Engineer reacts: Southwest's tech leadership

I did some LinkedIn spelunking, to answer my own question wondering about what SWA's leadership in the tech and operations space looks like.

It's *super* hard to say anything specific just based on some LinkedIn searches, so take everything I'm saying with a giant slab of rock salt. I wanted to get a general picture for how SWA runs its software and technology, for my own curiosity. And it's hard to watch a tech meltdown and not wonder about what it's like working there. I think I wasted enough time looking at LinkedIn profiles to answer that question for myself, at least. Counterexamples welcome.

Overwhelmingly, folks at the director and senior director level are very long term SWA employees. It sounds great to have a promotion ladder like this, but in practice, what this tells me is that SWA is hiring "safe bets" that preserve the company culture rather than hiring for excellence. The chances of a random guy who started off as a network technician growing into a competent senior leader who would outcompete external candidates is very slim indeed.

Folks might counter with: but this preserves SWA culture. Yes, but it's also inbreeding. If your core company culture is strong, and you hire really well, your new hires will learn it and adapt to it, because it will be the fastest way to get things done. But they will also bring in new ideas and new energy. Really long term staff know what kind of ideas fly (heh) and which ones do not, so they don't typically rock the boat. They also know where the skeletons are; the projects they know not to touch otherwise they'll get their face blown off.

I think this inbreeding produces a "Bc hire Cs" culture since there is no way someone promoted to senior leader of an area in which he or she has limited experience (and zero outside experience) can really know what an A player looks like. To them, an A player is going to be someone like themselves, who stuck it out for the long term and gets along with everyone. An outside A player with the energy and expertise to solve the hardest problems is going to look like a troublemaker who "doesn't understand our culture".

(note: the military kinda solves this by keeping people moving. By time boxing their tenure, leaders are highly motivated to make the most of it, and push for whatever changes they can get behind. And it means new leadership is constantly coming through and coming for you. It has other problems, but it's a very clever way to stave off decrepitude)

At the VP level, we start to see the pernicious effects of management consulting. I found two in the tech area who were fast-tracked into VP positions from PwC and Accenture. Terrible sign. Hiring business school or management consulting people and then putting them in charge of domains they know nothing about, because hey they are "professional managers" is like deliberately giving your body cancer because cancer is "good at replicating" and you heard cells like to replicate. Suffice to say that this simple fact alone dooms an organization to mediocrity at best, and I wouldn't work there. To paraphrase Strongbad: these guys wouldn't know majesty if it came up to them and bit them in the face.

Another red flag: senior leaders with titles such as "Business Transformation" and "Innovation". Decades of research into manufacturing, TPM, lean product development, DevOps, we know that you can't bolt "innovation" on as a leadership position, just as you can't do DevOps by hiring a "DevOps person". Innovation is a cultural component cultivated and regulated by leadership at the C-level; if your organization lacks innovation then those are the lightbulbs that need changing.

Speaking of which: the COO (beneath whom all technology appears to report) is primarily a finance guy, not an ops guy, which is telling. This just means he will see his position as primarily a fiduciary responsibility to shareholders and be allergic to spending money. Ideally you want a COO who is an outstanding operations guru kept in check by an assiduous CFO. Separating those roles and creating some tension between them gets you a better result. Don't make a fox the manager of the henhouse. I've seen this mistake up close and personal.

CTO: missing, they don't have one. Other things they're missing include any careers in technology on their site. "0 opportunities". They of course lack any presence on GitHub which is kind of table stakes these days, even if it's mostly a "how do you do, fellow open sources?" gesture. So it's hard to know anything about their core values, technology stack, DevOps practices, or anything you'd really be mindful of if you wanted to work there.

Anyway let's get to the rating. Southwest Airlines: a time capsule of the 1990s. 0/10, I wouldn't eat it.