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Ask HN: What was the biggest leadership challenge of your career?

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Re: Ask HN: What was the biggest leadership challenge of your career?

#201

I was leading a team of thirty five people in the US and India and working weekends and holidays powering through a death march of one terrible release after another. I got a lot of accolades for work; called out at town halls and even a hand written letter from our CTO thanking me for everything I'd done. Things were slowly improving as we collected metrics to improve poor code quality and shoddy releases that were…

Thanks for sharing. Had a somewhat similar experience to yours that your comment took me back to.

I used to lead a global team of 80+ devs at a senior management level. I inherited my team which was an absolute train wreck with a poor track record of poor performance who delivered nothing causing much angst to the business. Over 3 years, rebuilt the entire team, let go of these who brought toxicity/incompetence, set strategy, tightened comms and developed leaders with clear lines of responsibility and accountability. Shipped one product after another. Put the team on the map internally and externally. Accolades from every part of the organization. Made my leaders look like world-beaters. I was known to be an authority on my subject area and the rising star. My reports looked up to me, I inspired my team buy being an empathetic leader and I was hailed as a change-agent. Frankly, I outdid myself and it was one of those times, we sometimes have in our careers where we fire on all cylinders without a single misstep.

Come time for promotion, I had a rude awakening when my boss got promoted thanks to my back-breaking work but I got passed over and to add to the insult my newly promoted boss decided to fill the vacancy by bringing in a transplant from another part of the company to add an new layer. The new guy was well known to be the biggest ass-kisser in the organization so a total smooth operator to his credit despite being clueless in the domain. My challenge was to continue leading my team with a straight face despite taking this gut punch every day when faced to my new reality. It was a depressing time when I was also dealing with a personal loss in my family. I had naively assumed my work did the talking and my personality, relationships and overall competence/qualifications would continue my ascent. Its hard articulating this but the amount of time my own achievements were reinforced by outcomes and my prior leadership made me feel I could do no wrong until this point.

My big mistake was that my ego fed a sense of entitlement that made the change harder to deal with. My reports were now well entrenched and confident as I had always wanted them to be with large teams. I sensed a feeling of disappointment from my own teams over my lack of elevation and the impact it would have on their careers. Over a period of time, I went from being the shining star to someone about whom everyone wondered as to what’s wrong. I felt vulnerable in taking decisions that I once took confidently and my confidence took a beating. I mentally beat myself up as well for not playing my political cards well as well as sometimes questioning my own abilities. Added to the daily ignominy of reporting to someone obviously not qualified, was every decision/outreaches/opportunities/credit that were usually mine in the past due to my domain expertise now being passed over to my new boss who would emphasize the same with a lack of class and competence. I also got a sense that the new guy resented my abilities and would now start having direct lines of communication with my reports sometimes even not giving me visibility. He just wanted to get rid of me since my presence probably constantly reminded him of his lack of involvement in this teams prior success. People who would consult me for critical decisions would tend to leave me out as I was not deemed that important considering I was no longer the main decision maker. There were so many incidents that I unfortunately still recall that happened over a 1 year period that I stayed on after this development.

For me though, that was a lesson in humility and my own vulnerabilities. My swagger is gone and I don’t things for granted as I once did. Thanks to my own qualifications and experience, I had several external opportunities the beckoned that I could execute on and did do so. However, that feeling of being totally ripped off, a sense of anguish at losing something I built, sadness at dealing with a team that you built and loved that turned on you still remains and part of me is still bitter. I still love leading teams and getting the best out of people but the politics is toxic and can seriously damage your physical and mental well-being. I know why some of the best leaders I know remain relegated to lower levels of their organizations and I respect them even more knowing the balancing act they deal with. I don’t get too attached to teams, products, jobs anymore and am prepare to lose it overnight and rebuild. I continue leading large teams but I could still get a job as an individual contributor and be happy with it if it ever came to that.

Re: Ask HN: What was the biggest leadership challenge of your career?

#203

Earlier quoted context omitted.

My bad. I see they were responding to the leading question of my post, not the situation part of it.

You are right, I should have quoted the top so it was clearer what I was answering to.

I was up basically all night so I just wasn't reading straight. I think for most people it would have been apparent even without the quote.

Re: Ask HN: What was the biggest leadership challenge of your career?

#204

Earlier quoted context omitted.

There are a couple of terms here that I'm not familiar with. What is "elevating code"? (I'm trying to work out of autocorrect has screwed up the word "deploying".) What is an ASC?

I use elevate and deploy interchangeably sometimes. The package or files are already deployed in the test region, so you are elevating them to the next region (PRD). You could deploy the same code to the test region again, which wouldn't be an elevation since it's already there, and deploy would make more sense. ASC is Application Security Champion. Essentially the role requires some internal security training then y…

Many thanks for the explanations.

Re: Ask HN: What was the biggest leadership challenge of your career?

#205

Earlier quoted context omitted.

What motivated you to rewrite it rather than fixing the debt in the old product?

It was a ~8 year old mix and mesh of tech was not really fixable. We also got too many requests for enterprise clients for Java. And that would have been impossible. We more than doubled in revenue after the rewrite because now we could go for fortune 500 countries. It was a different time: the product was a combi of perl, php, c++. And then the business world, at least here, went over to java backends.

Many thanks for the explanation. If the product is built using different tech from what you want to use then a rewrite does make a lot of sense.

Re: Ask HN: What was the biggest leadership challenge of your career?

#206
post #141

Earlier quoted context omitted.

IMHO having this as a rule that keys in dictionaries are sorted alphabetically can be a valid rule. But this should be enforced in tooling, not "rules", and not through micromanagement. Much like using opinionated code formatters - like `prettier` you mention. It makes lives of everyone easier down the line. Sometimes this comes from years of experience (mostly pain ;)). Some leaders, while coming from a good place -…

> having this as a rule that keys in dictionaries are sorted alphabetically can be a valid rule Ordering keys to prevent randomness is very helpful to spot changes when using "git diff", doing code reviews, comparing files side by side. Often it helped me spotting bugs due to a missing or unwanted element. I wish code linters had enabled by default with the ability to disable it with some simple syntax.

I had a look at prettier's github issues in the mean time and

> No, prettier tries not to change the semantics (specifically, the AST) of the program, and sorting imports/keys could break that guarantee. See here for more details and context, as well as links to similar/duplicate issues: #1684 (comment)

it makes sense not to make it a default.

https://github.com/prettier/prettier/issues/2460 https://github.com/prettier/prettier/issues/1684#issuecommen...

Re: Ask HN: What was the biggest leadership challenge of your career?

#207
post #193

Earlier quoted context omitted.

Yes, see https://headrush.typepad.com/creating_passionate_users/2006/... and https://signalvnoise.com/archives2/beautiful_code_testfirst.... I don't have good memories from the whole thing.

Haven’t read the articles, but wow, this idea needs a new name

Why? Does something being "girly" strike some kind of negative emotion? I don't think it is bad to associate organized and elegant code as feminine. You probably should read the article

> And there you have it. I think "girl code" is quite a compliment. Because caring about things like beauty makes us better programmers and engineers. We make better things. Things that aren't just functional, but easy to read, elegantly maintainable, easier--and more joyful--to use, and sometimes flat-out sexy.

Re: Ask HN: What was the biggest leadership challenge of your career?

#208

Learning to let my go of my ego and trust... Understanding that delegating tasks, instead of doing them myself, was of the utmost importance the more people I managed... especially, greenfield work. Literally: do not steal the fun. This also means inherently trusting people, and if you can't do that you shouldn't be working with them. two important notes about that: 1. If you just thought of someone you can't trust i…

I don't think trust is something you can just decide to do. It's like loving someone or believing something. You either trust them or you don't. Is your advice to pretend you trust them? Some kind of "fake it til you make it" approach?

You can work on it. Trust people with small things (or at least bite your tongue while they do it their way). Observe that nothing goes wrong. Trust more.

Re: Ask HN: What was the biggest leadership challenge of your career?

#209
post #193

Earlier quoted context omitted.

Haven’t read the articles, but wow, this idea needs a new name

Why? Does something being "girly" strike some kind of negative emotion? I don't think it is bad to associate organized and elegant code as feminine. You probably should read the article > And there you have it. I think "girl code" is quite a compliment. Because caring about things like beauty makes us better programmers and engineers. We make better things. Things that aren't just functional, but easy to read, elegan…

Whether you see a trait as a positive or a negative does not mean it is useful to anyone to ascribe gendered terms to it.

A female software engineer who does not strive for beauty in code, is she less feminine? A male software engineer who strives for code beauty more feminine than the female one?

It is a useless argument to get into, when the actual way to describe the type of code would be a choice of "beautiful, sorted, structured, consistent" instead.

Gender, as such, has nothing to do with it.

Re: Ask HN: What was the biggest leadership challenge of your career?

#210
post #193

Earlier quoted context omitted.

Haven’t read the articles, but wow, this idea needs a new name

Why? Does something being "girly" strike some kind of negative emotion? I don't think it is bad to associate organized and elegant code as feminine. You probably should read the article > And there you have it. I think "girl code" is quite a compliment. Because caring about things like beauty makes us better programmers and engineers. We make better things. Things that aren't just functional, but easy to read, elegan…

Not at all, I'm just wary of reinforcing gender stereotypes.

Even in the conclusion quoted here, the author says "I think it's quite a compliment". As if when you first hear the term "girl code", you're supposed to think "ew", and the author is there to convince you otherwise.

Why not just call it neat or organised instead? Using a gendered term does nothing but appeal to stereotypes and solidify them.

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