One of the most common problems I come across when speaking to cyber security company CROs is frustration with the speed of deals. Essentially, they feel there is a lack of momentum or too slow a pace to bring sales opportunities to completion. This is a challenge at almost every company - and one I experienced, too, in my time running a cybersecurity sales team.
In fact, I don't think I know any team that's selling deals of any real significant size who claim to be really happy with the length of their cybersecurity sales cycle. There are always things that seem to slow deals down. And it causes problems: it causes problems with forecasting, it causes problems with delivering on promises, and it causes problems with meeting internal goals.
And there are lots of reasons why deals are slow.
Though, of course, things vary across organizations, there are some common things that happen again and again. There is a big problem in the selling world where we're trying to get a whole bunch of people on board. And this is where deals die or slow down, so this is where the change that has to happen: The very beginning.
A big challenge is sensing confusion and inconsistencies in what cybersecurity sales prospects tell us. It might be just that the prospect not entirely sure themselves about all the different things are going on. So when they speak to us, they say things that they're not entirely sure about and they may seem to contradict each other. But also, there are other inconsistencies. They might be telling us things that we want to hear. And they say that in the meeting, but then go and do something differently afterward. And those inconsistencies come home to roost a little bit and leave you feeling confused by the incongruency between their words and ultimate actions. Then that can be challenging to call out.
That’s why initial conversations are so crucial to a smooth deal in cybersecurity sales.
On the first discovery call and even a second call, it can feel a little bit challenging to sense fully that something funky is going on here, but it’s important to listen to those feelings and listen out for those inconsistencies. Don’t just let them go by because these will have big effects further down the sales cycle when that lack of clarity that will come home to roost and deals slow down and fall apart.
So taking control of a situation earlier rather than later is at least going to help avoid some of the slowdowns that might come from these inconsistencies. We might avoid some of the misunderstandings that we might have about what's important or not important to prospects. So how do you have that conversation? What's the way to get into that?
Challenge your buyer by starting conversations with four particular words: “I’m confused. You said…” This sentence starter helps you to hone in on inconsistencies between what buyers say they want vs. the decisions they’re making to solve that problem. Your ability to identify call out or resolve these inconsistencies show the added value you bring as a salesperson, so you need to get good at it.
And it's not always easy. Challenging your customers without tact can make them feel incompetent or insecure, which is not what you want from a conversation. You don’t want them to shut down. So, you don’t call them out or frame it as a “gotcha” situation. By starting off with “I’m confused,” it softens the call out. You’re inviting discussion, not making accusations. It lets you talk through contradictions not invite defense.
Let yourself shoulder some of the vulnerability. “I’m confused” makes you seem more authentic and open while starting an important conversation. Make a conscious effort when you hear inconsistencies or confusion from the customer to not avoid a discussion, say: “I'm confused, you said…” and then lead that into a conversation that needs to be had.
Solving these inconsistencies and understanding the roadblocks or hesitancies a prospect has at the very start will prevent changed minds and dragged feet at the end and reduce your deal slowdowns by reducing initial confusion. So now that we understand this concept, we need to make it a cybersecurity sales habit.
You might also like this blog: Improving the discovery process for B2B sellers with 1 powerful tip
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