Sales Takes Vulnerability

“We’ve decided to go in another direction.” My least favorite words to receive when selling. Not only have I just lost a deal. But the rejection is nebulous. It’s impossible to salvage an immediate lesson. I’m going to have to excavate to uncover what happened. In short, I feel powerless; the seller’s equivalent of curling yourself up in a ball, and crying yourself to sleep.

I’ve given a great demo. Even on Zoom, I can feel my prospect leaning in. She’s asked me about pricing. I’ve given a convincing narrative around her deriving enough value from our product to return at least a 10X multiple on her investment. She’s asked about implementation – more buying signals – and I made the case that “it’ll be dead simple” to get onboarded. In comes a wave of heightened alertness: time for the close. I buckle up, “Is this something you’d like to move forward with?” At that instant, the deal hangs in the balance. Time stands still. Even if my prospect were to respond in a matter of seconds, it would feel like an eternity. I check to ensure I’m not holding my breath (most times I am). And I brace myself to handle the barrage of objections that might come my way. Despite some positive signs, this deal could come unhinged. The outcome is at the mercy of my prospect. And I hate feeling this exposed.

I spot the startup CEO I admire at a conference I’m attending. His company has grown like a weed for the last three years and he recently locked up their Series B round, led by A16z. TechCrunch and Forbes have been covering them closely since they raised their seed; drooling over their against-all-odds founding story. Not only have I looked up to him for a while, but I know that his startup would be a game-changing customer for me. I start daydreaming, ‘Man, what I would give for some of his attention. I might even be able to sell him our product. How cool would that be?! But what if he’s too busy to even chat with me?’ I snap out of it, swallow my pride, and approach him anxious to strike up a conversation. “Hey Ben, been a big fan of yours and what you’re building for a while now. Congrats on the new round. I’m Paul. What’d you think of the guy that just got off stage?” I’ve gotten the brush off before at conferences. I hold my breath and pray this isn’t a repeat.

What do these three scenarios have in common? 

They all contain vulnerability while selling. Sales is all about being vulnerable. 

We’re forced to confront our vulnerability, be in touch with it, and come out on the other side. One of the reasons some of us avoid selling is because it confronts us with our vulnerability. We think we’re not comfortable selling. Most often, what we’re not comfortable with is the vulnerable feelings sales elicits. Vulnerability is far from comfortable. It makes us squirm; manifesting as a tightness in our abdomen, preventing us from being at our best. We feel naked. Unprotected. Unable to control our destiny.

Here’s where things get interesting. We often confuse our feelings of vulnerability with feelings of ickiness. Of disgust, even. In our minds, we all too conveniently go to the ’70s used car salesman stereotype, as the quintessential example of “bad sales”. The last thing we want to be is that slimy salesman. We rush to that image to comfort ourselves in our disgust of sales instead of going within and examining ourselves closely. What we’re actually afraid of is staying with our feeling of vulnerability; not sounding like an overgrown frat boy hawking automobiles.

The truth is the overgrown frat boy’s demeanor is a self-protecting alter ego. An overcompensation. A coping mechanism that enables some sellers to keep their shields up, and proceed with selling, all while not exposing their most sensitive parts to themselves and their prospects. 

I’ve found that the best salespeople stay grounded in reality. Instead of being defended, they open up and experience the world fully. They interact with their prospect without having to clam up and protect themselves. They care for themselves in real-time while staying intimately connected with their prospect. These sales men and women show up authentically. The prospect can feel it. And the connection between the two is pure; un-muddied by the seller’s contortions to cover up his soft underbelly.

So how does one stay open to the world – and thereby – the prospect? 

It takes personal work. Among other things, you want to cultivate what some folks will call an abundance mindset. Said differently: the ability to approach each sales interaction with equanimity. Can you hold yourself in a way that allows you to feel a sense of okay-ness whether or not you win the deal? If yes, you’ll be more courageous in the face of battle, and allow yourself to be more open and vulnerable throughout. 

You’re also going to want to deal with your trappings. Sometimes, things we’ve been through hold us back from being fully open and present with our prospects. If you had been humiliated as a child after giving an oral report to your 5th-grade class, you might carry a shame response when presenting to others. And that happens to come up to bite you every time you are in front of people. It may take working through the traumatic childhood episode with a therapist or coach to get over it completely. 

You’ll want to develop an ability to care for yourself in real time. Again, this might be something a therapist can help with (I know, I did). If you ever become aware that you shut down in your sales interactions or become less connected to your prospect, you might want to use tools like positive self-talk, or mindfulness, that can get you to a place where you open back up anytime you feel like you’re closing off.

The discipline of sales takes being in rapport with vulnerability. Whether you’re chatting up a new prospect at a conference, asking for the order, or dealing with rejection, you’ve put yourself out there. Your pride was on the line. And the outcome in limbo. In the realm of the interpersonal – where sales resides – if we want to influence others, it takes an ability to connect with them. Strong connection only comes with a dose of vulnerability. Without it, people won’t be able to feel you, or even trust you. Your capacity to co-exist with your vulnerable feelings plays a large role in how good of a salesperson you become.