Wednesday, February 11, 2026

Doing Discovery Pro Tip: "Why" Questions Drive the Conversation Upwards

 

And help uncover Critical Business Issues.

 

True story:

 

I asked a sales manager, “What’s the biggest challenge you face in your job today?”

 

He responded, “We need more good leads.”

 

“And why is that important?” I queried.

 

He replied, “Without good leads we don’t have enough opportunities to pursue.”

 

“I understand,” I said, “and you are not alone…! But tell me, why is that an issue? What happens if you don’t have enough opportunities?”

 

He grimaced, slightly, and said, “Well, without enough good opportunities, we won’t hit our numbers…”

 

“Uh huh,” I responded, “So the main challenge for you is achieving your numbers: making quota. Is that right?”

 

“Oh!” he exclaimed, “Exactly!”

 

In discovery, “Why” questions tend to drive the conversation upwards, towards uncovering Critical Business Issues (goals and objectives), as opposed to drilling downwards into more detail.

 

You’ll find more on using “Why” questions starting on page 180 in “Doing Discovery”

https://www.amazon.com/Doing-Discovery-Important-Enablement-Processes/dp/B0B8RJK4C2/

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