snydeq writes: Sure, nobody's perfect. But for those in charge of enterprise technology, the fallout from a strategic gaffe, bad hire, or weak spine can be disastrous, writes Dan Tynan, in an article on the biggest management mistakes in IT. "Some of the most common IT gaffes include becoming trapped in a relationship with a vendor you can't shake loose, hiring or promoting the wrong people, and hiding problems from top management until it's too late to recover." What are some other career- and company-destroyers you've witnessed in your years in IT?

Brian Merchant, writing for Wired: There are some 269 billion emails sent and received daily. That's roughly 35 emails for every person on the planet, every day. Over 40 percent of those emails are tracked, according to a study published last June by OMC, an "email intelligence" company that also builds anti-tracking tools. The tech is pretty simple. Tracking clients embed a line of code in the body of an email -- usually in a 1x1 pixel image, so tiny it's invisible, but also in elements like hyperlinks and custom fonts. When a recipient opens the email, the tracking client recognizes that pixel has been downloaded, as well as where and on what device. Newsletter services, marketers, and advertisers have used the technique for years, to collect data about their open rates; major tech companies like Facebook and Twitter followed suit in their ongoing quest to profile and predict our behavior online. But lately, a surprising -- and growing -- number of tracked emails are being sent not from corporations, but acquaintances. "We have been in touch with users that were tracked by their spouses, business partners, competitors," says Florian Seroussi, the founder of OMC. "It's the wild, wild west out there." According to OMC's data, a full 19 percent of all "conversational" email is now tracked. That's one in five of the emails you get from your friends. And you probably never noticed.

Lorenzo Franceschi-Bicchierai, writing for Motherboard: Google has released a powerful tool that can help security researchers hack and find bugs in iOS 11.1.2, a very recent version of the iPhone operating system. The exploit is the work of Ian Beer, one of the most prolific iOS bug hunters, and a member of Google Project Zero, which works to find bugs in all types of software, including that not made by Google. Beer released the tool Monday, which he says should work for "all devices." The proof of concept works only for those devices he tested -- iPhone 7, 6s and iPod touch 6G -- "but adding more support should be easy," he wrote. Last week, Beer caused a stir among the community of hackers who hack on the iPhone -- also traditionally known as jailbreakers -- by announcing that he was about to publish an exploit for iOS 11.1.2. Researchers reacted with excitement as they realized the tool would make jailbreaking and security research much easier.

An anonymous reader shares a Bloomberg report: For months Lovkesh Joshi was quietly terrified of losing his job as a manager at a top Indian tech services company. Joshi didn't want to burden his wife or friends so he turned to a chatbot therapist called Wysa. Powered by AI, the app promises to be "loyal, supportive and very private," and encourages users to divulge their feelings about a recent major event or big change in their lives. "I could open up and talk," says the 41-year-old father of two school-age children, who says his conversations with the bot flowed naturally. "I felt heard and understood." Joshi moved to a large rival outsourcer two months ago. The upheaval in India's $154 billion tech outsourcing industry has prompted thousands of Indians to seek solace in online therapy services. People accustomed to holding down prestigious jobs and pulling in handsome salaries are losing out to automation, a shift away from long-term legacy contracts and curbs on U.S. work visas. McKinsey & Co says almost half of the four million people working in India's IT services industry will become "irrelevant" in the next three to four years. Indians, like people the world over, tend to hide their mental anguish for fear of being stigmatized. That's why many are embracing the convenience, anonymity and affordability of online counseling startups, most of which use human therapists.

Hidden software that can record every letter typed on a computer keyboard has been discovered pre-installed on hundreds of HP laptop models, BBC reported on Monday citing the findings of a security researcher. From the report: Security researcher Michael Myng found the keylogging code in software drivers preinstalled on HP laptops to make the keyboard work. HP said more than 460 models of laptop were affected by the "potential security vulnerability." It has issued a software patch for its customers to remove the keylogger. The issue affects laptops in the EliteBook, ProBook, Pavilion and Envy ranges, among others. HP has issued a full list of affected devices, dating back to 2012. Mr Myng discovered the keylogger while inspecting Synaptics Touchpad software, to figure out how to control the keyboard backlight on an HP laptop. He said the keylogger was disabled by default, but an attacker with access to the computer could have enabled it to record what a user was typing. According to HP, it was originally built into the Synaptics software to help debug errors. It acknowledged that could lead to "loss of confidentiality" but it said neither Synaptics nor HP had access to customer data as a result of the flaw.

A medium-sized company just hired a new IT manager who wants advice from the Slashdot community about their two remaining IT "gofers": These people have literally been here their entire "careers" and are now near retirement. Quite honestly, they do not have any experience other than reinstalling Windows, binding something to the domain and the occasional driver installation -- and are more than willing to admit this. Given many people are now using Macs and most servers/workstations are running Linux, they have literally lost complete control over the company, with most of these machines sitting around completely unmanaged.

Firing these people is nearly impossible. (They have a lot of goodwill within other departments, and they have quite literally worked there for more than 60 years combined.) So I've been tasked with attempting to retrain these people in the next six months. Given they still have to do work (imaging computers and fixing basic issues), what are the best ways of retraining them into basic network, Windows, Mac, Linux, and "cloud" first-level help desk support?
Monster_user had some suggestions -- for example, "Don't overtrain. Select and target areas where they will be able to provide a strong impact." Any other good advice?

Leave your best answers in the comments. What's the best way to retrain old IT workers?