"What are you working on?"
This question gets asked all the time. In between meetings. Over coffee. Checking in with my team.
"How are you doing?"
This gets asked too. Often in the same conversation.
But here's what I've noticed: they don't land the same way.
"What are you working on?" invites a project list, updates, timelines. All useful information but it's more transactional. It keeps the conversation safely in the realm of tasks and deliverables.
"How are you doing?" invites a more truthful answer.
The truth sounds like: "Honestly? I'm drowning." Or "I've been stuck on this problem for weeks and I don't know who to ask." Or sometimes just "I'm tired."
The difference isn't in which question you ask. It's whether you treat the second one like a formality or an actual question.
I remember a young manager once telling me she dreaded her one-on-ones. They felt like performance interrogations. Then her leader started asking, "How are you really coping?" and suddenly she felt seen and supported. The whole dynamic shifted.
In my work with leaders, I see this pattern everywhere. We focus so hard on the ‘what’ that we miss the ‘how’. Last month, a senior leader told me she'd been asking both questions in every check-in. But she realised she was rushing through the "how" to get to the "what." Very efficient, but then one of her best people resigned. Turns out they'd been struggling for months. She was asking the right questions but not listening to the answers.
So what might shift if every check-in wasn't just about progress, but about people? If you took the time away from the hustle to listen intently to the answers?
Today is World Mental Health Day. It's a reminder about the importance of wellbeing and investing in care. As you move through the day, reflect on:
When was the last time you checked in on someone beyond their workload?
What would your team say if you asked them how they're really doing?
How honest are you being with yourself about your own wellbeing?
Caring about your people isn't soft leadership.
It's smart, sustainable, and deeply human.
Onward and upward,
Jackie
