Picture by Talia Cohen

Unlimited vacation is a dark-perk and you should use that to your advantage

Ask the tough questions during the negotiation portion of your next job interview

Unlimited vacation time is a “perk” that companies have figured out works in the US. Some countries protect employees from their employers by making shenanigans like this illegal but in the US we get freedom.

Unlimited vacation time, sounds great right? Yeah, that’s what friends in SF thought when their companies one by one added the latest greatest cost-saving-mechanism-disguised-as-a-perk to their compensation packages.

Here’s the rub. People don’t use it. I know, I know: you won’t be one of those people, you’re going to take advantage and use more vacation time than you would have before. You’re wrong, chill. Everyone thinks they are an outlier. I do, you do, we’re all outliers. A few questions:

  • Are you going to get your work done and still take advantage of the unlimited leave? Do you ever get your work done? I don’t. Of course, I finished the thing assigned to me but I’ve never worked at a company where the work finished. There is always more work, always a next thing, always an important thing that would have started already if only that last project hadn’t gone late. You’re not going to take more vacation.
  • The person sitting next to you hasn’t taken leave in six months, who wants that promotion more?
  • Who is counting the leave? Someone is and you know it. What’s the limit? How will you know? Will you know before it’s too late?

The game is rigged and honestly, you should have seen it coming. Suddenly vacation time is restricted socially instead of by policy.

Frankly, it’s surprising to me how many people underestimate the material value of unused vacation time. Not the value to themselves as humans, the material value. The value to the company; The red ink at the bottom of the balance sheet. Adopting an unlimited leave policy is a cost-cutting measure for a business. Cost cutting? Yes, they no longer have to pay out unused vacation when someone leaves the company. They no longer carry debt to every single employee who hasn’t taken this year’s two, three or four weeks of paid vacation.

Negotiating for compensation at a company with an unlimited vacation policy.

Say this with me: “What is the average number of vacation days taken by employees in the last twelve calendar months?”

That’s your question to the recruiter who mentions the unlimited leave policy. I can tell you from experience that most recruiters freak out. I mean they freak out in their head, you won’t see it on the surface. “Must be professional!” It’s fun and telling all the same time.

We’ve already established that someone is counting. The recruiter’s willingness to share the numbers depends on the company (which I happen to believe is a reasonable approximation how they treat their people). Information asymmetry is the recruiter’s biggest gun in salary negotiations and let’s be clear, you are massively outgunned. Asking questions that they aren’t willing to answer is the most effective way of exposing and leveraging this asymmetry for yourself. It’s time to push.

Imagine your annual salary, your monthly or weekly rate. Now break that number down into a daily increment, your pay-per-day rate. In a company with a static amount of leave where unused leave is paid out when an employee leaves, this is basically the rate at which those unused vacation days would be paid out. Under an unlimited leave policy however, no leave is paid out. I also happen to believe that my leave days are more valuable than a regular day. After all, I get to do whatever I want with my time, not what someone else wants me to focus on.

My advice is that you take this pay-per-day and multiply it by the average number of vacation days that you would have expected to come in the compensation package. In the US this is generally something along the lines of fourteen days: per-day*14). If you’re like me and value your vacation time more highly you might use: per-day*1.5*14, meaning vacation days are worth 50% more than regular working days.

Now you’ve got a little bit of leverage and you’ve got a number. Ask for it. It’s not that hard, something like: “Given the benefits on offer, I think my total package should be x amount higher.” Keep in mind, the person on the other end of the conversation is a professional negotiator. You won’t surprise them, this is literally the bread and butter of their employment.

Other dark-perks

Warning: Some of these are personal opinion. In some cases, there are two maybe three exceptional companies actively practicing and proselytizing these ideas. For truly exceptional cultures these things may work to that culture’s benefit.

  • Open plan offices
    You’d think that noise canceling headphones being a standard part of the dress code would be a sign that something is wrong.
  • Many (but not all) “flat” org structures
    Any company with more than 300 employees that is “flat” usually means leadership doesn’t have their act together or hasn’t been able to recruit truly great management talent. A red flag at best. Soul crushing culture problems at worst.
  • “You decide what to spend your time building”
    There were two technology companies that actively promoted this way of working and both had significant and public fallouts that were directly associated with the culture that arose from this way of working. Unfortunately, without leadership setting focus for a company and mandating that focus, companies tend to devolve into a more professional version of Lord Of The Flies. I honestly wish this worked but I just don’t think it does.
  • Dinner
    This is actually great for a fairly narrow but over-represented group. That a company is spending this much money catering to said narrow and over-represented group should be a call to look more closely.

But I want the job

The point is not to call-out companies or insinuate that they are awful because of dark-perks. There are truly great companies among dark-perk practitioners. Additionally, there are companies that have perks that I would assume to be “dark” that are actually legitimately perks of those because the leaders have been careful about building a culture that affords for those perks to be used properly.

No team is perfect and if after meeting a few members of that team you’re convinced that it’s a great place to work, go for it. That being said, the natural information asymmetry of salary negotiation will always work against you. If you believe that you’ve interviewed well and have convinced them that you would be a valuable hire, I kindly suggest you take advantage of any leverage that you can find while negotiating.

Don’t get screwed. Keep your eyes open and investigate the package.

Wesley Walser is the founder & CEO of askinline.com which automates the painful parts of collecting and actioning customer feedback. You can follow him on Twitter or on Medium.