“Did I miss the deadline?” I get asked this all the time. If you run live promotions with deadlines, you’ll get asked it too. Someone misses your cutoff, reaches out, and wants in. Do you take the money anyway, or do you stick to the deadline?
I’ve handled this a few different ways over the years. There was a time I was incredibly strict: miss the deadline, you don’t get to buy. I’ve eased up on that, but my answer still depends on what I’m selling. For a live cohort with a real start date, I stay strict, because I need to know numbers and I don’t think people should join a live course after it has started. For an evergreen program where the deadline is about a discount or a bonus going away, people can still enroll, but the discount and bonuses are gone.
In this episode I walk through why bending a deadline can feel unfair to the people who bought on time, why a late exception of days or weeks hurts your brand, and why “we’re reopening by popular demand” trains your audience to wait for the next chance. I also get into the times I say yes (a 24-hour grace period, and a bank blocking a payment before the deadline), the times I say no, a coach who took a late $3,000 client after a launch with no sales, and a woman I turned down who respected me more for it.
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Questions I ask before I make the call:
- How late is it? Within a day, or a week later?
- Was there a real reason (forgot, tech issue, family emergency)?
- Would I be comfortable telling the people who bought on time that I made an exception?
- Was this person already in a sales conversation with me?
Takeaway:
A deadline only works if your list believes it. Decide your rule before your next launch (grace period or not, how long, and for what reasons), apply it to everyone, tell people why the deadline exists, and if you hold the line, offer a next-round email or another option instead of slamming the door.
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- Website: kendraperry.net
The Deadline Passed. Do You Take the Money Anyway?
“Did I miss the deadline?”
I get this question all the time. If you run live promotions with real deadlines, you’re going to get it too. Your cart closes on Friday. On Monday, someone reaches out. Maybe she meant to buy and forgot. Maybe her payment got blocked. Maybe life just got in the way. Either way, she wants in, and now you have to decide what to do.
Do you take the money anyway, or do you stick to your deadline?
I’ve handled this a few different ways over the years. There was a time in my business when I was incredibly strict. If you missed the deadline, you didn’t get to buy. Period. I’ve eased up on that, and these days my answer is usually “it depends.” That’s not a cop-out. It really does depend, and in this post I’m going to walk you through what it depends on so you can make the call yourself.
I’m not going to tell you there’s one right answer, because there isn’t. What I will give you is the things I think about, the times I say yes, the times I say no, and a short list of questions that make the decision easier. Because the worst time to figure out your rule is when a message is sitting in your inbox and you need the money.
Why This Decision Keeps Coming Up
Deadlines are everywhere in online business. A discount that ends Friday. A bonus that disappears at midnight. Enrollment that closes before a cohort starts. Good promotions have them, and for good reason: a deadline pushes people to make a decision instead of letting it drift.
And when you have a deadline, some people will miss it. It’s not a question of if. It’s a question of what you do when it happens.
This is one of those decisions that feels small in the moment and ends up shaping how your whole audience treats you. One late sale feels like no big deal. But your list is paying attention, whether you realize it or not. What you do with that one message teaches people how seriously to take everything you say after it.
That’s why I think this is worth deciding on purpose, before the message shows up.
Start With What You’re Selling
The first thing that changes my answer is the type of offer. I treat a live cohort very differently from an evergreen program.
If You’re Running a Live Cohort
A live cohort has a real start date and a real end date. Everyone goes through the material together. If I’m launching a live cohort course, meaning a course with a start date and an end date, I’m very strict about the deadline. I have two reasons.
First, I need to know my numbers. I need to know how many people are coming so I can plan the content, the support, and the sessions. A fuzzy headcount makes all of that harder.
Second, I don’t think it’s good for people to join a live course after it has already started. They miss the early sessions, they feel behind, and everyone else has already moved on. That’s not a great experience for them, and it’s not great for the group either.
So for a live cohort with a legit start date, the deadline is doing real work. It’s not just a marketing tactic. It’s part of how the program runs.
If You’re Running an Evergreen Program
Sometimes you don’t have a live cohort at all. You have an evergreen program with ongoing enrollment, and what’s expiring is a discount or a bonus, not access to the program itself.
That changes things. If someone misses the deadline for a discount, nothing breaks. They can still enroll. They just don’t get the discount or the bonuses anymore. My answer in that situation is simple: “Yes, you can enroll, but unfortunately that discount and those bonuses are no longer available.”
That keeps the deadline honest. The offer that expired stays expired. And the person still has a way in if they want one.
So before you decide anything, get clear on which situation you’re in. What is actually closing? A spot, or a perk? The answer tells you how much room you have to bend. It also tells you what you can offer the person without undercutting everyone who already bought.
What Bending a Deadline Actually Costs
Let’s talk about the downside, because there’s a real one. It just doesn’t show up right away.
It Can Feel Unfair to the People Who Bought on Time
Think about the people who respected your deadline. They saw the date, they made a decision, and they bought before it closed. They did what you asked them to do.
Now imagine you let someone in three days later, with the same bonuses and the same deal. It can feel a little icky. It can feel disrespectful to the people who took action when you said to.
I think about this a lot. If I wouldn’t be comfortable telling the people who bought on time that I made an exception, that tells me something. Fairness matters, and your buyers notice it, even when you never say a word about it.
A Late Exception of Weeks Can Hurt Your Brand
There’s a big difference between someone asking a few hours after the deadline and someone asking a week later. Or multiple weeks later.
When the gap gets that big, the exception stops being a kindness and starts looking like you don’t mean what you say. Suddenly you come across as loosey-goosey. Your deadlines start to look like suggestions.
And that hits trust. If you say there’s a deadline and that deadline turns out to be meaningless, why would anyone respect the next one? Trust with your audience is built on your words matching your actions. Every deadline you bend a little chips away at that.
The “Reopening by Popular Demand” Trap
This is one I see people do, and I really don’t love it.
An enrollment or a bonus closes on a Friday. Then on Monday, the email goes out: “We’re reopening due to popular demand!”
Sometimes that happens because the launch didn’t bring in any sales, or the person wasn’t happy with the number of sales, and they’re trying to get a few more people in. I get why it’s tempting. But your audience catches on. They start to see the pattern, and they start waiting for the next chance.
If you do this every time, you train your audience that your deadlines mean nothing. Why would anyone rush to buy on Friday when they know the door will swing back open on Monday?
That’s fake urgency, and I don’t like fake urgency. It wrecks the exact thing you’re counting on when you set a deadline in the first place: people believing you.
So if you reopen, make sure the reason is true. Don’t say “popular demand” unless it actually is.
The Case for Saying Yes
None of that means you should always say no. There are good reasons to say yes, and I say yes plenty of times. It’s your business, and you get to make the call. Here’s when I do.
A Short Grace Period
Depending on the launch, I often have a 24-hour grace period. I don’t do it every single time, and it really does depend on the launch. But when someone messages me and says, “Oh my God, I really meant to buy and I totally forgot,” or tells me something happened, I’ll often say, “No problem. Here’s the link, but you’ve got to buy before midnight tonight.”
That keeps the window tight. It gives people a little bit of humanness, and it doesn’t stretch into days or weeks. If it were a live cohort with a hard start date, I’d likely still say no. But even then, if it’s within that 24 hours, I might make an exception.
The key is that the window is short and the rule is the same for everyone.
When Someone Tells You About a Problem Before the Deadline
This is the one exception I always honor.
During one of my previous webinars, our deadline was Friday at midnight. A woman was trying to buy, and for whatever reason, her bank was blocking the transaction. She couldn’t pay. She emailed us before the deadline.
It was Friday evening, close to midnight, so nobody was available to answer. We didn’t get back to her until Monday.
We honored it. We could see she had been trying to purchase, and that the bank blocking her wasn’t her fault. So we kept the discount in place and let her buy.
That led to a rule I follow now: if you email me before the deadline and tell me you’re having trouble checking out, because of a technical problem or an issue with your bank, I will always honor the deadline. My team isn’t answering emails after about 4 p.m., so I know there can be a delay on our end. The fact that she reached out in time is what matters.
If you have a team, this is a good rule to adopt. It’s clear, it’s fair, and it protects the people who did the right thing.
When You Already Had a Sales Conversation
Sometimes the person asking isn’t a stranger. You’ve been talking back and forth. She was interested, she meant to buy, and she just didn’t get to it. She already has a relationship with you.
That’s a situation where I’d likely honor the deadline and let her enroll, as long as it fits within a pretty tight window. A real conversation is different from someone who looked at your page once and then disappeared.
When the Money Really Matters
Here’s a story where I said yes, and I’d say yes again.
A coach had a launch that didn’t go well. She didn’t get any sales. Then, a few days later, someone came out of the woodwork who wanted to join. This coach was earlier in her business, and she needed the money.
I said, “Take the client.” It was $3,000. And she took it.
That $3,000 was the difference between her launch making no sales and her launch being incredibly successful. That’s a big swing, and for someone who had just been through something stressful, it mattered a lot.
Launching for the first time is stressful. It takes a ton of work. If you make no sales, or just a couple, and someone comes out of the woodwork, I think you should probably take the sale. If it’s the difference between making money and not making money, that’s a good reason.
But I’d add one thing: don’t make it a habit. In your next launch, be a little stricter with your deadline. Let the exception be a one-off, not a pattern.
The Case for Holding the Line
There’s a strong case for saying no, too. It’s okay to let people miss out. It can build trust and credibility.
And here’s something I’ve noticed: the people who miss out are usually the first in line for the next round, or the next time the promotion comes up.
I remember a woman reaching out several days after a launch who wanted to buy. It was a while ago, and I honestly can’t remember whether it was a closed enrollment or a discount. I told her the deadline had passed several days earlier, that our forms had already switched over, and that it would feel unfair and disrespectful to the people who had stuck to the deadline.
She told me she was disappointed, of course. But she said she respected me even more for saying no, because it meant I was true to what I said. I was honest, and I was telling the truth.
That stuck with me. She was the one who didn’t get what she wanted, and she still respected the boundary. People will be disappointed, and some of them will push back. But holding the line tells them your word means something.
And you don’t have to slam the door. You can tell them you’ll email them when enrollment opens again, or when the promotion is back. You can point them to another option. A no can still be warm.
Four Questions to Ask Before You Decide
When a late request lands, these are the questions I’d run through.
- How late is it? Is it within a day, where you might have a grace period? Or is it a week later, where an exception stops making sense?
- Was there a reason? Did they forget? Did they have a technical issue? A family emergency? A real reason is different from “I just didn’t get to it.”
- Would you be comfortable telling the people who bought on time that you made an exception? If that makes you feel really uncomfortable, it probably means you shouldn’t make the exception.
- Was the person already in a sales conversation with you? If you’ve been talking back and forth and she has a relationship with you, a tight exception can be reasonable.
If you answer those honestly, the decision usually gets a lot clearer.
How to Say No Without Being Harsh
If the answer is no, how you say it matters.
I like to explain why the deadline exists, so it feels logical and not harsh. Something like: “The reason we have this deadline is that I need to know numbers, and we start on Monday. I’m really sorry, I just can’t let you in.” Or, if it’s been a few days: “Our forms have already switched over, and it would feel really unfair to the people who stuck to the deadline.”
Then I give people another option. I’m still enrolling people into my 101 program, so we could jump on a call about that. Or I offer to message them when the promotion is available again.
That’s the pattern: be kind, tell people why, and give them somewhere to go.
It also helps to explain the reason behind a deadline or a bonus in the first place. In my previous launch, I offered a free strategy call with me for people who enrolled before a certain time. I told people exactly why it expired: I only have so much room on my calendar, and I can’t offer it to everyone. When people understand the reason, they respect the deadline more. When you don’t explain it, the urgency and the scarcity can feel false or fake.
Whichever Way You Go
Once you’ve made the call, there are a few things that keep it from blowing up on you later.
If You Say Yes, Keep It a One-Off
Tie it to a rule you already have, like your grace period. Don’t make it up on the spot and don’t make it sound like a favor you do for anyone who asks. The person should feel like they caught a break, and everyone else should still feel like the deadline meant something.
And if a yes starts to become a habit, that’s your sign to tighten things up before the next launch. One exception is a judgment call. Five exceptions is a new deadline you forgot to announce.
If You Say No, Don’t Slam the Door
A no is a lot easier to hear when it comes with a next step. Offer to email them when enrollment or the promotion opens again. Offer them a spot on the waitlist. Offer another option, like a different program or a call. Whatever you pick, don’t leave them standing there with nothing.
People who hear a warm, honest no often come back. The people who hear a cold one usually don’t.
Tell the Truth About Why
This goes for both answers. If you’re saying yes because it’s within your grace period, say so. If you’re saying no because your forms have already switched over, say that. And please don’t invent a reason. If you say you’re reopening due to popular demand when the real reason is that the launch was quiet, people can tell. It might not be obvious right away, but it adds up.
A deadline with a real reason behind it is something people respect. A deadline with a made-up reason is something people learn to ignore.
Decide Your Rule Before Your Next Launch
This is the most important part of the whole thing. Don’t wait until the message lands in your inbox.
Before your next launch, decide:
- Do you have a grace period? You don’t have to have one.
- If so, how long is it?
- If so, for what reasons will you use it?
Then write it down. If you have a team, make sure they know the rule too. And apply the same rule to everyone.
That last part matters. The moment you start making different calls for different people, it stops feeling like a rule and starts feeling like favoritism.
Having the rule ahead of time also takes the emotion out of it. You’re not scrambling when someone asks. You’re not deciding under pressure, or because you really need the sale that day. You already know the answer.
The Deadline Only Works if Your List Believes It
Here’s what all of this comes down to. A deadline only works if your audience believes it’s real.
Every choice you make on a late request, or on extending a deadline, is something your list learns from. If you’re consistent, they learn that when you say something closes, it closes. If you’re fickle, they learn to wait.
So make your rule. Apply it the same way every time. Make exceptions when it genuinely feels okay to make them. And keep your word.
Don’t be fickle. And don’t lie.
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