Top Sellers are Skeptical, Not Optimistic

Welcome to the Same Side Selling Podcast. I'm your host, Ian Altman.

I was having a conversation with a colleague recently, and he said, as far as I'm concerned, all salespeople are positive. In fact, the really successful salespeople are always positive, and they're always optimistic. And I disagree. Because I actually think that the most successful salespeople are not overly optimistic. In fact, it might surprise you that they're somewhat skeptical.

Now, here's what I mean by that. The optimistic salesperson believes that every time they have an interaction with somebody, that individual is likely to become a client. They just don't know it yet. So I'm going to share all about our products and services and capabilities, and you're going to get all excited, and you're going to buy our stuff, and they chase every deal down to the end. And what that does is it repels a lot of people. And it makes people say, Oh, I don't want to deal with this person because they can't take no for an answer. It's like the overly ambitious person at a bar, at a restaurant, whatever. It's like, get this person away from me. In fact, it's the reason why we walk into a store, and we see a salesperson. The salesperson says, May I help you? And we say no, thanks, just looking. Why do we say no thanks, just looking? It's because we believe they're looking out for their own interest, not ours.

So I would say that top-performing salespeople are not overly optimistic. They don't believe that everyone's the right fit. In fact, the top performers who I see are always a little bit skeptical. Now, what do I mean by that? They're not skeptical about whether or not their company can deliver. They're not skeptical about whether or not they can deliver what the customer needs. They're not skeptical about whether or not they can do a better job than their competitors. But instead, the top-performing salespeople are always a little bit skeptical about whether or not the client is as committed to finding a solution as the salesperson is.

So top-performing sellers are always taking that little bit of skepticism that says, I would like you to convince me that your problem is worth solving, that you're committed to dedicating the resources to actually solve that problem, and that if you saw a solution to it, that you would actually move forward with that, and execute whatever it took to achieve the outcome that you're looking for. Now, that may seem a little bit far-fetched, but what it means is that top performers, instead of always trying to be convincing before they ever start talking about their solution, they asked great questions about what's the issue that the client is trying to address? What's the impact of not solving that problem? How important is this compared to other things on your plate? What does success look like? Because if I don't know what success looks like for you, there's a chance that I won't be able to deliver it. And if I'm someone who sells with integrity, I can't take a risk that you're going to go down the path of something that isn't going to generate the right outcome. That'll make me look bad, and you'll regret ever buying anything from me. So I need to make sure that we have a mutual understanding about the outcome. And of course, I need to make sure that I understand who needs to be involved so that if someone critical does need to be involved, that we include them in the process in a way that's comfortable for you.

What that means is that, before I ever present anything, I take people through what we refer to as the Same Side Quadrants. And the same side quadrants cover those four key pieces of information. So you take a blank sheet of paper, draw a vertical line down the center, horizontal line across, creating four equal quadrants. In the upper left quadrant, we take notes about the issue. Namely, what is it that inspired you to meet with us today? And you're not looking for them to say, Well, I was hoping to learn about your software. Oh, great. You're excited about our software? Let me tell you all about it. You say, really, what was it about our software that caught your attention? Well, I was hoping you could do X, Y, and Z. Okay, how do you do X, Y, and Z today? Well, here's the way we do it. Okay. Well, what do you like about that? What don't you like about that? What happens if you don't solve that? That question, what happens if you don't solve that is what takes us from the issue/upper left quadrant to the impact, which is the upper right quadrant.

And impact is not only what happens if you don't solve it. Can you quantify what that impact is if you don't solve it, but also, how important is this compared to other things on your plate? Because if it's costing them a lot, but it's not one of their top priorities, they're probably not committed to finding a solution for it.

Then I say, Well, just because you engage us, just because you buy our products and services doesn't mean that we would be successful. So what could we measure together down the road? Now I ask questions about their outcome and what it is they're trying to achieve. So when I ask those questions about their outcome and what it is they're trying to achieve, now I'm getting a sense of, okay, I know what they were trying to solve initially. I know what happens if they don't solve it. They convinced me why it was so important. And I know what the outcome looks like. Now I get to do some soul searching and say, as the seller, do I feel I can actually deliver what it is that they need.

And if I feel that there may be a chance for that, now, I want to get a sense of so who else would have an opinion about how this has impacted your organization? Who's the most directly impacted by this problem? Who else would have a strong opinion about how we measure success? That'll give me a sense of who else needs to be involved.

And now I have a structure for having a conversation where my skepticism gets rewarded because they might convince me that though they would like to solve this, it's not that big of a deal, and they're not going to invest the resources to pursue this. Or they might convince me that, in fact, this is important enough for them to solve, it's a high enough priority, that our solution really matters to them and that it's worth considering, and it's worth spending more time.

Top-performing sellers know that you can't waste time pursuing the wrong opportunities. Top-performing sellers know that there are always more opportunities. We need to focus our time on the organizations where we can have the greatest impact on their results, not the people who just kind of don't really care about solving the problem at all. So the top performers are the ones who are skeptical. They're the ones who say, I'm not so convinced that they're serious about this yet. I haven't heard enough information that would tell me that if I were spending the money, I would commit the dollars to do this.

And if you take that approach, if you spend a little bit of time asking those questions and taking the role of being just a little bit skeptical, you might find yourself accelerating sales, working with clients who are less price-sensitive, and wasting less time on bad opportunities.

See you next time on the Same Side Selling Podcast.