Why You Really Lost That Deal - And What Your Buyer Isn’t Telling You

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REV UP Rebellion

Abbie White

86 episodes

2 weeks ago

This isn’t business as usual. It’s a full-on uprising. The REV UP Rebellion is the podcast for bold revenue leaders and teams ready to break free from outdated playbooks and rewrite the rules of growth. Each episode features unfiltered conversations with top-performing leaders and real-world experts—delivering battle-tested insights you can actually use. You’ll walk away with practical strategies to sharpen your edge, ignite team performance, and drive serious results in a fast-moving, AI-powered world. Mediocrity has no place here. Join the rebellion.

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Why You Really Lost That Deal - And What Your Buyer Isn’t Telling You

REV UP Rebellion

54 minutes 17 seconds

1 month ago

Why You Really Lost That Deal - And What Your Buyer Isn’t Telling You

You didn’t lose that deal because of price.

You lost it for reasons your buyers won’t share with you... unless you ask them.

In a climate where acquisition costs are up and win rates are under pressure, relying on assumptions doesn’t cut it.

In this episode of the REV UP Rebellion podcast, Cian McLoughlin, founder of Trinity, global win/loss expert and author of Rebirth of the Salesman, shares what buyers really think after the deal is done.

As an external advisor, Cian and his team have conducted thousands of post-decision interviews with senior buyers across some of the world’s largest B2B sales deals. They tell HIM what they won’t tell YOU: the real reasons behind their decision to buy, or walk away.

And from those conversations, clear themes emerge, patterns that separate the businesses who win consistently from those who are left guessing.

What we cover:

The most common themes behind why businesses lose
What separates the ones who win consistently
How one business used a loss review to unlock $100 million in revenue
Why your competitors are winning deals you thought were in the bag
How AI is changing the way we understand wins and losses
What today’s best sales leaders are doing to reduce cost of sale and lift conversion

If you're a business leader, sales and GTM strategist, or revenue owner, make this your top listen this week.

(00:00:00) Opening: The Customer Blind Spot in B2B Sales (00:00:20) Introduction and Welcome (00:00:54) The Missing Conversation: Bringing Customers Inside the Tent (00:02:13) Getting Two Bites at the Cherry: Customer Collaboration Tactics (00:03:19) Formal vs Informal Customer Feedback Approaches (00:05:11) The Rebirth of the Salesperson: Adapting to Modern Sales (00:05:54) Professional Development: Taking Responsibility for Your Relevance (00:08:33) Learning Differently: Micro-Learning and Creative Enablement (00:11:47) The Future of Sales: AI, Human Skills, and Customer Success (00:14:59) The Birth of Win-Loss Analysis: Kean's Journey from SAP (00:25:26) Common Reasons for Lost Deals (00:28:31) Why We Win: Risk Management and Thought Leadership (00:32:01) Differentiation Beyond USPs: Making It Customer-Specific (00:36:07) Sharing Risk in Complex Deals (00:39:31) Getting Started with Win-Loss Reviews (00:42:40) The ROI of Win-Loss: Leaving Value on the Table (00:45:37) AI's Role in Modern Win-Loss Analysis (00:48:35) Final Thoughts and Book Recommendations

Book Recommendations:

Careless People by Sarah Wynn-Williams: An critical behind-the-scenes expose of Facebook’s rise in influence on the global stage, from their former director of public policy
What’s Your Message? by Cam Barber: A must-read on mastering communication and presentation skills.

Connect with Cian:

Website: https://tinyurl.com/trinity-sydney
LinkedIn: https://tinyurl.com/Cian-LinkedIn

Sales Redefined:

Be an Insider: https://tinyurl.com/Be-an-Insider
Order your Shots here: https://tinyurl.com/Order-your-Shots
Ready to REV UP: https://tinyurl.com/mr3tuzh8
Follow us in LinkedIn: https://tinyurl.com/Follow-SR-on-LinkedIn
Follow Abbie: https://tinyurl.com/Follow-Abbie-on-LinkedIn