Sales Discovery: The #1 Reason Why Deals Are Won Or Lost

Sales discovery

Watch the interview

Listen to Cuvama’s interview with Dan Head about why Sales Discovery is the number one reason why a sales team is inefficient, unproductive and loses deals. He also discusses the reasons bad discovery happens and the ways to avoid it. 


Dan Head has over 25 years of experience as a B2B software leader. He was Chief Revenue Officer at customer engagement platform Braze, establishing the European arm of the business and growing it over the next 7 years to a successful IPO in 2021. 

Dan is also a former Regional Vice President at Salesforce, where he was responsible for launching Marketing Cloud. He also led the acquisition of ExactTarget.

We caught up with Dan to discuss the number one way to improve sales productivity and efficiency, as well as the bad behaviors that lead to salespeople wasting time and losing revenue. 

Q: What’s the #1 thing sales leaders need to consider now?

Dan: “If you ask any sales leader in any business anytime over the years, at what stage you win or lose deals, they will all say it’s discovery. 

“So, the first area is how can we make that better? How can we improve that so that we’re wasting less time, winning more deals, and being more efficient?” 

Q: How does discovery help with efficiency?

Dan: “The sales discovery process, first and foremost, needs to be effective at deciding if we are going to take this even further. Discovery is so important with helping the business be confident that its expensive resources, the people in the sales team, and all the assets surrounding them, are being spent in the right places on the right opportunities.” 

Q: Why is discovery often not done well if it is so important?

Dan: “If you think about the average or below average member of the sales team, it’s very easy for them to do the opposite. They get seduced by shiny objects. They believe that being busy is the same as being productive. And it isn’t.”

Q: What leads to bad discovery?

Dan: “The kinds of things that lead to poor discovery is if you don’t know what questions to ask, or how to ask, how to drive towards outcomes, how to speak to the right people. How you are going to educate the client, how you’re going to qualify the client, how you’re going to be consultative for the client, and what competitive traps to lay. There’s a lot in discovery. 

“You can see that it’d be very easy if we’re the sales team that is worried about not being busy to decide to embark and commit to a whole bunch of opportunities that they’re not going to win or you don’t want to win.

“On an individual basis, that’s bad. But you multiply that across 10, 50, 100 salespeople—now you’ve got a chronic problem across the business of wasting time and money.”

Q: How are deals lost in discovery?

Dan: “Deals are lost in discovery because when you move beyond discovery into the demo, or perhaps the technical deep dive or the second demo, or the client reference or the negotiation, and problems arise, they are always from things that could have been better understood earlier on. 

“There are always things that could have been positioned for, that could have been qualified earlier on every single time.” 

Q: What can sales leaders do to solve this?

Dan: “If you speak to a group of salespeople in a room in any business, and when you have a deal, that’s halfway through the sales process or towards the end, and you say, “Why do you lose those deals?” Every single person will say exactly the same list of things in every single business. 

“So you say to the teams well, you know the reasons why you lose those deals. Are there things that you could have done to set the client’s expectations to overcome those problems earlier on? 

“And the answer is always yes—the benefit of hindsight. Except the benefit of hindsight, in this case, is going to play out every single cycle you’re in.” 

“So given that we know why we lose deals and given that we all agree that we can do something about that earlier on. It now comes all the way back to saying let’s not just pay that fundamental, universal truth lip service. Let’s actually do something about it during discovery.”

Why Is Discovery in Sales So Important?

It’s clear from what Dan says that bad discovery reduces sales team efficiency because it causes salespeople to pursue poorly qualified leads. 

This results in salespeople:

But how does this happen? After all, most salespeople know the importance of qualifying leads.

The truth is that while many salespeople think they do a good enough discovery, most don’t go deep enough. 

Instead, they jump straight to talking about features and functions before fully assessing whether the prospect is a good fit. 

Good discovery involves:

  • Identifying the reason to change and the pressing business problems the prospect is looking to solve
  • Uniquely positioning your solution as the answer to these issues, and
  • Understanding all of the drivers and influencers that could affect the deal closing or being delayed — including competitors, internal decision makers, the champion, etc. 
Why Is Discovery in Sales So Important?

If you don’t uncover this critical information, then you are more likely to pursue deals that you end up losing.

And losing can come in many forms. The obvious one is losing to a competitor. However, losing can also mean that the customer:

How Do You Conduct Sales Discovery?

You can read about how to perform good sales discovery in our Ultimate Guide to Value Selling and Value Selling Framework

Here’s a brief overview of the process, along with an explanation of how each stage makes your sales process more efficient:

1. Earn the right to ask questions

Many salespeople struggle to get prospects to engage in deep discovery sales. Many are busy people who want to get your pitch over and done with so they can move on to the next one.

You need to give them a reason to listen and spend time doing proper discovery with you. Usually, the best way to do this is by providing the prospect with valuable insights—we recommend a value hypothesis explaining the common challenges others face in their industry. 

This “buys” you the right to ask deep discovery questions. 

2. Uncover the prospect’s business challenges

Ask probing questions that identify the prospect’s pain points and the root cause of the problems facing their company. 

This allows you to find out whether there is a need for change at the prospect’s business. 

How Do You Conduct Sales Discovery?

3. Identify KPIs

Next, Identify which KPIs will overcome these challenges and the scale of the impact they will have on the business. This helps identify how urgent the need for change is.

4. Link the prospect’s value story to your solution’s unique capabilities

For example, your prospect might say they need good data security. If your competitors aren’t SOC 2-compliant but you are, then highlight that to your prospect. 

This not only ensures that the customer knows why to choose you but it also frames you as the only choice. 

5. Co-create a business case using your prospect’s numbers

Here you refine your assumptions and create a financial justification for choosing your solution. Make sure you use your prospect’s numbers so that it suits their business case. This will make it more convincing to them and other stakeholders. 

This makes the need for change using your solution even more urgent by showing the customer what improvements they could be missing out on by delaying or not making a decision. 

6. Empower your champion

In recent years B2B buyer groups have grown larger. This slows decision-making and often leads to no decision. 

You can speed up customer decision-making by arming an internal champion with the assets needed to drive consensus for your solution across other stakeholders. 

Tech Is Critical to Nail Sales Discovery Business case

Tech Is Critical to Nail Sales Discovery

Most sales leaders know that effective sales discovery is the foundation of value selling and more efficient sales operations. 

The problem is that getting their whole sales team to perform good discovery is challenging because:

  • Training rarely sticks.
  • Managers can’t be on every sales discovery call to coach reps live.
  • Recording sales discovery calls and performing post-sale diagnoses which often involves analyzing why you lost.

Instead, the key is to provide them with a live enablement tool like Cuvama that allows them to guide their prospects through structured discovery.

Cuvama allows them to guide their prospects through structured discovery

This allows every salesperson to perform good discovery and sell like a top rep. It also means that new or inexperienced sales reps learn on the job—which is the best way to make this knowledge stick.

Cuvama’s platform enables your salespeople to start selling value—not products

It allows them to guide prospects through the sales process by helping to:

  • Lead conversations with a hypothesis of customer challenges and KPI impacts.
  • Drive deeper discovery by asking the right questions.
  • Agree and align with the prospect on their problem, solution, and ROI.
  • Empower all team members by sharing a digital discovery record with them.

Boost your sales team’s performance with Cuvama today.

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  • The Ultimate Guide to Value Selling – Taking you from what selling value really means, to how to implement it
  • Value Proposition Guide – How to structure your value prop to enable great value selling
  • Value Discovery Guide – To drive deeper discovery and better sales discovery