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How Not to Get Circle-Back-After-the-Holidays-ed

Strategies to help you conquer circle-back season.

November 19, 2025

By Alicia Oltuski

Last year, Atlassian named December 17 World Circle Back Day. “Let’s circle back on this after the holidays” can be a relieving response to receive or write.

The other day, I saw an online post that went something like, “Don’t worry folks, it’s almost ‘Let’s circle back after the holidays’ season.” You’ve probably seen some of those “Happy ‘Let’s circle back after the holidays’ to those who celebrate” wishes.

The phrase can translate to happily knocking an item off your full (what’s the opposite of delicious Thanksgiving?) plate. It can also mean obstruction that costs you time, money, momentum, and maybe even a deal. So, how do we get ahead of it?

CALL ME MAYBE

Don’t take that literally. Not every business relationship needs a constant phone call (though there are certain opportunities where a phone call is always going to be better than an email). What almost every prospective deal does need? Regular communication. This is true for many different reasons, but let’s talk about why it’s useful for our purposes.

  1. You stay top of mind

    It’s fair to assume that tasks that we’ve forgotten about that suddenly come calling around the busiest time of year are likelier to be shelved than those you regularly interact with.
  2. You avoid the snowball effect

    Tasks that lie untouched for longer tend to necessitate more legwork once you do return to them. Keeping in regular touch with prospects and clients means that there are fewer opportunities for things to collect and become unmanageable (or even just appear unmanageable). It’s a lot easier for people to take on a few bite-sized tasks that allow them to close a deal stage.
  3. You keep momentum going

    If you’ve taken Maestro’s DRIVE training, you know the (purposefully) provocative maxim: “A deal in motion stays in motion. A deal at rest dies.” The pre-holidays are a time when people often prioritize. What has to get done now? Keeping a deal’s momentum flowing can infuse it with a sense of urgency.

And if you are going for that call? Introduce, frame, and use it intentionally. “My go-to,” says Becky Gilman, Maestro’s SVP of Product Marketing, “is to shorten the timeframe, so instead of asking for a full 30 minutes, I’m asking for a short 15 minutes with a hard stop. The 15 minutes need to be very intentional, so make sure there are just one or two key points you’re covering, and be transparent ahead of time about what those are. Ensure they know it’s a hard stop and it’s not a bait and switch just to get time on their calendar. If you’re already following Maestro’s practices, they should know that you stand by that already! And finally, make sure there are clear next steps coming out of the 15 minutes. The call should leave you and your contact feeling productive and accomplished in a short bite of time.”

COMMUNICATE VALUE

It’s good to continually communicate—or, better yet, demonstrate—the value of your solution, your proposal, or whatever it may be, but it’s especially important before circle-back season arrives. It seems simple, but it can also be easy to forget: showing what your product brings to the table, which pain points it prevents or eases, and which goals it helps accomplish, keeps it from appearing more optional or, worse, unnecessary. If you are selling something that’s continuously useful and necessary, it’s probably a bit harder to push the meetings or tasks it requires to a later date.

STAY AHEAD OF THE GAME

Is there a reason why pushing off your meeting, implementation, or whatever else it might be until after the holidays puts your client, prospect, or coworker at a disadvantage? Use that! But in this case, offense may be better than defense. Trying to use this tool after you get a circle-back email is a lot harder than subtly communicating it before circle-back day even arrives, when it has the potential to feel less pushy. Don’t wait to share the benefits of getting this set before the new year. Depending on how blunt or tactful you want to be, you can state this explicitly (e.g., “I want to make sure we get you set up with…before the holidays/new year, so that you can take advantage of the…discount”) or use a more subtle approach to make your prospect or client aware of it.

WHEN YOU SHOULD NOT AVOID CIRCLING BACK OR BEING ASKED TO

  1. When it’s bullying.

    There are a lot of ways to introduce the proverbial circle-back. “Can we circle back to this after the holidays?” “Let’s circle back to this after the holidays.” “I suggest we circle back to this after the holidays.” “We’re going to need to circle back to this after the holidays.” Some of these feel more optional than others. But the power structure of any given relationship probably has even more to do with how the phrase lands than exactly how it’s worded. A “Can we circle back after the holidays?” asked of a sales-development representative (SDR) by their CEO is a lot harder to contest than an officemate of equal rank asking the same question. Relatedly, it would take a lot more gumption for an SDR to even think about asking that of their boss.

    If you are in a position of power, sometimes it’s up to you to respect circle-back season even if your employees/team members don’t have the capital to ask for it. On the flipside, it’s also up to you to know when asking them to delay a meeting or [fill in the blank] would have a negative impact on their income, work, or even just sanity. Basically, just remember the influence you have.
  2. When you need to circle back

    You’re human. Sometimes we all need to circle back. The ability to is a privilege that not everyone gets to enjoy. But if you do, try to know when you are the one who needs to deploy the circle-back option.
  3. When haste will make waste

    There are times when we know that pushing for a sooner close date is going to result in a poorer job. If that’s the case, you generally won’t want to sacrifice quality for timeliness.
  4. If it’s going to negatively impact a relationship

    This is a tough one. Urgency is important, but there is such a thing as too much of it. You’re not looking to make someone lose patience with or resent you. You don’t want to be the reason their November stinks. It’s a difficult balance to strike. You know your business relationships best, but since every situation is different, it can be helpful to consult a mentor or coach if the answer isn’t as obvious to you. Just make sure you’re speaking to someone who is familiar with the situation or even—in an ideal world—the client themselves.

It’s a lot to take into consideration, I know. There isn’t always a perfect answer. But giving a bit of advance (or not-so-advance) thought to circle-back season can help you navigate it more effectively. Now go eat yams or whatever.

Looking for some help with your go-to-market strategy? Get in touch now (no circling back) at mastery@maestrogroup.co.