Training for Confidence: Enabling Reps for the Modern Sales Environment

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Armed with more information today than ever before, buyers are gaining more confidence – and sellers need to match it to win.

Over the past decade, there has been a substantial shift in the dynamic between salespeople and their prospective buyers. A cornerstone to this shift is the advent and widespread implementation of digital research tools and communication channels that are primarily online.

Whether it be product reviews and comparisons or simply a website overview, buyers now have access to a wealth of information that they historically had to gain from a salesperson. This transfer of purchasing power to the buyer can leave sellers feeling like they have less control over conversations with prospects, causing a decrease in seller’s confidence and an increased fear of contention.

It goes without saying that building confidence in any situation requires time and diligence; both of which are sparse in the fast-paced world of sales. In sales enablement, where training is a focal point, this makes for a cruel reality when it comes to equipping sales reps with the unique skills needed to overcome fears and sell with confidence.

Here are some beginning steps for sales enablement professionals to take in designing training initiatives to help reps build the confidence needed to win in the modern selling environment.

1. Train Skills vs. Product Knowledge

Often, companies think of training in terms of developing deep product knowledge and proficiency. While being well-versed in the product is certainly essential to selling, it is just as essential to design training that teaches reps the skills needed to identify buyer needs and provide value in customer interactions.

Before the digital age, sellers held all of the cards in buyer interactions. Thus, an abundance of product knowledge was key to seller confidence because the selling process leaned heavily on technical information. Now that most product information circulates liberally in the public domain, the most important asset to a seller is malleability – the ability to adapt to a customer’s situation and unique needs.

“If you know your buyer persona…it almost doesn’t matter what words you’re saying,” said Chris Orlob, senior director of product marketing for “That’s a cosmetic issue. If you understand the buyer at a very deep level, the right words come out automatically.”

By teaching the skills necessary to access the source of a buyer’s pain, for instance, a seller gains control of the conversation and thus grows more confident. Contrarily, an overemphasis on product knowledge is consistently accompanied by a general lack of contemporary selling skills like objection handling or the aforementioned understanding of pain points.

“I would put it at a 70/30 split,” said Hillary Anderson, senior sales enablement manager at Host Analytics Inc. “The 30% being product knowledge because you know they’re going to start using that ongoing and that’s going to develop, and then the 70% being the actual application and selling.”

In general, hyper-focusing on product knowledge in training for sales reps can end up pulling them away from their primary function within the company and begins to encroach on the duties of more technical roles like sales engineering.

2. Leverage Peer-to-Peer Training

One simple way to support reps and help them build confidence is to encourage peer-to-peer knowledge sharing and initiate internal practice prior to allowing reps to communicate with real customers.

Traditionally, this is where companies rely on roleplay. Roleplay can be a great place to start, however, it tends to be rather one dimensional and can oftentimes grow to be redundant for both the rep in training and his or her counterpart in the roleplay scenario.

In addition to roleplaying, sales enablement professionals should take this internal practice a step further by tiering practical exercises in a dynamic way that allows them to practice a range of skills. This will help teach reps how to handle real-life sales situations as independent sellers in a low-stakes environment where they can receive candid feedback and adjust their approach. Here’s what this might look like:

  1. Roleplaying with a fellow rep
  2. Shadowing a top-performer
  3. Mock-calling common positions internally (e.g. VP of sales, gatekeepers, CMO, etc.)
  4. Making a structured outbound call with managerial presence

Just as a weightlifter wouldn’t max out before warming up or a dancer stretch before practicing a routine, it is critical to arrange practical exercises in a manner that continuously challenges reps, thereby creating opportunities for growth.

Intra-company practice builds confidence in handling a variety of scenarios and reduces the chances that reps will stumble through interactions with real clients.

“We remember the things that go poorly much more often than we remember the things that go well,” said Anderson. “So, use your internal team to help replicate the buying process; have them get in front of the CFO, have them get in front of your CMO, have them get in front of your CEO, pitch the product, and hear the objections.”

3. Create a Fail-Safe Environment

Failure occurs frequently when attempting anything for the first time – and sales is certainly no exception. It’s what happens when reps fail during training that has the biggest impact on their confidence rather than the failure itself.

“What shatters confidence is when you push so hard to get a number and the kid doesn’t hit that number,” said John Barrows, CEO of JBarrows Sales Training. “And then it’s this self-defeating prophecy and it just gets worse because now they just feel worse and then they do the wrong activities more and more and more.”

One successful tactic used by enablement professionals is creating an environment in which failure is adopted as a tool for understanding what not to do in certain seller situations rather than imposing penalties or shaming failure. In this environment, when a rep fails, he or she simply has more knowledge highlighting what not to do in order to be successful next time. As more failures pile up, consistency and clarity begin to emerge, and eventually, confidence is more easily acquired.

While creating a fail-safe environment, it’s essential to focus on fostering friendly competition that serves to deflate some of the stressful aspects of selling. Selling is chalked full of stress, primarily due to the fast-paced, high-stakes atmosphere created by quotas. Reminding reps to have fun lowers tension and encourages comradery – two important boxes to check when creating a fail-safe environment.

“Just have some fun with it,” said Barrows. “Realize we’re selling stuff – we’re not brain surgeons here. That would be my tip for something actionable you can do to help build confidence right out of the gate.”

Creating seller confidence begins with teaching and reinforcing skills to have more effective conversations with buyers. Then, it relies on practice internally in a low-intensity environment where failure isn’t ridiculed but instead expected and used as an opportunity for learning.

By thinking of training as a multi-dimensional, continuous process, sales enablement professionals can provide meaningful training that nurtures sales rep confidence.

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