The Secret to Closing More Sales? Learning How to Lose Them First.
Here’s a hot take: the best closers know how to lose. Whether it’s a prospect that passed or a long-time client who moved on, losing with grace can turn a “no” into a “not yet.” In sales, your biggest wins are often hidden in how you handle the losses.
The Art of Losing (and Why It Matters)
Something I always preach at The Middle Six is this: the biggest part of closing a deal… is losing a deal. (Yes, I went full cLosing pun. You're welcome.)
First, let’s talk about the deals you pitch and don’t win. It’s the most common (and most feared) type of sales loss. But it’s normal. In fact, most reps lose about 80% of the deals they go after. That’s why we built our name around The Middle Six: you’ll lose 2, win 2, but it’s what you do with the middle six that determines your success. This is called the Pareto Principle.
If you're serious about learning how to close a sales deal, you’ve got to get good at sales loss recovery. That means building a smart sales follow-up strategy, understanding why clients leave, and most of all, losing clients gracefully.
Let’s get into it.
1. Losing the Pitch: A Lesson in Grace
This is the loss we all fear: the one where you almost win. You pitch your heart out. You feel the energy. And then...crickets. Or worse, “we went with someone else.”
That sting? Completely normal.
Most salespeople lose around 80% of the deals they chase. The numbers are real, and so is the rejection. But that doesn’t mean you failed.
Remember our company name? The Middle Six. Based on the Pareto Principle: 20% of deals are nearly guaranteed wins, 20% you’ll lose no matter what, and it’s what you do with the middle 60% that defines your success.
So what do you do when you lose? You lose with class.
Thank them for the opportunity.
Stay visible.
Stay helpful.
Why? Because the vendor they did choose? Might not deliver. And when the shine wears off, you want to be the easiest, most comfortable “yes” they’ll ever make. No ego. No guilt. Just grace.
2. Losing a Client: When They Walk Away
Now this loss stings in a whole different way. Maybe you worked together for years. Maybe they were a dream client. And suddenly, they’re out. Gone. Replaced.
You may never get the real reason: cost, change in leadership, or just vibes. But here’s the one rule that always applies: Let them go with grace.
Keep that door open. And mean it.
Case in point: we once got fired for being “too optimistic.” (Direct quote. And yes, we framed it.) That same client? They came back. Turns out, aggressive positivity is exactly what they needed all along.
Let this be your sales follow-up strategy: make them want to come back, not regret leaving.
3. Why Every Loss is Still a Win
As we head into the season of reflection and gratitude, here’s your reminder:
Be thankful for every single client:
- The ones who buy from you
- The ones who might buy from you
- And even the ones who didn’t buy or walked away
Why? Because each one is shaping you. Sharpening you. Teaching you how to show up, sell better, and serve smarter.
In short: you didn’t lose a deal unless you burned a bridge.
Takeaways: Your Sales Loss Recovery Plan
Here’s how to make peace with the “no” and position yourself for the “next time”:
Follow up without being clingy. Check in 60-90 days later with something helpful.
Be the first call when the new provider drops the ball. Keep adding value—even without the contract.
Know when to move on. Some losses aren’t about you. Release them with respect.
Keep a re-engagement plan handy. An email series, a free workshop, or a new offer can re-open doors.
Need help crafting a graceful follow-up strategy or re-engagement plan? Let’s chat about how The Middle Six can help you stay visible, valuable, and always in the running. Contact us here.
About Lisa Proeber
Lisa Proeber is the force behind The Middle Six®. With more than 20 years of high-performing sales experience, she brings a breadth and depth of knowledge to her solo venture. The Middle Six® is not a gatekeeper; it opens the gates for anybody to learn how to succeed at sales. Sales is not a dirty word; it's equal parts art and science, starting from the bottom up. Ready to become a salesperson with a roadmap in hand? Join us, and let's make waves together.
