Here’s how to avoid obscuring the truth with too little — or too much — information.

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I’m proud to share a personal milestone in a pursuit that’s very dear to me. To those who didn’t know, other than my full time role of managing a software engineering team (and, of course, in between trying to keep this blog updated), I spend a lot of my free time running a small independent record label called . And being a career software guy, I’ve always wanted to eventually find a way to use what I know about software and technology to solve real problems in the music business.

Just a few days ago, we reached a milestone…


Do more by recognizing when “good” becomes “good enough”.

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Not to brag (well, maybe a little), but I’ve always gotten a lot of positive feedback about how much I’m able to get done in a limited amount of time. And I think there’s really one key secret I’ve learned throughout my work to accomplishing this, which I’m happy to share a bit more about.

This particular gleaning also comes in the light of recently starting to read Lean Startup by Eric Ries. Throughout the book, Ries talks (almost lovingly) about that first version of the software — buggy, seemingly missing important features, and generally not something the team can…


Here are some things I’ve learned about people leaving en masse.

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Half of 2021 has gone by so quickly and I hardly even noticed. It’s undoubtedly been a challenging year to say the least. In fact, from where I stand, it has felt even more difficult than 2020 — who would’ve thought? At this point, the pandemic has now stretched out for nearly a year and a half. Vaccine rollouts are happening, but I think it’s safe to assume it won’t be fully effective until at least this year ends.

To make matters more difficult, a lot of the people in my team have been leaving since the start of this…


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

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 . 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…


Here’s why the QCD triangle might be a little misguided.

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As with a lot of managers, I’ve lived my career by the QCD triangle — that is, quality, cost, and, delivery. If the term is not familiar, perhaps the old adage is — “ build it right, fast, or cheap: pick two. “ And I definitely still believe in this idea. There’s no better way to illustrate how certain expectations from management can be, well, downright impossible.

However, conversations I’ve had recently with people has led me to believe that the QCD triangle, or at least some interpretations of it, might be a little misguided. …


In a remote setting, accountability is important. But equally important is safety.

Here’s another lesson from 2020 and this one comes in the light of working fully remote for almost a year now and reflecting on all the organizational complexities that come with it. What complexities, specifically? First off, the lack of visibility. Without a physical space to gather, we’ve lost all visual cues as to how people are actually doing (and, admittedly, what they’re actually doing). Secondly, when you can’t just pop your head up and ask a question, there’s an inevitable slowdown of information and obvious challenges in decision making that comes with that.


I’m lucky to have come out of it relatively better off, but I also wish I could have done more for others.

I find it funny when I look back at , where I wrote that it was highly unlikely that I could beat that year in terms of being “transformational”. It turns out that was kind of true. But while I’ve personally decided to stay the course for this year, the entire world just happened to change super drastically. A little bit forward to early this year (still pre-COVID) and on where I was at at the time, and even that seems ages away now. …


A few things I wish for you and for all of us after such a challenging year.

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Hey there! I know you’ve probably been having a rough year. I assume we all have, in varying degrees and each our own unique circumstances. My problems may not be the same as yours, but I believe regardless of what you and I have been through this year, we all deserve a break these next few days to enjoy time with the people we love or simply time with ourselves. And, yes, we deserve to have a better year ahead.

So here are a few things I wish for you (and all of us) this Christmas:

  • I wish for some…


We want to solve problems but we also have to admit that we can’t solve all of them.

In , I talked about failing to address rumors as one of the things that seem harmless on the surface but can do quite a lot of damage if left unfixed. I felt that point alone merited an article of its own. Consider this my 2020 reflection (or at least the first of several).


Here are four silent culture killers you need to watch out for, and some tips on how you can avoid them in your organization.

Company culture — a holy grail that most companies hold in very high regard and rightfully so. Yet, despite all the motivational speeches and slogans plastered throughout our office walls, we often find ourselves in holes that are a bit difficult to climb out of and cycles that seem… counterproductive, to say the least.

There are, of course, the obvious red flags you need to watch out for — power struggles and in-fighting, incompetent or absentee leadership, expectations of overtime as a norm… the list goes on. …

Derwin Dexter Sy

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

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