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Will you pay for my haircuts from now on? Here’s what to do with unusual employee requests


Will you pay for my haircuts from now on? Here’s what to do with unusual employee requests

Picture this: It’s a normal day at work. A nice day, even. The number of emails coming in is less than the number going out, and no one called out sick. You just might make it out of here without having to put out any fires.

And then…it happens.

A random employee – one of your good ones – suddenly sends an email that says, “We need to  talk.”

You knew it was too good to be true.

Immediately, your mind fast-forwards to them handing over a resignation, you needing to post a job ad, figure out the new pay scale, cover their clients… but you’re wrong. They’re not quitting, It’s actually kind of worse – they have a non-work-related request. Instead of “I quit,” they ask, “Will the company pay for my gym membership?”

Wait, what? This is a good employee, so you don’t just want to say “NO!” and slam the door.

But what do you say?

Things Employees Ask For
If this hasn’t happened to you yet, it will. An employee will ask you for something that saves them money but costs you. It can be an awkward conversation, not only because the employee is likely nervous to ask, but you’re hesitant on what the right answer is. And the requests can range from relevant to downright strange.

Here’s a breakdown of the four types of things employees typically ask for, and tips for how to answer them.

1. Things that will help them do their job better
We’ll start off easy. When your employees ask for tools or resources to do their jobs better, say yes (even if you think they’re silly and not really necessary). They want a bigger monitor? Yes. A new keyboard? Okay. A sit/stand desk? No problem. 

What they’re really saying is “I want to work more and get more done and this object will help.” Accommodating that request should be a no-brainer, as long as it’s not exuberant or immensely expensive, like a private jet to help them avoid rush-hour traffic.

I can already hear your objections: If one person gets a bigger monitor, everybody else will want one too! You’re probably right, but your answer should still be yes. Compared to the monthly price of an employee, the cost of equipment they need to do their jobs well will ultimately be trivial.

Consider the morale hit of saying no. Someone has gotten up the nerve and courage to ask for something, they’ve decided it will help them, in their judgement, it’s something they need. When you say no, you’re saying – “your judgment is bad, you are wrong, and you should feel bad about yourself. I do not trust you to decide what you need to do your job, I know better than you.”

I promise, that kick-in-the-junk will cost you a lot more than the thing they want.

That said, this does depend on your company’s financial health. If things aren’t going well and you literally can’t afford what they’re asking for, adjust your answer to “yes, but.. “We’re about to go bankrupt, so I have to say no for right now, but yes as soon as we can afford it.”

Side note: Do not ask a $75k-per-year employee to “justify” why they need a $200 keyboard. It costs them more to write the email explaining it than it does to give it to them. It also probably makes them feel like they’re in preschool and need a key to go to the bathroom.

2. Education benefits
This one is a lot more expensive than buying monitors. The best course of action here is to establish a company-wide policy that lays out how much money the company will spend per employee per year on education benefits, and what is included. 

For example, “education” should be clearly defined as classes or certifications that are directly related to either improving an employee’s current role or preparing them for a future goal. (No, your accounting firm is not paying for an employee to take art classes at night.)

As a thank you to your longtime employees, consider awarding education benefits based on job title and years of service. For example, employees who are Level 2 engineers get $500 per year for job training, Level 3 is $750, and so on.

3. Random, non-work-related benefit requests
The biggest mistake you can make here is to treat one-off requests as one-off requests. That can get messy, quickly. Instead, establish one rule to rule them all, and make sure the policies are clearly written and easily understood. It only needs one word: NO.

If you say yes to one request, you’ll open the floodgates – trust me. And once you’re paying for one person’s gym membership, you’re paying for everyone’s gym membership.

Take it from the guy who was once paying for 13 people to lift weights after work.

Your policies on non-work requests should be simple and well-defined. Make it crystal clear that the company pays its employees money and offers certain benefits, like health insurance, retirement, and whatever else you decide to offer – and nothing more.

For example, let’s say an employee claims that another job offered them the same pay, but will also pay for the tolls along their commute. If they’re a good employee and you want to keep them, you can give them a raise equal to the amount of the tolls – but never the tolls themselves. Once your other employees find out (and they will), paying for everyone’s commute will become an expectation.

Here’s a trickier situation: A female employee based in Texas asked for relocation assistance because she wanted to be closer to one of her children. Her supervisor, a mom herself, was torn. The supervisor’s oldest lived far away too, and she understood the loneliness that brings. But on the other hand, she worried about setting a precedent.

If a request is made based on emotion, it’s essential to give an answer that’s based solely on business – even if it’s gut-wrenching. In any other non-work-related circumstance, would you offer relocation assistance? If an employee said, “Will you pay to relocate me? The weather here is terrible,” the answer would be a clear no.

From where I sit, people get paid a salary that they can use however they wish. If they want to move, they can use it for that. If they want to hit the gym, they can use it for that. The emotion-based decisions that don’t directly relate to their job need to stay with them, not you.

4. More money
This is probably the most common employee request you’ll encounter. (Just keep in mind when an employee asks for more money that it probably took them a week to muster up the courage just to ask for the meeting, and their heart is probably beating out of their chest as they sit down. If your answer isn’t what they were hoping for, be gentle.

The good news is that If an employee simply requests a raise, getting to a yes or a no is straightforward. It starts by evaluating their salary. Is it fair? If it’s below other comparable salaries for the position, then adjust their salary to match the market. If it’s already in line with the market, then show them the numbers and tell them no.

It gets more complicated if your employee tells you they got an offer to do the same job at a different company for more money. The first thing to do in this situation is ask for a copy of the offer. I can’t count the number of employees who have used this tactic to try and fake a raise. When you ask to see the offer, those conversations come to an abrupt, awkward end.

In real job-offer scenarios, it’s also good to see the offer because the employee honestly might not fully understand whether the offer is actually better. (I once had an employee who was hoppin’ mad that they were being underpaid. They came with a new offer, but didn’t realize it was a temporary contract job. Yes, it was 35% more in pay … but it only lasted three months, with no benefits, and no employer-paid taxes. Going over the offer together helped them avoid making a big mistake.)

Offers often get misconstrued as “better” because the employee focuses solely on the annual dollar amount and glazes over the rest. This can be a costly error, because if you go from free health insurance at one company to $200 a month at another, your expenses just went up by $2,400 a year. Does the raise in salary justify that?

The same goes for PTO, which is basically the money you earn without having to work for it. Earning a slightly higher salary but reducing your PTO from 4 weeks to 2 isn’t necessarily a step up. Here’s why:

If I offer an annual salary of $52k, I value each week at $1k. If I give 4 weeks of PTO, that’s a value of $4k. If their new offer is $54k but only has 2 weeks of PTO, they’re just making an even exchange.

Tips and advice
If an employee is hesitant to show you the new offer, tell them it’s okay to redact the name of the company or any other identifying info. Reassure them that your only intent is to help them ensure they’re making an apples-to-apples comparison. 

Sometimes, your conversation will reveal that the new apples aren’t as ripe as your employee thinks they are. In those cases, you might find them slinking out of the office and back to their desk with a sheepish look on their face. 

If the new offer is comparable or better, however, then double-check your math. Are you sure you’re paying fairly? If so, and the new company is overpaying…that’s a them problem. And sometimes we just have to let good employees go. It’s not a smart business decision to start doling out ruinous raises because you’re afraid of hiring – that’s not sustainable in the long run.

If employees come to you with requests, be mindful about establishing precedent. Anything you do for one, you’ll end up doing for all. For unusual requests, even from your favorite, hardest-working employee, it’s imperative to consider the ripple effect that will happen if you say yes – because it will happen. And faster than you could ever imagine.

Take it from the guy who once paid for 13 gym memberships.


Once you’re paying for one person’s gym membership, you’re paying for everyone’s gym membership. Take it from the guy who was once paying for 13 people to lift weights after work.

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