Tactic 6 of 10: Take a Challenging Approach (without being a jerk)

Teach, personalise, and take control without being pushy. Create healthy tension that leads to better decisions and stronger outcomes.

This is part of a limited series of sales tactics from my forthcoming book ‘How To Sell’ to help you sharpen your conversations, close with confidence and hit targets faster. You’ll get two tactics each week until the book launches on Nov 25th, when I’ll drop my pre-launch subscribers a best-price alert so they can grab a great launch-day deal.

Today’s tactic comes from the chapter Step-3: Understand your customer

Take a challenging approach

The heart of the understanding step of the sales conversation is to ask questions and listen actively to what your customer has to say. However, before we look at how to do that, let’s take a step back and consider the approach you should adopt as you do so.

In Chapter 1, I introduced the importance of balancing courage and consideration – balancing your courage to actively lead the sales conversation with consideration for the customer’s needs. This concept is so important that it’s embedded within our sales philosophy, to help people make informed buying decisions by exploring and targeting win-win outcomes.

This principle explains why, as a salesperson, not only is it OK for you to challenge customers (in the right way and for the right reasons), it should be something you wholeheartedly embrace.

This principle of challenging customers is explored in more detail in the 2011 book The Challenger Sale by Matthew Dixon and Brent Adamson. This book is based on a global study by the Sales Executive Council that examined the behaviours of more than 6,000 B2B salespeople. In the study, researchers found that the highest performing salespeople were much more likely to display the following behaviours.

• They teach their customers. They take the sales conversation beyond just the features of their solution, offering insights that provide a fresh perspective on the customer’s situation. They also educate the customer – often revealing problems or opportunities the customer wasn’t aware of.
• They personalize their sales message. They have a finely tuned sense of their individual customer’s values and objectives, and they use this knowledge to effectively personalize their sales pitch.
• They take control of the sale. While not aggressive, they found that high-performing salespeople are much more likely to be assertive and comfortable with tension, and are unlikely to give in to their customer’s every demand.

In short, the researchers found that although the best salespeople weren’t pushy, they were often happy to challenge. Unsurprisingly, the researchers termed these salespeople challengers.

They also identified salespeople who were more relationship-led. Those salespeople focused on developing strong relationships with customers, were generous with their time, endeavoured to meet their customers’ every need, and worked hard to resolve any tension. While those characteristics weren’t necessarily absent in challengers, they weren’t the skills and behaviours that defined a challenger’s customer interactions.

In addition to challengers and relationship builders, the researchers also identified three other types of salespeople: hard workers, lone wolves and reactive problem solvers.

When they analysed the sales performance of these different groups, the researchers found that challengers accounted for almost 40% of the high-performing salespeople in the study and, as a result, The Challenger Sale book focuses on how salespeople can develop these characteristics. But as good as that advice is, it’s not the full story.

Considering complexity

The study also noted that when the researchers cut the data by complexity of sale, separating out product-selling reps from complex solution-selling reps, they found that challengers increasingly dominated as the sales process got more complicated.

This is an important insight that often gets overlooked.

Frontline salespeople like you, typically sell through a single or short chain of sales conversations, with a single or short chain of decision makers. The sales you make are no less difficult and no less important than those of your long-chain peers, even if the sales conversations you have and the solutions you propose are less complex.

So although the study shows it’s always more effective to challenge than it is to just blindly comply with your customers every request, the degree to which you challenge is important. The more complex your sales conversations and solutions are, the more important it becomes to challenge your customer’s pre-existing ways of thinking.

Got a question? Drop it in the comments or in a DM and I’ll be happy to help.

Managers: Comment COACH and I’ll send you a one-pager on how to coach this with individual reps or in your next team huddle, plus the pitfalls you need to avoid.

Next up: Simple FAB presentation examples (you can mirror today)

Reading on LinkedIn? Join the pre-launch list for email-only perks, including the chance to win a signed advance copy of my book every week until launch.