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  • Writer's pictureBenny Fluman

Uncovering Customer Needs through Strategic Questioning

Updated: Jan 29

Mastering need-finding conversations accelerates deals and forges enduring partnerships. This guide compiles field-tested questions for unveiling client challenges and mapping solutions. 


While extensive sales education promotes questioning techniques, real-world application matters more. Having conducted thousands of C-level engagements over decades, I've seen meaningful inquiries catalyze growth. 


Success requires understanding executives' motivations, measuring relevant KPIs, aligning capabilities, and coordinating stakeholder buy-in.











Introductory Questions


  1. What pressing needs drove exploring our offerings? 

  2. Walk me through key decision makers' typical day. Where could our solution integrate?

  3. Which critical business objectives can our services impact?


Addressing Challenges


4. Tell me about situations where current solutions are recently disappointing.

5. What obstacles impede hitting targets around [X KPI]? 

6. How have needs shifted over the past year? What changes do you anticipate?



Envisioning the Ideal


7. Forget constraints. What would the dream solution entail?

8. If you had an unlimited budget, what capabilities would get priority?  

9. How might we deliver 10X, not 10% improvement?



Uncovering Values


10. What principles guide your decision-making?

11. How does sustainability factor into your selections?

12. Describe your vision for a mutually-beneficial partnership.



Navigating Decisions 


13. Who approves final purchases? 

14. Take me through your typical evaluation process.

15. What evidence carries the most weight?



Addressing Concerns


16. What reservations remain about our fit?

17. What else should I know about your needs?  

18. May I clarify our offerings further?



Finalizing Next Actions


19. What follow-up would you find valuable?

20. When could we reconvene?



I welcome any opportunity to hone need-finding skills while uncovering growth opportunities. Please reach out with additional questions or to further discuss deal acceleration approaches.


You are invited to arrange a telephone/online conversation at a time that suits you at this link and we will ask you smart questions😊

It is also possible to send WhatsApp to +972 52-420-3043 or send an email to benny.fluman@match-b2b.com

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