11 Principles of Engineering Management

More than 2 years ago, I decided to try to create a brief, digestible manual on the expectations of management for senior engineers at my company who are considering making the shift. At the time, I had about 3 years of management experience, including two prior companies. Enough to feel like I knew how to do the job, but not enough to feel like I should be some kind of authority on management. After letting this marinate for a couple years, I’m ready to share what I have learned.

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Employee Equity: Understanding “qualifying disposition” is a must

If you have worked for a tech startup, you have probably earned incentive stock options (ISOs) as part of your compensation. ISOs are notoriously difficult to understand, let alone to strategize. In most cases, it frankly doesn’t matter, because most startups will not become spectacularly successful, and therefore, the options will never become a dominant part of the money you made during your stint. But, if you are lucky enough to hitch a ride on a unicorn 🦄, it can get very complicated, indeed.

The tax treatment of ISOs encourages employees to take financial risks, in return for potential tax advantages. If there were no tax advantages to be gained, it would be advantageous in all cases to exercise options as late as possible—either just before expiration or when you want to sell the stock—because you would have maximal certainty of the value of the shares. But because there are holding periods for tax advantages and triggers for taxable events, there is pressure to exercise earlier. This means locking up cash for years, before knowing when, or even if, the shares can be sold for profit.

The one thing you must understand about ISOs is the concept of a qualifying disposition. I’m going to first explain what that means, and then present a brief case study from my own situation.

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Ableism: the sneakiest “ism”

Fighting the prejudice within myself is a lifelong battle. One of the -isms I struggle most with is ableism. It comes through in my language, and as I’ll explain, I believe it underlies a stubborn prejudice in my heart. It is completely normalized to demean things and people as “stupid” or “crazy”. If you want to know why this is a bad thing, this article does a good job of explaining. Please read it, and do try to suspend the voice in your head that thinks it’s maybe being a bit excessive. Just for a minute.

All done? Great, because instead of stating the point they’ve made so well, I want to talk about why I accept it.

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Why does the world want index investors?

I have no financial training or credentials. This article represents my understanding from synthesizing many sources of information, but I am likely misusing terminology, and I may be factually incorrect on some points. Apply this information at your own risk.

Don’t invest in anything you don’t understand.

This is the first rule of investing. In a world where people want your money, it’s a good way to avoid becoming mark, swindled out of your life savings. In other words, it’s important to understand:

  • What your money will be used for
  • Where the new money to pay your return-on-investment will come from
  • What the risks are

If investing for building personal wealth has a second commandment, it is to continually pump excess income into low-cost index funds that track a large chunk of the US stock market. It’s not the purpose of this piece to justify this, but mountains of research indicates that this almost absurdly simple strategy—when executed with discipline and an iron stomach—has historically outperformed pretty much every complex investment strategy implemented by active traders, especially once fees are accounted for 1.

I have found these two pieces of advice to be in conflict. This piece is my attempt to sort this out.

Where is the investment?

The word investing literally means that I take money I don’t need to day and I give it to another entity that needs it today. In return, I expect to eventually have more cash out than I put in, either because they have paid me back with interest or given me a cut of profits. It’s pretty straightforward. The philosophical problem I’ve grappled with is that it’s not obvious how buying an index fund constitutes investment, in this most literal sense.

When you put money into an index fund, that manager of that fund buys shares in every company in the index from the secondary market for stocks—the “stock market”. By secondary market, I mean that the money you put in isn’t going to the companies in the index. It’s going to existing shareholders, who are selling shares that they might have bought from the company. But more likely, the shares have passed through dozens of hands since a person or entity actually provided capital to the company. You know: investment.

This is well and good, but the burning questions in my mind are:

  • Why should this be the gold standard of personal investing?
  • Why does the market reward people so lucratively for not actually investing directly in companies?
  • And furthermore, for not exercising any personal judgment on individual companies whatsoever?

It’s been surprisingly difficult to get a straight answer to these questions. I’ve posed them to people I know who are very sophisticated. I often get answers that are vague or too loaded down with jargon for me to understand. But it’s more than an academic question, because those questions underlie the real questions in my mind:

  • As index funds become more popular, is dumb money (like mine) indiscriminately increasing the demand for shares?
  • Is this just a giant game of hot potato?
  • Will this last until and through my retirement?

A proposed answer

As I’ve been needling and challenging folks to draw out nuance, I’ve continued to do my own reading, and combined all of this with the bits of econ I still remember from my minor. I present my two answers, which feel somewhat satisfying:

  1. Share price extremely important to the executives of every public company, and they will do damn near anything to keep it increasing. It drives their own wealth and the determines the ability of the company to raise capital in the future. So, while they don’t need your money in the form of literal investment, by being a shareholder, you are along for the ride. By being an index fund shareholder, this extends to the massive chunk of equity in American industry that trades on the stock market.
  2. What you are literally investing in is the cash needs of the faceless people or entities who your index fund is buying a share from. Maybe they’re retiring. Maybe they’re buying a house. Maybe there’s a hot deal they want to participate in. Maybe they’ve lost faith in the US stock market and want to hold cash. Maybe they’re starting a business. Who knows. On some level, the stock market is simply serving our economy as a giant pool to park and retrieve cash. 2

Presumably, the stock market is in a unique position for Answer 2 because whatever spending the seller is using their newfound cash for, that money probably isn’t going too far before passing through the hands of publicly traded companies, helping those companies meet their goals, and increasing demand for their shares.

I guess the brilliance of the whole scheme is that I, as an investor, don’t really need to know who needs my money or how it will eventually help the companies I’m investing in. I can trust in the dollar-based economy to work it out, and I can trust the huge number of active traders on the stock market to determine the value of companies. The lack of specificity of my “lending” of cash to the economy diffuses the risk and increases efficiency, as long as the dollar-based economy remains functional and growing.

The stock market is likely to have crises of confidence and the economy is likely to periodically break down, but historically, things have always recovered and achieved new peaks. Maybe that won’t always be true, but if the trend ends, I’ll probably find myself more concerned with short-term survival than wealth growth.

So to recap:

  • What your money will be used for — the general wants and needs of previous investors
  • Where the new money to pay your return-on-investment will come from — the increased valuations of companies, driven by the spending and further investment of
  • What the risks are — permanent breakdown or devaluation of the dollar-based economy 3

I hope this doesn’t sound too convincing, because I’m still not totally satisfied with this reasoning. But it’s a lot better than where I was before I started asking questions, and I hope I continue to get a better grip on these questions.

If you are an expert in this topic, I would love to hear more perspectives.

1 See, for example, the Buffet Bet.

2 Interestingly, it’s not even the biggest such pool of money. The US stock market is $50T, but the US credit market, consisting of bonds and loans, is three times larger. The stock market is much more transparent and liquid, however.

3 There are also risks inherent to the instrument of an index fund, risks of the dominance of indexing strategies, and risks of the companies that offer them, for argument’s sake, I’m not getting into it.

The kindest things anyone has ever done for me

Recently, I’ve gotten into a podcast called Invest Like The Best. The host ends every episode by asking his guest “what’s the kindest thing anyone’s ever done for you?” To be honest, this didn’t stick out to me until I heard a couple guests answer with some pretty trivial shit. I won’t say which guests, but imagine it’s something like “someone lent me $100 the other day”. And, I must admit, I felt pretty judgy. Like, how privileged must your life be to have something so trivial be the kindest thing anyone’s ever done for you?

To be fair, maybe they were just put on the spot and didn’t have time to think deeply about it. And really, I don’t really know their life, so whatever it was they actually said really made a difference.

Anyway, it got me thinking: what would I say? I’ve got two answers.

Trigger warning: severe depression is discussed.

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Screening developers should be easy

I’ve been thinking about programmer hiring for several years now, and I have a new theory for how to do it:

Make it clear what it is your software team does, and hire people who can make a compelling case for why they want to join your team.

That’s pretty much it. Class dismissed.

I guess I should justify this theory. The remainder of this piece describes my journey to this radical realization.

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An epic Webpack mystery

Webpack logo

For reasons I’ll explain elsewhere, I’m building a desktop app, which stores its data locally. It’s built using Electron, a toolkit for writing desktop apps using web technologies. and it uses a pure-JavaScript database called NeDB for persistence. Pretty quickly, I ran into a headscratcher of a problem. My data wasn’t actually being saved to a file but I wasn’t getting any errors or warnings.

As it turned out, it wasn’t a bug, but a complex situation involving Webpack defaults. Understanding and solving this issue took me waaaaaaay down a rabbit hole, and I thought it would be informative to share the story.

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