My brother Rob was born in October. He's not here anymore, so this month has a way of bringing him closer than the rest of the year does. Not in the dramatic, stop-what-you're-doing way it was in the early years, but more like a low hum. A reminder that the people in your life are carrying things you can't see, and that the distance between "fine" and "not fine" is often a lot shorter than anyone lets on.
I bring this up because losing Rob changed how I see the people I work with. Not overnight, and not in some clean before-and-after way that makes for a good story. Grief doesn't work like that, at least not in my experience — it doesn't arrive with instructions… it just settles into the background and reorganizes how you pay attention to the world. For me, that reorganization happened slowly. I started noticing things I used to look past: the analyst who went quiet in meetings when she used to be the first one to speak up, the engineer who started staying late every night (which everyone praised as dedication, but which looked to me like someone who didn't want to go home), the leader who was hitting every metric and looked like he was running on coffee, fumes, and willpower and not much else.
I started asking people how they were doing — and not in the hallway version where "good" is the only acceptable answer, but where you actually wait for the response and pay attention to what comes back.
What came back, more often than I expected, was that people were struggling with things that had nothing to do with work but were affecting everything about how they showed up to work. A parent with a new diagnosis. A kid failing out of school. A marriage falling apart in slow motion. Financial stress that made every day feel like walking a tightrope. These weren't occasional crises — they were the ongoing, grinding realities of adult life, the kind of stuff that doesn't show up on a dashboard but absolutely shows up in how someone performs, communicates, and engages.
I think most leaders know this on some level, and either don't know how to handle it or don't care to take action. The problem is that very few organizations are built to actually account for it. We design work environments around the assumption that employees show up as fully available, emotionally regulated, cognitively sharp professionals who leave their personal lives at the door. That assumption has always been fiction, but we've built entire management frameworks around it. Performance reviews, productivity metrics, meeting cultures, promotion criteria — all of it assumes a person who exists only as a worker. The whole human never enters the spreadsheet.
I'm not saying leaders need to become therapists. I've been in conversations where that pushback comes up immediately: "I'm not trained for this." "That's what EAP is for." "I don't want to open a door I can't close." I get it. Nobody signed up for management expecting to navigate someone else's mental health crisis on a Tuesday afternoon. But there's a vast space between being a therapist and being a person who notices when someone on their team is struggling. You don't need clinical training to say "how are you doing, really?" You need the willingness to ask and the patience to listen to whatever comes back. That's not therapy… it's just basic human attention.
What I am saying is that pretending the rest of someone's life doesn't exist, or that it shouldn't affect their work, is a form of organizational delusion that costs more than most companies realize. It costs you in turnover, because people leave managers who don't see them. It costs you in disengagement, because people stop bringing their best when they feel like their best is all anyone values. It costs you in trust, because the gap between "we care about our people" on the company values poster and "nobody here has ever asked me a real question about how I'm doing" is a gap people feel every single day.
I managed someone years ago — call her Sarah — who was one of the most capable people on my team. She could write policy, run an audit response, and present to executives with a level of clarity that made the rest of us look rough. Then she went through a divorce, and everything shifted. Not just her output — she was quieter, distracted throughout the day. She wasn't sleeping, which I could see in her face even though she never mentioned it. The version of Sarah who showed up to work was going through the motions of being "Sarah," and she knew it, and she knew everyone else on the team could see it too.
As always, I want you to learn from my mistakes. Here's what I didn't do, and I'm not proud of this. For about six weeks, I said nothing. I told myself I was giving her space. Honestly, what I was really doing was avoiding a conversation I didn't know how to have. I was afraid of overstepping. I was afraid she'd break down and I'd be standing there with no idea what to do. As a newer manager, I'd been taught that work is work and personal is personal and the line between them is sacred.
That line is a myth. It's a convenient myth because it lets leaders off the hook for paying attention — but it's a myth. Sarah's divorce was affecting her work because Sarah is a whole person, and you can't partition a human being into functional modules. The personal stuff was the work stuff, and ignoring one meant ignoring both.
When I finally did talk to her, I didn't lead with performance. I led with: "I've noticed you seem like you're carrying something heavy, and I wanted to check in." That's it. Not a script from a management training book, not a formal sit-down with HR talking points — just one person saying to another: I see you, I'm paying attention, and you don't have to pretend everything is fine if it isn't.
She told me what was going on. Not everything, I'm sure, but I didn't need everything — just enough to understand. We talked about what she could realistically handle for the next couple of months, and we adjusted her workload. Not as a favor, and not with a guilt trip attached. Just a practical acknowledgment that she was a human being going through a hard time, and that the work would still be there when she was ready to take it back on.
What she told me later stuck with me more than anything else in that conversation. She said the six weeks where nobody said anything was worse than the divorce itself, at least in her work life — because she knew she was slipping, and she knew everyone could see it, and the silence felt like either pity or indifference, and she couldn't tell which was worse. She said my asking felt like someone throwing her a line — not pulling her in, just letting her know someone noticed she was in it.
I've thought about that a lot. Just how little it actually takes to make someone feel seen, and how rarely most of us do it. Not because we don't care, but because the workplace has taught us that caring is someone else's department. HR handles the personal stuff. EAP handles the mental health stuff. We've divided the human experience into functional silos the same way we divide an org chart, and then we wonder why people feel like nobody at work actually knows them.
I had another team member — call him Marcus — who had an attendance pattern that was starting to create problems. Not dramatic absences, just a persistent drift: late arrivals, early departures, occasional Fridays that disappeared without much explanation. The easy management response was procedural — document the pattern, have the corrective conversation, follow the progressive discipline playbook. I've seen other managers do that. It fixes the attendance and breaks the relationship.
Instead, I asked him what was going on. Genuinely, without an agenda. "I've noticed something, and before I make assumptions, I want to hear from you." He told me he was dealing with some things at home. He didn't elaborate, and I didn't push. But the fact that I asked — instead of leading with the policy manual — changed the entire dynamic. We worked out an adjusted schedule that gave him some flexibility without leaving his team guessing when he'd be around. The pattern stabilized. And importantly, he started talking to me when things got complicated instead of just going quiet and hoping nobody noticed.
That's the part worth emphasizing. When people believe their leader actually cares about their wellbeing — not as a performance strategy but as a basic human commitment — they communicate earlier, more honestly, and with less fear. The relationship shifts from transactional to something closer to real. Not friendship exactly, but a level of real trust. The kind where someone can say "I'm not doing great" without worrying that it'll show up in their next performance review as a weakness. They tell you when they're struggling before the struggle becomes a crisis. They flag problems before the problems become emergencies. They bring you the uncomfortable truth instead of the comfortable fiction — not because you demanded transparency, but because you created an environment where transparency didn't feel dangerous.
I want to be clear about something: paying attention to people's wellbeing isn't the same as having no standards. I've seen that confusion play out, and it doesn't end well. The leader who responds to every struggle by removing expectations isn't being compassionate — they're being avoidant. Compassion without structure creates its own kind of harm, because the person who's struggling doesn't need you to pretend the work doesn't matter. They need you to help them figure out what's realistic while they get through whatever they're getting through. Lowering the bar without saying so isn't a kindness. It's a slow erosion of someone's professional identity, and most people can feel it happening even when nobody names it.
The leaders I respect most are the ones who can hold both realities at once. Yes, you're going through something difficult. Yes, the work still matters. Let's figure out together what "good enough" looks like right now, with the understanding that "right now" isn't forever and that the standard will come back up when you're ready. That's not a contradiction. That's just honest leadership.
There's something else I've learned that I wish someone had told me earlier in my career: the conversation doesn't have to be perfect. I spent years avoiding check-ins with struggling team members because I was afraid of saying the wrong thing. What if I make it worse? What if they don't want to talk about it? What if I accidentally cross a line? Those fears feel reasonable in the abstract, but they're almost always worse than the reality. In my experience, the conversation where you stumble a little but show up with genuine concern does more good than the perfectly articulated silence where you say nothing at all. People can tell the difference between someone who's awkward because they care and someone who's polished because they don't.
I think about the signals we send without realizing it. The manager who eats lunch at their desk every day and never takes a vacation is telling their team something, whether they intend to or not. The leader who sends emails at 11 PM and then says "I don't expect you to respond right away" is sending two messages at once, and the team hears the louder one. The organization that offers an employee assistance program but makes the culture around using it so awkward that nobody calls is checking a box, not supporting people.
Wellness isn't a program you roll out at the all-hands. It's not the meditation app in the benefits portal that nobody uses. It's not the monthly newsletter with tips for managing stress, written by someone who has never had to manage a team through a reorg while their own job was on the line. Wellness is a culture. It's whether people feel safe saying "I'm not okay" to the person who controls their next promotion. It's whether taking a mental health day feels as unremarkable as taking a sick day when you've got the flu. It's whether your one-on-ones include a real question about how someone is doing, or whether they're just status updates with a calendar invite.
I know a technology leader who, within the last few months, lost a team member to suicide. He told me afterward that he'd noticed something was different in the weeks before — the guy had gone quiet, stopped joining the team for lunch, seemed disconnected. He noticed, but he didn't ask. Not because he didn't care — he's genuinely a caring person — but because he told himself it wasn't his place, that it was probably nothing, that bringing it up might make things awkward. He now carries that with him. I'm not saying a conversation would have changed the outcome — nobody can know that for sure — but the regret of not asking is a weight I've watched him carry, and it's shaped how he leads now. He asks every time he notices something off. Especially when it's awkward.
I'm not perfect. I've gotten this wrong plenty of times. I've been the manager so focused on deliverables that I missed the person delivering them falling apart. I've been the leader who noticed something was off and told myself it wasn't my place to ask. I've been — I am — the one sending those 11 PM emails and genuinely believing my team didn't feel pressured by them. (They do.) Every one of those failures taught me something, mostly that the cost of not paying attention is almost always higher than the awkwardness of paying attention.
I also want to say something about the people who leave, because not every story ends with the adjusted workload and the grateful conversation. Sometimes you do everything right — you notice, you ask, you accommodate — and the person still leaves. It's not about you. They needed a change. The situation at home may require a move, or the role just isn't working anymore for reasons that have nothing to do with how well they're managed. Wellness-aware leadership doesn't guarantee retention, but it guarantees that when people leave, they leave knowing someone saw them. That matters more than you'd think, because people talk. They tell friends who are job hunting, tell former colleagues. The reputation of your team as a place where people are treated like human beings is one of the most powerful recruiting tools you'll never see on a slide deck.
There's a version of this that some leaders resist because it feels soft. I understand the instinct. We've been conditioned to believe that business is business, that sentiment is a liability, and that the best leaders are the ones who make tough calls without flinching. There's a kernel of truth in that — you can't lead effectively if you can't make hard decisions. But somewhere along the way, "make hard decisions" got confused with "don't feel anything while you make them," and those are very different things. The best leaders I've worked with felt the weight of their decisions. They could sit across from someone in pain and be honest without being cold. That takes more strength than the stone-faced version, not less.
Like most of what I write, I'm not writing this because I've figured it out. I'm writing it because I think about it constantly, and because I think more leaders need to say out loud that they think about it too. The mythology of leadership is all confidence and clarity and decisiveness. The reality is a lot of uncertainty, a lot of moments where you're not sure if you're helping or making things worse, and a lot of learning that only happens after you've already gotten it wrong.
The organizations that get this right don't do it because they have better benefits or bigger budgets. They do it because someone in a leadership position decided that noticing mattered. One person. One manager who asked a real question and then actually listened to the answer. That's where it starts. Not with a policy or a program, but with a single person.
What I keep coming back to is something simple that's harder to practice than it sounds: pay attention to your people, not just their output. Notice when someone's energy changes. Notice when someone stops laughing, or when someone who used to push back in meetings starts agreeing with everything because they don't have the fight left in them. Those signals are there if you're willing to see them, and most of the time, the person sending them is hoping someone will.
You don't have to have answers. You don't have to fix anything. You just have to let people know they're not invisible — that the person behind the employee badge matters to you, not just the work the badge gets access to.
Rob didn't have anything to do with management or leadership. But losing him taught me something I carry into every one-on-one, every team meeting, every hard conversation: people are dealing with more than they show you, time moves faster than you think, and asking someone how they're really doing is never the wrong call.
It's a small thing. It costs nothing. Most leaders still don't do it.