How to Keep Your Deals Moving When Everyone is in Holiday Mode

The holiday season is upon us, and while everyone is getting into holiday mode, the work isn’t done yet—especially in sales. In this mini-episode of C-Suite Sidekick, Summer Poletti shares her top nine tips to keep your deals moving forward when everyone (including you) is busy with year-end projects, holiday parties, and endless to-do lists. From using smart scheduling tactics to leveraging CRM and AI tools, Summer provides actionable advice to ensure your sales pipeline doesn’t freeze up as the year winds down. If you're trying to hit those Q4 targets or set yourself up for a strong Q1, this episode is packed with timely insights to keep you on track.

Tune in for reminders, pro tips, and a quick motivational boost to help you close out the year strong! Available on Apple Podcasts, Spotify, and all major podcast platforms.

Companion content:

• Podcast episode: Strategies for finishing your year strong
• Podcast episode: AI-powered strategies to close deals and ill up your 2025 pipeline

Show notes:

• Episode recorded and edited using Descript
• Repurposed content, such as this description created using CastMagic
• Visit Rise of Us for more information about Summer's services
• Connect with Summer on LinkedIn

Transcript

0:00

Hello. And welcome back to C-suite sidekick. I'm your host. Some are politely. And today we're going over. Something that I think is on everyone's minds. Are you in holiday mode already? I know I am. Shopping is in full swing. And we're watching all the holiday baking shows. I both love and dread this time of year. And I get along with family and in-laws, so it's not that. This is the time of year. When your prospects get distracted with time off holiday parties end of your projects. And you start to see deals bump out to next quarter into next year. And if you're trying to close a gap on revenue or quota or something like that, it can feel very stressful. Have you ever heard I'm slammed right now? We're going to have to revisit this next year. Yeah, we all have. And if you're like most kind people, I know do you dutifully schedule something in February? Well, it's a good idea to start filling your Q1 pipeline. I don't think we're there yet. So the topic today is nine things that you can do to keep deals moving. When everyone, including you is in holiday mode. This is packed with insights, reminders, and pro tips for anyone working in sales. Or anyone managing a sales team So let's get started. Number one. Schedule the next step. On your calendar and there's, Have you ever gotten a last minute cancellation? or had a no show to a meeting and it turns out it's because someone had time off. Yeah, we've all been there. So while you're scheduling, especially this time of year, don't forget to ask about time off during the holidays. And if you're working with a buying team of more than one, make sure you're asking about time off for the other decision influencers as well. Pro tip. The scheduling time on your calendar. And there's thing is something you'd be wise to do all year long. Have you ever heard check back in two weeks only to never speak with that person again? Yeah, we've all been there too. This helps with that. Schedule. On their calendar and yours. And it's easy. Sure. I'll call you in two weeks. Let's pull out our calendars and pencil something in. I like the word pencil. Even though, I don't know that anybody's actually using pestles anymore. Pencil makes it seem less permanent. Psychologically speaking. It's. Less of a commitment. They know that they can move it around if necessary. And so you're less likely to get pushed back. Number two. Leverage implementation guides or timelines to help people plan. Have you ever heard we'll address this after the holidays? And then when they do, they realize there's not enough time and then you have to bump it to next quarter. Let's avoid that there is of course, a natural inclination to put things off this time of year. Always thinking that there will be more time later and there never is. Your implementation guide is going to show them that they can't wait until after Thanksgiving. For example. Pro tip. Be very careful about who gets an implementation guide. You don't want to scare off an early stage prospect. This is to help inform folks who are close to making a decision. Number three. Leverage integration guides. Ever heard we have too much going on. We can't take on another project right now. Yeah, we probably all have, especially if you're in software. And integration guide is a helpful tool to show your prospects how easy it is to get started with you. And that you're helping them every step along the way. Pro tip. Like the implementation guide choose wisely. If you're not careful, this one is going to come across about as good as a marriage proposal on the first date. Number four use AI features in your CRM to track lead scoring and other indicators that show buying readiness. You won't have as much time in the office this time of your either. So it's best to focus your efforts on the deals that are most likely to close. If you've got a current prospect downloading case studies, you've got a live one. Pro tip. Remember those implementation and integration guides. We just talked about, put those on your website. When used as gated content, these are magical. They can show buying readiness to if someone you've never heard of or spoken to at a prospect's organization, just downloaded your integration guide. For example, there's a good chance. That's an it person figuring out. His or her part because the team is ready to pull the trigger and they got to get to planning. Number five. Work in tandem with partners. This is the perfect time to tag team and try to win deals together. And the bonus is that when times are busy, your partner, who's likely another sales professional is probably going to pick up. They'll probably book that coffee with you. So sometimes this is about. Winning deals together. And sometimes this is just finding someone who's willing to talk to you, which is great for your psyche. Number six. Remind them why you're talking. It's easy to procrastinate this time of year with so many things going on outside of work and such a crunch toward the end of the year. Reminding people of the business challenges and the impact that you're helping them resolve will ensure that you get prioritized. Instead of being seen as another chore. Is fill in the blank no longer important to you. Did you already resolve these challenges? Are you good living with this vendor you hate for another quarter or year? You're obviously not going to use the word hate, but you kind of get the jest, right? Pro tip, just like these scheduling we talked about earlier. This is something you can use all year. If you're doing your job and you're finding real business challenges that you can resolve. It's kind of up to you to not make it easy to procrastinate your deal. If you really can help them. Number seven. Use your marketing materials. B2B selling is all about helping your buyer confidently, make a decision. If you've got case studies or other materials that can help them answer some of their lingering questions, use those. And pro tip again, this also helps lighten your load since you're going to be doing more with less time. Imagine sending over the case study that talks about a similar business challenge and how you helped resolve it. As opposed to setting. An hour long meeting to go through some of their questions and objections. Save yourself some time to number eight. Think about does your next step have to be a meeting? I'm not going to belabor the point. We've all seen the meme, right? Be careful be mindful of the fact that with so many days off in the upcoming weeks, days in the office will be packed. I work heavily in financial services. So a three day weekend really just means you're cramming five days of work into only four. And I don't think financial services is the only industry. That feels like that. My personal rule is no discovery or price presentation in email, but lower stakes discussions. Don't always have to be meetings. And psychologically, they're going to be less likely to put you off if you're not asking as much time from them. Pro tip. Also try to avoid using the word meeting or conference, call those, bring about a feeling of dread in most knowledge workers. Number nine, when you are scheduling something, does it have to be an hour? If you do need to do a meeting or a conference call, try scheduling for 30 minutes and make sure that you get it done in that time period. Manage expectations in your opener and run a faster discussion by skipping the fluff and avoiding rabbit holes. Psychologically speaking. There are a couple of studies that show that this is a good tip. Just anyway. Number one. People's ability to pay attention in an online meeting is capped at about 39 minutes and 17 seconds. So that full hour people are already checked out. And also meetings kind of naturally expand to fill the time allotted. Because I think your brain, if you know, it's going to be an hour long meeting, you know, you take an hour, but if it's only half an hour, you know that you have to get it done in half an hour. So try shorter meetings. Pro tip. To end each meeting a little early, even if it is a half hour, you can go 20 minutes. And then remind people, but you're giving them back a few minutes in their day and they're going to be appreciative of the fact that you are mindful of their time. So let's wrap this up so you can get back to your day. This is do or die time in B2B sales resist the temptation to let status quo win by letting your prospects put you off. If you did your work, right? You've identified business challenges that you can help resolve. And a positive impact you can have on them. You owe it to them to help guide them toward a decision. If you found this helpful or inspirational, share it with someone in your network who works in sales or who runs a business. And I would appreciate a review if you liked it, it helps me expand my reach. Thank you for listening. I will see you next week.