In this conversational podcast episode, Shaun Whynacht and co‑host (Speaker A) discuss how small businesses and retailers should begin planning their holiday (Christmas) promotions well before the season arrives. They stress the importance of creating a promotional calendar early, breaking the season into phases, and tailoring both in‑store and online experiences. Topics covered include in‑store tactics such as bundled gift packages, extra staffing days, sensory‑friendly or pet‑friendly events, and targeted demographic sales. They explore discount strategies, charitable tie‑ins, and the use of multiple, niche sales. Online recommendations feature free‑shipping offers, surprise gifts, video countdown series, active social‑media engagement, and virtual shopping parties. The hosts also highlight the role of atmosphere—festive music, scents, décor, and inclusive brand messaging—in shaping customer perception. Finally, they advise on timing, suggesting that planning should start now, with public marketing rolling out in late November, while avoiding premature holiday music that can alienate shoppers. The episode blends practical tips with examples, aiming to help listeners craft a cohesive, multi‑channel holiday promotion plan.
Chapters
Talking about your brand personality and actually imagining your brand or your company as a person, and you know, what would they act like? What would they, you know, what would their emotions be? Hobbies? Like all those little silly things that don't seem that important are actually huge in determining your target audience.
Alright, here we're back. It's episode number 49. We're so close to season 5. I love this whole 10-episode season going there. So we are currently— we're still in the summer when we're recording this, but we're gonna talk about Christmas. Are you ready for this?
Yes, I won't be a Grinch.
No, perfect. I want to talk about like holiday promotions, and the reason that I wanted to do this now is is a lot of times most businesses wait to start to plan and promote their business when the season turns to that season or that holiday, right? So we'll get through the fall and then we'll start to get in November and people are like, oh, gotta think Christmas promotions. You gotta start doing it now, right? You need to start to allocate things and that's what I wanted to talk about in the episode are some ways to help you start to think about what could you do for, for Christmas to promote? Now, you had said, you know, I haven't promoted through Christmas yet, um, but you've obviously had a Christmas before, right? And there may be some things from your own personal experience that you've seen that kind of caught your eye. And a lot of times you'll see a lot of people jump on the board of Christmas in July, and they'll kind of flip it, you know, 6 months early and all that kind of stuff, which is a great idea, you know, to kind of stand out, but I think number one is preparing a calendar, right? Start to think about the content, and that's for any holiday. It doesn't have to be Christmas, right? So what would people start to think about, or what should people start to think about, even to prepare a calendar or a content or a promotional calendar for their business?
And I mean, even thinking about it in phases too. Like, I know, uh, you know, working retail, even you had that last week before Christmas that we always called the last-minute shoppers. And we would actually completely rearrange the store to deal with that. Putting our little bundles or packages right at the front because people are so stressed out that they're just like, "Okay, yes, whatever's easiest." Things that they didn't have to think about. Stuff that didn't have a size or was just kind of universal, those types of things. Planning it out in stages and thinking what's going to be best to do, you know, during the very beginning of December when people, you know, it's kind of that mid-range where people are like definitely ready to buy, but, um, they, they have like a couple ideas maybe and aren't exactly sure of what it is yet.
Yeah, and you'll see that the holiday season extends out even earlier than that. You got, you know, we jumped on that Black Friday trend in November, uh, with the US and You know, just getting in people's mind, right, to help them out. And a lot of times it's sales. And, you know, sales aren't always just like, okay, this is a sale for everyone. Don't have— it doesn't have to be, right? What you can actually do is you can have multiple sales. You could do, you know, here, you know, we have, you know, this week we're gonna have a sale for women. We have this week we have a sale for men. We have, you know, you see sales for, for people that, that, you know, cater to, you know, specific shopping nights. That's a new trend that's been going around the last couple years. You know, if you're dealing with, with families and that's your demographic, you know, a lot of businesses have like the autistic-friendly shopping experiences where the music's turned off, the lights are lower, and those sensory elements are really reduced, right? People really love that. Yeah. You know, if you're a pet-friendly business, like, you know, some of them that are out there, there's a lot of local businesses that allow pets in there. Maybe you can have some kind of pet event and really bring out that subsection of people. So there's a lot of ideas from the on-the-ground brick-and-mortar type businesses that are out there.
Absolutely. And I mean, you know, when we say promotions or, you know, something that's like a holiday special, a lot of times people think like discounts and stuff, which obviously that's the majority of it. But I remember seeing— I can't remember what store it was for, it was definitely retail, but They actually had a specific day dedicated where they had double the amount of workers that they normally do. So if you needed extra help or wanted somebody who was right there with you, shopping with you, especially men who are looking for gifts in a completely female store, they have no idea what they're doing, they're just lost. They actually had a day dedicated to double the employees so you can have all the attention you need, which I thought was really cool. Well, I mean, I guess that's still— you're paying extra money for the employees to be there, but the offering is extra customer service, not necessarily, you know, a price discount.
Yeah, well, I mean, if you're discounting your prices, you're still paying for— the business is paying for it. You're reducing your amount of income that's there. Another great thing you can do is trying to align yourself with certain charitable organizations in the area and really have fun with it. You know, there are businesses that just say, you know, we will do donate 5% of all sales to this organization. But how about this idea is, you know, get a bunch of those little like poker chips or little whatever they are tickets and have, you know, 5 different organizations and have some kind of like jars at the checkout. And then for everyone who makes a transaction, they get one, and for every token that's in the jar, you'll give $5, so let's say that amount, to that charity. So now you're still giving away, but now you're making it fun. The person can actually choose 5— one of 5 different places they want that $5 to go to. Yeah, right. So that's kind of a fun way to do that, right? If you've got online, I mean, there's, there's a million different ways to have different promotions that are happening, you know, with, with coupons, to buy one get one free, to, you know, buy this and we'll, you know, you get to choose who we can send another one to, or any, you know, any of those promotions that are, that are happening, right? You know, online shopping parties are, are becoming more popular, you know, with Zoom and things like that. Right, so, um, throwing in a gift. What do you think about that?
Throwing a gift, that's always a great idea. I mean, any time of year, but especially around Christmas, like, just giving that little added value is, is so special to people.
Yeah, no, not telling them it's there, right? Making that surprise when they either at the checkout or, you know, online, it's even better because you're packaging it and shipping it to them and they open it up and it's that pleasant surprise that's there. Right, right. That's a really cool idea. Creating videos, right? We're big on video, right? So, so how about creating like a, you know, a video series, a countdown to Christmas, you know, your stocking stuffer recommendations, all that common stuff. You know, what we used to do, or what I used to do years ago, was I go around to clients and get them to shoot their Christmas greeting video that they wanted to send send that message out. And we would do that, you know, October, November, because once December hits, they're run off their feet busy, they don't have the time to do it. And kind of getting it done early is a really cool idea around that. Now another idea is staying active on social. What you'll see is as people get busy, especially if they're in that small business world or they're doing a lot of online stuff, um, selling, is their time is taken away. They're also planning their own personal lives and they kind of step away or step back, take the foot off what they're doing on social media. This is the time people are online. Yeah, right, especially, you know, coming home, holiday breaks and things like that, and they're going online looking for ideas, last-minute ideas. So you need to be active on there consistently.
Definitely. Another thing that I just kind of touched on earlier, um, that we did in my store working retail was, you know, the convenience aspect, but actually making specific bundles or packages for Christmas that are providing customers with like more convenience. You know, so bundling things together that just make sense and offering it a little bit of a discount. Again, just making it easy for people because it's a stressful time of year, unfortunately, for a lot of people. You know, financially and also time-wise, like there's just so much going on that the easier you can make it for them, the more likely they are to buy.
Yeah, and you know, if you're selling online, if you can, can run a free shipping offer, right, that's— you'd be surprised how many people will actually decide who they're buying from if they don't have to pay for the shipping, right? It's just another cost, and you know, money is tight most times, so you know, if they can get the item they want, you know, you know, you can look at it where surprising how many people would buy an item that is 10% off and have to pay for shipping versus somebody who would buy a full price item and free shipping, right? They're actually probably saving more of the 10% off than the $10 shipping or whatever it is. But the fact that people hate paying for shipping, they will go the other route, right? So, you know, free shipping for the whole month of December or something like that, right? And you can do as much as, you know, orders over X amount, but that's a really good hook. To use.
Yeah, absolutely. And I'm definitely guilty as charged. I hate being shipped.
That's what leads to that whole cart abandonment issue, right? The number one reason that people don't buy online is they, you know, get to the shipping part and they abandon the cart that's there. So, um, and I think the last one that it really kind of stands out to me is, um, you know, the atmosphere, right?
Oh, absolutely, right?
I mean, you've got businesses that you go into, you know, and there's the other side too. It's like, you know, do I say Merry Christmas Do I say happy holidays? You don't want to offend people because, you know, we're in a very delicate world now where people get offended easily. My stance is if you celebrate Christmas, right, and you're okay with Merry Christmas, say it, right? You don't— it's okay. But the idea is it's a time of year that people really want to feel kind of warm and fuzzy. Yeah, right. It's, it's the reason that Hallmark ramps up all their movies on TV, like, very early on, is it's that warm and fuzzy feeling. So, you know, when people come into your store, they want to feel, you know, want to hear some festive music, they want to, you know, even, you know, the scents. So, you know, the, the chocolate scents, the cinnamon, the nutmeg, all that kind of stuff that's happening, and just kind of just walk into this, like, winter wonderland kind of feel, you know, is very, very beneficial. And I'm sure people come back to stores because of that feeling that's in there.
Yeah, I was just gonna say, and you know, that comes up in conversation, like, oh, I went shopping here the other day and it's so Christmasy, it made me so excited. And then other people go, right? So even just that alone, the environment, and I guess kind of the vibes of the store can really draw people in for sure.
Yeah, and you can get that coming across in, you know, the way that you, you know, build your website, adjust it, change it for the, for the seasons. Your social— this would be time where you could actually change your header on your Facebook page, your profile images and stuff. Maybe have one with you with a Santa hat on or whatever the case is. Really kind of make sure that your marketing reflects the experience in the store as well.
Absolutely.
So in closing, When do you think is the best time to start marketing for the holidays?
Hmm, see, a lot of people say after November 11th, which I think makes sense. I'd say like start the last week of November because there are those few people that are so annoyed. I saw all the time in the mall when the Christmas music would start like right after. Remembrance Day, and people would be so cranky about it. So I think a good middle is kind of towards the middle or end of November, right?
And that's the time that you start to roll it out to the public's eye. That's not the time you start to plan for it, right? Now is the time to start to think about it, right?
Exactly.
Doesn't necessarily mean that you're picking all your products and everything, but you know, you may have to order some stuff and things of that nature, but definitely start to think about it now, even though the weather's nice and there's no Christmas trees in sight right now. Excellent.
