Dealmakers Podcast

How To Talk With Confidence To A Business Seller

A practical episode on seller conversations, rapport building, open questions, negotiation confidence, and uncovering the real motivation behind a business sale.

Listen to the Episode

Episode 221  |  Runtime: 28:20  |  Audio Episode

Listen to the Episode

Hear the full conversation on how to speak with business sellers, build trust, ask better questions, and uncover the motivation that can shape the deal.

Episode 221
Runtime 28:20
Topic Seller communication & negotiation
Format Expert interview on influence & rapport

Key Takeaways

Three practical lessons for acquisition entrepreneurs who want stronger seller conversations and better discovery calls.

Selling Starts With Asking

Buyers damage trust when they talk too much. Strong seller conversations rely on open questions that help the owner reveal the real reason they may want to sell.

Start With The Owner's Story

Asking how the business began, what attracted the owner to the sector, and what changed over time builds rapport before the harder questions on revenue, profit, and deal structure.

Do Not Sound Needy

Confidence comes from positioning the next step as a mutual decision, not chasing the seller. The buyer should create space for the owner to move toward a meeting.

Episode Breakdown

This episode features Jonathan Jay speaking with Andy Harrington about the communication skills that matter when buying a business. The conversation focuses on the discovery call, where the buyer must build trust, understand the seller's story, and uncover whether the real motivation is retirement, stress, ill health, family time, operational fatigue, or another pressure point.

Andy explains why confident buyers ask rather than tell. Instead of pushing a proposition too early, the buyer should ask questions that help the seller articulate their own problem, their own urgency, and the outcome they want. That makes the eventual offer feel aligned with the seller's needs rather than imposed by the buyer.

The episode also covers defensiveness around financial information, how to label tension in the conversation, why closed questions reduce momentum, and how to move from a first call to a face to face meeting without appearing desperate. For anyone using direct mail, off-market outreach, or broker conversations to find acquisition targets, this is a practical guide to improving seller trust and deal flow quality.

Best For

  • First time buyers preparing for discovery calls with business owners.
  • Acquisition entrepreneurs using direct mail to generate off-market seller conversations.
  • Buyers who need to uncover seller motivation before discussing price and structure.
  • Dealmakers handling defensive owners who resist sharing revenue or profit figures.
  • Operators who want to move a seller from phone call to meeting without sounding needy.

Questions Answered In This Episode

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  • Step-by-step acquisition roadmap
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  • Due diligence checklists
  • Deal closing procedures