There’s no win more satisfying — and no loss more frustrating — than one you’ve spent months negotiating. Sales leaders know that the desire to close a deal can push even experienced sellers toward bottom-line-undermining discounts, unkeepable product promises, or ballooning scopes. Even the sellers who avoid these tempting traps might struggle with procurement, legal, and their ever-expanding list of paperwork requirements.

During Q4, negotiations are top-of-mind for every sales team. But the groundwork for successful negotiations in sales is laid long before the contract is signed. When they nail it, your sellers can avoid discounts and, dare we say it, perhaps even have a little fun?

In this article, we’ll address how Challengers approach negotiations differently, with the negotiation tactics your sellers need to win.

The role of preparation in negotiation

Challengers never walk into a sales conversation without a Commercial Insight, and that level of preparedness helps them prepare for negotiations, too. For one thing, preparation builds the confidence sellers need to negotiate effectively.

In our recent webinar, Negotiating Like a Challenger, Challenger’s Geoff Hendricks expanded on this idea.

“Sellers don’t naturally want a discount because it takes us further away from our own personal goal. But why does it happen? There’s a moment of fear that can take place when you’re looking at needing to make quota. At the same time, you know you have a deal towards the end of the stage, and you don’t want it to slip away. Simon Sinek actually found that you can turn that fear or that nervousness into excitement with proper preparation, training, and practice, because they’re [coming from] the same area of your brain.”

It takes adequate preparation for sellers to prevent late-stage value leaks. That kind of preparation might require your sellers to outline customer needs and priorities earlier in the sales process, including identifying what’s negotiable and what isn’t.

Quantify like a Challenger

To avoid late-stage negotiation stumbles, Challengers do a couple things differently. First, they constantly quantify value — starting with delivering a true Commercial Insight and using that information to emphasize the cost of delay, according to John Shea, Global Director of Sales Enablement at Databricks.

“On a day-by-day basis, we could actually quantify the impact of not taking action on the problem and not getting it over the line,” John said. “The discount is not really that effective or scalable or defensible of an urgency driver, in my experience.”

This calculation, called the Cost of Inaction (COI), brings the thread of the Commercial Insight through to negotiations in order to build a more urgent case for change. As John said, “If you’re not quantifying, you’re not challenging.”

How do you calculate the COI? Use this simple formula, detailed by our Head of Learning Design Lauren Graves in this short clip.

Be prescriptive

Next, Challengers are prescriptive. The prescription doesn’t even need to be correct. High-performing sellers offer the solution they think buyers need based on all the information at hand and then sit back and listen. Confident Challengers also use prescription to create Constructive Tension. They ask, “Where did I go wrong here?” Sellers can use this opportunity to probe key priorities and adjust based on those corrections.

“Be prescriptive,” John said. “Invite skepticism. That’s what confident Challengers do.”

When they recognize that buyers have realized the need to disrupt the status quo, they pivot to offering a solution — what we often call “Sizing the Pie.” The information they’ve gleaned throughout the sales process helps them build leverage during this phase, since they know customers’ pain points and their negotiables.

Build rapport with the right stakeholders

Once procurement enters the chat, sellers’ attention to multithreading and ability to identify Mobilizers is put to the test.

“If you’ve got one champion, you’ve got a problem,” John told our webinar audience.

With buying groups spending so little time — less than 17% of their buying time, spread across vendors — it’s essential for sellers to equip their Mobilizers to sell on their behalf. That might involve seeking out technical champions within your customer’s organization, or ensuring your Mobilizer can answer technical questions when you aren’t in the room.

This goes hand-in-hand with anticipating customer objections later in the negotiation cycle. Sometimes, it’s as simple as writing down the ultimate goal of the sale and understanding what is worth sacrificing in pursuit of that win; likewise, high-performing negotiators also know when the answer is a hard “no.”

As Geoff explained, it comes down to establishing value early in the sales process. Building value-based relationships with internal stakeholders empowers them to advocate on your behalf when procurement steps in with demands.

“Being a third-party facilitator of decision-making between your customer’s organization and your organization is a really powerful position to put yourself in,” Geoff said.

What high performers do differently in sales negotiations

As you assess what your team needs to close deals and prevent value leaks, remember that Challengers win by creating a better sales experience from the very first call. Likewise, high-performing negotiators don’t win in the final mile. Instead, they sell in a way that makes for smoother negotiations. Here’s how the difference between core performing and high performing negotiators might play out…

Core-performing negotiators

• Bring a must-win attitude to the negotiation
• Anticipate customer objections
• Write out opening remarks
• Repeatedly mention advantages of the proposed solution
• Prepare to win a debate at the expense of the counterpart

High performing negotiators

• Know where you need to win and can afford to lose
• Retain a reputation for reasonableness
• Anticipate customer objectives
• Write out ultimate goals
• Negotiate dealbreakers first, rather than easy items first
• Never stop looking for more opportunities to create value

Small changes early in the sales process can help transform core performing negotiators (and sellers) into value-protecting high performers. That’s good news for your bottom line and for the sales experience, which Challengers know is the key ingredient for longstanding customer loyalty.

For more on negotiations, don’t miss the full replay of our on-demand webinar, “Negotiating Like a Challenger,” and tune into Winning The Challenger Sale each month as we dive deep into Challenger methodology with expert guests.

The 2011 research that inspired “The Challenger Sale” revealed a surprising foundational fact: the sales experience is the single biggest driver of customer loyalty. Yet the gap between what buyers want and what sellers deliver is wider than ever. More than a decade of research shows us that sellers aren’t doing enough to engender that loyalty. What gives?

When we retested buyers’ opinions in 2020, they rated seller capability as down 40% from the previous year. The most critical skill to buyers, demonstrating unique insight, was down 52%.

This erosion of trust might be one reason that as recently as 2022, 75% of B2B buyers told Gartner they preferred a completely seller-free buying experience. Or why most sellers (89%) in our 2020 survey reported identifying their business problems themselves—without the input of sellers.

In an era of cringy AI-fueled outreach and “personalization at scale,” who can blame those buyers? To break through the garbage, sellers must deliver a story that deconstructs a buyer’s thinking, leads toward a new solution, and dismantles their underlying beliefs and assumptions. Challengers call it a Commercial Insight.

What is a Commercial Insight?

Challengers know to avoid the stale “What keeps you up at night?” question. Instead, they aim to tell customers what should be keeping them up. The Challenger Sales Methodology teaches sellers to execute this new approach through a six-step choreography that forms a Commercial Insight.

But what’s to be done in a new era of selling where buyers believe they already know what they need? Buyers move through nearly 90% of the sales process alone, and when they do finally reach out to sellers, these buyers arrive with solid perceptions. Sellers hoping to close in this environment must ask: “Is that perception reality? Do they truly understand their needs? And are they building consensus around something that exists in the marketplace?”
The second step in the choreography, known as the Reframe, gives sellers this opportunity. As they build their Reframe, they can directly address even the most entrenched beliefs of these highly-researched customers. Ideally, the right Reframe:

• Makes the customer think differently
• Drives toward action
• Leads to your solution
• And will reveal
  • An unrecognized problem
  • An underappreciated problem
  • A misunderstood cause of the problem

As sellers build their Reframes, our Principal Executive Advisor and Global Head of Insights and Messaging Michael Schaumberger recommends addressing three problems. Learn more in this short clip from our recent on-demand webinar.

How do you ensure your Reframe compels your prospects to act?

The Importance of Tailoring

Tailoring – one of the four foundational Challenger skills – happens when sellers use their understanding of what’s driving the customer to customize their message for resonance. Challengers know how to deliver the right message to the right person at the right time.

Many programs, approaches, and tools offer alternatives to Tailoring that promise significant results with minimal effort. However, Tailoring for resonance involves going far beyond knowing details about a person’s professional or personal experiences. It sometimes means delivering a different message to each stakeholder, understanding pain points throughout an organizational chart, and even changing your message in the middle of a call based on answers to your pointed questions.
It isn’t easy – and it’s often executed incorrectly.

Ineffective Tailoring looks like:

• Delivering the same message to everyone
• Tailoring to only one level
• Offering the wrong message to the right stakeholder (i.e., don’t give Procurement a demo)

Effective Tailoring looks like:

• Aligning messaging to industry and company
• Customizing to the role and personality of the individual stakeholder
• Drawing additional insights as new stakeholders enter the conversation and bring them up to speed

Tailoring helps sellers earn the right to deliver Commercial Insight. When executed correctly, the Challenger Choreography helps establish sellers as trusted advisors—a role that few can claim, according to our research on buyer perception. This is only possible with a level of understanding, perspective, and thoughtfulness achieved through intense planning and earned experience. While that may be daunting, one essential skill most sellers are already practicing that immediately helps them improve their Tailoring is listening.

While most successful sellers already practice “active listening” (if they didn’t, they likely wouldn’t be successful), few are skilled enough to listen in a way that allows them to synthesize and build a Reframe on the fly. In this short clip from our on-demand webinar, Challenger Account Executive Charryse Bigger explains why developing this muscle can aid your Tailoring efforts.

A Tailored Insight Earns Buyer Trust

Buyers are smart, savvy, and sick of generic sales pitches—but they’re also still looking for a guide. Challengers succeed by reframing their customers’ thinking and pointing directly to a solution only they can provide. No matter how far along buyers may think they are in a purchase process and how rep-free they may think they want their experience to be, a successfully Tailored Reframe can change their thinking and give sellers an opportunity to earn their place as trusted advisors.

For more on building a successful Reframe, including a tear-down of two real-life examples, watch our on-demand Winning The Challenger Sale Webinar, How to Build a Successful Reframe.

Last month, I achieved a new personal best at the gym: I hip-thrusted 130kg (that’s nearly 300 lbs for our American readers). To put it into context, that’s more than 2.5 times my weight (so there you go…now you know how much I weigh). I wouldn’t have gotten this far if my conventional way of thinking hadn’t been disrupted and someone hadn’t delivered a powerful Insight that made me feel some Constructive Tension!

I know what you’re thinking: wow, you’re strong! But you’re also probably wondering, “What’s that got to do with Challenger?” We’ll get to that. But for now, let’s focus on Prospect Theory.

As humans, we want to reduce tension, keep relationships amicable, and show the benefits of doing something — what we at Challenger like to call “the gains.” The Nobel Prize-winning Prospect Theory model, developed by Kahneman and Tversky, shows that the human tendency toward reducing tension is a less effective motivator than loss aversion. Loss aversion is a cognitive bias that describes why, for individuals, the pain of losing is psychologically twice as powerful as the pleasure of gaining. In short, the pain of losing money (or any other valuable item) is more significant than the pleasure of gaining an equal amount.

Or as John Legend recently put it:

When you prepare for a conversation with a prospect or client aimed at changing their current way of working, it is imperative that you include the negative consequences of sticking to the status quo. This is what I tell my clients every day, and yet it remains a difficult concept for many sellers. Companies then exacerbate this problem by ignoring Prospect Theory entirely and spending a lot of time teaching reps how to sell the company’s products and solutions rather than understanding customers’ problems and identifying solutions. For this reason, training and ongoing reinforcement is key. Irrespective of the industry, country, or region that your organization operates in , research shows that delivering a sales experience that challenges the status quo and helps the customer think differently will win more business.

But let me take a step back and remind you that I’m currently hip-thrusting 130kg. And to get to this achievement, I experienced firsthand what I tell my clients every day…

It all started a year ago: I grew tired of my workout routine and wanted to increase my strength as I felt I had plateaued. I am not new to strength training and nutrition, but I was eager for a new perspective – I read articles, watched videos, tried different exercises, and still felt stagnated. I have always been reluctant to spend money on a personal trainer ; but was willing to talk to some and see if it was worth it.

I did my research and narrowed down the three I wanted to talk to that specialized in strength building. All of them asked me the same questions: my goals, my current routine and lifestyle, my eating habits. I had some nice conversations and gained a few tips; but ultimately, they proved to me that my status quo was good enough and that with some tweaks, I could continue building strength. I didn’t choose any of them. One might say I chose nothing over something (like 40-60% of B2B buyers these days).

One key learning of Prospect Theory is that when people are presented with opportunities for gain, it naturally triggers risk aversion. For me, when the trainers made their positive suggestions, to be honest I was automatically triggered to be risk averse — and do nothing — as many buyers often do.

Then one day a new trainer approached me. I nearly told her, “no thanks”, but before I could, she said “I noticed you have abdominal separation like many of my female clients. They often have it from pregnancy. Is that the case with you?” No PT had ever spotted this, much less pointed it out so boldly. I felt a little self-conscious, even defensive. We started chatting, and she shared with me something I was completely unaware of about my current trajectory: If I continued to do heavy lifting as I was, I would weaken my core, my back would suffer, and eventually I could severely injure myself, therefore taking me away of exercise for a while. Clearly this would prevent me from achieving my goals. She shared a story of how it happened to herself as a new mother, painting a picture I could use as a frame of reference and lending power to her case for change. And then she shared that strength gaining with abdominal separation was her speciality.

That trainer perfectly executed the Challenger choreography, and I perfectly executed a buyers’ journey and committed to six months of personal training and to achieve my goal. In essence, she delivered a Commercial Insight by:

1. Considering her customers’ status quo and highlighting what the gap was – in this case, a literal abdominal one! (Warmer and Reframe)
2. Intensifying the consequences by showing the cost of staying the same and humanizing the problem with storytelling (Rational Drowning and Emotional Impact)
3. Identifying a new approach that was unique to her solution (New Way and Your Solution).

She helped me avoid loss — and mitigated my fears — to lead me out of decision by indecision.

At Challenger, we support organizations in refining their go-to-market strategy by helping them build the right message, for the right stakeholders, at the right time. We can’t promise you gym gains like mine — but we can show you how to use Prospect Theory, Reframes, and the Challenger choreography to show your customers a new way and your solution.

If you’d like to discuss how to develop commercial insights that disrupt the status quo for your customers, get in touch!

Let’s start with a familiar scenario. You’re choosing an operating system for your enterprise company. Your two options are both great companies with strong products and offer prices that work for you. So, what makes you choose one over the other?

When CEB (now Gartner) conducted a widescale study of approximately 5,000 individuals aimed at determining what exactly they look for in B2B suppliers and solution providers, what they found changed the way we look at sales. They revealed that buyers believe a high-quality product, a great brand, and reasonable pricing are merely table stakes. The only dimension where buyers truly perceived a difference was in the sales process. At 53% of the loyalty equation, this factor drives more customer engagement and loyalty than brand, reputation, service, quality, and price combined. The fact is that how you sell matters much more than what you sell.

What exactly do buyers expect during that sales process? Our 2019 B2B Buyer Study identified “demonstrating unique insight,” “helping me come to a decision,” and “understanding and addressing different stakeholder needs” as the top seller skills. In a 2024 study, LinkedIn and Ipsos validated these findings, noting that buyers most wanted sellers to “demonstrate a clear understanding of [their] business needs,” and “demonstrate a clear understanding of [their] industry/competitors.”

Challengers win because they create a better sales experience using a distinct set of skills: Teaching, Tailoring, and Taking Control of the sale. Through the entire sales process, they deploy an important fourth skill, known as Constructive Tension. Among these skills, we hear that Constructive Tension is the hardest to get right. More Challenger clients (97%) ask for extra help with this skill than any other we teach.

Let’s dig into how Challengers use Constructive Tension throughout the sales process to change the way buyers think about their problems and move them away from the status quo.

How Constructive Tension Helps Sellers Create a Better Sales Experience

In “The Challenger Sale,” authors Matt Dixon and Brent Adamson profiled sellers and found that star performers came from one dominant category: the Challenger. Of all the high performers in the study, nearly 40% were Challengers. The Challenger sales methodology is built around the behaviors that set these sellers apart. They found that Challengers consistently and frequently build Constructive Tension while Teaching, Tailoring, and Taking Control. They push their customers to think differently — even if they don’t immediately see eye-to-eye. Yet for those learning Challenger methodology, this skill can be particularly opaque.

Constructive Tension Is:

• A productive force used to compel a customer to take action
• Used strategically and empathetically to examine conventional ways of thinking, explore assumptions, probe for answers, and navigate your Commercial Insight choreography
• Created throughout the sales cycle
• A learned skill

Constructive Tension Is Not:

• Aggressive selling. Challenger’s Isabel Gillespie debunks this myth in this short clip
• Used to make buyers uncomfortable so they’ll pick your solution. Constructive Tension isn’t about personal discomfort but about discomfort with the status quo.
• A tactic to be rolled out only during negotiation and close
• Only for Americans. Like all Challenger skills, Constructive Tension can be used effectively outside North America. For more on this topic, check out Veronica Coli’s article “Beyond Borders: Debunking Myths About Challenger for International Markets.”

The best-performing sellers use Constructive Tension with the other Challenger skills to help customers realize they need to make a change. It isn’t about creating tension between the seller and the buyer but within the buyers themselves – a tension that tells them that the status quo isn’t good enough.

Getting Constructive Tension Right

Constructive Tension helps create the sales experience buyers want, but we know many sellers don’t use this correctly across the sales process, deploy it as frequently as they ought to, or tap into it early enough. In our recent webinar, 41% of sales leaders told us their sellers worry Constructive Tension will hurt buyer relationships, and another 34% just don’t know how to do it. Many wait too late, creating Constructive Tension for the first time during negotiation and missing the opportunity to use it during their Commercial Teaching, where it’s most impactful.

Here are a few tactics you can use to get Constructive Tension right:

Ask Powerful Questions

Questions create a dialogue with your buyer and help you to surface additional information. Not all questions, though, are created equal. Closed questions, those beginning with “is” or “are” or “have,” allow for incomplete responses. When you lead with these, you risk buyers responding with “yes” or “no,” effectively ending the back-and-forth. Even worse, they could perceive these as leading questions. To use Constructive Tension credibly in your Commercial Teaching, instead, opt for open-ended questions that require your buyer’s thoughtfulness.

This approach helps you develop trust and allows for an open response and helps surfaces additional information to use throughout the sales process. For example, instead of asking, “Are you happy with how much you’re spending right now?” ask, “What would happen if you continued losing money each quarter on this service?”
This approach requires research and prep but leads to a more productive conversation.

Investigate assumptions

When you use Powerful Questions to create Constructive Tension, you force your clients to consider their status quo. At that point, you can begin to uncover what’s unstated by your buyer by digging into their own assumptions about their business. You want them to ask themselves, “Am I approaching this business problem correctly, or am I putting myself and my organization at risk by not considering a new way?”
Use examples from other companies — both successes and failures — to illustrate their assumptions’ underlying problems. The goal is to highlight an unrecognized, misunderstood, or underappreciated problem or pain point. This investigation can help you identify a gap in the current state that’s in need of a reframing.

Use silence

Stop talking — really. When you ask a Powerful Question designed to investigate an assumption, you must give your buyer time to think and process. Strategically using silence is an extremely effective way to dial up tension. Just make sure you’re using it constructively, not awkwardly. Dive deeper into silence with this short clip from our on-demand Winning The Challenger Sale webinar.

Practice dialing tension up and down

What happens if you go too far in your quest to create Constructive Tension? Challengers aren’t afraid to overstep because they know how to read the Dial of Tension and pull things back when they’ve gone too far. Similarly, they know how to read that there isn’t enough tension to bring about change. Think about tension as a spectrum, with Constructive Tension sitting squarely between “too little” and “too much.”

Challengers gauge the tension in the room by looking for body language, signals of interest, and even signs of frustration or anger. When they sense too much tension, they use strategies such as naming the tension, refocusing on a shared goal, or summarizing to help shift the conversation and continue moving forward. These strategies take practice, but they’re the marks of a truly skilled Challenger.

Constructive Tension Isn’t the Villain. It’s the Hero.

It’s easy to think of tension as a villain, but Constructive Tension is a hero. By creating tension within the customer, this force actively moves them away from the status quo and towards change. Constructive Tension requires practice and planning, but like all Challenger skills, it’s possible — and arguably essential to Challenger selling — to learn how to get it right.

For a deeper dive into Constructive Tension, don’t miss our on-demand Winning The Challenger Sale Webinar, Crush Constructive Tension in Commercial Teaching.