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In many ways, building sales confidence is about expanding belief boundaries, addressing some underlying perceptions and providing the type of sales training and coaching that maximizes strengths, encourages risk taking and helps your customers think differently.

Confident salespeople believe in themselves. They’re secure in the knowledge that they have what it takes to deal with whatever challenges or setbacks come their way—and they behave accordingly. That’s a powerful quality to have when you’re in a high-pressure role like sales. It builds a kind of emotional resilience that’s vital for sustained sales success.

Confident salespeople also gain a lot of credibility with their customers. Think about it: If you suspect a salesperson isn’t all that sure of the value they’re bringing to you, how much confidence will you have in what they’re offering? On the other hand, the confidence of a salesperson who genuinely believes in what they’re doing is contagious.

Confidence isn’t a fixed trait, though, and that’s especially true when it comes to salespeople. Shifting market trends, changing buying habits, new products, unfamiliar technologies and upstart competitors can all shake a person’s confidence, no matter how much experience they have.

The most obvious recent example is the pandemic, which changed B2B sales forever. The majority of B2B decision-makers now prefer remote human interactions or digital self-service to the traditional face-to-face meeting. That means your salespeople have to get confident — quickly — with video, live chat and other tools and adjust to selling in ways that may be entirely new to them. Does that affect their confidence? You bet it does.

For sales leaders, building and nurturing sales confidence of your salespeople takes continual attention. Here are some key areas to focus on.


When it comes to remote sales, now that they’ve gotten a taste of it, B2B decision-makers want more of it. Research shows that even a percentage of larger sales ($1M+) are now happening remotely instead of in person. If your salespeople aren’t comfortable engaging with buyers in a digital environment, they’re going to lose deals, and their confidence is going to plummet even further.

Equip your salespeople not just with the technology but the skills and processes to use technology effectively in sales. Being proficient in the technical aspects will go a long way toward building their confidence. Just as important, they need to understand how to keep virtual buyers engaged. Nothing kills sales confidence faster than realizing your buyer is multitasking or has completely tuned out.


Forrester’s What B2B Buyers Crave report observed, “Too many B2B marketers underestimate the importance of branding to their success, focusing instead on a product-based appeal to buyers.”

This same concept applies to personal branding as well. Early in the sales process, buyers will care more about the value and insights you bring to them than the nuts and bolts of what you’re selling. Salespeople who take this customer-needs-focused approach are more likely to be viewed as credible and reputable, which helps reduce a common reason why deals stall out — the customer’s fear and perception of risk. The salespeople that can make their prospects smarter or think differently now are the one that will land the appointments later.

So why do so many salespeople skip ahead to product-focused discussions? Because that’s where they’re most confident. The reason for this is that the balance of sales training and coaching is often weighted toward things like product/service knowledge and sales techniques vs. effectively listening for cues, asking deeper questions, building up their beliefs about selling and overcoming mental roadblocks to success.  

Think about what your organization focuses on when it comes to sales development. Are you helping people build up confidence in themselves and what they’re capable of as much as you’re helping them build up their ability to recite product knowledge and use their CRM system?


Something as seemingly basic as asking good, probing questions isn’t always so straightforward. It requires that salespeople show a willingness to help buyers think differently or consider things they’ve never even thought about before. Being honest, transparent and ethical also takes strong self-belief. You have to have a healthy level of sales confidence to be bold enough to say the things a customer may not want to hear.

But many salespeople fail to do the work in advance to think about why they’re asking questions. Before they walk in or make the call, they need to be able to think of a compelling reason why that person would want to use their products. And it has to be an emotional why, like saving time or money or leading to better outcomes for their customers. The why is also often about risk mitigation. And if they can’t come up with good reasons for the client to make this change or why it reduces their level of risk, they’re not going to go into the meeting with a high level of confidence. They’ll revert back to spitting out product features.

Salespeople who do the necessary prep work around questioning have an advantage, because they’re able to bring real value that sets them apart. Instead of an aimless list of closed-end questions that lead nowhere, they can be strategic and ask open-ended questions with specific goals in mind. Knowing how your product or service will make a difference for the client is a big confidence boost, and that confidence will transfer to the client as well.


Any number of underlying perceptions and belief patterns can eat away at a salesperson’s confidence, and often, the person doesn’t even realize it’s happening. For example, a person who views selling as a way to convince or persuade people to buy something may feel conflicted about what they’re doing. They don’t want to manipulate someone into doing something. That conflict with their values and their perception of themselves will damage their confidence in ways that tend to show up in other areas, like call avoidance.

A person’s view of their abilities, whether it’s accurate or not, also plays a role in their sales success. Confident, high-performing salespeople believe that the next success is around the corner and that they have what it takes to get there. They know it might not be easy, but they believe it’s within their reach. And then they tend to turn that belief into a reality. That inner belief energizes them and unlocks their achievement drive, propelling them forward.

Those who don’t believe they have what it takes — whether it’s to make a strong first impression, to be effective selling remotely or to close the big deal — usually prove themselves right.

In many ways, building confidence in sales is about expanding belief boundaries. Some people naturally push themselves beyond these self-imposed barriers, but most of us need a good sales coach, someone who sees more in us and what’s possible for us than we might see in ourselves. Just like confident salespeople transfer their confidence to their customers, the confidence of a sales coach breeds confidence in their people.


Everyone is not going to be good at everything, and that’s okay. If you try to force mastery in an area that simply not a good fit for the person, they’re going to become demoralized and disengaged. Instead, focus on each person’s unique strengths and how they can put those capabilities to maximum use to achieve their goals.

Another effective way to build confidence is to share successes as well as failures. Peer coaching — “real play” vs. “role play” — is a powerful tool for helping salespeople get outside of their own heads, especially if they’re convinced that they’re the only ones struggling. Just as important, they can learn from each other’s experiences with similar challenges and help each other solve problems — a confidence boost in itself. It’s often easier to see a solution to an issue when someone else is going through it than when you’re the one in the middle of it.

With more complex sales involving larger and diverse buying committees, salespeople need the confidence to go after and win these much larger deals. Sales training that helps them build the mindset to navigate these kinds of deals and incorporates the collective insight of peer coaching will deliver massive dividends.


It takes confidence to go for it, especially in an evolving and increasingly challenging sales environment. If your salespeople are busy fighting that inner game of self-belief, they’re going to struggle to get the big wins. In fact, a low average deal size on your sales team can be one sign of lacking confidence to go after bigger wins.

In many ways, confidence and sales success are both self-perpetuating. As reps begin to use new skills, tools and processes and then experience mini-successes, it breeds a new level of confidence and expands paradigms. But for this to happen, the content and approaches must resonate; they can’t be in conflict with the person’s inner values and beliefs. The right training approach is also important. Learning must be accompanied by structured follow-up, bite-sized application over time, accountability, repetition, reinforcement and ongoing coaching.

As confidence expands, it leads to a real sense of commitment, not only to setting and achieving your own sales goals, but also to the broader purpose of the organization. As a result, alignment and synergy individually and collectively peak.

Confidence also has a direct impact on sales rep retention and turnover. If your salespeople are questioning whether or not they’ve got what it takes or feeling a lack of progress and growth, their performance will likely start to fall off and their confidence will take yet another hit. Without effective coaching and training to prepare them for today’s realities and expand their belief boundaries, turnover (either voluntary or involuntary) is bound to follow.

With so much change going on right now, you can’t assume anyone is immune from a crisis of confidence. If you want to your team to remain confident and successful, help them see what’s possible for them to achieve and then support them in developing the self-belief to make it a reality.

About the Author
Mike Esterday
Mike Fisher

Master Facilitator

Mike Fisher began his 30 year career in sales as a college student, selling books door-to-door in the summers. He...
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