How do you balance time off requests?
A reader-submitted Q&A about so much more than scheduling
Did you know you can submit reader questions and seek advice by replying directly to this email? You can!
I’ve always said I’m not planning to repackage my knowledge into a PDF or an online course and charge you for it, because my #girlboss phase is officially over, but if you’d like me to turn your current dilemma into a writing prompt, I welcome the opportunity. I dislike the idea that I'm giving advice to anyone, so let’s think of it more as a reframing, a validation that I’ve also grappled with this stuff, and probably at least 12 other shop owners have as well. Maybe they’ll even post additional thoughts in the comments!
So! On to Storefront Revolt’s first reader-submitted letter. (And yes, if you write to me, I can keep it anonymous.)
If someone asks for a weekend off during the busy holiday season and they normally work every weekend day, do they end up with the days off? Do you ever not give people the days off they want? What happens if every staff member requests the same day off? Do you have a policy for that?
Do you have different expectations of manager folks working during your busy season? Like they can’t request certain days off?
I’ve got an employee who I’ve always done my best to be accommodating of. I do my best to be accommodating of everyone, sometimes feeling as though I am bending over backwards to get them the time off they need. We all work collaboratively to really get the schedule to work for folks, so that people can have the time off they need. I schedule a month in advance, and a month at a time. I send an email saying “tell me when you can’t work,” and don’t schedule people at those times. Maybe the biggest fault, if someone asks for a week off, or their normal workday, I don’t always create extra hours to fill the time lost. So let’s say you request a day where you work 8 hours off, you will miss 8 hours at the next pay period.
But ok, back to the employee. She’s worked with us for 2 years. She’s got lots of retail experience. She’s taken over some backroom tasks and since our manager went down to 1 day a week she’s stepping up and I’ll most likely ask her to be manager next year. She took 16 days off in August and September which we accommodated without question. She requested to work 30 hours a week, which is more than she did this summer, so she could drop her summer waitressing gig. And so when employees all got more hours when the manager left, she got the most. I prioritized her request. But she also wants to stay working that number of hours and can’t work more come Christmas season. In December we usually average a non-holiday month's worth of sales in a week, it’s bonkers crazy. She emailed saying “My boyfriend and I will be going on a weekend trip December 1-3 and I’d appreciate if I can have it off." She’s asking for two of her normal work days off at a time when we need all hands on deck.
Not giving someone the time off they request feels yucky to me, yet I want to have a conversation with her where I share that I feel she’s on the manager track, and that we've accommodated her needs and that it’s hard for us to be down our normal weekend employee during a weekend where we will sell four times what we normally sell in a weekend. So I’m torn between feeling yucky—we don’t live to work, we work to live, her needs should come before the business—and also wanting to share how her absence would be really impactful and a manager can’t really have weekends off in December.
One thing really stands out to me about your question, and that's your use of the term "yucky." You feel yucky having a conversation with this could-be manager about why their schedule request conflicts with your need to adequately staff your shop during your busiest season. I don't think you have to feel yucky about it, and I think feeling yucky about it is the real issue here.
On the one hand, I get it. It's not like I come to work excited on the days I have to tell someone they can't have what they're asking for, or that they need to, you know, "improve performance." Those conversations are never fun, but they're necessary, and after years of managing people we get better at having them. Maybe that's all you mean by "yucky" in this context, but I suspect it's something more because of the whole "we don't live to work" comment. So let's dig into that.
There is an element of perfectionism in your letter. I sensed it when I read that part about failing to balance time off requests by shifting the schedule so people get the same number of hours even when they're taking days off. It's nice if you can swing that for folks, but it's not a fault if you don't. I think that's normal for part-time retail.
I have a feeling that you probably have some toxic workplace experience in your job history, because your question reads to me like you actually have no idea what's normal. And look, that's not a value judgment! I didn't have a "what's normal in a workplace" compass either when I opened Fernseed. We can't model something we've never experienced. For example, I've had part-time retail jobs where if I asked for a Friday off that I usually worked, I might get even further de-scheduled! But managers also screamed in people's faces at these jobs. In other words, I never saw a healthy example of a retail manager doing something that made sense for the business where it also felt like they still cared about their team. Have you?
It sounds like you would rather bend over backwards to please everyone on your team in order to demonstrate that you are not that toxic manager than enforce what are, in fact, very reasonable limits on time off. But somewhere you've lost the map on what's reasonable, so you think any limit at all is cruel. In the absence of past good examples of reasonable, but compassionate, boundaries, you're striving to be an ideal boss based on standards no one can ever meet.
Maybe it's not your personal work history, but your relationship to work as a boss and business owner. We're living in a cultural moment right now of recalibrating our entire relationship to work. There are a million points of data in this cultural moment—comprised of each news story and Instagram post about going back to the office, labor strikes, gig economy jobs, the Great Resignation—and the connect-the-dots picture it's all painting is that work sucks and the system is broken. Now, if you're someone who is asking people to come in to work in this moment rather than granting vacation requests, it probably feels like you're not getting the memo.
But you know what? It sounds like you are getting the memo. It sounds like you're keenly aware that there's an unfair division between who has access to capital and who performs the labor, and that there is often immense income inequality between entry-level and C-suite work. But it also sounds like you're overcompensating for the parts of the memo that don't belong to you. Yes, the old way of trading time for dollars is in a moment of reckoning and rightfully so, but you, as a tiny storefront business owner, don't have the financial resources or personal stamina to grant someone's 17th day off, especially if you're working those hours yourself, and that doesn't mean you're not part of the collective work-life recalibration.
You said this employee has been with you for two years, which by my calculation means they were not working for you during the COVID shutdowns and immediate aftermath. You WERE there. So was I. I'm pretty sure you and I both pulled some all-nighters packing up online orders while the rest of the world stayed home, and then more all nighters expanding and contracting physically and financially in the wake of fickle consumer spending post-COVID. One day you're opening up a second storefront to accommodate the massive influx of orders, the next you're borrowing $8k from your personal savings to make payroll because "July is just a really bad month." I'm not saying your employee had to go through that with you in order to deserve a weekend off. I'm saying after going through all that, you probably need a weekend off too. You're protecting yourself from burnout by not constantly filling in for people, even if you have nothing else to do on a Saturday.
So I'm going to push back on this notion that your employee's needs trump the needs of the business, because the business itself doesn't have needs, you do. You have tasks to accomplish that some people on your team don't know exist. You have also taken on all the financial risk, which means that, unlike your employee, you can't just walk away from this job whenever it doesn't feel like a fit. You don't have to explain these things to your team in order to get their buy-in on the reasons you can't work Saturday, either.
You have no idea whether anyone working for you is part of the marathon or just here for the sprint. All you know is that you are in the marathon, so you can't default to sprint-like behavior, like working 14 days in a row and missing doctor appointments. Conserving your marathon energy also means staying healthy enough to cover for sprinters when they really need it, which aligns with your compassionate (but not perfect) boss values. This specific employee request—to take a weekend off for a vacation with her boyfriend—is not a need, especially if she's had 16 days off in the past two months. You're conserving marathon energy to cover when actual needs arise, like illness and emergencies, so you can compassionately and without reservation say, "Go take care of your life, I've got this."
You can honor someone's whole self and inherent human value AND ask them to work both weekend days because that's part of the job at this store. It's normal! But you can't start expecting your employees to believe that's normal until you believe it's normal. You have to find your own path to getting there. I'm still finding mine.
But here's where it gets a bit tricky.
It sounds like you have a situation where this person isn't quite a manager, but is "on track for management," and you're giving them this information in fits and starts, never in a concrete way that clearly outlines the path to management. It's probably not a great time to tell them they're on track to be a manager in the same conversation as, "You need to stop casually asking for weekends off." I am the WORST at this, by the way. I think somehow that the way to explain why I want someone to see why what they're doing is a problem is by... telling them I can see them being a manager in the same breath?
"You are making so many mistakes in these finance reports, and that's costing us a lot of money. But the reason I want you to start catching these errors is because I really see you managing this place one day." That doesn't sound logical, does it?
A better, but harder, way to get this not-yet-a-manager to work all the weekends in December might be to say: “I got your request for December 1-3. I'm not going to be able to swing that for you, I'm sorry. I'm sure you remember from last year that we're super busy during that time, so we need everyone working their usual shifts plus additional hours when possible. I'm not asking that you work beyond 30 hours, which is already an accommodation, but I really do need you here all the weekend days that month."
You know how you know if she's manager material? By how she handles that conversation.
Performance reviews are also a great time to have conversations about people's interest in management and what you see as the clear track to getting there, but I know having meetings off the floor in a retail setting, especially when payroll budget is limited, is challenging. Despite the scheduling challenges, we started doing annual performance reviews at Fernseed two years ago, and they’ve made it easier for me to set the cadence by which we offer raises and job promotions. It (mostly) stopped me from mumble-promising new job roles to people randomly, or agreeing to raises the second anyone expressed ambiguity about their role.
Wherever you can in your business, seek realistic clarity over generous ambiguity. Right now it sounds like you're generously, but ambiguously, offering unlimited time off, but now you need to turn off that faucet of unlimited generosity because it's harming you and the business. You know it doesn't make sense to accommodate this time off request, but you've unwittingly created a culture where you always say yes. How can you now say no, and on what grounds?
When I started Fernseed I aspired to be the most generous boss, and I thought cool perks was one way to get there. These perks included sparkling water in the fridge, reimbursement for using personal phones or computers for work, expensive hygiene products in the bathroom. The problem with these perks is, unlike the tech companies I worked for in the past that I modeled them after, my tiny retail business couldn't afford them, so when the cash flow dipped, they went away. While that doesn't sound terrible—budget cuts are budget cuts, right?—it actually sets the tone that the little benefits you come to rely on as an employee, whether it's sparkling water or a relaxed attitude about time off, could come and go at any moment. I'm talking about psychological safety! In the five years of doing this job, I've learned to underpromise and overdeliver on perks, which means starting off by saying no to a lot of things and learning not to feel bad about it, because I feel worse—and my team feels worse—when perks disappear. Keep that in mind the next time you say no to something. While it may feel yucky in the moment to deny a request, you're actually building the scaffolding of psychological safety that allows people to know what to expect, even if it's less than they would wish for, and that's healthy. That's what a compassionate boss does.
Clearly defined job roles also help eradicate ambiguity. Perhaps working all weekend days in December is a requirement of the manager role, in which case, you can outline that at the offer stage versus springing it on someone as a loose requirement of a future position they may or may not be promoted to.
I got a great piece of advice last year about the difference between expectations and agreements. The idea is to move away from expectations, which are easy to misinterpret and change constantly, and shift instead into agreements, which are clear and mutually agreed upon. Consider the difference between a management conversation where you say, "I expect you to work all weekend days in December," and one where you say, "When you agreed to this role, part of that agreement included working all weekend days in December. Right now I see you pulling back on part of that agreement."
It doesn't help you to have someone in a management position who's only doing part of the manager job but abandoning another critical part, even if the parts they are doing are stellar. You have to find a way to define what all the parts of the job are so you can take them off your plate, because there's psychological safety there for you. Under the terms of a less ambiguous agreement, if a manager won't work weekends in December, or work beyond 30 hours per week, you have permission to find someone who does.
Honestly, I don't think you have to be in charge of scheduling anymore, either. I recommend promoting someone to management and having them take over the scheduling, in part because once someone else in the business is tasked with it, it becomes pretty obvious just how difficult this stuff is and how, no matter what you do, someone isn't getting their ideal schedule. It also removes you as the gatekeeper of time off requests, which can be influenced by your emotions. Having someone else do the schedule is actually more democratic!
I do love that you're doing the schedule a month in advance. We do that, too. Informally, if it's still a few weeks out, we're cool with adjusting the schedule for last-minute things that come up. But once we're at the point of no return, which is different in every business, we ask people to arrange their own shift coverage before reaching out to management. Our scheduling software (Homebase) makes this easy, so if you don't already have one, I recommend using a shift scheduling software. That way you're not emailing everyone to ask for their time off requests, either, they can just make them in the software. This helps people who are shy about asking "the boss" for time off, because they can just mark off dates in a software versus wording a request to you directly. More scheduling democracy!
The end-of-year holidays aren't our busiest time, ours are Valentine's Day and Mother's Day, during which, to answer your question, we do expect everyone—not just managers—to work. Our current GM suggested this next scheduling stroke of genius, which I'll suggest to you: vacation black out dates. Long in advance of busy holidays, we "black out" dates on the schedule where no vacation requests will be granted. If you work here, you know you'll be required to work those days unless you arrange something with a manager. We talk about this in the hiring process, and it becomes part of our working agreement.
Remember, it's an agreement, not an expectation. It's explicit from the moment of signing, which means that even in serious matters, like someone requesting Mother's Day off because it will be their first Mother's Day after their mom died, I can reasonably, and with compassion, say, "I completely understand that it's a difficult day, and I'm here with you in that experience. As much as I would like to accommodate that request for all the reasons that make me human, this is a really small team, and I can't give you this incredibly busy holiday off—and tax everyone else—for something that isn't an immediate and pressing need to be away from work. I know that's not what you want to hear, and I'm sorry, but I'm more than willing to arrange with the team that you won't have to work any customer-facing retail that day, if it helps."
Might that person quit after hearing that? Maybe. If they do, I'll feel okay that I handled it as compassionately as I could while maintaining reasonable boundaries for what it takes to run a small business. I feel more okay doing that when we outlined that part of the job a pretty non-negotiable upfront.
We also use black out dates to earmark days we're already saturated with time off requests, so no one else can ask for and receive that day off. It's okay to normalize the idea that if you want to work at this little shop, these are the required working days. But we balance that with a few compassionate and easy to execute practices around time off.
We accommodate requests on a first-come, first-served basis.
We discourage our team from providing a reason for time off requests. If it's available and you have PTO, take it! We don't want people to feel as though they have to justify the reason.
We make it clear that we can make black-out date exceptions for important family gatherings, surgeries, religious observances—the stuff of life that can't be simply shuffled to the next weekend.
We don't require a doctor's note for a call in, and we don't want you to tell us why you're calling in sick unless it's a matter of pandemic contagion.
I'm not saying you're not doing any of this. Rather, I'm highlighting that these are all ways to show a compassionate balance between staff needs and the needs of the business, which are really just the needs of everyone who works in the business to maintain a healthy work-life balance, including you.
You know what else helps? An employee handbook. Do you have one? I know it sounds like a LOT of work if you don't have one already, but I suggest starting from a template, or just jotting down a bunch of stuff that's floating around in your head each time you wish you could explain to your team why what they're asking for doesn't work. Start turning those requests into policy! Have your team read and accept the terms of the handbook before starting the job. When I created our employee handbook I printed everyone a bound copy and had my current team read and agree to it after a period of open feedback. I was surprised when several people told me they appreciated the clarity, and that they hadn't had that type of clarity in any previous job.
You can outline your time off policies in your handbook! It sounds like right now you're giving people unlimited (unpaid) time off, which is exceedingly generous, but in a retail business, can be paralyzing. We have a paid time off policy that's official and managed by software, but we also have a semi-official unpaid time off policy outlined in our handbook. I don't have the exact wording in front of me, but it's something like, "At a certain point, you kind of have to be here frequently enough to do your job." This normalizes the idea that if you have a specialized role and someone else has to frequently do a task that you are responsible for, we may need to reassess.
Of course we're talking about discretionary requests and not chronic illness, FMLA, parental leave, situations involving domestic violence, housing insecurity and other reasons people need to take time off of work where legal issues are involved. I can't give HR advice here, but I can say that I feel more confident in my ability to manage complex employment issues now that I feel a bit more firm in my sense of where I draw the line on discretionary ones.
In the immediate, I recognize that it might be hard for you to say no to this request for December 1-3 because you've already—generously!—allowed so much time off without clarity—agreements!—on what the expectations of this person's job is right now, not when they may one day become a manager. Working those days for her might be one more hit you take for the team so you don't have to have a hard yanking-away-perks-without-warning conversation today, and it's up to you to decide if it's worth spending your marathon energy on this sprint. As an alternative, you could ask her to switch with someone else on the team, because you're "trying to move away from covering already-scheduled weekends except in emergencies."
The next steps will be for you to decide what you really need in a manager, and what compensation and perks the business can afford to offer someone who, let's say, works 35+ hours a week 49 weeks of the year, and works every weekend day in December unless they can figure out a better scheduling system because they handle the schedule. Then you clearly and unambiguously post that job role internally for anyone on your team who may be interested in it, which of course includes this could-be manager, but also anyone else on your team who might be interested in entering into that agreement with you.
This process takes time, but so does any worthwhile recalibration of reasonable work-life balance, whether it's systemic and cultural, or internal to your business. The point is, both are justified.