There’s a moment most managers dread: sitting across from a team member who is clearly not okay. The work is slipping, their energy is gone, and something personal is written all over their face, even if they haven’t said a word.
Most managers default to one of two bad options. They either push through it professionally (pretend not to notice, focus on deliverables) or they offer an empty “Is everything okay?” that signals they don’t really want the answer.
The managers who handle these moments well do something different. They go first.
You can’t always leave that baggage at the door
Early in my career, I hit a wall. I was going through something hard, the kind of hard that doesn’t stay home when you walk into the office. My work suffered. I wasn’t performing the way I had been. And I was lucky: my boss noticed.
He didn’t lecture me. He didn’t put me on a performance plan. He sat down with me, told me he’d seen the change, and asked what was going on. Then he told me about something I didn’t even know existed: short-term disability leave. He suggested I use it.
That conversation changed everything for me. Not just because of the leave, but because someone with authority over my career treated me like a human being first.
“You can’t always leave that baggage at the door. And as a manager, it’s not your job to pretend otherwise.”
Years later, I had a team member going through something similar. A death in the family. A sick partner. Two major life crises happening at the same time. I could see it in everything: his energy, his focus, his work. I knew this look.
Because I had been there.
I sat down with him. I didn’t open with performance metrics. I told him what I’d seen, I told him I wasn’t there to judge, and then I shared something personal: I told him about my own experience, what I’d gone through, and how a manager once helped me the way I was trying to help him now.
Then I told him about short-term disability. And I told him something specific, something I only knew because I’d done my homework: the company we were at offered 100% coverage during leave, not the 60% I’d had at my previous employer. That detail mattered. The difference between 60% and 100% can be the difference between whether someone actually takes the time they need.
He went on leave. He came back. He did really well.
What Brené Brown gets right about leadership
Brené Brown has spent decades studying vulnerability and trust, and one of her central findings applies directly to the 1-on-1: leaders who show vulnerability first give others permission to do the same.
When you walk into a meeting projecting invincibility (all competence, no cracks), you send a signal without meaning to: this is a place where weakness isn’t safe. And your team members hear it, even if they never say so.
The opposite is also true. When you share something real (a mistake you made, a hard season you went through, something you wish someone had told you earlier), you lower the barrier. You signal that humanity is allowed in the room.
“What would you have wanted someone to say to you? That question is where empathy starts.”
This doesn’t mean oversharing. It doesn’t mean turning 1-on-1s into therapy sessions or making your struggles your team’s emotional burden. It means being a real person, and letting that realness create space for theirs.
Rapport isn’t built in one conversation
Tuckman’s stages of team development (forming, storming, norming, performing) describe how groups move from uncertainty to trust over time. The same arc plays out in the 1-on-1 relationship.
In the early stages, there’s caution. Your team member is feeling you out. They don’t know yet whether you’re safe, whether you’ll use what they say against them, whether you actually care or you’re just doing the management thing.
Rapport is what moves them through that uncertainty. But rapport isn’t a single gesture; it’s the accumulation of small, consistent signals that say: I see you, I remember you, I’m here for you.
That’s why taking notes matters so much. Not just operational notes: personal ones. When someone mentions their kid has a big game this weekend, write it down. When they’re dealing with something hard, note it. Then ask about it next time. That small act (“How did the game go?”) signals more than any speech about psychological safety ever could.
Consistency does the same work. Showing up to every 1-on-1 prepared, present, and engaged is a form of empathy. It says: your time matters. You matter. I didn’t forget about you this week.
Know your resources
One of the most underrated aspects of empathy in management is preparation. I wrote about this in the psychological-safety essay, and the short version holds: know your company’s EAP, know how short-term disability works and what the coverage percentage actually is, and know who in HR is a safe person to involve without betraying a confidence. You can care deeply about a team member who is struggling, but if you don’t know what options exist, your empathy has nowhere to go.
“Knowing your resources is an act of empathy. It means you’re ready to help before you’re asked.”
Key takeaways
- Vulnerability is a leadership tool. Sharing your own relevant experiences doesn’t undermine your authority; it builds trust.
- Ask yourself “What would I have wanted someone to say to me?” That question is a compass for empathy in the moment.
- Rapport is built through consistency: small, repeated acts of presence and remembrance, not a single powerful conversation.
- Take personal notes. Remembering what matters to someone is one of the clearest signals that you actually care.
- Know your company’s resources before you need them. Being prepared to help is itself a form of empathy.
- The goal isn’t to be a therapist. It’s to be human, and to make it safe for your team member to be human too.