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How to Challenge Buyers without Pushing Them Away

Not all sellers are comfortable with the idea of challenging their buyers.

For some, this discomfort stems from a preference for building relationships and currying buyer favor with a "nice guy" approach.

For others, the idea of challenging a buyer seems disrespectful or overly aggressive.

There's a fundamental misunderstanding in both responses. Sellers who shy away from challenging their buyers don't realize that doing so is a service to buyers. What's more, buyers want to be challenged and place a higher value on time spent with sellers who challenge them.

Challenging buyers is what builds a strong relationship with them. Not challenging them is what's disrespectful.

Of course, there is a right way and a wrong way to challenge your buyers.

Challenging shouldn't be done in the context of a competition with your buyer. It's not meant to be a battle of wills, a duel or a demand. These may be the dictionary definitions of "challenge," but that aggressive posture is different from what buyers want.

Buyers want to be challenged in a way that makes them think, gives them pause, heightens their awareness, and causes them to reconsider. They want sellers who bring something new and will engage with them in fruitful discussions that go beyond what they already know. They want to be challenged with thought-provoking questions and new information.

Consider these 10 distinctions to better understand how to challenge your buyers in a productive manner:


Drawing out your buyers with respectful, well-intentioned challenges will position you as a trusted advisor. You'll differentiate yourself from other sellers who misunderstand and don't challenge buyers. You'll also differentiate yourself from sellers who offer no challenge and are, therefore, conducting low value transactions and conversations with buyers.

Best of all: by challenging your buyers you will also be building and strengthening your relationships with them.

The CONNECT2Sell Blog has been discontinued as our focus has shifted to leadership at every level. Research with buyers demonstrates that buyers respond favorably when sellers show up as leaders. If you'd like to step into your full potential as a leader (and boost sales!), take a look at our free and affordable courses on