t afraid to look at the pain and say, “I see you, and I will sit with you.”
Check out my podcasts, contact information and other blogs at arikhousley.com. Or you can get a copy of my bestselling book Always November: Lessons in Loss, Love and Resilience.