I spent the better part of last week hiking through the Grand Tetons backcountry with my friend Brian. Upon emerging from the mountains and getting back to Jackson, we soon learned that there had been another mass shooting. In between showering for the first time in days and treating sunburns, we learned some of the early details: young white man, white supremacist, legal gun, channer, rambly manifesto. The story, by now, is painfully familiar. And then, before we each flew out back home early the next morning… it happened again.

The other week, before another mass shooting claimed another media cycle, there was a brief debate about the slowing pace of Progress in our society. What causes Progress, they asked? How can we get more of Progress? The authors, somewhat disingenuously, threw up their hands, flummoxed, and suggested that this question was unanswered and must be studied. (Meanwhile, historians and economists fumed, because these questions are, in fact, anything but under-studied.)

There’s a lesson to be gleaned in the timing of these events. Namely: what do we mean by Progress?

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FAQs on Remote Product Management

One of my basic beliefs is that virtually every job function in knowledge-based industries can be done effectively regardless of geographic location. Living in New York obviously does not magically make one a better stock analyst any more than San Francisco makes one a better software developer. “Clustering” effects and the legacy of pre-internet geographical concentration of knowledge-based industries are real, but their grip over the distribution of modern companies is demonstrably weakening every year. “Distributed” working is a fundamentally disruptive organizational technology that is going to eat – indeed, is eating – “the office.”

Most discussions of “remote” working* in tech have thus far centered on software engineering – mostly due to recruiting pressure. But that’s really just the beginning. The same reasons why recruiting “remote” contributors and managers is good for engineering teams apply equally to marketing, sales, operations and finance roles – as well as to Product Management.

I’ve held Product Management roles where I’ve lived and worked “remotely,” as have many or most members of my teams. Guess what? It works. In this blog, I’m going to talk a little about my experiences, what works and what doesn’t, as well as answer some FAQs I’ve fielded about what “remote product management” looks like.

* – I don’t like the connotation of this term, but given its broad adoption, I feel like fighting it is sort of futile. For what it’s worth, this thing on why “remote” is the wrong way to think about distributed working is my most-read post ever.

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On Professional Distance and Courage

Something that I’ve thought a lot about over the years, but never quite formed an opinion about, was work cultures and the relationships forged through them: what makes for a good work culture? How can you identify (and remediate) bad ones? How do we as individuals, and independent of the environments we happen to be in, create positive and productive cultures around us?

I finished a book recently that really helped me crystallize and put into words my ideas about this: The Courage to Be Disliked by Ichiro Kishimi and Fumitake Koga. It’s a terrific, and quick, book. While it doesn’t address work culture specifically, its ideas are directly applicable, and they run directly counter to many popular myths about good “company cultures” in a way that finally made sense to me. Specifically:

  • Healthy work culture isn’t about everyone making friends or meeting others’ personal expectations
  • Instilling and fostering courage on the part of your employees is necessary for them to collaborate
  • The basis of a strong company is community, whose empowered members want to contribute to it

I want to talk a little bit about what this means in practice.

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AI is not coming for you

A current joke that has been circulating around the tech world for a while now is that the way to get VCs to eat out of your hand is to slap the words AI, “machine learning” and/or “blockchain” on your pitch deck.

As they say, the best jokes are indistinguishable from reality.

I’ve come to the conclusion that most of the exuberance about artificial intelligence is founded on sand. I’ve gotten there both from a closer look at what amounts to “artificial intelligence” today, as well as a good understanding of both how software itself works and, importantly, how it is developed within a corporate setting.

A very large majority of the AI hype out there today is pure attention-seeking nonsense. Generously, one might see it as just yet another example of a certain genre of tech hucksterism (see: self-driving cars, internet-beaming drones, 3D printing). Less generously, however, it isn’t hard to see the lavish marketing machine around AI as a strategy to depict deliberate choices by dominant software platforms as technical inevitabilities.

“AI” is not something anyone needs to be worried about. A world mediated by unaccountable corporate software platforms is.

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What you need to know about retirement planning

Chances are, if you’re a twenty- or thirty-something, and especially if you’re a dude, you’ve given some thought as to what you’d do in the event of a zombie apocalypse. What you’d do, where you’d go, what you’d stockpile, and what kind of ranged weapon you’d specialize in (obviously, melee arms are not the way to go). Don’t be embarrassed. I have a plan too. We all do.

You ask these same people what their plans are for retirement, and most freeze. Many/most have not done any real planning at all. Of those who have, their planning is hazy at best. If they have retirement accounts at all, they’re not sure what those accounts are invested in, what those are, or how they work.

Many, if not most, of my peers and younger have given a lot more thought to the first scenario than the second. This is a well-researched phenomenon that basically boils down to a human aversion to planning for stuff that feels distant, scary and kind of unresolveable. Who knows what the future will look like in 30 or 40 years, after all? Why bother?

I’ve written before about how disastrously unprepared the Boomers are for retirement, and how their penury will likely cause major economic strain for our generation. But here’s my gist for this post: you should plan for retirement. At its most basic level, understanding this stuff is easy. I’m not selling you anything. But unless you have plans to die young, you’re probably going to need this stuff. So do future-you a favor and give this a little thought.

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Taking control of your internet

A while back, I finished Matthew Crawford’s latest book, The World Beyond Your Head, whose subtitle is, unusually, a pretty good summary of his topic: “on becoming an individual in an age of distraction.” (I tweeted some thoughts at the time.) There are an awful lot of books out there on “focus” or eliminating distractions that approach the topic from a sort of techie-hustler Tim Ferriss sort of angle, and this is not one of them. Crawford is both a philosopher and motorcycle mechanic by profession. (Not in a sort of precious way, either – he actually owns and operates a motorcycle repair shop.) I’ve been thinking a lot about this book ever since. In particular, it touches on how I’m working to better master my own attentional resources by taking control of my experience of the internet.

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How-to for new dads

A few days ago, Penny turned 17 months old. Around the two-year mark, people generally stop denominating baby ages in months and start going with years, so it won’t be long now until we’re in that category. That’s pretty wild for me to think about. We’re solidly into life with a toddler now, and I’ve taken some time to think back over the last two years and how we got through it.

I’m the sort of dude who went out and consulted the literature in preparation for Penny’s arrival. What I found was that the genre of “mother-to-be” books is bulging at the seams, and the vast majority of other “how to baby” books are mostly oriented towards women. The “books for new dads” segment is far smaller, very religiously oriented, and much hokier. I found about 75% of it to be more or less useless.

Most of my friends are now in the process of having or raising kids. A close buddy of mine and his wife are now expecting their first in just a couple of months. I wrote up a few practical things that I thought he should know, and then decided – you know what? Lemme just dump this on the internet. Maybe this could be useful to other soon-to-be dads too. So what follows is a bunch of stuff I wish I’d known before Penny graced us with her presence.

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Software engineering as a sign of the future

They say that the future is already here, just unevenly distributed. One area where this adage is manifest is in working arrangements – or, if you like, the organizational technology – in software companies.

At most software companies, there are two business functions that are very commonly staffed with a heavy complement of “remote” employees: sales and engineers. On the sales side, the reason is pretty obvious. Where in-person sales calls are a part of the business, you want sales personnel geographically near the client. On the engineering front, the reasons are a little more interesting.

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Why aren’t there more software engineers?

One perennial area of debate in the tech industry centers around who’s in it (and who’s not). The constant background noise about the supposed scarcity of developer talent has led to any number of new approaches aimed at bringing more skilled candidates online. All manner of “bootcamps,” career-switcher programs and innovative approaches like Lambda School have emerged to meet labor market demand for skilled software developers, with varying levels of success.

A lot of people have wondered why more people, particularly young people just beginning their careers, don’t go into computer science. Dan Wang wrote what is probably the best summary of the common reasons proffered: that CS is hard, it’s unwelcoming to women and minorities, the degree isn’t strictly necessary, etc. These are all true points.

There’s a bigger question at stake, though – are there, in fact, “too few” software engineers? I’m not convinced there actually are. And if you do grant that this is true, then the reasons for it seem clearer from outside the Valley bubble.

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