Why You’re Losing Deals You Should Be Winning

Picture of Meridith Elliott Powell & Mark Hunter

Meridith Elliott Powell & Mark Hunter

Sales Logic Podcast

Salespeople work hard to prospect, build relationships, and get in front of decision-makers. But too often, deals slip away—sometimes to competitors who shouldn’t have won in the first place. 

On the Sales Logic Podcast, Mark Hunter and Meridith Elliott Powell tackled the question every salesperson faces: Why am I losing deals I should be winning?

The Discovery Problem: Buyer Intent and the MOD

Many salespeople lose because they don’t dig deep enough into discovery. Mark emphasized the importance of uncovering buyer intent and recognizing the moment of demand—the point when the buyer realizes they have a problem and are ready to solve it.

Rushing to the close before reaching that moment is a surefire way to lose deals to someone else who takes the time to understand the buyer’s real need.

Desperation Kills Deals

Another hidden reason sales fall apart? Neediness. Buyers pick up on desperation fast. Meridith shared how communication is far more than words—it’s tone, confidence, and presence. If you appear desperate for the deal, you’ll drive prospects away.

Mark reminded listeners: “Are we selling on our journey, or are we allowing the customer to buy on their journey?” The customer drives the timeline, not the seller.

Narcissism vs. Listening

One of the podcast’s standout moments came when Brynne Tillman commented, “Deals are lost because the salesperson is a narcissist.” Too many sellers focus on themselves—their product, their pitch, their needs—instead of listening to what the buyer actually wants.

As Mark said, “The customer doesn’t care what you do. They care about solving their problems.” Winning deals requires shifting the focus entirely to the buyer’s world.

Confidence, Proposals, and Customization

When it comes time to present, a generic proposal won’t cut it. Meridith advised tailoring proposals in the buyer’s own language, reflecting what they said during conversations. That shows you were listening and ensures the buyer feels heard.

Mark added that proposals should remind buyers of their own problems, creating urgency to act. “It’s their proposal, not some template pulled off the shelf.”

Why Follow-Up Wins

Even when you get everything right, timing often derails deals. That’s why follow-up is non-negotiable. Meridith compared it to being “a barnacle on a boat—you can’t chip me off.” But persistence must come with value.

Mark agreed: following up doesn’t mean nagging. It means bringing consistent insights, reminders, and solutions that keep you top of mind until the buyer is ready.

Matching Buyers Where They Are

Both hosts stressed the importance of meeting buyers on their terms. That includes mirroring tone, dress, and communication style. Meridith shared how she once lost a deal by showing up overdressed on a farm call, creating immediate disconnect.

Respect your buyer’s world, and they’ll respect you back.

Lightning Round: Top 10 Follow-Up Moves

The episode closed with rapid-fire tips for mastering follow-up:

  1. Build a strategy—70% value, 30% ask.

  2. Take the lead—don’t wait for the buyer.

  3. Schedule your follow-ups.

  4. Reference past conversations.

  5. Use multiple channels.

  6. Bring timely, relevant value.

  7. Personalize every message.

  8. Show expertise with examples.

  9. Keep it simple.

  10. Commit like a barnacle—persistent but valuable.

Final Thought

At the end of the day, winning deals comes down to integrity, confidence, and focus on the buyer. If you’re losing deals you should be winning, take a step back: Are you truly listening? Are you aligning with the buyer’s journey? Are you following up with value?

When you sell with integrity and confidence, uncertainty becomes your competitive advantage—and the sale becomes logical.

Lightning Round: Top 10 Follow-Up Moves

Question: Lucia in Seattle asks, “Love the show–I am a new listener. Here’s my question: I’m killing myself and cannot get one of my deals across the finish line. I get to proposal stage and then they go cold or I lose to my competition. I really need help.”

Book: Gap Selling by Keenan