Empathy is not a soft skill. It's sharp
How to stop managing spreadsheets and start managing humans
As a manager, you’re going to fail.
Not constantly. But sometimes, without doubt.
You’ll miss a signal from someone who needs support. You’ll fill an awkward silence in a retro when someone else was about to speak. You’ll rush a 1:1 or forget to follow up on something you promised.
Why? Because management is hard.
So how do you get better?
Try asking yourself this simple, quietly-horrifying question:
Would you like to be managed by you?
If you’re like me, there will have been times in the past when the answer was “No thanks!” Perhaps you feel like that right now.
Would you enjoy being managed by someone who’s half-distracted in meetings, always rushing, and never listening?
Would you feel seen? Heard? Trusted?
This isn’t about guilt. It’s about empathy, and not the feel-good kind you’ll find in 1000 psychology self-help websites. We’re talking about the practical, daily kind. The kind of empathy you exhibit when you listen, notice, and sync with someone. When you manage like a human being instead of a walking spreadsheet.
Empathy isn’t a vibe. It’s a skill.
And this question is how you start honing it.
How I’ve failed as a manager
There have been countless occasions where I’ve failed. Lots I’ve not even noticed, many repressed and forgotten, but some have stuck with me. As Functional Introverts, we’re destined to overthink these things forever.
Here’s just a few:
Setting up a contractor to fail, with a loose remit and no clear expectations… then blaming them for their low output
Avoiding difficult conversations, allowing a bad situation to fester and get worse
Failing to communicate important organisational updates to my team, or only doing so by dropping ad-hoc comments in slack thread replies
Let's use our killer question to dial up the empathy in each of these cases. How would it have helped?
“Would I like to be managed by me, when I don’t set clear expectations? My success criteria are undefined... I’m doomed!”
Getting poor direction is stressful. What’s expected of me? What even counts as success?
“Would I like to be managed by me, when I know that there’s an issue with team dynamics but I’m burying my head in the sand, hoping it fixes itself?”
If it’s me doing something wrong, I’d really hope someone would tell me and I can do something about it
If the issue is with another team member, perhaps toxic behaviour or unwarranted negativity, then this needs addressing ASAP. It erodes team spirit like acid
I want my manager to lead by example and and show what thoughtful, human feedback looks like, not hide from difficult issues
“Would I like to be managed by me, when I don’t provide the context the team needs?”
I need my manager to not assume everyone knows everything
As a team member, my exposure to the wider machinations of the company are limited. I need a manager who can filter useful information and pass that through, while shielding me from the noise
You can instantly see by framing things through this question, our ability to empathise is turbocharged. It helps us see our management through the eyes of the managed, and spot exactly where we fall short.
Although this process can be hard, it’s the first step to being a stand-out manager.
What does good look like?
Let’s run the empathy test in the other direction. Imagine you’re being managed by someone who does get it right. How does that feel?
You’re trusted. You’re not being micromanaged, but you’re also not left floating in space. You have the autonomy you need, but with guardrails of sincere support. You’re not on your own, you’re just in the driving seat.
Your manager has your back and you know it. They notice things. They remember. They ask, “What do you need?” not “What went wrong?”
They give feedback that helps, not hurts, even if it’s hard to hear - it comes from a place of care and concern. They encourage you to stretch, but also to pace yourself, to recover and know your limits. And when they challenge you, it comes with the scaffolding to succeed, not just pressure to perform.
None of this is about being nice. It’s about being useful.
And it can’t be faked. People always know.
You don’t need to be an emotional guru. You just need to care enough to try. That’s what empathy looks like in practice. Tuning in, being there, connecting.
Empathy is a skill you can build. You sharpen it by asking better questions, by listening more than you talk, by sharing your own failings and vulnerabilities. And of course, by regularly reflecting on your own blind spots.
The best way to support others is by helping them support themselves. Empowering people doesn’t mean fixing everything for them. It means helping them build the tools they need, then getting out of the way.
The Mirror Test
So turn the spotlight on yourself.
Ask the question that every manager should ask, at regular intervals. Stare into the mirror and ponder:
Would I like to be managed by me?
“Yes” - Great, now prove it.
“Sometimes” - Welcome to the club.
“Not right now” - Good news: you’ve already started improving as a manager by reading this blog! Right?
Because empathy isn’t a soft skill. It’s sharp. When wielded well, it cuts straight to what matters most.
Ask It Again Next Month
Like honing any skill, you need to form a habit to exercise it.
Set a reminder to revisit the question next month. You might be surprised how your answer changes. And if it doesn’t? That tells you something too.
If this piece hit close to home, you might like my Engineering Manager OS, a Notion template built to give managers the structure I wish I’d had when I started.