Most managers don’t care enough.
Most managers fail for one simple reason - they don’t care enough about the people they are managing.
They care about performance, optics, and their own trajectory, but not the human, and the team always knows.
You see it in the surface-level questions... in the way they listen to words instead of motivations… in how they treat outputs as the whole story instead of the final 3% of it. They think they are leading but they are really just supervising the visible parts. The way I see the distinction? Managers see performance, leaders earn the truth. Performance is the rehearsed version, truth is the raw version. You don’t earn the raw version unless people believe you see them, understand them, and won’t turn around and weaponize their honesty. You can’t create that belief without caring enough to look below the surface.
I’ve lived in five countries and worked across dozens more. That forces you to pay attention to context, culture, and subtext. High-context versus low-context communication is not a theory when you are managing a direct New Yorker, a nuanced Japanese PM, and an engineer in Singapore who reads between the lines, because directness can feel like confrontation.
Caring is not sentimentality or being “fluffy”, rather it’s precision.
Caring deeply also makes accountability easier. When you understand someone well, you aren’t guessing why they’re off track. You know if it is fear, misalignment, burnout, or lack of raw capability. And people accept accountability faster when they know you have taken the time to understand them.
The best managers read what people are not saying. They notice hesitations, nervous laughs, defensive shifts. They ask the inconvenient question that reveals the truth (this is hard, I find it hard).
“What have I learned about people during my travels?”
Here’s ten things I think are *mostly* true:
“If you look back 12 months from now, what bullet points do you want on your resume? What narrative do you want to build?”
Most people don’t know. So that’s the thing to work on. A single question unlocks ambition, insecurity, misalignment, and hidden constraints. It’s the fastest way to understand motivation.
I don’t rely on scheduled 1:1s to find out what’s going on. Good managers catch problems as early as smoke, not fire. I learned this working in cultures where forecasting risk upwards is not a conditioned or perceived virtue. Surfacing truth is often easier than asking your team to reveal it. (But I hate the phrase “trust and verify”.)
I’ll say things like: “Here’s the part I’m not sure about.” Or, “tell me why I’m wrong.”
This disarms defenses instantly. People match the vulnerability (also a word I hate) level of the leader. If you’re guarded, they’ll be guarded. If you’re open, they’ll be open. They know more about any given subject than I do.
When giving feedback, I’ll say: “You’re strong at X. The role also needs Y.”
This avoids identity threat. It stops people from hearing “you are wrong” when the truth is “the role requires something more and we can work on that together.”
I comment on the signal, not the output. My job is to enable people to do their best work, not know the answer.
“You hesitated before answering. What was behind that?”
“That joke/laugh - is something feeling unclear or risky?”
“Are you saying yes because I am asking you to say yes?”
I share the “why,” the tradeoffs, the parallel considerations, the incentives, the pressure... Not every detail - but enough for people to understand how decisions get made and so they have the same context I would want.
Information asymmetry creates fear and suspicion. Context creates alignment and speed. The extra time context sharing always pays back.
I don’t let problems metastasize. If something feels off, I say it. If expectations are misaligned, I reset them immediately. If accountability is required, I handle it directly and transparently. This can be hard - and I find it hard - but teams run toward truth when they trust it won’t be used against them.
Trust is the entire game. You know someone trusts you when they tell you what they’re actually considering, not the safe version. Early warnings beat late confessions.
“When someone gives you the truth early, everything else becomes easy.”
This is not just about culture, it’s about context, and sometimes it takes months to learn. Words are only half the equation. Show people you remember your last conversation. Be explicit, but listen for subtext, invite challenge, and earn the right for them to open up. Give people time if they need it - a quality answer a couple of hours later is always better than now.
I used to think a lot about what I wanted my brand to be, and projected that. Now I think about what the person I am talking to needs from me. Sometimes it’s just 15 minutes to vent, and that’s ok!
I would always pay someone more to tell me “something’s weird” before it’s a problem, than try to hide it and fix it alone. They still might do that, but I need to know it is a risk and be prepared if they cannot.
I try things in front of the team - even things I might get wrong. Whether it’s product strategy, brand decisions, or telling a story about fixing an AC unit with YouTube and a wish (it blew up). I try to explicitly call out when I am guessing rather than guard my own limitations.
Caring doesn’t take more time, it takes presence.
These observations can take seconds, and managers who claim they do not have time are usually avoiding the discomfort of truly dialing in. Good managers collapse the distance their position creates by being consistent, principled, and human.
“Caring is not softness. It means telling the truth early, not shielding people from consequences.”
The irony is that caring deeply produces better business outcomes than the mechanical version of management that obsesses over KPIs but ignores humans. When people believe you care, they tell you the truth earlier and make better decisions because they are not protecting themselves from you.
And that is the real point. Managers only see the performance; leaders earn the truth. The best way to cross that line?Caring.
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