For myself, I once had to forego an assignment that I wanted because my boss didn't think he could do without me. This was a wake-up call for me that I needed to "hire my replacement" to give me the ability to move on.
I wish the article expanded further on this in the section on firing beyond the mantra of "fire fast." Taking the infamous Netflix presentation as an example, there may be plenty of other jobs that need to be done at the company, but the reality is the generalist wearing multiple may need to be swapped for a specialist wearing one or two. So there may not be any other jobs for that generalist, and it isn't necessarily a critique of their performance.
While the article touches briefly on this, it doesn't seem to follow through and connect it with the examples of questions/concerns people voice during phases of growth and team changes.
Unfortunately, unless it is deeply ingrained in the culture, it is often not a great approach as a manager to tell a team "well, your concerns are justified and we'll be evaluating whether there's still opportunities that are a good fit for you here." But that is ultimately the candid answer I think a lot of employees might be looking for in response to the sorts of questions the article gives as examples.
I ask because it's come up before in other contexts that money isn't enough. If someone says here's $26 million, start 4 projects that should supposedly take 2 years each and have them done on time! Assume each of those projects takes 25 people. Somehow you need to find 100 people all on day 1 to meet your deadline. Few companies can find 100 good people quickly. Can you find 1 a day? Well then 5 months until you're fully staffed. 1 a week? It will be 4 years until you have the people.
Maybe it works for Netflix but most companies struggle to find people to hire.
That said, I personally think there is a lot of value in certain types of generalists, but not all (or rather, not in all cases).
You see, when a company is very young, they may not have the best and brightest, but rather the people that were willing to shoulder a ton of risk, burn the midnight oil, etc. They may have been lucky to get both, but optimizing for one is not a guarantee of getting the other. So you get to a point where you can afford to hire more experienced individuals, and suddenly you might be faced with the ability to replace your current generalist with a much more experienced generalist, or a generalist that is T-shaped in their skill set.
I used to think I was T-shaped (wide range of skills, very deep in one), and then I started becoming more M-shaped because I've gone very deep down multiple paths in my career. That was when I realized the sum of the parts is greater than the whole, and it enabled me to work exceptionally well in cross-functional technical environments. Specifically in my case, I started out in the marketing/advertising world, then went deep in analytics, and have gotten progressively more technical over the course of my career in terms of coding. Turns out that happens to be a valuable generalist combination.
But even certain combinations may not be right for a company that wants someone who specialized in X for their entire career, and I respect that.
Ultimately, experienced, high-performing generalists will have a relatively easy time finding jobs either elsewhere, or within their current company as it grows. Often times that turns into leadership roles. When it doesn't is when I could see you running into more issues with finding something new to do at the current company if they have fewer generalist individual contributor roles.
I imagine at some point I will no longer be useful and I can leave the company entirely doing some occasional consulting for them.
As a generalist, I welcome this day and look forward to another place to whip into shape.
Yes, in practice companies will need more specialists, but the thing about a generalist is they do lots of things, so there's always something else for them to pick up on and dive deeper on. By the end of their tenure they may even find themselves in the specialist bucket! But in any case, this transition doesn't happen overnight anyway. You will always need people to explore new areas, and you will never be able to find the perfect candidate for every role you dream up. In practice you want to hire great people whenever you can get them and help them find their own role.
Scott McNealy called an all-hands meeting, and made grand sweeping gestures with his arms while imploring everyone: "Stop hugging your trees! Everyone has to let go of their tree! No more tree hugging!"
As if we understood what the hell he was talking about because we'd all read the same management self-help books about preventing tree hugging in large corporations that he had, and that by making tree hugging and releasing gestures, everybody would be able to empathize with him and figure out what the the fuck he meant.
After the meeting, I confronted my manager: "You never game me a tree! Why didn't I ever get a tree? I want my tree! I promise not to hug it, but I want one too!"
Legos make tomato paste.
Sidenote: If you're trying to coin a catchy phrase - make sure it's correct and doesn't play into a grammatical flame war.
I'm not lego's marketing department, I'm not their lawyer, I'm not their CEO. It's not up to me to give a crap about the pedantic nonsense that is their preference for how you refer to their product. It's not brand confusion. Lego, Legos, LEGO, LEGOS, whatever. People know what you're talking about, and they aren't getting the name "lego" mixed up with anything. People that see the Megabloks and other knock offs and think that they're legos are what they need to worry about. But an informed child, consumer, etc. knows better already. It didn't take very many Megablok sets before I realize they were incredibly inferior in quality and the colors were way off. Lego is obviously the superior product even to a child.
Okay so I lied. I do care, a lot. More than I should. But I'm just so sick of pedantic idiots hopping into conversations like some sort of know it all "WELL ACTUALLY....". Fuck off. Lego, legos, LEGOS, LEGO, doesn't matter we all know what's being talked about. And derailing discussions over that nonsense is obnoxious.
I couldn't bring myself to read it and wasn't alone and it annoyed me enough to say something. Should she have known better or care - maybe not. Her audience is probably just Silicon Valley and extend to the rest of the US.
But this is the Internet, so welcome to the wider world.
"I need more legos to finish off this house" sounds, to a Brit, like someone saying "I need more sands to finish off this sandcastle," or "I need more ices to finish this ice sculpture". Lego is kind of like a substance in our language. Pluralizing it is just wrong.
I do not believe this at all. Being the default word for its category is the truest sign of the penetration of a brand.
Companies seem to think different about this.
In the UK I've only heard Lego referred to like:
"Give me that red brick",
"Give me that red Lego brick",
"Look at all my Lego",
"Look at all my Lego bricks"
Not even Lego has Legos. 
Just a little reminder from Xerox / prepared by Needham, Harper & Steers Advertising, Inc. -- Not even Xerox can Xerox / prepared by Needham Harper Worldwide, Inc. (March 1985) -- Once a trademark, not always a trademark / [Xerox Corporation].
Though it was a long time ago, I recall that my law school Business Torts casebook contained a copy of Xerox’s old ad, “Not Even Xerox Can Xerox”, which Xerox used to promote proper use of its trademark and fight genericide. Back in the day, Xerox was by far the most well-know copier brand, leased by offices all over. In this day and age, now that most people have a copier at home (as part of a multifunction printer) and it could be a Canon, HP, Brother, Epson or other brand, I think the younger folk are not so likely to refer to copying as “Xeroxing”. It poses an interesting quandary: Xerox may be winning the genericide war but they are no longer dominating the competition. Which is preferable?
Proper Use of the LEGO Trademark on a Web Site
If the LEGO trademark is used at all, it should always be used as an adjective, not as a noun. For example, say "MODELS BUILT OF LEGO BRICKS". Never say "MODELS BUILT OF LEGOs". Also, the trademark should appear in the same typeface as the surrounding text and should not be isolated or set apart from the surrounding text. In other words, the trademarks should not be emphasized or highlighted. Finally, the LEGO trademark should always appear with a ® symbol each time it is used.
It's now being used as the filler word in podcasts.
Wikipedia has a good list of names that are in the process of becoming generic, much to the dismay of the companies that hold the trademarks.
They are meant to protect each in different ways.
Tangential to the article. But, I find it kind of surprising that the employee to user base growth was linear. I would expect it to be closer to logarithmic in a well run company. Although I have no data points. Am I off base?
To the point, I would not be surprised if 5,500 was the "settling" point. In my experience, the hiring pendulum takes some time to swing far enough to include an adequate number of employees in a rapidly scaling environment. (e.g., I would not be surprised if 500 million users were served by 750 employees.)
Especially if you know it's going to explode midair once it's launched and you don't have to be in it when it does.
And there are plenty of people who eat that shit up. I know a lot of engineers are a bit socially retarded, but is it helping us to progress to accept this infantilization? Can we stop pretending to be "big kids"?
sadly it's central to the silly con valley ploy, so don't expect change to come out from here. there's plenty company out there that value professionalism out of its workforce, but those aren't building cool toys for mid twenties bros.
I've spent the last 17 years working for (and now running) tech startups in Boston; the worst of them ceded all fun to cube farms, but the best of them never went all-in on the culture described here. Perhaps there is an east/west coast division here?
I look at the folks working alongside me now, building an incredibly sophisticated machine learning engine for cybersecurity, and I wouldn't think to draw upon a Lego metaphor for what they're doing. It's hard, substantive, mathematical work, and certainly not akin to playing with toys. I expect my senior engineers, sales guys, and marketers to be both protective of the brand we're building and understanding of the need to grow fast and expand our teams.
Of the tech companies that have tried to woo me, most fall into this infantilization trap and its such a big turn-off. If the reason I should come work with you is because you have a foosball table and on fridays you put a keg in the break room......I want to build things! I want to create. I will take your company and move it forward, I dont have time for ping pong.
Shouldnt the goal be to make your comoany rich, so you can be rewarded enough to buy the comforts YOU want, instead of lounging in the comforts of an employer as you work?