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The One Thing That Separates Great Engineering Leaders from Good Ones


Just to recap, this is part 4 of a 4 part series (the finale of this opening series!), the four parts being the four lessons I learned from my time as a financial advisor:

  1. Basic sales techniques, including but not limited to, being ok with silence, looking for buying questions, and how to take what someone tells you and turn it into a story where you can help them solve a problem (and not to be marginalized, how to write upside down)
  2. Every job is a sales job (you’re selling a product or yourself, but you’re always selling)
  3. Never turn down a free lunch (I would sometimes have 3 lunches in a day where I bought food for other people… and no I wouldn’t eat three lunches… but I’d for sure get a lunch to take home for every lunch after the first one!)
  4. If your job discourages you from being empathetic then your job sucks

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If your job discourages you from being empathetic then your job sucks

This sounds obvious. And maybe it is, but to me, this is a huge factor in my decision making when I’m thinking about whether I’m in a role and a company that I can invest myself in or if I’m just collecting a paycheck and need to start looking for new opportunities.

And let’s get this part out of the way, I realize the privilege that I’m coming from to be even able to make that kind of a decision, or have that kind of thought. I’m not ignorant to the fact that most people are only ever able to do the job that sucks because it’s their only way to afford to live. And this isn’t meant as a disparagement to people in those jobs. They aren’t the ones who are deciding to make their jobs not be empathetic, normally there’s some combination of “all corporations are inherently greedy” and “society is set up to fail people” and “some industries are just predatory” and probably many more impacts as well.

But that’s not the point that I’m trying to make, I’m trying to make the case that if you have opportunity and options, you should be thinking about whether the place you work is worthy of your time and effort.


To talk a little more about how I came to this conclusion and things that I look for when I’m at a company, I have to go back to a story in the last post, about the family I took out to lunch that just wanted help to pull out money they’d saved for retirement to use while the main earner was dealing with ALS. (Link to story here in case you hadn’t caught it already!)

I talked about how I didn’t help in that story. But that’s not the WHOLE story. It’s for sure true that I didn’t help, but there’s another layer I want to unpack.


After that lunch, I went back to our offices.

At the office, I had two “mentors”. One that was specifically assigned to me, and he was a guy who had been doing the job for a year or two, but by no means someone who was an “expert” in the field (he started as a car salesman, which created so much stress for him that he had a heart attack in his 30s and had to switch careers and change his entire life to manage stress), and then a branch manager who you could talk to… but honestly he was someone you tried to avoid bothering if you could (especially as a newbie like me).

I took this families situation to my mentor to try and figure out what options we even had to help him, because even though I realized that there wasn’t going to be a ton of money in it for me, my goal in doing the job of a financial advisor was to make it so that people’s money could work for them to live their lives and this seemed to fit perfectly in that goal.

When I asked him to help me out, his basic response was, “why would you bother there’s nothing that they need you for here.”

The response hit me like a freight train. Like what do you mean why would I bother? I met a family in crisis. I want to bother because I care and feel like we’re uniquely positioned to help. That’s why.

I stewed. I was so angry that he didn’t just immediately understand the way I felt about this family and the pain that I saw. I wanted to fix it, so I did what I thought was right… went to one of the computers in the office and started to do research.

Mind you, this is 2005. The internet was alive and well, but not nearly as easy to use as it would eventually become. So I did my research, there was some conflicting data, but I felt like there was a clear path that I could help on, but it would take me time and energy and I’d probably need some help to make it happen.

I knew my mentor wasn’t going to help me. So I again did what I thought was right. And I went to the branch manager.

Full disclosure… I should have known the branch managers response. This guy was clearly of the mold where he wanted to be Alec Baldwin in Glengarry Glen Ross or Ben Affleck in The Boiler Room. He WANTED to be that asshole. He saw them as heroes not as slimy pieces of shit. Exemplified by the fact that he loved telling a story of when he made it big. His first move once he made a ton of money and knew he could just splurge… was to walk into a Porsche dealership. And he specifically went in a t-shirt, and shorts and flip flops and a hat. Because he wanted to see if any of the sales people would talk to him or just ignore him. And he wanted the person who saw through his clothing to be the one who got his commission. But you know this kind of person… even if that story was true, the reason he did it wasn’t about the sales people — its as so HE could tell that story. God I still hate him.

I walked into his office, asked if he had a minute, and then sat down and went through the story of this family, the research I’d done, the things I think we needed to do to help them and the things I needed either his approval or his assistance with.

He very patiently listened. And then when I was done, he looked at me, with such disappointment and sadness. I was hoping it was sadness at the plight of this family and wanting to be a positive change agent. But that’s because I was naive.

He then starts in on everything that’s wrong with what I’m doing. We’re not a charity, we don’t have time to waste on people that can’t pay us, there’s no avenue that’s worth anyone’s time here — as he gave me the litany of reasons his voice just turned into an adult in Charlie Brown going “Wah wah wah wah wah”.

After he was done, I walked out and just felt numb. I felt a sense of loss. I felt like a failure and a terrible human being. I felt like nothing mattered. I honestly just wanted to sit down and cry. And, it’s when I decided I needed to quit.


Let’s be real for a second, this wasn’t the ONLY reason I decided I needed to quit, there was other stuff going on in my life that was making me not happy, so I’m not saying, “I was altruistic and good while everyone else was bad!” And I also look back and can say that I get where they were both coming from — we had strict quotas. They had families. They needed to feed their families just like the folks I was trying to help needed to feed theirs.

But their logic wasn’t what made me realize I was in the wrong place. It was their complete and utter lack of empathy.

In business and life we often have to make choices that have a negative outcome. It’s about balancing the negative and the positive to create the most good/least bad in any given situation. For example, I personally believe that crypto is nothing but a scam to funnel money from ordinary people to rich people (please don’t try to convince me otherwise, that’s not what this is about lol). But, while working at FIS I was presented with a situation where I could either a) build a crypto trading app or b) pick 6 people who would need to be let go.

High level the budget I already had couldn’t support those extra six folks, but the crypto folks had enough budget to support them! They just had to… build a piece of functionality that I thought was inherently evil and meant to trick ordinary people. But I had to choose, which one does the most good/bad — and I chose to save those 6 people. Luckily, I was saved by a bitcoin crash that made the app never see the light of day, but these are the kinds of decisions that business people make every day.

And I don’t begrudge people who make a decision that they think is the right one. I don’t have all the right answers, so you disagreeing with me isn’t a problem. The problem I have is when that decision is made callously.


It’s very reasonable to expect that I could have come to the exact same conclusion about the crypto app but just because “this is a way for FIS to make more money and possibly get myself more money by bringing in a huge win”, without any consideration to the people involved. It also would have been reasonable to say, “I think this is a scam and I don’t want any part of it” without any consideration to the people involved.

But I think both of those decisions would have been a huge mistake. Not because of the outcome, but because of the process.

If all I’m thinking about is my bottom line and my companies bottom line, I start missing the things that create that value. The people are building the applications. They build better applications when they’re happier! They build worse applications when they feel like their job is constantly on the line, or that a small screw up will cost them a promotion or a raise. They have families where they might have responsibilities heaped on them that they can’t possibly deal with on top of a heavy work load at the office. They may be facing health issues. Or they may have a family member in crisis.

Making decisions and ignoring the human elements makes us robotic. It makes us replaceable! It makes us less human.

Seeing the face of someone in truly dire situations and ignoring them in order to make a profit isn’t business. It’s lechery.


So what the hell is the point of all this other than that it’s very cathartic to write for myself (and trust me it really is… I don’t even know when I last told the story about that family, but it haunts me even though it’s almost 20 years ago).

Well, the point is, you should be analyzing not just the decisions that are made by your peers and leaders. You should be analyzing motivations and thought processes. You might have a leader who has excellent outcomes, but if those outcomes are based on a decision making process that isn’t empathetic, do you really trust them? You conversely might have a leader that doesn’t always get the greatest outcomes, but they always have the backs of their team members, and thinks things through in a really positive and well thought out way.

Don’t get too hung up on those outcomes. Get hung up on motivations. Motivations need that empathy included to make a difference.

And I’ll leave you with this, because this whole article was supposed to say that without empathetic leaders you likely have a crappy job. And that’s very reductive, so I tried to elaborate. But there’s one thing that I think you should be thinking about while you’re doing this exercise of analyzing motives not just outcomes.

Analyze YOUR OWN motives and empathy. If you have a leader that you would trust regardless of what they say and do, you’re not being loyal, you’re in a cult. If you have a leader you would never question for fear of retribution, you’re also in a cult, you just haven’t bought into the cult yet.

You need to be in a position where you have the safety to have your own thoughts and motives, and to question your leaders thoughts and motives. Otherwise, you’re just waiting to be replaced by a robot.