10 min read · 1,870 words

Empathy is exhausting


Obviously I’ve been spending a lot of time thinking about empathy and its role in the workplace, and how it makes better work environments, work outputs, work products yada yada yada. And I keep thinking that things I’m saying are fairly obvious and that people would pick up what I’m putting down and overall it’d be easy enough to take some of my learned lessons and turn them into something else.

But the more I’ve been thinking about it, the more I’ve been thinking that the problem isn’t about not knowing when and how to employ empathy, but rather that the process of doing it is just really hard. And, like parenting, it doesn’t get easier the more you do it, it just changes (we could have a LONG talk about that with parenting but today we’re talking about work lol).

So today, I wanted to go into a few examples of why it can be so hard, how you can overcome the overwhelm, and how sometimes you can embrace the lack of empathy. Because we’re all exhausted by (gestures at the world) everything. And we need to give ourselves as much empathy as we’re trying to put out into the world.


So why is it so hard to practice empathy at work?

I’ve given a ton of reasons already why it’s worthwhile and doable, but not exactly what keeps people from doing it. Keep in mind this is all anecdotal so I’m not trying to say “this will work for everyone!” or “this is why everyone fails!” I’m just trying to give some examples and show some options for how to better identify when you are and are not practicing empathy and how to either shift your mindset. And sometimes, why it’s ok to be in a space without empathy. WHICH I KNOW IS A WEIRD THING FOR ME TO SAY. But it’s also true. There’s no one quick solution. There’s no right answer. There’s just opportunities to learn and grow.

So let’s jump into it.


Mistaking Your Expertise for Empathy

I feel like this is the most common reason that we neglect to have empathy in work. Especially when you’re in a product company. This also happens in consulting scenarios, but I want to focus on product companies because you’re more entrenched in a specific business and product. Which one the one hand is great, because you have an incredible amount of knowledge and experience in a specific industry.

But sometimes that experience and knowledge blinds you. It’s easy to interpret your situation and expertise as definitive. And often, when you’re working in a product company, you’re always up against deadlines. You have a limited budget, you have limited time, and you have limited flexibility. And while most of the time product folks start off doing user interviews and deep research on expectations… as you get more knowledge and more experience, you tend to lean less on those interviews and research items and more on your own expertise.

And the second that you start making that shift, the empathy muscle starts to atrophy. Because instead of finding real world examples to prove how your users or your employees or your stakeholders are thinking, you start using your experience.

And you might even find some success! Some of the time, it’s important to not just listen to what people say they want but to see what’s coming and push your clients toward a better end state.

But that takes a specific kind of skill and recognition of ones own limitations that is rare. Being able to point out a new way of working that’s against your experience takes a lot of humility that’s tough to use when you’re an expert in your field!

So, I guess the idea here is that I should suggest options for how to overcome this right? Well, I think the main way to overcome it is, to start by accepting as a reality that your expertise isn’t the same as empathy. The only way to tackle a challenge is to admit that the challenge is there and needs to be tackled!

The next step is to constantly question your own comments. Which is really tough to do, but a GREAT exercise to run through whenever you’re making a decision. Instead of simply making a suggestion or putting out an idea, interrogate your idea. Ask “why is this right” and then force yourself to put detail around it. The more you confront your opinions and expertise with genuine curiosity the more likely you are to find the empathy that you’re looking for in your solutions!

One of the greatest keynotes I ever heard was while I was at Smith Barney, where the speaker was talking about the lessons she learned going from being a nun to being a financial advisor to being an advocate for financial advisors (she was so cool lol) — but her entire premise was that when someone gives you an opinion ask them why at least 3 times. Each time you clarify yourself, you end up seeing more of your answer and in the end, finding more empathy for yourself, your end users, and your solutions!


You Don’t Just Focus on Solutions

On top of all the roadblocks we just covered, there’s the fact that you’re not ever able to live in a world where we’re JUST debating ideas and backlogs when we’re at work. There’s egos, people’s feelings, and just general emotions you have to navigate at the same time!

Now try and throw empathy on top of all those roadblocks. How do you REASONABLY do it. Notice I didn’t make that a question. It’s a statement. How on earth do you reasonably expect someone to navigate all of the complexity of human emotion in addition to the complexity of large scale technology problems, and still maintain empathy.

You have to make a decision about whether or not your empathy has guardrails against it.

I spent a lot of my early career doing the exact opposite of what I suggest in this whole substack. I would completely ignore people’s feelings and just focus on solutions. And I’d be so direct that a ton of people I worked with probably just thought I was an asshole. Because I was absolutely being an asshole.

I was trying to be empathetic toward my stakeholders, the people who were taking advantage of whatever value I was providing. But I wasn’t thinking about the people that supported ME and our company!

It ranged from yelling at bosses and telling them that they didn’t know what they were talking about (it doesn’t matter if I was right I was because they couldn’t hear me because I was being a jerk!), to completely ignoring the needs of our main stakeholder because his asks were clearly stupid (they WERE but I was still wrong!), to constantly assuming my expertise was the same as empathy and acting like everyone who disagreed was just too dumb to see it (they weren’t, I was just being an ass).

And while all of that was the wrong thing to do, there’s one other pitfall I want to call out…


Sometimes, Empathy Isn’t Needed

Dude, Scott, it’s post #4 and you’re already like “the entire premise of this blog sometimes isn’t relevant”?! What the hell man.

Yea, it’s true. Sometimes the problem with empathy in the workplace is using it too much or in the wrong place.

As you can tell, I’ve done a lot of dumb stuff at work. And my typical reaction when I realize I have done something dumb is to ensure that I never do it again (or at least if I do it again I brace for the impact lol).

So I took some of the examples of ways that I wasn’t empathetic toward my colleagues then turned it too far in the other direction.

I ran a team that was remaking a mobile solution, using a proven technology, with no real unknowns involved. But the stakeholders wanted a proof of concept. And earlier in my career I would have explicitly said, “that’s dumb and you don’t need that because you don’t have anything to prove.” But because I had tried to “learn my lesson”, I wanted to work with them to find a common ground to get us to the end goal.

Mind you, my team was telling me in real time “this is dumb and we shouldn’t do this and you should tell them this is a waste of time and money”. And I would calmly say “yea, but we need to be good partners and try to get everyone on board.” I was trying to exhibit empathy for our stakeholders. And I did! I DID exhibit empathy toward them! But I didn’t show it to my team. I erred in the wrong direction. And then we spent 3 months building “proofs of concept” of things that we knew we could do. And because of the terminology the team didn’t understand that this wasn’t just throw away work I was hoping for, I was hoping for us to reuse what they wrote!

But my empathy was misplaced. It was placed where the money was and not where the work was. And that’s an easy trap to fall into, especially if you’re like me, and you’re trying to make amends for pushing so hard against the trap in the past.

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Ok, so what who cares dude. What’s the point of all this? The point is, that none of this shit is easy. And none of it is straight forward. And if you’re looking for a silver bullet, go watch a werewolf movie, because that’s the only place you’re gonna find it.

In the real world, things are messy. You’re going to think you’re doing everything right and then be shown in stark terms how wrong you were. Then you’re going to try and compensate for it, and go too far, and realize you need to back track.

But that’s when the magic starts. Because you start narrowing in on who you want to be and how you want to act.

I ended up realizing that I would have rather had the entire team that held the purse strings hate me if it meant that my team was successful. I ended up realizing that people are much more important to me than even the outcomes of any given project. I realized that when I said things like, “I just want to do cool shit at work” there was a missing “with cool people” element to it.

While I’ve focused a lot on the difficulties of empathy, the thing that I hope you take away is that just because it’s hard doesn’t mean it isn’t worth doing. The hard is what makes it good. The hard is what makes it worthwhile.

As I frequently tell my daughter, you can’t be brave without first being scared. And you won’t be scared if you’re comfortable. So get out of your comfort zone, try to be your authentic self, then learn from it. That learning from it? That’s empathy for yourself.