Strategies to help you conquer circle-back season.
November 19, 2025
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?
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.
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.”
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.
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.
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.
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