Want to close more deals? Just show a little vulnerability

If you want to build a prospect’s trust, stop acting like a sales hero.

Prospects don’t care about superhuman confidence. And they don’t expect you to have all the answers. They just want to see some vulnerability.

Why is this so important?

Because prospects already feel pretty vulnerable. They’re talking to you because they need help. They have a problem only you can solve. But prospects aren’t looking for saviors—they’re looking for partners. They want vendors who are empathetic and understanding. They want to work with people who can be vulnerable, too.

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At some point, prospects are going to ask questions you can’t answer. And they’ll have demands you can’t meet. It’s important to be honest and authentic, even if it leaves you open to criticism or disappointment.

Most salespeople are so afraid to let down prospects that they overcompensate. They promise things they shouldn’t promise. They talk in absolutes. They bullshit and bullshit and bullshit.

But prospects know when you’re not being honest. They know when you’re scared to look vulnerable. They know when you’re pretending to be sales hero.

So how can you show your vulnerable side and still close deals?

Ask for help

What four words unlock any difficult sales conversation?

Help me out here.”

When prospects aren’t making sense, or you’re missing a critical piece of information, don’t start making educated guesses—just ask the prospect to provide some clarification.

Here’s how it looks in action:

“Okay, you said earlier that your #1 priority is high-volume sales, but you also said you don’t have many leads to call right now. So what am I missing? Help me out here.”

Some salespeople might think asking for help is a sign of weakness, but that couldn’t be farther from the truth. You’re not a mindreader. When something’s confusing, get unconfused. By asking for help, you actually empower the customer to give you the information you need to close them.

Say “I don’t know”

If you don’t have an answer, just say so.

We all want to be the smartest person in the room, but nothing says idiot quite like getting caught in a lie.

And I get it. It’s difficult to say, “I don’t know,” when you feel like it’s an answer you should know. But ad-libbing or freestyling isn’t going to get you anywhere. You see this a lot with new sales reps—they’re asked a question they haven’t prepared for and they just. keep. talking. It’s like watching a crash in slow motion.

So let me be clear: there is absolutely nothing wrong with saying: “You know, that’s a great question. I don’t know the answer, and I don’t want to give you the wrong information, so let me talk to one of our experts after this call and get an answer for you.”

If you’re new, say, “That’s a great question, but I don’t know the answer. This is my first week, so I’m still learning the ropes. But I’ll talk to one of our experts and get you an answer right away.”

It’s an awkward and vulnerable thing to say to a prospect, but nobody's going to be mad that you're new. We’ve all been there. We’ve all had first weeks. As long as you’re honest—and you show that you’re eager to find the right answer—they’ll be encouraged to continue the conversation.

Admit you were wrong

At some point, you’ll provide a prospect with incorrect information. It happens to all of us. You’ll misquote a launch date or overquote a discount.

In these situations, most reps try to ignore the problem and hope prospects don’t notice or care—which is the dumbest thing you can do.

Instead, call them right away and correct that false information. It sucks, but it’s the right thing to do. Just say:

“I wanted to check back with you about the call we had a couple hours ago. I told you we’d build this feature within the next eight weeks, but I talked to our product team and it turns out I had the timeline wrong. This was pushed back on the roadmap, so it’s probably going to be more like three or four months before we have this completed. I apologize for getting the dates wrong.”

Or, if you’re dealing with a price negotiation, say:

“I know you really wanted a 20% discount, and you had a very good reason for why that’s the only price you can pay. I told you I could make that happen, but I went back to the team and, even though I fought tooth-and-nail, our finance department won’t approve it. No customer has ever received a 20% discount. The best I can do is a 15% discount, which is still an amazing deal. I think this can work, and I hope you agree with me.”

What’s the takeaway? Call the prospect immediately and tell the truth. You’re going to feel completely naked, but it’s the only way to move forward and re-establish their trust.

Learn to say no

When you’re qualifying leads, don’t be afraid to tell people, “I don’t think our solution is right for you.”

It’s never easy to turn away money, and this kind of honesty occasionally leads to disappointment and anger—especially from enthusiastic prospects—but selling to the wrong customers can kill your startup.

Saying no to feature requests is equally worrisome for sales reps. No one wants to say, “Look, I understand you want this feature, but it’s not on our roadmap and we’re probably not going to build it any time soon. So if this is an absolute must, you shouldn’t buy our product.”

It’s scary when you don’t know whether that’s the last straw for a prospect. You may feel vulnerable in the moment, but you’re actually taking a position of strength. For one, you avoid bringing on a bad customer—who will undoubtedly hound you about the feature for the next six months—and, when you ask if this feature is a really deal-breaker, you usually find out it’s not a deal-breaker at all. The prospect isn’t going anywhere.

Roll with the punches

Product demos are nerve-wracking enough. But when something breaks, most salespeople start looking for the nearest exit.

Don’t hide from these moments. Don’t overcompensate. Don’t pretend like you’ve never seen an error message before.

Welcome the unexpected. Say something like:

“Okay, great. Here's an error message. Let me show you what happens when you run into a bug. This is how you get in touch with support. See this support link? When I click it, I’ll be connected with an engineer. Hi Thomas, can you help me? I’m giving a live demo and we’ve received the following message.”

Confront the problem and coach them through the support process. When you don’t hide from an issue, and you treat the situation as an opportunity to learn, you show prospects that they have an entire team working to make their lives better, not just one sales hero.

Embrace the chaos

During a crisis, you’re going to feel incredibly vulnerable. Customers will be pissed, solutions will be delayed, and you won’t have anything to say other than, “Sorry.”

You may feel like ignoring phone calls and emails, but you have to show up. You have to call the customer and apologize. You have to listen as they scream and shout about taking their business elsewhere. Even if you’re not in a position to help them, it’s on you to be present.

This shit sucks, but it’s possible to turn these vulnerable moments into opportunities for growth.

A while back, we had a technical problem with our telephony provider, so we called our customers to apologize. After talking about how committed we were to solving the problem—and how committed we were to our customers—we asked if they were happy with our product overall. Many said yes. So we recommited to the relationship long-term. In order to do that, we pitched pre-paid, annual contracts at a discounted price.

And quite a few customers took us up on our offer.

We communicated transparently and admitted we’d let them down. We let them say what they needed to say, then we pushed the conversation forward. We weren’t afraid to look vulnerable. In the end, we turned an outage into a real opportunity.

So what’s the lesson?

The coffee’s for closers way of selling is over. Well, it’s almost over. If you really want to connect with prospects—if you want to establish trust and close more deals—you don’t need to be the smartest, fastest, and strongest sales rep in the world. You just need to understand that we all feel vulnerable from time to time. Even salespeople.

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