5 simple strategies for scheduling sales meetings during the holidays

Posted December 11, 2017

Chelsey feldman headshot

By Chelsey Feldman

Product Marketing at Outreach

Meetings can be really stressful during the holidays. And no I’m not just talking about “meetings” disguised as holiday parties where Meredith overindulges, Michael messes up secret Santa, and everyone stands around uncomfortably, looking for an exit. I’m talking about the meetings with prospects you’re working tirelessly to book -- the ones that required months of work but could entirely be derailed by conflicting vacation schedules and long weekends. However, not all is lost because as the holiday season approaches. With a few simple strategies, you can maximize the time you have left in office to ensure the meetings you do have on the books are successful.

Be kind, remind

Sending your prospect a reminder is critical before meetings during any time of year. But it’s especially important before meetings that occur around the holidays, when your prospect is battling the stress of how to pretend they’re eating Aunt Judy’s jello cake during family dinner, and your meeting is the last thing on their mind. If you're booking a meeting more than 48 hours in advance, don't let that time pass without a scheduled email reminding your prospect about when you’re meeting and why. Mention that you're looking forward to the conversation, remind them of your value prop to reignite their excitement, and offer an extra value nugget from marketing, like an ebook or infographic, to keep you on their mind. You can also connect on LinkedIn or engage with their posts to stay top of mind between booking and holding the meeting.

Make the meeting convenient

You know what’s not convenient? Getting through TSA at 5pm on the Friday before Christmas. Close your eyes, and imagine the stress of that scenario. Your meeting should be the exact opposite of that experience for your prospect. Make the task of meeting with you completely effortless for them. Some strategies you can use:

  • Insert your schedule availability directly into your email to send 3-4 time slots that work for you, so they don’t even have to think about scheduling. Sometimes, having a blank slate and figuring out from there when to meet can be daunting!
  • Make sure your meeting invite includes a detailed description of why you decided to meet and what you hope to cover. Conference links and phone dial in options are also necessary.
  • Send a same-day reminder with the dial in info and meeting link so it’s convenient for your prospect to find.
  • Track clicks and opens to ensure your prospect opened your meeting invitation. If not, give them a call the day before or the morning of to get your schedules squared away.

Don’t fall for the easy bait

Calendars tend to be more open around the holidays for good reason-- and unfortunately that reason isn’t to attend a sales call for a sweet new product. Don't take the low hanging and tempting fruit of a meeting the day before a holiday. Like many Friday meetings, they are easy to lose. Let’s be honest - if someone’s schedule is unusually empty, it’s for a reason. Either they’re focusing on tackling their to-do list so they have time to brave Toys-R-Us, or they’re not actually planning on coming to work in the first place. Play it safe and book your meetings well in advance of the holidays so your prospects are more likely to show, and so you have a buffer if they need to reschedule. You can also send your own availability over via your personal Outreach Meetings calendar link and give your prospects a handy way to book time on their terms.

Schedule around your stakeholders

I personally don’t travel over the Christmas holidays (staycation ftw!), but many people on my team do. Ask for the holiday schedule of all the key stakeholders and decision makers in a deal so you don’t get caught on an empty conference call line. Additionally, you can leverage Outreach’s “book on behalf of others” feature to see your account executive’s schedule when putting meetings on their calendar. This is important both internally (make sure your AE isn’t on vacation before you pass them a meeting) and externally (make sure all decision makers are available before you assume your deal will close in 2017). That way, you can plan for what you realistically can close before the end of the year and spend your time wisely.

Sequence seasonally

Nothing is going to kill your prospect’s holiday party vibe faster than realizing they forgot to turn off their work email notifications and seeing that a sales email is what disrupted their celebration. There are 2 ways you can update your sequences for your winter break:

  1. If you have our “Exclude Federal Holidays” feature turned on, Outreach will automatically turn off email sends for the appropriate upcoming holidays: 12/25 (Christmas Day) and 1/1 (New Year's Day).
  2. Many Sales Reps will be out-of-office for additional time beyond just the holidays, if you’d like to pause Outreach campaigns for additional time, you can manually reschedule emails or simply pause your sequences.

Take some no pressure downtime

If you work in an industry where you know your prospects are all talking the holidays off, or you’re just feeling that end of year burn out, take the holidays as an opportunity for some no-pressure time off. Some teams, anticipating the holiday slow down, ramp quota down for December or consider their months closed by the 20th to reduce stress and focus their time on creating memories with family and friends without worrying about missing leads. After all, the most rested and rejuvenated reps are the ones who are ready to bring their A game on January 2nd.


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