Maybe you remember the moment. Life had gotten heavy, whether it was a sick parent, a child who needed you, or a stretch where the work piled up faster than any one person could carry it, and you finally worked up the courage to tell your leader you were struggling. You chose your words carefully, hoping for a little understanding, and what you got back was a reminder of the deadlines, the numbers, and the fact that you were hired to do a job. You walked out of that conversation feeling smaller than when you walked in, and you probably spent the next few weekends trying to catch up, wondering whether anyone there saw you as a person at all.
Or maybe you remember the other kind of leader, the one who noticed something was off before you said a word, who closed the door and asked how you were really doing, and who moved a few things off your plate so you could breathe again. Chances are you would still go to bat for that person today.
If you've been working long enough, you've likely had both. I know I have, even after I stepped into leadership roles myself.
I'd love to tell you I've always been the second kind of leader, but I haven't. I've made my share of mistakes over the years, and much of what I believe about leadership today I learned the hard way, by getting it wrong and paying attention to what happened next. Those two leaders, and my own missteps along the way, have shaped the leader I've chosen to become. I'm still evolving, and I keep learning and growing with every team I have the privilege to lead.
What I took away from those experiences is simple. I'm human, and there are going to be seasons in my life when I need a little more support than usual. The same is true for every person on my team, whether that's the high performer who always goes above and beyond, the steady employee who does great work and heads home on time, or the newest hire who is still learning the ropes. I truly believe most people want to do their best work, and when something in their life changes, every one of them deserves the second kind of leader, a leader who truly cares.
Being that leader doesn't happen by accident. In my experience, it comes down to four things: leading with curiosity, listening past the first answer, lightening the load, and learning what lights your people up.
Lead with curiosity
Think back to the leader who noticed something was off before you said a word. That leader was curious, and curiosity starts with how you open the conversation. I like to begin with a simple question: "Can I offer you some honest feedback?" It sounds small, but it gives the person a gentle heads-up that the conversation might be a little uncomfortable, and it lets them decide whether they're ready to have it right then. In my experience, most people say yes.
From there, I share what I've noticed without building a case against them. I might say, "Lately, it seems like something's off, and I wanted to check in with you. Is anything going on?" I want them to know that I care about them as a person and that I'm there to listen if they want to share, while making it clear that how much they tell me is completely up to them.
Listen past the first answer
When you finally told a leader you were struggling, you were hoping for a little understanding, and understanding only comes from listening. This is the part that's easiest to rush. The first answer is often "I'm fine," so keep listening and give the person your full attention. So much of our work happens remotely now, and on a video call that means letting the emails and chat notifications pile up for a while, keeping your eyes on the person instead of your other screen, and resisting the urge to plan what you're going to say next. Ask gentle, curious questions that help you understand what they're really dealing with, because that's how you find out what's actually going on.
None of this works without trust, and trust takes time. You build it in all of the everyday moments long before the hard conversation ever happens, so that when someone is struggling, they already know you're safe to talk to.
Listening tells you what's going on, and what you do next tells them whether you meant it.
Lighten the load
Remember the leader who moved a few things off your plate so you could breathe again? That's what this step looks like in practice. Sometimes it means moving work around for a little while, whether that's asking someone else to take a project for a few weeks or stepping into the weeds yourself to fill a gap. It doesn't have to be forever; it just has to be long enough to help your person get back on their feet, so they aren't spending their weekends trying to catch up.
This is where a leader really earns the title. It's your job to decide what matters most right now, to be honest with the people above you about what your team can realistically handle, and to make sure that one person's flexibility doesn't become everyone else's burden.
Your team doesn't need to know the reason behind the change. If someone is on family medical leave, for example, that stays between the two of you, and the team only needs to know what's shifting and who's covering what. I've found that on a team built on trust, people will often jump in to help before you ever have to ask.
Lightening the load also doesn't mean lowering the bar. The person who needs extra time still deserves clear expectations and a realistic deadline, because meeting someone where they are and holding a standard can absolutely go hand in hand.
Learn what lights them up
Seeing someone as a person also means knowing what they love to do and what they're great at. I've seen people go from muddling along to on fire when they're challenged in the right way, and finding that challenge starts with really knowing your people.
Some people love a complex project, and if you hand them a problem that's been sitting out there for months, they'll dig into the research and come back with a plan. Others love the steady, detailed daily work and take real pride in getting it right every single time. When work has to move, I try to send it to the person whose strengths fit it best, so that covering for a teammate becomes a chance to do more of what they enjoy, or to stretch into something new.
That includes your steady employee who has been doing the same work for years. Find out what excites them, give them ownership of it, and let them see the impact their work has on the people around them.
Your strongest people need something a little different. You hired experts, so your job is to give them the vision and the goals, be clear about the boundaries and the timeline, and then get out of their way.
Lead the way you wanted to be led
People remember how you treated them when life got hard, just as you remember both of those leaders. When you lead with curiosity, listen past the first answer, lighten the load, and learn what lights them up, the person who was struggling comes back ready, and from that day on they'll have your back, because you had theirs when they needed it most. Years from now, you'll be the leader they would still go to bat for.
So I'll leave you with this. Think about the last time someone on your team told you they were struggling. Did they walk out of that conversation feeling smaller, or did they walk out able to breathe again?