The One Thing That Separates Great Engineering Leaders from Good Ones

Let’s get this part out of the way — the one thing? It’s empathy.

I’m going to use a lot of words (and lots of posts) to explain how I came to that conclusion and how my background set me up to utilize that one thing, but if you’re busy and don’t have time for all that, you’re welcome, there’s the answer!

Throughout this substack, my goal is to show how I formed my belief system that allowed me to build engineering organizations that deliver impossible transformations while putting people first. And while this applies to being an engineering leader, I think these lessons and stories will be valuable for anyone leading an organization or group of people.

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My first job out of college was as a financial advisor. Classic start to a career for an engineering leader! I had a business degree (Business with an emphasis in Cinema and Television - again, CLASSIC engineering leader story!), so I figured, I could handle the management of finances and help people along the way. Little did I realize, that entire career hinges on your ability to sell yourself! And honestly, I wasn’t great at it. I also had the difficulty cranked to 11 (just imagine, a 23 year old California guy, trying to convince people in the Cleveland Ohio Metro Area that they should trust him with their money… not gonna happen).

While I didn’t have any real success at it, it did teach me some important lessons:

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)
Every job is a sales job (you’re selling a product or yourself, but you’re always selling)
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!)
If your job discourages you from being empathetic then your job sucks

Importantly, all four of these lessons lead back to our main topic… empathy!

Today, we’re going to just cover lesson 1:

Basic sales techniques

I had no idea how to sell anything. My jobs had been being a gopher at a tech company, working in a bike store stock room and as a driver, and working at a summer camp, along with various tv internships. None of that prepares you for a “real job”.

Add on top of that, before I was officially hired, I had to pass all the licensing exams. This just reinforced all my assumptions about work; I could learn quickly, pass the test, then I was good to go! Wrong. I studied, then passed the tests, showed up day one, and the first thing I got? A script for how to talk to someone during a first meeting.

My expectation when it was handed to me was “this is the basic framework of the conversation you need to have”, but boy was that wrong. It not only was something to memorize, but part of my job was to present it to the regional director verbatim. And, to add insult to injury, the verbatim INCLUDED all the purposeful grammar errors. To make it seem more “natural”.

I absolutely hated it. I’d go out to the back of the building with a Hi-Bounce Pinky ball and throw it against a wall (channeling my inner Toby Ziegler) while trying desperately to memorize all the drivel in this script. I eventually got there - the ball throwing was necessary because I learn best while being active. But while I did, we had plenty of trainings to tell us about why the script was structured the way it was. And what a real sales pitch looked like.

Because of that, I was able to turn it into a sociological experiment instead of just a sales pitch. We started with basics, what kind of investment vehicles we used, we then talk about how we tailor our approach to the individual, and how our different options could work for them to create growth that they were not seeing from their existing advisor. We then asked leading questions to get them to ask buying questions in response (Would you like to have your money grow at 10% / year instead of what you’re getting today? — yes… but how would you do it?! — Great question…. Then back into the script). Then we flourish back to the end, where we drop the hammer and say “We’d like to do business with you, what would it take for you to say yes right now”. Then you shut up.

This was my favorite part. You shut up. You wait. You let the silence linger as long as you could so that they were forced to break the silence. They had to come up with SOMETHING. Either they’ll say “here’s what I’d need”, you then say “if I gave that to you right now, can we sign the deal”, and then you know EXACTLY where you stood. If they said they had to think about it, or they needed more time, you’d just create a sense of urgency and make it so they either had to tell you yes or no on the spot.

Now sometimes that led to a no. But that’s ok! Sales isn’t about getting yeses every time, it’s about at bats. The more at bats, the more important your batting average became. Instead of each at bat being do or die it makes it so you just want to get to an answer. Don’t be left waiting.

Ok cool Scott, fun story, but what the hell does this have to do with being an empathetic leader?

I hated the script because it was forcing a fake empathy and understanding. It’s a ruse. It’s like when we were cold calling and you’d drop the phone after saying, “Hi this is Scott, calling from…” so that way the person on the other line felt bad for you and wanted to let you finish.

It’s pretending to be a person while really just being robotic and formulaic. Right up until you ask what it would take for them to say yes. Then it became a game of empathy. I have to understand their problem, I have to understand what gets them to yes, but more importantly I have to understand WHY that will get them to yes. Otherwise the whole game falls apart. If you clearly don’t care, or if you won’t learn what your potential client needs and then provide it to them, then you’re going to lose. And I hate losing.

But I found that other people didn’t grasp it. They’d interject, they’d add context, they’d keep trying to sell sell sell. And… people hate that. They don’t like being sold to but they hate it even worse when you’re badgering them into a sale. Because people want to make their own decisions and be seen. So the whole point of silence is, it makes the client vulnerable. It makes them start to think about what I’m asking and come up with an answer.

But if you don’t have empathy for the person across from you, you’re just going to keep talking because YOU need the sale. You need the win. But the client doesn’t care about that. They have other interests, and no matter how engaging, attractive, or intelligent you are… you are not their interest.

It’s hard to have empathy when you are selling for your life. So I am not trying to say that these people didn’t have any empathy or weren’t worried about anyone but themselves; that’s not the lesson. The lesson is, it’s so hard to put your own interests aside in order to figure out what the person across from you needs. Because we’re all complicated and have so much happening inside our heads that no one else sees. And when someone can break through that, and see you, truly see you… that changes your entire perspective. And that’s what the silence created - an opportunity for you to understand the person sitting across from you.

To win a sale, or run an organization, you have to get people on your side, and you can’t do that looking inward. You have to look outward. You have to see the people you’re looking to win over, whether it’s a prospective client, or your internal team, or just a friend. If you can’t see what motivates them, what scares them, what excites them… then you can’t possibly know enough to make them buy in.

So how do you actually DO that? How do you find that empathy in a conversation? The first part is to turn off all the questions and comments in your head. Most of the time we’re just waiting for the last person to stop speaking so we can make our point. I do this ALL the time. And it’s NOISY in my head, so I had to come up with strategies to calm down the noise.

To break that streak I have to be overly attentive. I have to stop waiting for my turn to speak and instead take the time and actually take in the information I’m hearing from the person across from me.

Once you actually start listening, the focus of your next point isn’t to bring it back to your sale, or your pitch that you want to make… instead you can steal a trick I learned in my days at Smith Barney… just ask why.

“I really just want to make this app that does this thing” - why?

“I just need this functionality added to my website” - why?

“I am feeling so burnt out today” - why?

At first blush it feels SO uncomfortable. Like they’re pouring a whole problem on you and you’re asking WHY it’s a problem? But when people have to start explaining and you show that not only are you listening but you CARE, it’s going to change their brain chemistry to start wanting to explore the problem with you. And then if you can come in after with a specific solution, it’s so empowering to both of you!

“Are you telling me that if you were able to show your clients the most important products first then it’s going to enhance your business by making it easier for people to buy your best product, then that would be a success?” is such a better response than “we can put your best products first if that’s what you want”.

And the only way to get there… is to have empathy!

Thanks for reading, be on the lookout for posts every Tuesday and Thursday!