Outside Sales Training: Preparing for the Field
Improving win rate

What is Field Sales?
Field sales (also known as "outside sales") is the practice of selling a business’s products or services outside the office. Field sales professionals often travel to the customer’s location to engage them directly in a sale. This includes traveling to attend networking events and trade shows, conducting sales presentations, and building relationships with prospects and customers.
Field sales representatives often have irregular working hours in one or more specific sales territories. At its core, though, outside selling refers to conducting face-to-face interactions with customers. Their counterpart is inside sales. Inside sales involves interacting with customers and prospects through phone calls, email, social media, cold calling, or other mediated means.
Why Field Sales Training is Critical
With so many business activities done digitally, businesses see interactions with inside sellers as more convenient. However, sales organizations require both inside and outside sellers to succeed in today's technological age. With a sales interaction at every digital corner, businesses see in-person, real time interactions as more authentic. With better relationship-building, field reps can close higher-stakes, complex deals.
Today, purchasing decisions involve an increased number of stakeholders, increasing the complexity of the sales process. With more stakeholders, a seller faces more indecision and scrutiny. Addressing more stakeholders requires better interpersonal skills to conduct successful in-person meetings. To prepare sellers to navigate these circumstances, organizations need effective field sales training.
Outside Sales Roles and Responsibilities
Achieving business goals has become more complex than ever. This trend stems from increased competition.
Positioning solutions that address these challenges requires training sales professionals on deeper questioning. Often, a sales professional can more easily accomplish this on site with the customer. Fully-engaged customers yield longer-term relationships and greater revenue.
Being adept at customer-facing scenarios is an essential skill built during field and outside sales training. Field sales professionals must be able to approach the conversation with authenticity by engaging in a questioning strategy that uncovers the customer’s needs.
The field sales process can be difficult because it forces both sides to acknowledge the stature of the business challenges. Openness illuminates the specifics that will give effective professionals an edge over the competition. The most critical part of outside sales lies in field sales professionals' ability to build relationships.
Top Challenges in Field Sales
Outside sales training must require professionals to have a superior skill set. One-quarter of business sent out for bid is never awarded to any sales team. This inertia means leaders need to train a field sales team that can perform at a level that earns the customer’s trust.
Earning the customer’s trust is more difficult than it has ever been. As technology advances, outside sales professionals face escalating business needs and aggressive procurement practices. Reaching quotas means training professionals to deliver on these challenges. Failing to do so carries a heavy expense given that 71 percent of the sales force today consists of field sales professionals.
Time in front of the customer is short and outside sales professionals need to make every interaction meaningful. Doing so means engaging in consultative selling characterized by a shared commitment to the business challenges at hand.
Research from McKinsey underscores the value of this skill. One company credited a move from transactional selling to consultative selling with “$500 million in new bookings and a 40 percent improvement in productivity.” The difference comes from deeper customer relationships. This depth cannot develop without authenticity.
Building Critical Skills for the Field
Time in front of the customer is short and outside sales professionals need to make every interaction meaningful. This requires sellers to use consultative selling, characterized by a shared commitment to the business challenges at hand.
Sellers that use a consultative approach create deeper relationships with buyers. When using a consultative approach, sellers deliver value in the buying experience and differentiate themselves from the competition. Instead of pushing a product, they become advisors that prioritize customer needs.
Research from McKinsey underscores the value of this skill. One company credited a move from transactional selling to consultative selling with “$500 million in new bookings and a 40 percent improvement in productivity.” The difference comes from deeper customer relationships. This depth cannot develop without authenticity.
Outside Sales Essential Selling Capabilities
With customer interaction at the forefront of field sales, sellers need specific selling capabilities to reach their goals. At Richardson, we created a sales capability framework to guide all types of sales interactions. While field sellers can benefit from all capabilities in the framework, navigating their in-person sales activities requires the following capabilities:
Sales Meeting Execution
Successful sales meeting execution requires sellers to lead effective meetings to explore and address customer needs. It also requires collaboration with colleagues to win sales opportunities. Specific selling behaviors underpin this capability, including:
- Preparing for Sales Meetings
- Opening Sales Meetings
- Selling with Teams
- Closing Sales Meetings
Demonstrating Conversational Agility
To demonstrate conversation agility, sellers must master the art of connecting with their customers. This means understanding their messages and presenting compelling information that resonates both intellectually and emotionally. Specific selling behaviors underpin this capability, including:
- Projecting Presence and Relating to Connect
- Authentically Questioning and Actively Listening
- Positioning Persuasively and Checking for Feedback
Managing High-Stakes Conversations
Outside sales reps often face higher-stakes deals. This requires them to successfully lead critical conversations with a higher propensity for greater risk and reward. Specific selling behaviors underpin this capability, including:
- Resolving Objections
- Positioning a Price Increase
- Asserting a Point of View
- Addressing Misalignments
- Navigating Challenging Conversations
Stakeholder Management
With more stakeholders involved, field sales reps rely on effective stakeholder management. To do this, they need to drive stakeholder engagement and expand presence across the organization. These actions create impactful strategic account outcomes. Specific selling behaviors underpin this capability, including:
- Accessing Power
- Engaging Executive Decision Makers
- Aligning Stakeholders on Vision
- Analyzing Stakeholders

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Learn MoreOur Approach to Field and Outside Sales Training
Richardson's Accelerate Sales Performance System brings these capabilities and behaviors to life. The selling behaviors are mapped to modular, high-impact digital learning assets. With so much time spent out of the office, field/outside sales professionals require flexible, digital learning.
Mobile-optimized tools afford the option of training on the go without having to step off the field. Mobile learning leverages the power of recency. Users can take skills learned just moments ago and immediately apply them to real-world selling interactions. Mobile learning is especially effective in selling scenarios requiring a team of field sales professionals.
This flexible training engagement ensures that skills become uniform throughout the field sales team. Synchronicity is critical for teams that need to be cohesive in front of the customer.
Developing these skills often requires some classroom training as well. Though field sales professionals want to limit their time out-of-market, there are a few learning techniques that are best achieved with instructor-led training, namely, role-play exercises. This approach gets learners comfortable with being uncomfortable. It pushes them outside their comfort zone so that when faced with the pressures of a high-stake sale they know how to perform.
Want to learn how Richardson Sales Performance can help your team achieve outside sales success? Contact us to speak with a sales expert today.

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