What We Need to Remember About Empathy

Are you putting yourself in the shoes of others or doing the opposite?

Derwin Dexter Sy
The Startup
5 min readJan 25, 2021

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Here are four things I’ve learned to keep in mind when it comes to building better empathy.

I started TechManagement.Life with an article I originally posted on LinkedIn about empathy. Back then, I wrote that empathy is hard. I was at a pivotal point in my life where so many changes were happening — most notably my daughter Harper being born and, secondly, starting a new job after 12 years in my first and, at that time, only employer.

Both of these changes required enormous amounts of empathy, which I always considered a weakness of mine. A newborn child can’t speak for herself — you need to be present and try to best understand what she needs from all the subtle cues. Likewise, moving to a job where I had little experience in the domain, I needed to listen well and understand what my team was going through so I could have a good grasp on what I might be able to do for them.

Comparing then to now, empathy is still hard, and I suspect it always will be. But along the way, I’ve learned a few lessons that have helped me and which I hope would be helpful to you as well in your own journey.

Here are four things I’ve learned to keep in mind when it comes to building better empathy.

#1: It’s mainly just listening.

It’s important to overcome this nature by listening to understand first and not to respond.

We get this advise so frequently, it feels like there shouldn’t be any need to mention it any more. But there’s good reason why it’s always brought up — it’s because it’s really hard to do. Regardless of what field you’re in, most of us have been raised at home, educated, and rewarded for being problem solvers, so it’s natural to want to find immediate solutions to problems posed to us.

Still, it’s important to overcome this nature by listening to understand first and not to respond. I struggle with this, for sure. Every few sentences in 1:1s, I hear something I have a good answer to, or that I want to refute. But I actively decide to withhold that response until after they’re finished. Taking notes might help you do this with less strain on your brain, as you then won’t have to fret trying to remember everything. Of course, take notes respectfully and don’t let that distract you from hearing the rest of what the other person has to say.

#2: Put yourself in the shoes of others (not vice versa).

Don’t try to guess and anticipate needs — you’d be lucky if that works half the time. Listen instead.

This is another one that seems reasonable enough by concept, but takes a lot of mental gymnastics to truly pull off. In our attempts to put ourselves in others’ shoes, we end up doing just the opposite. It’s not for any lack of character — these opposites are more similar than it seems on the surface. It’s simply more natural and instinctive to analyze situations based on our own limited viewpoint.

To get over this challenge, we have to go back to #1 — it’s really about listening and, at the same time, trying to get a better sense of what the other person is experiencing. Perhaps more importantly, it’s also about accepting you’ll never truly understand his or her viewpoint and that you’re simply trying to learn enough to help him or her through it.

To put this as concisely and as practical as possible: don’t try to guess and anticipate needs — you’d be lucky if that works half the time. Instead, listen well and engage in joint problem solve, instead of trying to figure it out on your own.

#3: Common sense is often not as common as you think.

The fact is, there’s very little that’s truly common.

Here’s a quote to live by from The Great Gatsby:

Whenever you feel like criticising any one… just remember that all the people in this world haven’t had the advantages that you’ve had.

This is something I’ve always kept in mind whenever someone makes a mistake or doesn’t meet my expectations. In cases like this, we should first ask, “was I clear about what I actually expected?” It’s easy to excuse quick judgment by saying it should be common sense, but the fact is, there’s very little that’s truly common. We’re all raised differently — some in polar opposites in terms of environment, education, and culture — and we all experience life in our own unique ways. It’s important to remember that whenever you disagree with someone. Instead of arguing, let’s ask why — and I mean really ask, with a sincere intent to understand.

#4: Your preferences are not universal.

Tools are only effective with the right mindset. It helps to be in an inquisitive “growth mindset”.

I wrote an article previously about how the golden rule needs to be exercised with care. This is the same point I’m making now. What you enjoy or like may not necessarily reflect on others. In fact, it’s highly unlikely it will reflect on others. Understanding different personalities and just broadening your perspective in general helps.

Again, it’s about listening, instead of assuming. It’s about being there, and not about immediate action. In more practical terms, 1:1 conversations, surveys, and pulse checks are all incredible tools for managers for good reason. These all help you get a good understanding of what people like and don’t like, and allows you to make better decisions on their behalf — or better yet, actually engage them in the decision making.

Of course, tools are only effective with the right mindset. So it helps to be in an inquisitive “growth mindset” and be keenly aware that what’s true for you may not be true for others.

Do you have any of your own tips on how be a more empathetic leader or colleague? I’d love to hear your stories so do share them!

If you liked this post, do subscribe to my mailing list for more leadership stories and lessons. Originally published at https://techmanagement.life on January 25, 2021.

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Derwin Dexter Sy
The Startup

I’m an engineering manager and entrepreneur who loves exchanging ideas and helping others become better at what they do. I run a blog at techmanagement.life