Everything I Know About Sales I Learned From My Worst Deal

This one is personal. Tara walks through the deal that cost her more than money — the CEO meeting where she did everything right on paper and still lost. And the three specific changes that changed everything that followed. ConvoControl.com

Transcript

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Welcome back to Everything's Sales. I'm Tara. And I want to do something a little different today. I want to tell you a story, specifically my story, about the deal that cost me more than money. The conversation that went wrong in a way that I still think about and and what came out of it that now lives at the center of everything I teach. A few years into building my practice, I had what felt like a dream client situation. A mid-sized company, strong growth trajectory, real budget leadership team that was genuinely excited about what I do. I had done the initial discovery. I had a solid proposal. I had done everything right on paper. The proposal meeting was with the CEO and two senior leaders. I walked in confident, maybe a little too confident. I had rehearsed everything. I knew my material cold, and I started presenting. I walked them through the framework, the approach, the outcomes they could expect, the investment required. I was smooth. I was organized. I was honestly pretty impressed with myself. And I watched the energy in the room slowly drain. I could see it happening, and I could not figure out what was going wrong. The CEO's face, which had been open and engaged in our initial conversations, became unreadable. The two leaders on either side of him were polite but clearly checking out. And by the end of my presentation, the response I got was, this is interesting. We'll have some internal conversations and get back to you. They never got back to me. I spent weeks trying to figure out what happened. The proposal was solid, the price was fair, the fit seemed genuine. What had I missed? What I had missed was the person sitting across from me. In all of my preparation, all the slide refinement and the talking point practice and the outcome articulation, I had spent zero time in that meeting trying to understand where he was in his thinking, what he was actually worried about, what his real question was, underneath the one he'd already asked me. I had prepared to impress him. And what he needed was to feel understood. That's a distinction that sounds small and is enormous. Impressing someone requires them to evaluate you. Understanding someone requires you to engage with them. And the first experience puts them in judgment mode. The second puts them in collaboration mode. Those are completely different conversations with completely different outcomes. After that loss, I rebuilt how I approach every proposal meeting. The first change, I stopped presenting for the first 15 minutes. Instead, I asked, before I said anything about what I do or how it works, I asked, What's changed since we last talked? What's on your mind going into this meeting? What would a successful outcome of today's conversation look like for you? And I listened to the answers, actually listened before I said a single word about myself or my work. The second change, I built explicit check-ins into every presentation, not just at the end. Every few minutes. Does this match what you were thinking? Is this landing the way you hoped? Where does this feel off? These check-ins do two things. They keep me calibrated to the actual person in the room rather than the imaginary person I prepped for. And they signal to the person across from me, this is a conversation, not a performance. I care what you think. The third change, and this is the one that changed everything. I started treating the no as information rather than verdict. That deal I lost was not a verdict on my value or my capability. It was information. Specific, actionable, useful information about where my approach was missing something important. And once I started treating every no that way, they stopped breaking my confidence. They started building it because every no that teaches me something makes me better at the thing I do. And there are only so many lessons before you stop making the same mistakes. Here's what I want you to take from this episode. The conversation that went badly, the pitch that fell apart, the relationship that didn't develop the way you hoped, those are the things that contain the real curriculum. If you're willing to sit with them honestly, to ask not what went wrong with them, but what went wrong with me. What did I miss? What was I so focused on that I stopped paying attention to what was actually happening? The Convo Control Framework exists because of the mistakes I made before I built it. Every tool in the system came from a conversation where the tool didn't exist and I needed it. Every principle came from a moment where I violated it and saw what happened. You don't have to make every mistake yourself. That's actually part of why this podcast exists. I've made a lot of them, so you don't have to make as many. But the ones you do make, I want you to mine them. Sit with them, pull out what they're trying to teach you. Because that's where your real edge is built. If you're ready to go deeper to work through not just the skills, but the mindset underneath them, head to convocontrol.com. Everything is there. And if you want to do this work seriously, with direct access to me and the full system, ask about the black belt program. That is where people who are serious about changing how they operate come to do the real work. Find me at convocontrol.com. I'm Tara Schuller. This has been Everything Sales. Thank you for being here all season. Go make something happen. I'll see you on the next one.