Why Conversations Stall Out (and how to fix it!)

Most business conversations don’t fail because of bad timing or weak value props—they fail because we make them about ourselves, miss the real points of alignment, or forget to actually listen.

If you’ve ever felt a sales call, partnership chat, or even an internal sync just… fizzle, you’re not alone. The real reasons are subtler—and fixable. Let’s break down why so many promising conversations stall out, and what the best operators do differently.

We Make It About Ourselves (And Don’t Realize It)

It’s a classic trap: you’re excited about your product, your numbers, your roadmap. You launch into a pitch or update, thinking you’re building credibility. But the other person’s eyes glaze over, and the conversation goes nowhere.

According to a 2023 Gong analysis of 100,000+ B2B sales calls, reps who spent more than 60% of the call talking about their product saw deal conversion rates drop by 23%.


Don’t get stuck in presentation mode, a founder friend told me about a recent pitch: “I was so eager to show how much we’d built, I barely let the prospect get a word in. They nodded politely, then ghosted us for weeks.” Sound familiar?

Why It Happens:

• We’re wired to showcase expertise and passion.

• We assume more information = more value.

• We fear silence, so we fill it.

What Great Founders Do:

• Flip the script: Make the customer or counterpart the hero.

• Use frameworks like “You > We > I”: Start with their world, then how you can help, then your credentials.

• Ask open-ended questions early (“What’s your biggest headache with X?”) and actually wait for the answer.

At Stripe, early sales teams were trained to spend the first 10 minutes of every meeting just learning about the other company’s business model and pain points—no product talk allowed.

We Don’t Find (or Build) Real Alignment

Alignment isn’t just about agreeing on a goal—it’s about discovering if there’s enough shared ground to move forward. Too often, conversations stall because we never clarify what “success” really looks like for both sides.

A recent McKinsey survey found that 68% of B2B deals that stalled did so because “stakeholders could not agree on priorities or next steps.”

Throughout my career I’ve worked to build channels, in which creating partnerships are key. Nearly all of my succes has been dependent on finding and securing wins for partners, by learning their needs and creating alignment for both sides. While this is easy to identify for others, mantaining objectiveness in my conversations is a real challenge.

Why It Happens:

• We assume alignment because we’re in the same room (or Zoom).

• We avoid the hard questions (“What does success look like for you?”).

• We don’t map the other side’s incentives or constraints.

What Great Founders Do:

• Explicitly ask about priorities, incentives, and constraints—early and often.

• Use tools like a “decision matrix” to map out what matters to each stakeholder.

• Summarize and confirm alignment in writing (“Here’s what I’m hearing: your top priority is X, and you need Y by Q3. Did I get that right?”).

Figma’s enterprise sales team is famous for their “mutual success plan”—a shared doc that both sides update live, listing goals, blockers, and next steps. It’s not just a formality; it’s the backbone of every big deal.

We Don’t Really Listen (or Learn)

It’s easy to nod along and wait for your turn to talk. But real listening—where you’re actually learning, probing, and adapting—turns a stalled conversation into a live wire.

A Salesforce study found that 78% of business buyers say they’re more likely to buy from companies that “listen and understand their needs.” Yet only 38% feel that vendors actually do this.

A startup CEO told me: “I realized I was treating every demo call like a checklist. Once I started asking follow-ups and digging into their stories, our win rate doubled. People want to feel heard.”

Why It Happens:

• We’re multitasking, or mentally rehearsing our next point.

• We fear going “off script” or losing control of the meeting.

• We underestimate the value of silence and follow-up questions.

What Great Founders Do:

• Practice “active listening”—paraphrasing, clarifying, and probing.

• Take real notes (not just action items), and refer back to them.

• Treat every conversation as a chance to learn, not just to sell or persuade.

When I added a sales rep, my call conversion rate took off! We put in a new practice; call reviews. Early on that involved looking into my call performance. It’s easier now to identify presentation and listening flaws, then work to predictively shut those practices down with new opportunities. Take advantage of the tech that surrounds us to improcve our human effectiveness.

Putting It All Together: The Conversation Flywheel

When you make the conversation about the other person, find true alignment, and actually listen, you unlock a flywheel:

• People feel heard → They share more real information.

• You find alignment → You co-create solutions, not just pitch them.

• You learn faster → Every conversation gets easier and more productive.

It’s not rocket science, but it is a discipline. And in a world where most B2B conversations still stall out, it’s a real edge.

Links & Signals

 Why Most Sales Calls Fail (Gong)
Breakdown of over 100,000 sales calls, with data showing how “talking too much” kills deals. Must-read if you want to see the numbers behind the intuition.

The Mutual Action Plan Playbook (Figma)
How Figma’s enterprise team keeps every deal moving forward by co-authoring a shared success doc. Steal this template.

How to Listen Like a Pro (Harvard Business Review)
Practical tips for active listening—great for anyone who wants to level up their conversations (not just sales).

The Real Reason B2B Deals Stall (McKinsey)
Short read on how misaligned incentives and unclear priorities are the silent killers of revenue.

Why Your Revenue Meetings Suck (and How to Fix Them) (Lenny’s Newsletter)
Lenny Rachitsky on how to make every meeting more actionable and less painful. Relevant for anyone tired of endless “update” calls.

The Bottom Line

If your conversations keep stalling, it’s probably not your offer, your timing, or your product.
It’s the basics:

• Make it about them.

• Find real alignment.

• Actually listen and learn.

The best operators treat every conversation as a chance to discover, not just to deliver. Try it this week—then hit reply and let me know what you learn.

If you found this useful, forward it to a friend or share your own “stalled conversation” story. See you next week!

-G

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