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People have been trying to simplify and improve the sales process since cavemen started peddling flints and arrowheads. It’s amazing how little the art of selling has changed—even as the life of the customer has gotten more complex and difficult.

Buyers are busier than ever these days. At their disposal, they have more information that’s easier to access than at any time in history. That’s both a blessing and a curse: customers can get up to speed on just about any subject (including your products and those of your competitors) in no time, but they also get lost in endless data swamps.

Most buyers aren’t making purchasing decisions on their own anymore. The decision-making process involves many different constituents in their companies, sweeping in a variety of functions, points of view and, often, time zones. All that impedes the sales process, slowing it down and making it much easier to short-circuit. A recent Harvard Business Review article notes that in just two years, the average number of people who weigh in on B2B purchasing decisions has jumped to 6.8 from 5.4.

What does this mean? It suggests that successful salespeople have to be empathetic in two senses. They have to figure out the customer’s challenges and pain points to provide a solution. And they have to understand how difficult it is for the customer to sell that solution in his company.

Appreciating these hurdles, there’s an approach that teaches salespeople to bring new insights to enable customers to take the next steps in the evolution of their company—and to reduce their risks in speeding the sales cycle. The idea is that salespeople become trusted advisors to buyers, helping them to overcome the challenges to their businesses and the roadblocks that can detour or derail a deal.

There’s a lot of good and helpful literature on salesmanship that’s emerged over the last few years, including The Challenger Sale, which identifies five different types of B2B reps: The Hard Worker, The Relationship Builder, The Problem Solver, The Lone Wolf and The Challenger, which stresses dialogue with the customer and a keen appreciation of his business.

The challenger rep is a useful model that is useful to focus on three key areas: teaching, tailoring and taking control.


Just as buyers have scads of information a tap or swipe away, salespeople should access enough research to learn about the prospect’s business, including its current projects and challenges. This develops insights that can help demonstrate how their customers’ lives will improve once they become customers. Teaching isn’t promoting your product or service per se; it’s recognizing someone else’s problems and suggesting helpful ways of tackling them.


Customizing starts with the ability to listen and ask questions, and requires a flexible approach. A government agency with a fixed budget has very different needs and means from a corporate client with multiple divisions and a far bigger purse. Multiple pricing models are a good start in tailoring. But being alert to different situations is also key. A potential client may want to test drive your system without throwing out the incumbent one. Customizing a solution relieves the client of some of the risks of buying.

Take control

Manage the sales process by understanding the buyer’s journey, from the initial point of contact, along the windy road of procurement, to the ultimate decision to buy. In becoming your prospect’s trusted advisor, you not only must demonstrate your appreciation of the particular problem he’s trying to solve, but you also have to establish your experience and knowledge of his dilemmas as he navigates his own internal purchasing process. “I’ve seen this situation before; I’ve helped other customers through the hoops” goes a long way toward reassuring your prospect and building trust. There’s nothing like proven competence to instill the sense that no hurdle is insurmountable.

These days, selling is harder than ever, not just because the buyer has more choices but because the once-simple act of buying has become such a fraught process. Customers are faced with more information and alternatives than they can possibly handle. And they have to get far more signoffs from different factions. Salespeople have to understand everything their prospects are up against—and use every tool available to help make the task of purchasing as easy as possible.

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