SO

Soft Skills Engineering

Jamison Dance and Dave Smith

Episode 459: Am I cutting edge and how to compliment someone who went from super jerk to super nice

May 5, 202522 min
Summary

In episode 459 of Soft Skills Engineering, the hosts dive into a mix of technical strategy and complex interpersonal dynamics. The discussion opens with an inquiry from a listener at a fintech startup who is struggling to find resources for integrating various systems, such as CRMs, CDPs, and data warehouses, in a way that remains scalable alongside a rapidly evolving product. The hosts analyze the situation through the lens of Conway’s Law, noting that such technical fragmentation often mirrors an organization’s internal structure. They suggest that instead of searching for a "holy grail" of documentation, the listener should consider writing about their current approach to spark public discussion and attract insights from others in the field. Later, the conversation shifts to a softer skill: how to properly compliment a colleague—now an engineering manager—who has undergone a significant personality transformation from being a notorious "jerk" to a supportive, approachable leader. The hosts discuss the risks of bringing up past negative behaviors and offer advice on how to frame the appreciation by focusing on the recipient's growth and current positive impact, while allowing the individual to determine how much they wish to discuss their own personal evolution.

Updated Apr 27, 2026

About This Episode

In this episode, Dave and Jamison answer these questions:

  1. I work for a B2C fintech startup as a senior engineer. Our onboarding funnel has a lot of moving parts due to regulatory compliance and a litany of requirements from various parts of the business. As a startup, we also live and die by optimizing for and demonstrating growth, so we need to gather data from our product and pipe it to various analytics platforms. Finally, we need to offer customer support for high-touch edge cases. All of this is connected together in a very patchwork way between our own code and various secondary and tertiary systems (CRMs, CDPs, data warehouses, etc).

    I am torn between two ideas. One is that we may very well be doing something “state of the art” in terms of integrating all of this together. The other is that we are engaging in wheel reinvention on a massive and incredibly wasteful scale. I have no way of knowing though, because I am having such a hard time finding holistic accounts from anyone who has done something like this. My gut says that this is something dozens, if not hundreds of companies have had to build at some point, but I don’t know where to find people talking about it.

    How do I find documented, real-world case studies for how to build a complete package like this? Everything resource I can find online is a myopic, narrow slice of the entire pie focused on only one aspect of the problem. No one is talking about how you integrate e.g. a sane and scalable analytics stack with a fast evolving product. All they want to talk about is how to make a “webscale backend” or “do growth hacking” while assuming someone else is going to draw the rest of the owl.

    Where do I go to find these people or these resources? Maybe these constitute some form of “trade secrets” - does anyone even want to give this information up freely? If my higher-ups saw me go outside the company for resources, would _they_ think I’m leaking important secret sauce?

    Sorry that got so long. I love the show! Keep being awesome.

  2. I’ve been at my company for about four years, and I’m currently a senior engineer. When I first joined as a mid-level engineer, there was a certain tech lead who wasn’t exactly known for his warm personality. On my very first day, I joined a Zoom call and witnessed him verbally berating someone. This type of behavior was fairly common at the time and earned him quite the reputation as a jerk, though thankfully it became less frequent over the years.

    Fast forward to today, and he’s genuinely transformed. The intensity has dialed way down; he’s now approachable, supportive, and even recently earned a promotion to engineering manager. It’s honestly been impressive to watch.

    We have a friendly relationship, and I’d like to acknowledge his growth because I genuinely admire it. But here’s the catch: How do I, as someone junior to him, respectfully bring this up without accidentally implying, “Hey, congrats on no longer scaring everyone at work”?

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