How to Cure Happy Ears Once And For All

The most common reason behind closed-lost deals won’t show up in the CRM, but it’s a notorious deal killer nonetheless. In this post,’s Director of Sales, Jake Carter, shares three strategies for beating happy ears for good.

Jake Carter

Stop me when this sounds familiar.

Your first meeting with an ICP feels like it goes well. They’re excited by the product and keen to get started, which of course makes you seem like it’s a sure thing.

Everyone leaves the meeting in high spirits. Next day you send a follow up email. A couple of days pass with no response. So you send another chaser.

Two weeks pass. No correspondence. The deal’s gone completely cold. 

Defeated, you mark it closed-lost in the CRM.

This scenario plays out all too often in the life of a B2B salesperson.

Deals fall apart for all kinds of reasons. There’s never usually a single factor to blame. But there is one phenomenon that plays a role in pretty much every deal that falls through.

Happy ears.

AKA hearing what you want to hear instead of what’s really going on.

With 5 years of B2B sales under my belt, the above scenario has happened more often than I care to admit. Happy ears has been one of my biggest deal killers.

So I’ve decided to do something about it.

If you want to learn from my mistakes instead of making them for yourself, read on for the three strategies I’m using to turn things around. Let’s get rid of happy ears for good, together.

First, a definition:

What is “happy ears” in sales?

Happy ears, sometimes known as happy ears syndrome, is the optimistic yet often misleading tendency in salespeople to only hear what they want to hear from prospects. It’s almost always caused by the same thing: 

Misguided assumptions based on insufficient discovery.

It’s a plight that affects all salespeople, no matter how experienced. But with a little self-awareness, curiosity, and a touch of healthy skepticism you can cure happy ears once and for all. 

Here’s how:

1. Deeper discovery that gets to the root of the problem

2. Building airtight & stress-tested business cases

3. Demos that address prospect’s specific pain points

Let’s dig into each.

Deeper discovery to find the root of the problem

Deals are made or broken in discovery.

The goal of discovery is to get to the root cause of the problem your prospect is experiencing and ultimately determine how effectively your product or service can address this problem.

Not all deals that make it to discovery are going to close. For bad-fit deals, it’s better to rip off the bandaid and disqualify them quickly than keep them in the pipeline for a few more weeks till they’re inevitably moved to closed-lost

To combat happy ears during discovery, you must:

  • Ask probing questions to help prospects clarify any ambiguities.
  • Identify potential blockers such as budget constraints or lack of buying authority.
  • Develop a healthy skepticism to differentiate between mere pleasantries and genuine interest.

Remember, being skeptical doesn’t mean being abrasive.

Healthy skepticism is the ability to ask the right questions at the right time to truly understand your prospect’s intentions.

Consider this real-life example from a recent deal:

The prospect’s surface-level problem was their cold emails weren’t landing with prospects. They weren’t getting the results and replies they wanted.

If I’d let my happy ears get the better of me, I would’ve jumped on that and only that.

The resulting generic demo would have most likely led to closed-lost.

Instead, I dug a little deeper:

  • Probing question: “There’s tons of reasons why cold outreach gets low responses. But because you have solid delivery and open rates, that leads me to believe the issue is with either a lack of personalization or your ICP.”
  • Answer that reveals the real problem: “Our ICP is solid; it’s based on strong customer data and reviewed regularly. We do have a bandwidth issue when it comes to personalization, though…”

As it happens, personalization at scale is something we specialize in. So I was able to tailor the pitch for the rest of the sales process around this specific pain point.

The lesson: Deep discovery uncovers the root cause of the problem.

Build airtight business cases for each deal

With the root cause uncovered, you can now prepare a business case.

This is what you’ll present to the economic buyer in a proposal as you go for the close. Before you get to that all-important conversation, it’s important to make your argument as strong as possible so you can handle any objection likely to be thrown your way.

This is how you do it:

Create a customer problem statement report in your CRM

Do this immediately following the discovery call so the information is fresh in your mind.

(As an added bonus, you’ll quickly become your RevOps person’s new favorite by making this a regular practice.)

Next, write out how you solve this problem.

Following on with the example above, this is how I wrote up my CRM notes for my prospect.

  • Problem statement: “Prospect has bandwidth constraints around personalizing prospecting emails. As a result, response rates are falling below expectations and benchmarks.”
  • Solution: “ addresses this problem by using AI to automatically conduct extensive prospect research to uncover information which can be used to create personalized outreach messaging.”

Writing it out like this also helps you really solidify your thinking and tighten your argument.

The next step is key.

Review the problem/solution with your sales director. 

If you don’t have one, or you are the director, review it with a peer. If you’re at a small company like I am, review it with your CEO.

The purpose of this is to roleplay the conversation between you and the buyer. 

You want to try and find any flaws in your plan. Come at it from every angle. If your sales director/CEO can poke holes in it, then so can your prospect.

Refine, refine, refine till it’s airtight.

Now for the ultimate stress test…

Test the pitch on your champion.

No one’s got a better read on your target company’s pain points than your champion.

💡Reminder: A champion is your advocate and go-to contact within your target org. While they may not always have final decision-making and buying power, they have significant influence over those that do.

A champion’s insider knowledge can transform a pitch from pretty good to we’d-be-stupid-not-to-do-this-deal good.

Test your pitch on your champion by:

  • Repeating their current state and pain point back to them. You want to build consensus here to ensure you’re not embellishing the problem.
  • Summarize how you can address that problem—this is your value proposition. Gauge their response to this and ask how it may be received by others at the company.
  • Confirm your account map. This is a blueprint of everyone involved with the deal. The point of this is to make sure no unexpected stakeholders pop up and take you by surprise.

Then ask these two critical questions.

  1. “What’s your process for buying a product like this?”
  1. “If I create this business case, can you get it in front of the economic buyer?”

Your champion is your litmus test. If they can't sell it internally, neither can you. How they answer these questions will determine which way the deal will go and reveal the credibility of your champion and the validity of the deal.

If you’re not careful, happy ears can do some damage here.

So listen carefully.

Tailor demos to your prospect’s unique pain point

No one wants a feature dump.

The best demos show your prospects you know them.

In this context, “knowing them” means distilling all of the insights and knowledge you uncovered about your prospect’s pain points—the same pain points you did all that work internally and with your champion to build a business case around—and tailor your demo towards them.

Don’t sell product features. Sell how they solve a specific, agreed upon problem.

Now, you’ll need to excuse me while I turn once again to my own experience.

(I wouldn’t be doing so if I didn’t think there were actionable lessons that can help you avoid making the same mistakes.)

Reflecting on recent deals:

  • Closed-won deals: I had a comprehensive understanding of the prospect's pain point AND what was causing it.
  • Closed-lost: I had a loose grasp of the prospect’s challenges led by gut feel.

These insights certainly aren’t groundbreaking.

But even though they’re obvious, they are essential to understanding how happy ears can lead to insufficient discovery and lost opportunities.

If you take anything from this, let it be this

Asking probing questions is hard. Digging for the truth is hard.

It can feel uncomfortable and awkward and pushy.

But it almost always leads to good things. Whether that’s the gold nuggets of insight you need to build a solid business case, or the indicators that tell you this prospect may not be the best fit.

The key is asking the hard questions in a gentle way. 

The interaction should feel like a conversation, not an interrogation—and you always need to have a sincere intent to help.

Sales is about communication. Listening is one half of communication.

When happy ears syndrome affects what you hear, you’ll feel the impact on your pipeline, your career, and your commission cheque. 

So listen up and don’t let it.

Jake Carter

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