Sales POP - Purveyors of Propserity
Q4 Strategic Questioning
Blog / Sales Professionals / Oct 23, 2025 / Posted by Brian Sullivan / 3

Q4 Strategic Questioning

0 comments

With the 2025 selling year’s Q4 well underway, most of us have a pretty good idea what our actual Dec. 31 number will be. Looking in the year’s rear view mirror likely shows us some deals filled with promise that unfortunately fell short. We can see a few very nice wins, of course, but we are infatuated by the “what ifs” that haunt those losses.

I have a friend who likes to say, “There’s a reason why car windshields are 24 square feet and rearview mirrors are 24 square inches”. His meaning, of course, is that we should spend our time looking ahead and not backwards. And there’s no better time than Q4 in a selling year to prove that true with the time to impact your 2025 performance getting shorter and shorter by the day. Simply put, we can’t waste it on those January through September “what ifs”. It doesn’t serve your purposes and more importantly, those of your clients. Neglecting their year-ending interests is a selfish and foolhardy strategy. For in the end, your customers depend on your support. 2025’s Q4 and the upcoming Q1 of 2026 are not only about your numbers and your commissions. They are about your clients and their needs. As such, making rational decisions about how to spend your limited time is critical. Think about what you might learn from your clients by asking this simple question now – “What’s most important to you as the year wraps up and how can we be helpful to you in meeting your Q4 needs?”. Right, I get it. You’re already thinking about the answers you’ll get.

I’ve often mentioned my early selling days at Xerox, where we viewed deals from a nourishment standpoint as breakfast, lunch or dinner. You need them all but most importantly, at any time of year, your clients need the value you deliver regardless of deal size. And deal size, like meal size, does not dictate value. That’s up to your client. A relatively small deal for you may deliver great value to your client. OK. It’s time for my mantra about the four most important words in selling – “It’s not about you”. And how can you discover the client’s view of value? I’d say a really good place to start is to pick up the phone after this article and call a client asking that golden question, “What’s most important to you as the year wraps up and how can we be helpful to you in meeting your Q4 needs?”. It will likely be a very different question for the client to be hearing as opposed to what is being asked by your commission-obsessed competitors spewing discounts, sales and the like. Be different.

And as you gain newfound client knowledge over the next few weeks with strategic questioning, you’ll likely also find that some new opportunities are entering your funnel. It’s funny how that works out but there’s often a ripple effect to doing the right thing. And as you get closer to the month of December, add this question to your repertoire – “What’s most important to you as the new year kicks off and how can we serve you most effectively in Q1?”. Be prepared to listen well and follow up intently.

Q4 represents the end of the selling year but it also represents the end of the calendar year for your clients. A simple change in your thought process of customer questioning can be refreshing for both parties and help you be viewed as more of a partner and less of a vendor. After all, from a client’s perspective, you’re not at your best when you’re selling to them but when you’re serving them.

About Author

Brian Sullivan is a best-selling author, consultant, and enterprise selling expert. He spent eight years at Sandler Training, developing and growing the Sandler Enterprise Selling Program on a worldwide basis. Prior to Sandler, Brian was in sales, sales management, and P&L management positions with The Capgemini Group for thirty years.

Author's Publications on Amazon

The comprehensive 6-stage selling program from Sandler Training-- "Top 20 Sales Training Company" by Selling Power Magazine Competitively pursuing large, complex accounts is perhaps the greatest challenge for selling teams. To keep treasured clients and gain new ones, you need a system to win business…
Buy on Amazon
Comments

This website uses cookies. By continuing to use this website you are giving consent to cookies being used. For information on cookies and how you can disable them, visit our privacy and cookie policy.