Jeff Rosset says stalled deals usually fail because sellers miss early warning signs, not because of competition or price. He recommends diagnosing when the deal stalled, then either sending a vulnerable email acknowledging your own misstep or presenting a hypothesis about the buyer's changed priorities and explicitly asking for the truth.
Every time I have a deal that stalled, which, let me tell you, was by and large the number one reason I lost, it was never competitors. It was never not never. It was rarely competitive, rarely price. It was just like, sure, we could train our people to be better or we could just not, right? Like, that's a perfectly viable option. And people don't always choose better in our regular lives and elsewhere. When I had a deal that was stuck, I would always go back to my initial conversation and one of two things would happen. I would either see, hey, I got happiers. Like, someone came in when I was selling Challenger and said, like, I read the Challenger sale, I loved it. I want to train our team. And I went right to, well, let me tell you exactly how we can. And that was a misstep on my part. Or two, there was an actual true deep conversation where I understood the trigger event and the problem that was behind it, but something along the way fell off. So the first step is to isolate. Like, how did I start the conversation? Did I drop the ball or did it happen elsewhere? If I dropped the ball early, I always am in favor of just having a honest conversation with buyers. If I think about the people I'm closest to in my life, it's the people I feel like I can candidly talk to and not worry about being judged. I think sometimes we get so fearful of hearing bad news, we just make our jobs harder by just kicking it down the line until they finally tell us. So what I would do in those instances is I would say I would send an email that said, maybe, like, remember our first conversation on X, whatever their problem was, and then the email, I would take ownership of the problem and I would just say, in reviewing our first conversation, I think what happened is I got happy ears because I heard you saying a lot of great things about Challenger and I neglected to do the right work to understand what else might get in the way of this might make it hard for you to socialize this with other people. And essentially what I'm saying is I think it might be worth going back to the drawing board to figure out if there's another way in. And I think when we lead with honesty and vulnerability and authenticity, it becomes much harder for our buyers to not reciprocate that. When I am trying to convince someone to do something, it is really easy for them to be put off because no one likes to be convinced. So that's what I would do. If I dropped the ball early, if I got mid stage and realized something changed, I would What I'm trying to do here is I'm trying to make it easy for them to give me the honest truth. I'm then going to go and say, like, hey, I have a hypothesis. I might be totally off base. My assumption is maybe something else became more urgent. Or maybe you got stuck trying to figure out, how do I get everybody else on board the bus. If I'm anywhere in the neighborhood of this, I've got a couple ideas. Or maybe it's something else. Hoping you should set some light. And yes, like, transparency, right? Like, that is transparency. And when we open the door for bad news, we can have an honest conversation. I think the deals that I lost were places where I just wasn't making it easy for the buyer to give me the truth because I was too busy trying to convince them so I could hit my own target.
