When speaking to a seller for the first time, what are your go-to questions?

searcher profile

July 23, 2025

by a searcher from Boston University - Questrom School of Business in Newton, NH, USA

I thought it might be helpful to exchange ideas on this topic. I like the question "If you were starting this business over, today, what would you do differently?"
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commentor profile
Reply by a searcher
from HEC School of Management, Paris in París, Francia
Having a good research about their products can open the conversation to understand the value proposition, differentiation and even competitor's landscape. Also understanding their structure can be helpfull to learn about succession plans and mid-line leardership
commentor profile
Reply by an investor
from Concordia University in Montreal, QC, Canada
I agree with Foley, biggest mistake is forgetting the Human side. Blend Information Gathering with a Human side. I've been in situations where the seller was hesitant to discuss why he was selling, you start diving into it thinking its an operational issue, and then you realize it's a very delicate health situation forcing the sale. Need to balance both.
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