Challenger Sales: The Ultimate Guide (+5 Examples)

The challenger sales model has potential to transform your sales approach from the ground up – and help you close more deals.

That’s why I made this guide to challenger selling.

But also because being a “challenger” just sounds cool.

Ready? Let’s jump right in!

What Is the Challenger Sales Model?

The challenger sales model comes from the bestselling book The Challenger Sale, by Matthew Dixon, Brent Adamson, and their CEB Inc. colleagues.

I’ve covered sales methodologies based on decades-old books, but The Challenger Sale is more modern, first published in 2011. That’s important, as you’ll soon see.

Here’s the introductory premise of the book: today’s customers are changing how they buy, so salespeople need to change the way they sell. (At least when it comes to complex B2B deals).

How?

The Challenger Sale uses empirical data to define and explore five major types of sales reps, based on personality traits, habits, and overall sales styles.

Among these five personality types is one that stands above the rest: the challenger.

The 5 Types of Sales Representatives

These are the sales rep types as defined in the book:

1. The hard worker.

The hard worker is a driven, ambitious individual. They’re willing to put in lots of effort to achieve their goals and please customers, but they tend to lose sight of prospect perspectives.

2. The relationship builder.

Relationship selling is a sales methodology worth exploring and considering for your team. But in the challenger sales model, the relationship builder is ineffective.

This personality type attempts to become a trusted advisor to prospects, offering free information and insights and networking hard.

This tends to be a slow and somewhat inconsistent process for certain types of customers.

3. The lone wolf.

The lone wolf attempts to work by themselves as much as possible. They can be high performers, but they don’t collaborate well with others – and they struggle to build good relationships.

4. The problem solver.

The problem solver’s approach revolves around identifying a problem faced by a prospect and spinning your core product as a solution to that problem.

It works in a variety of cases, but it’s not a perfect approach.

5. The challenger.

Here we have the focal point of the challenger sales methodology: the challenger type.

A challenger is someone who is brutally honest and upfront with prospects. They’re not afraid to challenge their prospects’ perspectives and they’re willing to have frank conversations about money and budget.

Good challengers use strategic pressuring and leverage to get control of conversations and ultimately lead to a sale.

Of all the types, challengers tend to be the highest performing – and the authors encourage you to tailor your style to challenger selling as a result.

But there are a few caveats.

First and most importantly, the challenger selling approach is only demonstrably superior at sales in certain conditions.

In a B2C, transactional sales model, it’s no more effective than the other types – and in some cases, it’s inferior to relationship builders, problem solvers, and lone wolves.

Challenger sales reps are usually better when it comes to large, complex B2B deals. You’ll see why when we dig into the core tenets of challenger selling.

It’s also worth noting that the “challenger” mentality is something that any of the four other major personalities can evolve into. Regardless of whether you feel like more of a hard worker, or a lone wolf, you have the potential to become a challenger.

The 7 Key Elements of the Challenger Selling Model

So what can you do to become a real challenger?

Like with most of the sales methodologies I’ve covered previously, it comes down to your habits and processes.

Generally speaking, the challenger approach encourages you to follow the “three T’s” when engaging with a prospect: teach, tailor, and take control.

You’ll have to teach your prospect new information and new perspectives. You’ll need to tailor your sales pitch to match their needs and current situation exactly.

Then you’ll need to take control of the conversation.

Here are the key elements of challenger selling:

1. The complex sales cycle.

Challenger selling is custom made for B2B situations with complex sales cycles. The longer the process and the more complicated the decision is, the better challenger selling is going to work.

2. Teaching over relationship building.

Relationship building is crucial for networking and many types of selling, but if relationships are your only priority, your bottom-line sales performance may suffer.

You have to be a teacher, taking the role of an expert and a confident outsider in the process.

3. Owning the conversation.

Take control of the conversation. That doesn’t mean you should be talking the whole time; in fact, active listening is as important here as it is for other sales methodologies.

Instead, this is about staying focused and on point. Gently guide the conversation back where it needs to go if it drifts.

4. Constructive tension.

Challengers truly do challenge their prospects. It’s a premise known as “constructive tension.”

If your prospects feel a bit of tension and a bit of pressure, they may be more likely to comply with your requests and think carefully about your arguments.

Just don’t push too hard or too far, or your prospects may walk away before you can close the deal.

Part of that constructive tension can be wrapped up in casual debate. If your prospect has an outdated or incorrect idea, engage them in a constructive debate.

Introduce new ideas, new facts, and new arguments to persuade them to adopt a new way of thinking.

5. Disruption.

Challengers are agitators.

You can’t afford to be a passive, placating friend to these prospects; you have to stimulate discussion, get uncomfortable, and disrupt the status quo however you can.

6. Understanding the customer.

It’s not enough that your product has the potential to solve a prospect’s problem. You have to make sure the customer understands what the problem is, what the product is, and how the product solves it.

That’s part of where your job as a teacher comes into play.

7. Transparency and openness.

You still need to respect the rules of business etiquette, but you can afford to be more blunt and straightforward in a challenger sales environment.

Be fully transparent and open about your ideas – even the ones that push your prospects to think in new ways. No subject is taboo, including money.

As long as you’re still complying with the fundamentals of challenger selling, you can incorporate and utilize a wide range of other tactics and philosophies.

The 5 Phases of Challenger Selling (+ Examples)

Most of the deals you’ll navigate as a challenger sales rep will go through a set of familiar phases. I’ve outlined each below, along with challenger sales examples for each phase.

1. The warmup

Everything starts with the warmup.

Here, your goals are to pique your prospect’s curiosity and establish some trust. It’s also your opportunity to form a good first impression by “challenging” your prospect.

• Establish the “why.” Why are you reaching out to this person? You’ll need to think about the question from both a low level (e.g., how did you get this email address?) and a high level (e.g., what problem are you trying to address?).
• Showcase your expertise. Find a teaching moment and start to build your own credibility. Build yourself as an expert in this field.
• Stoke curiosity. You’ll also need to stoke the prospect’s curiosity naturally. Don’t bombard them with reasons why they should be interested in a product like yours. Instead, guide them to figure out their curiosity on their own.
• Facilitate engagement. The more you interact with a prospect directly, the more they’ll come to trust you. Try to get interactive during the discussion.

Example:

You start the conversation just learning more about this prospect.

Who are they? What is their current advertising strategy? What do they struggle with? What’s their favorite ice cream flavor?

Something like, “How much do you spend on advertising? What kind of results are you seeing” can get the ball rolling.

Remember, don’t be shy – be blunt and open about the topic.

2. Reframing

At some point, you’ll need to reframe the conversation. The goal here is to take a casual, objective conversation and turn it into a thought-provoking, hypothetical, future-based one.

For example, let’s say the initial warmup conversation reveals that this prospect is dealing with a stretched, thin budget.

Your goal could be reframing that conversation to talk about the opportunities available for a small budget – and tactics that can free up more money for higher levels of spending.

• Address misconceptions. This is a great opportunity to focus on misconceptions related to your product or industry and address them – or talk about how most businesses solve this problem incorrectly.
• Keep control over the topic. No matter what, you’ll need to keep control over this topic. Don’t let the conversation drift.
• Be authoritative. Stay confident and authoritative to build yourself as a true expert.

Example:

Here, your job is to be a bit of a contrarian – and reframe the conversation. Start challenging your prospect with surprising facts or new lines of thinking and guide them to a more appropriate position to be sold.

For example, “Did you know most PPC ads in this category actually end up losing money?”

3. Emotional connection

Throughout your meetings, the challenger sales methodology will encourage you to form a true emotional connection with your prospect.

Get to know who they are and what they’re feeling – and use that information to your advantage.

Use a combination of stories, hypothetical situations, metaphors, and genuine questions to stoke more emotions from your prospects – and guide them to take action.

Example:

It’s time to start stoking emotion (with caution).

After building some trust, don’t be afraid to challenge your prospect with something like, “Aren’t you worried about overspending on ads that aren’t working?”

Or “Do you ever feel stressed that you can’t keep up with your campaign management?”

4. The value proposition

Once you’ve established more authority and an emotional connection, you’ll be in a position to give your prospects a value proposition.

Your prospect has a problem. There’s an issue that needs solved, or a set of conditions that are seen as negative.

What’s the thing that’s going to make those bad feelings and bad situations disappear?

Your job as a challenger is to present a clear picture of a better situation. How could someone address the problem in a productive way?

What would that product look like? How much value would it add to their career or their life?

Example:

Here’s where you’ll convince the prospect on your general value proposition.

“Wouldn’t it be easier if you had a comprehensive platform that let you manage everything in one place – and saved money in the process?”

5. The product

If you can get the prospect sold on the conceptual idea of your product’s value, you can easily sell them the product itself.

To close the gap, you’ll just have to effectively demonstrate the product and prove that it can add value the way you say it can.

Example:

All those “what ifs” need to fall away. Prove that your product can do everything your dream hypothetical promised.

Use facts, good arguments, and demonstrations to close the deal – and don’t be afraid to seize control of the conversation if it drifts.

Using Email in Challenger Selling

In the challenger sales model, like with many other sales methodologies, much of your success is going to be contingent on your ability to email quickly, efficiently, and with specific relevance to your target audience.

One of the best tools for understanding and improving your sales email communication is EmailAnalytics.

It lets you see a detailed breakdown of your email activity, complete with graphs, charts, and statistical analyses to help you see essential sales KPIs like average email response time, and much more.

Sign up for a free trial today and see for yourself! There’s no risk, no credit card, and no software to install.