I used to blame lost deals on the obvious things.
The pricing was too high. The timing wasn’t right. A competitor got there first. The champion left the company. Budget got cut.
Some of that was true. But when I actually sat down and went through 20 consecutive lost deals. I waslooking at notes, call recordings, email threads — a different pattern emerged.
Most of them broke down in the conversation. Not in the proposal. Not in the pricing negotiation. In the actual human exchange, somewhere between hello and the silence that followed my last voicemail.
What I Found
Across those 20 deals, a few patterns kept showing up:
Pattern 1: I moved too fast for the buyer.
Several of my losses were with buyers I’d read as engaged and ready. In hindsight, they were being polite — not decisive. I pushed for commitments they weren’t ready to make, and they went quiet. I’d confused openness with urgency.
Pattern 2: I led with the wrong thing.
For buyers who needed data and proof, I’d opened with vision and story. For buyers who wanted to feel understood first, I’d come in with slides. I was pitching to myself, not to them.
Pattern 3: I missed the real objection.
The stated objection (‘We need to talk to legal,’ ‘The timing isn’t right’) almost never matched the real one. The real one was usually trust, they weren’t confident that what I was promising was real. I handled the surface objection and left the real one untouched.
Pattern 4: I didn’t flex mid-call.
I had a plan for the call and I stuck to it even when the signals were telling me to change course. Adaptability — real, in-the-moment adaptability — wasn’t something I was practicing. It was something I was hoping for.
The Uncomfortable Truth
None of these deals were lost because of the product. The product was fine. The pricing was competitive. The timing was actually pretty good for most of them.
They were lost because of communication…my communication. How I showed up, how I read the buyer, how I responded to what they were telling me both explicitly and between the lines.
This isn’t a comfortable thing to admit. It’s much easier to point at external factors. But it’s also incredibly empowering because communication is something you can actually fix.
What I Changed
After that audit, I started doing two things before every call:
1. Running a buyer profile. Using Dextego’s Chrome extension, I’d pull up the prospect’s LinkedIn and get their DISC and OCEAN breakdown. Not to overthink it — just to know whether I was walking into a conversation with someone who wants data first, relationship first, or bottom-line first.
2. Roleplaying the hard part. Whatever I thought the most likely objection or friction point would be, I’d practice it. Out loud. Against an AI that pushed back the way that buyer type actually would.
Within a month, my call quality changed. Not dramatically at first. But deals started going to next steps more consistently. Objections started feeling like conversations instead of walls.
Know your buyer before you pitch. 👉 Install the Dextego Chrome extension free here.
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