4 Red Flags That Signal Questionable Work "Opportunities"
Find out why I'm especially leery of jobs that require "highly motivated" candidates, offer "full-time contract positions," and employ doublespeak.
Welcome to the 10th edition of This is Not Advice, a "not-advice" column for premium subscribers of What Works! If you’re not yet a premium subscriber, enjoy today’s excerpt—or upgrade your subscription to read or listen to the full piece! You can get 20% off an annual subscription when you subscribe today, Monday, September 11.
This week's question is from Will. Will wanted to know if I had any guidance for finding companies that aren't in the business of squeezing every last ounce of juice from their workers.
And, in true This Is Not Advice fashion, I don't. Or, rather, I don't have direct experience in the actual "getting hired at a company that doesn’t bleed you dry” part.
What I do have, though, is a long track record of hearing about the absurd expectations of employers (both from those setting the expectations and those who are subject to them). I also have limited experience with hiring and a bit more experience with working with people from (ostensibly or in fact) progressive companies. And I have more recent experience with combing through job ads and daydreaming about having a steady paycheck and 401(k) match in an ideal role.
All of that experience adds up to having a keen eye for red flags.
As in, there are certain words and phrases that—rightly or wrongly—I've come to associate with bad jobs.
Now, before I get into those red flags, a note for the small business owners and independent workers who are reading: this is absolutely relevant to you, too.
The line between traditional employment, non-traditional employment, and self-employment is fuzzier than it's been since the 1940s. While you may or may not be combing the job boards on LinkedIn or ZipRecruiter, you are encountering projects and "opportunities" that employ these same warning signs.
You might also be considering hiring help yourself. And it's amazing how quickly a progressive business owner can turn into an authoritarian employer.
Finally, these red flags apply to your own job description, too. Your expectations for yourself may be out of alignment with your values or priorities. See how many of these red flags are just "business as usual" for your own work.
Highly Motivated
This time last year, when "quiet quitting" was the anxiety of every Wall Street Journal reader, I read a line that makes my hyper-literal brain spasm. It was something to the effect of:
Most jobs require going above and beyond.
Read within our small-scale reckoning with undue expectations at work, it's a tiresome idea. But read within my words-mean-something-specific brain, it's ludicrous.
A job can't require going above and beyond.
If it's a requirement, it's not extra. The notion that we have to do more than the job description to fulfill expectations would be silly if it weren't so pernicious.
When an employer states that they're looking for someone "highly motivated," they mean that they're looking for someone who will see a job description not as an accounting of the actual job but instead as a jumping-off point from which the right candidate will imagine all sorts of new responsibilities, projects, and tasks.
"Highly motivated" means that nothing less than "above and beyond" will cut it. And when "above and beyond" is the baseline expectation, more is always the prescription since "above and beyond" serves to normalize ever higher standards of performance.
Are there exceptions? Sure. But it’s still a red flag.
To be clear, I consider myself pretty highly motivated. My quarrel isn't with highly motivated people. My issue is with "highly motivated" being a stand-in for "no boundaries," "easily exploited," or "willing to work harder and harder without guidance."
Full-time Contract Positions
Anytime I pull up job postings, it takes between zero and ninety seconds to find one advertising a "full-time independent contractor" position. Just now, I found a job for an independent contractor advertised as a "Full-time, Monday through Friday, 9 am to 5 pm; work-from-home position."
If a position is 40 hours per week with no end date or specific deliverable marking the end of an engagement, it is not an independent contractor role in the United States. It's full-time employment—and, depending on the rate of pay, may be subject to overtime rules.
Aside from the legalities of offering a position classified this way, accepting a position like this is a minefield. Without a W-2, a worker doesn't have the benefit of worker's compensation insurance or unemployment insurance. They also pay a higher tax rate, often have a harder time qualifying for credit, and have to purchase health insurance on the open market.
If you’re not in the United States, please know that our employment policies are draconian.
And aside from the financial implications of accepting this type of position, one must consider what kind of ethical framework the employer is operating with. They are opting (consciously or unconsciously) to heap all risk onto the worker while maintaining profit from the worker's labor for themselves. The employer is accepting almost no responsibility for the person whose time they're monopolizing.
Given all that, the working conditions for such a position are bound to be cruel. Even if the employer somehow does their best to maintain their contractor's boundaries, pay them fairly, and honor the responsibilities the contractor was hired for, they are willingly inflicting psychological instability on their team member.
Set Up for Failure
I often come across job descriptions in which the title of the job and the responsibilities described are clearly a mismatch. Most often, the title corresponds to the pay offered, while the responsibilities would generally command a far higher wage.
For example, I just spotted an ad for an "executive assistant" for $20 per hour, part-time (the ad doesn't mention whether it's W-2 or 1099... let’s just say that I have my suspicions). That pay would be at the very bottom of the executive assistant pay range, but let's go with it.
The job description, however, reads more like an operations manager or director. The job doesn't seem to be so much assisting the executive but managing the operations of a small team. To wit, the posting includes this chef's-kiss line to describe who this position is right for:
…if you are a team player and "that's not my job" isn’t part of your vocabulary...
When an employer hires an executive assistant for below-average pay with part-time hours and expects them to be the force of will that makes the company function, well, they've set themselves up to fail. But more importantly, they've set up the worker to fail. And the employer ignored that fact—which doesn't bode well for day-to-day working conditions.
This is one fairly common example. But it happens with many kinds of roles in many different industries. This "set up for failure" scenario is more common among small businesses and startups than it is with larger employers. Small business owners are often used to pushing themselves to the breaking point, and they've normalized that kind of "work ethic" in a way that makes it seem appropriate to expect others to do the same. While startups bank on “venture labor”—employees making a bet on better work conditions in the future.
Doublespeak
Doublespeak is a term for language that either obfuscates the truth or says one thing while meaning something else. And doublespeak is everywhere. Many of our most cherished values—such as life, liberty, and the pursuit of happiness—don't seem to stand for the actual meaning of those words.
I'll spare you my more overt political rantings today, though, to focus on doublespeak in the ways we talk about jobs and work.
The meaning of language is created not by the lexicographers at Oxford or Merriam-Webster but through its usage. Word usage—and therefore the meanings ascribed to words—vary by group, even when different groups speak the same language. For instance, when I say "freedom," I mean something very different than when Tucker Carlson says "freedom." That's doublespeak.
Oops. I said I'd steer away from politics.
I find the brand of doublespeak that occurs in job listings and company about pages particularly confounding. There are plenty of words that, in one context, mean something legitimately good about an employer while, in another context, mean something abysmal about working conditions.
Take the notion of family.
The word "family," when used to describe work environment, can mean two opposite things. A workplace can feel like a family in that team members look out for each other, offer caring feedback, and handle conflict with grace. Or, a workplace can feel like a family in that those with power expect those with less power to clean up their messes, make their proverbial meals, and attend to all of the emotional labor components of the work.
Insisting that a workplace "feels like a family" has also been used to break up labor organizing for decades.
I can't list all the ways doublespeak is employed in the way employers recruit and interview prospective new employees because doublespeak is always a moving target. As workers make new demands on employers, employers tend to take those demands and say they're meeting them. The language of the demand turns into a red flag that the opposite is happening behind closed doors. But at the same time, some employers really are meeting those demands and even, ironically, "going above and beyond."
Like I said, it's confounding.
I tend to approach any language that sounds good with a mindset somewhere between cautious optimism and healthy skepticism. If a company says they care about "work-life balance" in a job ad, I look for signs of "work-life balance" in their customer service policies, for instance. If a company says they're committed to an "inclusive work environment," I look for evidence of inclusivity in their product descriptions or content. Without talking to people with first-hand experience, there's no way to know for sure. But I try to do my due diligence when it comes to spotting doublespeak.
What about a green flag?
The best job descriptions, and hopefully then the most promising positions and work environments, are specific and full of information. Ambiguity is always a red flag. Meanwhile, well-considered details are often a sign that the people you'd be working with consider more than just how fast they can tear through one project to get to the next.
I wouldn't only look for specificity in a job description, though. A company's website should also display a level of thoughtfulness and transparency. Don't just tell me about your brand's values; tell me how those values are applied to policies and expectations. Don't just tell me you maintain a "positive work environment;" tell me what I can expect that to look like on a day-to-day basis.
Specificity doesn't only tell you that a job is well-defined or that a company means what it says.
Specificity most often signals that thoroughness and thoughtfulness are part of everyday operations.
It's a strong cue that even if you're working in a "fast-paced environment" or "disruptive industry," you won't be expected to work with undue urgency or cut corners. And that makes work better for everyone.
This piece is hardly an exhaustive list of red flags to be on the lookout for when it comes to finding less exploitative employment or being a less exploitative employer. But my hope is that thinking through these red flags (and one green flag!) helps you consider other potential pitfalls that might be specific to your needs, role, or industry.
Finally, if you're a small business owner or independent worker with no plans to hire, this is a good opportunity to assess the work environment you've created for yourself. What red flags might you notice if you were considering a job at your company? What do you put up with in your business that you wouldn't put up with from an employer? And is that working for you?