Robin Schooling

Open Enrollment Is a Foreign Language

When Pam first went into HR, she pictured herself across the table from nervous job candidates as the company representative who would calm their jitters and help them navigate a successful job offer process. She imagined having career conversations with high-potential employees and the occasional difficult performance discussion that would leave a manager better at managing people when he left her office than when he had walked in.

What Pam did not imagine, at any point during her coursework in organizational psychology or the two summers she spent interning, was that she would one day spend 7 days standing beside a folding table in the breakroom, flanked by the broker’s rep and a bowl of branded stress balls, explaining to a warehouse supervisor why his free preventive visit produced a bill because the doctor also asked about his knee.

And yet every October, there she is, fluent (or fluent-ish) in a language she never set out to learn and wondering, somewhere between her tenth and fifteenth explanation of coinsurance, whether plunging the salad fork from her desk drawer into her eyeball might offer a merciful exit from open enrollment season.

Pam, if you haven’t guessed, is a composite of nearly every HR generalist I’ve worked alongside. And more than once she’s been me.

A Language Re-Learned Once a Year

Each fall, organizations ask employees to make some of the most consequential financial and medical decisions of their year using a vocabulary (deductibles, coinsurance, out-of-pocket maximums, HSA versus FSA) that most people are never formally taught and yet need to relearn every autumn. It’s a bit like being handed a phrasebook at the airport in Paris and being told that you have until mid-November to negotiate a lease, a car loan, and a surgical consent form entirely in French. (You also come to understand that you’ll then forget all of it by spring and be handed a slightly revised phrasebook next year.)

The research on this all is interesting. In 2013, Carnegie Mellon behavioral economist George Loewenstein and a team of colleagues surveyed a representative sample of Americans who had private health insurance, and more than 90% of the survey respondents felt confident they understood copays, deductibles, and out-of-pocket maximums, and 57% said the same about coinsurance. The confidence of all involved was misplaced; measured comprehension fell well below what the respondents believed they knew, as a mere 14% of survey participants turned out to be adept in their self-declared understanding.

The PUSH/PULL of the Norman Door

And yet HR’s instinct, and I say this with love and a fair amount of personal guilt, is to treat benefits illiteracy as a failing by the employees. They didn’t read the email. They skipped the webinar. They opened the benefits guide – saw a stock photo of a family laughing on a beach – and promptly closed it. But when a majority of reasonably intelligent adults consistently struggle with understanding the language and then ultimately choosing insurance options, perhaps the problem sits with whoever designed the choices.

Cognitive scientist Don Norman made this argument decades ago in The Design of Everyday Things, and designers now use the term “Norman door” for any door so poorly built that someone must tape a sign reading PUSH to the glass. A door that needs instructions is a badly designed door. By that standard, the American health plan is a Norman door with a forty-page user manual, and the Affordable Care Act’s requirement that health plans and insurers provide a standardized Summary of Benefits and Coverage along with a uniform glossary of terms is essentially the federal government taping PUSH to the glass. (When a product requires a legally mandated glossary, we’ve got some problems. Know what I mean?)

Pam in HR can simplify the menu and redesign the comparison charts in her pamphlets all she likes, but she’s still speaking in a language that nobody uses the other eleven months of the year.

How in the World Did This Land in HR’s Lap?

Nobody sat down, once upon a time, and decided that the person who recruits your engineers should also explain your prescription drug formulary. The arrangement arrived by accident, in stages, and mostly because of a war.

The prehistory begins in 1929, when Justin Ford Kimball, an administrator at Baylor University Hospital in Dallas, offered local schoolteachers a prepaid plan covering a set number of hospital days for a modest monthly fee, a model that eventually grew into Blue Cross. The real turning point came during World War II, when Congress passed the Stabilization Act in October 1942 to freeze wages and prices and hold down wartime inflation. Tucked inside was a carve-out that exempted “insurance and pension benefits in a reasonable amount” from stabilization, and employers who were desperate for workers but forbidden to raise pay did what any enterprising employer would do and started competing on benefits instead. In 1943, the IRS ruled that workers didn’t owe taxes on premiums their employers paid, and the National War Labor Board reaffirmed that fringe benefits were outside the wage freeze.

And thus, what began as a clever wartime workaround hardened into permanent HR infrastructure.

Melissa Thomasson, an economic historian at Miami University who has studied this period extensively, told a Senate committee in 2017 that when the tax exclusion was codified in the 1954 Internal Revenue Code, it prompted employers to enrich existing plans and more firms to begin offering coverage, cementing the employment-based system along with several distortions, including lower wages and workers afraid to leave jobs for fear of losing coverage. Somewhere along the way, the personnel department inherited the paperwork, and the paperwork eventually became a profession.

Today, employer-sponsored insurance in the U.S. covers 154 million people under the age of 65, and the average annual premium for family coverage reached $26,993 in 2025, with workers contributing $6,850 of that on average. Pam, who wanted to spend her days coaching managers, is now the primary customer-service representative for what amounts to a $27,000 annual purchase per family, made on behalf of people who didn’t even get to pick the vendor.

HR’s Been Deputized

The translation work is exhausting, but it’s the enforcement work that troubles me more. Over the past two decades, employers have been encouraged (by brokers, carriers, and the steady upward creep of premiums) to manage costs by managing employees’ bodies, and HR has been handed the badge.

So now we administer the tobacco surcharge and collect the signed affidavits. We run the biometric screening events, track the wellness points, levy the spousal surcharge, and cheerfully promote the step-count challenge in the company newsletter. And then, on a different day and in a different meeting, we ask those same employees to trust us with their complaints about a manager, their accommodation requests, and their candid thoughts about their career goals.

It’s difficult to be a strategic advisor, a professional confidante and the health police – and I’ve never been convinced that employees consider all of those to be compatible roles for one person.

Of course, most of the developed world decided long ago that none of this should run through the employer. Coverage in the UK, Canada, France, and the Nordic countries doesn’t hinge on where you work, and even Germany, whose system is funded through payroll contributions, lets people choose their own sickness fund rather than asking an HR generalist to curate a plan menu and teach coinsurance in the breakroom.

I’d happily trade our arrangement for any of theirs.

Workers could change jobs without doing an actuarial calculation first, employers could compete on wages and work design rather than on formularies, and Pam could go back to recruiting. But that isn’t the system we have, and it won’t be the system we have during this fall’s open enrollment season.

Translating Anyway

So every HR professional learns to translate, and the best HR teams I know have gotten remarkably good at it. They pare down the menu offerings, set sensible election defaults, and replace the convoluted coverage grids with real-world scenarios that walk through what happens if you break your arm, have a baby, or fill a monthly prescription. They talk about HSAs throughout the year instead of cramming the whole curriculum into two weeks in the fall. And those top HR teams have also stopped assuming that when an employee makes a poor choice, or can’t remember what her coverage entails, it’s because she didn’t care or was lazy.

What bothers me, though, is that every single improvement Pam makes renders the arrangement a little more tolerable – and a tolerable system is far easier to leave alone than a broken one. The better HR becomes at explaining a language that shouldn’t exist in their world/role, the less pressure anyone feels to stop speaking it. And honestly … I’m not sure whether Pam’s hard-won fluency is part of the solution or one of the reasons we’re still stuck with the problem.

Your “Best Practice,” According to Whom?

Every mattress I’ve owned has arrived with a small white tag stitched into one seam, warning in capital letters that it must not be removed under penalty of law. For years I left those tags alone, as did nearly everyone I know, because the wording carried enough menace to discourage any further inquiry. Only much later did I learn that the warning was aimed at manufacturers and retailers, and that I, the person who had paid for the mattress and slept on it every night, was free to snip the thing off whenever I liked.

The phrase “best practice” works on HR people in much the same way. It sounds official, it discourages follow-up questions, and very few of us could tell you who decided it or whom it was meant to govern. So when someone asks me which HR best practice I think is nonsense (and someone always does), I find I can’t answer without first taking issue with the premise.

A Conduit to Conformity

In Real HR I wrote that best practices are a conduit to conformity, and I haven’t changed my mind. At their most useful, they’re a starting point for thinking, but far more often they become a way for HR to borrow someone else’s answer without doing the work of understanding our own question. A practice that works beautifully at a 40,000-person manufacturer was built around that company’s history, its workforce, and its particular dysfunctions, so when we lift it wholesale and drop it into a 200-person software firm, we shouldn’t be surprised when it lands with a thud.

Part of the problem is that HR has been conditioned to reach for the template. Understandably so, since we’re asked to move fast, do more with less, and avoid risk at every turn — and a downloadable or borrowed-from-a-friend best practice promises all three at once. But replication isn’t strategy, and what we frequently end up copying is the homework of a classmate who also got a C, since many of the organizations whose practices we borrow aren’t executing them particularly well themselves.

I’d much rather HR professionals think of themselves as artists working with the materials in front of them than as lab technicians faithfully replicating someone else’s experiment. Nothing at all against lab techs — I used to hire them — but those are very different jobs.

Still, for purposes of this blog post, I’ll play along and pick a few of the most ridiculous best practices, provided you keep the premise at arm’s length while I do.

Longevity Masquerading as Evidence

The annual performance review earned its best-practice status largely through longevity. We keep doing it because everyone else keeps doing it, and everyone else keeps doing it because we do. When Deloitte tallied the cost of its own process roughly a decade ago, the firm found it was spending close to two million hours a year on forms, meetings, and ratings, and it redesigned the whole thing from the ground up.

The more instructive part of the story is what happened next. Deloitte’s shift, along with Adobe’s earlier decision to abandon annual ratings, was promptly written up, packaged, and circulated as the new best practice, to be adopted by organizations whose problems bore little resemblance to either company’s.

In the years since, and in true HR fashion, we’ve managed to turn a rejection of conformity into a fresh opportunity to conform, except that we now do it through quarterly check-ins and an annual sync-up conducted from our phones.

A Peculiar Welcome

The 90-day introductory period is another best practice that’s treated as sacred in employee handbooks across the country, even though in an at-will environment it offers little in the way of legal cover and, if it’s worded carelessly, can imply that anyone who survives the first three months has earned a form of job security the organization never intended to promise. Mostly, though, it signals to new hires that they’re on some sort of provisional trial, which strikes me as an odd and faintly unwelcoming way to greet people we’ve spent months (and a fair amount of money) persuading to join us.

Naturally, the evaluation of a new hire happens whether there’s a policy or not, and as most of us have learned, the ones we should keep an eye on rarely wait for day 89 to reveal themselves.

Doors and Hallways

Then we have the open-door policy, which declares that any employee may walk into any leader’s office at any time to raise a concern. We adopt it because we like to think we’re transparent (we often aren’t) and that our leaders are friendly and approachable (they often aren’t). It also reads well in the handbook even though it bears little resemblance to calendars booked solid for weeks, or to the career consequences that everyone understands come with going over your manager’s head.

As I noted a few weeks back when writing about workplace nostalgia, the person most fond of the open door is very often the one sitting behind it, at the far end of a vestibule guarded by an executive assistant, with the door itself closed more often than not. And anyone who has spent time working in an organization knows that even if the door is open, the hallway leading to it is often a minefield.

Feelings, Annually

And finally, the much-dreaded annual engagement survey, in which we ask people how they feel once a year, spend three months analyzing the results, and then roll out an action plan to a workforce whose feelings have long since moved on to something else. The survey itself isn’t the trouble so much as the cadence, which treats employee sentiment as though it were a fiscal-year metric rather than something that shifts every time a manager leaves, a reorg lands, or the parking lot gets repaved.

Leaving the Tag On

I’ll grant that not every inherited practice is decorative. As I wrote recently about the rules nobody remembers writing, some of them exist for sound reasons that simply went unrecorded, and telling the structural from the ornamental takes more effort than we usually budget for.

But I suspect the deeper appeal of a best practice has less to do with its results than with the protection it provides. A borrowed practice comes with built-in cover — if it fails, we can point out that we did what everyone else does — whereas a practice we designed ourselves fails with our name attached. That’s a considerable comfort, and it may explain why so many of us leave the tag stitched in place long after learning we’re free to remove it. What I can’t quite work out is whether we’d make better decisions with the tag cut off, or simply more visible ones.

____

I was thinking about best practices last night because the topic was front and center on Q Chat yesterday. Come join us one of these weeks!

Who’s Flying the Plane?

Those of us of a certain age once kept a small directory in our heads, stocked with the phone numbers of our best friend, our grandparents, Domino’s, and the cute guy/gal we crank-called during slumber parties. And then, when our phones began remembering the numbers for us, that directory was cleared out so gradually that most of us can’t say when it happened or what moved into the vacated space in our brains.

That trade-off is relatively harmless; the contacts app on my iPhone rarely fails when it’s time for me to call the dogs’ groomer. But the same sort of switcheroo looks considerably different when the skill being traded away is the ability to fly an airplane, which is precisely what worried an American Airlines captain named Warren Vanderburgh nearly thirty years ago.

Following the Line

Vanderburgh, who spent 27 years in the Air Force before flying for American, was asked by the airline in the mid-1990s to figure out why so many accidents, incidents, and violations seemed to trace back to what came to be called “automation dependency.” In 1997 he stood in front of a class at the American Airlines Training Academy in Dallas and delivered a presentation he titled Children of the Magenta Line, borrowing the name from the magenta course line that a plane’s flight computer draws across the cockpit display. His concern was that pilots had grown so accustomed to following that line – managing the automation rather than flying the aircraft – that their own hand-flying skills were wearing away. And his team’s analysis attributed 68% of the problems they reviewed to automation mismanagement.

What makes the talk worth watching today (it lives on YouTube in all its late-nineties video glory) is that Vanderburgh was no Luddite. He laid out three levels of automation, from manually flying the plane, to the autopilot, to the full flight management computer, and argued that the professional skill lay in choosing the right level for the moment and being willing to step down a level when the situation called for it. The problem, as he saw it, was a culture that pushed pilots to always operate at the highest level of automation – a culture, he pointed out, that the industry had built for itself.

The Magenta Line Comes to the Office

The office version of the magenta line is the AI-generated first draft. It’s the meeting summary we skim in lieu of attending the meeting, and it’s the tidy synthesis of a forty-page report we never open.

And it arrives with a similar promise of reduced workload.

By their own account, employees have started to feel the drift Vanderburgh described. In a survey of 2,500 workers and IT leaders released this spring by GoTo and Workplace Intelligence, half of employees said they rely too much on AI, 39% said that reliance is eroding their skills and making them less intelligent, and 28% said they’ve begun trusting AI more than their own judgment. (That the research was commissioned by a company selling AI-enabled software gives the findings an almost confessional quality.) Six in ten also reported feeling pressured to use these tools in the name of productivity, which suggests that the culture pushing everyone toward the highest level of automation is not confined to cockpits.

Measured Decline

Self-reported worry is one thing and measured decline is another, and medicine has started producing the latter. In 2025, gastroenterologists Krzysztof Budzyń and Marcin Romańczyk of the Academy of Silesia in Poland and their colleagues published a study in The Lancet Gastroenterology & Hepatology examining what happened after four endoscopy centers introduced AI tools that flag polyps during colonoscopies. When those same doctors later performed colonoscopies without the AI, their adenoma detection rate fell from 28% to 22%. The researchers came across the finding by accident and were careful to frame it as a hypothesis about deskilling rather than a verdict, but a six-point drop among experienced physicians is not the sort of number we want to merely shrug off.

None of this would have surprised Lisanne Bainbridge, the cognitive psychologist whose 1983 paper Ironies of Automation remains one of the most cited works in human factors research. Her central irony is that automation absorbs the routine work and leaves humans responsible for the rare, difficult exceptions, which happen to be the moments when skills that have gone unused for months are least likely to show up.

The better a system performs day to day, in other words, the less prepared its human operators are for the day it doesn’t.

Who Learns to Hand-Fly?

For HR, the most uncomfortable part of the magenta line problem has less to do with the experienced workers sitting in our companies today than with the people coming up behind them.

Carl Hendrick, who spent eighteen years teaching in classrooms and now works on the science of how people learn, has been circling these ideas for a while – his March piece carries Bainbridge’s ironies straight into the modern knowledge-work office – and this summer he borrowed Vanderburgh’s phrase for a terrific essay in his Substack, The Learning Dispatch, about what chatbots are doing to students. In it, he draws a distinction that ought to make anyone responsible for workforce development a little uneasy. The pilots Vanderburgh worried about had learned to fly by hand long before the flight computers took over, so what they lost was ready access to knowledge they already possessed.

Novices who reach for the chatbot before building any foundation of their own, Hendrick argues, never acquire that knowledge at all. And nobody can drop down a level to fly a plane they were never taught to fly.

Skipping Ground School

Hendrick’s subject is the classroom, but the argument travels easily into the office. The Polish endoscopists, like the pilots, had years of unassisted procedures behind them before the AI arrived.

That 24-year-old claims analyst you’ve just hired, on the other hand, may never write the clunky first draft, reconcile the spreadsheet line by line, or struggle through the first set of investigation notes that once built judgment through sheer repetition.

We tend to think of AI deskilling as a loss – the gradual wearing away of something a person once had. But for a growing share of the workforce, the skills aren’t eroding at all … they can’t erode because they were never laid down in the first place. Medical educators have been wrestling with the same problem among residents and trainees, and the vocabulary has made its way into the New England Journal of Medicine: deskilling describes the loss of a skill someone already had, while “never-skilling” describes the failure to acquire it at all, because AI did the work during the period when the skill should have been forming (not to be confused with its unfortunate cousin, “mis-skilling,” in which the trainee learns the AI’s mistakes as if they were facts).

And our HR processes and systems aren’t built to notice these things either. Performance management rewards output, and the magenta line produces a great deal of output. Competency models assume that a skill, once demonstrated, stays put. And most L&D programs (and budgets) are planned around adding new capabilities rather than protecting existing ones from atrophy.

Manual Override

Aviation eventually responded by encouraging pilots to step down a level and hand-fly on purpose, and I think it’s fair to wonder what the workplace equivalent might look like. Perhaps a periodic exercise in drafting reports from scratch? Or a performance conversation that asks someone not only what they produced but whether they can explain how they produced it?

Pilots do have one advantage the rest of us lack though, because when an autopilot disconnects, an alarm sounds and the crew knows the plane is theirs to fly. When Claude or Grok or ChatGPT hands the work back to us – with a fabricated citation or a plausible but wrong summary – it doesn’t point out that it’s wrong. No alarms are buzzing on our desktops.

I’m not sure how many of us can recognize those moments when they come … let alone remember what to do with the controls.

“No White after Labor Day” and Other Authorless Rules

Nobody knows who made the rule. There’s no founding document showing us there was an etiquette board that convened in 1903 and took a vote. No one has found evidence of a memo that was circulated among the summer houses of Newport announcing that white linen would be retired on the first Monday in September. Historians have theories of course, and the most persuasive one has very little to do with fabric weight or autumn mud.

White was what you wore when you weren’t working.

You wore it when you had somewhere cooler to be for three months and no particular reason to think about what a day’s labor does to a hemline or the cuffs of your pants. This rule that ended the season became a way for the people already inside the room to sort out who shouldn’t be allowed to enter the room. You either followed the rule or you didn’t — and knowing who didn’t, or couldn’t, follow the rule was entirely the point.

The rule has now outlived its own explanation by roughly a century. Vogue has pronounced it dead more than once. Every September though, somebody’s grandma still says something about people who shouldn’t be wearing white shoes.

I think about this a lot at work. But not because of the shoes.

The Unwritten and the Unexplained

Every organization I’ve been part of has carried a set of rules whose origins were lost in the same way — not written down anywhere anyone can find, not defensible under even gentle questioning, and enforced with a gravity wildly out of proportion to anything at stake.

The expense threshold set at $25 because of an incident in 2011 concerning Rory from Facilities that nobody can describe but everybody vaguely remembers. The dress code prohibition on open-toed shoes at a corporate office where the primary hazard is the carpet. The standing rule against scheduling anything before 9:30 AM, which has now survived by five years the departure of the executive who wasn’t a morning person. The PowerPoint template with the mandated shade of blue and the very specific hex code that’s not even in the company logo.

Ask about any of them and you’ll get a pleasant answer with no defensiveness whatsoever (because nobody really feels the need to defend anything). After all… “It’s just how we do it here.” (shrug)

But… whatever these rules were originally built to do, what they do now is sort and separate people.

Who Followed and Who Didn’t

Learning these types of work rules is how you demonstrate you’ve been around long enough to have learned them, and following them without comment is how you signal that you’re one of us. Which is why the new hire who asks “why do we do this?” is being more disruptive than she realizes. She isn’t challenging the rule so much as pointing out that there’s no there there and nothing is holding it up. And no one wants to hear that.

Now HR is not an innocent bystander here; we’re frequently the ones who wrote the rule down and memorialized it. Somebody did something ill-advised and a policy got drafted in response. The policy then outlived the person, the circumstance, and eventually anyone’s memory of why it had seemed necessary. And now it continues to survive in the department SOPs or the employee handbook — seemingly forever.

The complication is that not every unexplained rule is a white shoe in November; some of them are substantive and necessary. The requirement that feels most arbitrary is occasionally the only thing standing between the organization and a regulator, or between the organization and something genuinely bad that happened once and has not happened since. The challenge is that from the outside, structural and decorative look identical. Both are inherited, both go unexplained, and telling them apart takes more effort than we often bargain for.

Because without that discernment, we keep these rules — often for the same reason the white shoes go back into the closet come Labor Day. Not because anyone can explain them, but because asking about them may cost more than complying.

*****