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Sales Training Techniques for the Modern Manager

Daniel WeissLast updated on September 1, 2023
11 min

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Selling is a paradoxical profession. It’s always changing but it’s also staying the same.

For managers, that means balancing sales training techniques to promote both time-tested methods and promising new approaches.

Sales Persuasion Guide

This guide will cover the strategies, tips, and structures you’ll need to keep your full sales team engaged, prepared, and poised to win deals.

Tips for training new sales reps

Before we get into specifics, it’s important to acknowledge the different ways sales training can be structured. Old or new, all these methods are smart ways to train your sales department’s newcomers.

What are the best ways to train new sales reps?

In-house. Sometimes, the best — and definitely the most accessible — sources of knowledge come from within your own sales team. These in-house training sessions can take many forms. The most obvious is when the sales manager or department leader presents training focused on team best practices.

But also, you shouldn’t let your individual contributors’ talents go unnoticed. If sales managers observe one employee excelling in a defined area, why not encourage those individuals to share their observations in a formal setting? (ex. Samantha will be presenting “How to Scan Linkedin for Ideal Customer Profiles.”

Hands-on. One proven way to teach your new sales employees about the product they’ll be selling is to have them use it themselves. If you’re selling software, have a company training account set up — someplace where mistakes can be made without consequence.

The sales automation tools your team uses to conduct sales operations also require a breaking-in period with new employees. Novice sales reps should have a “sandbox” experience in these platforms as well, where they can experiment without fear of disturbing active sales deals.

Shadow. Nothing trains new employees quite like watching an experienced sales professional. This approach is more than a “fly on the wall” strategy. During breaks in the action —after sales calls, in between meetings, during scheduled 1-on-1s, new reps should ask follow up questions based on what they’ve observed.

Mentors. Onboarding and training new employees goes much smoother when each hire has a direct point of contact for questions, concerns, and examples. These mentors should be experienced sales professionals on your team and can be assigned on an individual or pod-based structure, where multiple sales reps report to one main lead.

External Resources. Onboarding and training new sales employees is as much about immersing them in the culture of sales as it is teaching them how your specific team operates. Give all new employees as set sales reading list for their first few months on the job. Maybe even give them a “book report” assignment where they have to list 10 interesting takeaways from each resource.

Sales managers should also recommend blogs and podcasts to help new reps continuously hone their skills. They’re likely to be more engaged in their work (and more successful sellers) when immersed in the right environment.

Quizzes. When important information has been communicated to new sales people, it can be solidified using formal quizzes during the onboarding process. The subject matter of these tests can vary, but good areas to focus on include:

Create a mentor program for your new sales people

Why should you use mentors to help train new sales employees?

New employees will require the most attention from a sales training standpoint. With so many processes, names, and faces to learn, it’s easy to see how they could become overwhelmed. This detracts from the training spirit and hurts the end results.

By assigning a mentor to each new employee, you give them a reference point for questions and guidance. Many parts of your sales training program can be automated, but the mentor-mentee relationship humanizes the beginning of a new role.

Furthermore, consulting with a deskmate if often the fastest feedback loop. Slack is a great way to communicate across teams, but indirect forms of communication can still be isolating for new employees. Assigning mentors within the same team avoids delayed messages and prevents roadblocks during the onboarding process.

How do you choose the best mentors for sales training and onboarding?

Sales mentors need to possess certain characteristics that may not be present across every member of the team. That is to say, your whole sales team should be knowledgeable, persuasive, and welcoming. Sales mentors, however, will be able to communicate culture and best practices effectively; they’ll be inherently good teachers. Sales mentors will be:

Top Performers. Naturally, you’ll want new employees to emulate the best practices and sales strategies of your top performers. Furthermore, these high-achievers will seek knowledge and tips outside of working hours. They’ll listen to sales podcasts and read professional literature to gain insights. If new employees take on the same desire for advancement and sales training, coaching will be much easier.

Articulate. It’s often taken for granted — we assume just because somebody is good at what they do that they’ll naturally be able to communicate their processes and thoughts. However, this isn’t always the case. Good mentors should be able to break down what they do (and most importantly, how they do it) into digestible and measurable steps. Your sales reps don’t need law degrees, but they do need to present a coherent case for your sales system.

Enjoy the Success of Others. The best sales teams are competitive. They see each other succeed, and they want to match performance or do better. So long as sabotage and trickery aren’t in their operating vocabulary, this competition can be healthy and productive.

However, the best sales mentors will want to succeed alongside their colleagues. They should be energized by their students’ success — not nervous, jealous, or threatened. Closing big deals makes them happy, but so does seeing their students succeed.

Patient. Some new sales reps are going to soar instantly, like peregrine falcons on the hunt. Others will need some nudging before they leave the nest. Learning curves vary between employees, and your sales mentors should be able to identify problem areas and work through them without resentment or impatience.

How to match sales mentors with less experienced salespeople

Ideally, there would be no disastrous mentor-mentee matches within your organization. So long as you hire amicable individuals and everyone goes through the same onboarding process, there won’t be any incompatible-personality-type issues.

When a structure is already in place, your sales team is far more likely to buy into the mentor system. You can try to match new employees with more experienced ones based on personality, but this subjective system could be seen as unfair or biased.

Another possible mentor-structure is some type of pod system, whereby new sales hires report directly to a team leader. These leaders can be either account executives, or more experienced development reps, depending on your current sales team structure.

This sale mentor system has three big advantages:

1. It gives new hires direct access to more experienced sales reps during their onboarding and first months on the job.

2. It fosters a sense of both community and competition amongst your sales team. When both individual and team performance are rewarded, sales reps will be encouraged to go out of their ways to help each other out.

3. It gives lower-level sales employees a goal to pursue. Without a clear promotion structure to aim for, energy and morale can quickly slide in the wrong direction. If sales are successful and the team grows, reps will have more chances to move into these positions.

Each individual contributor can be rewarded according to quota attainment, but the teams can also compete in internal sales competitions that incentivize overall team success.

Pod leaders can meet with team members on a regular basis that encourages candid discussions of sales performance and constructive criticism for the immediate future.

Ongoing sales training and encouragement

Sales training isn’t a single event. If your training regimen ends just after employee onboarding, your squad will struggle to stay on top of industry trends. What’s more, performing the same tasks repeatedly with no variation or progress could lead to burnout. This is why training has to be an ongoing objective for your sales team.

What are the best ways to conduct ongoing sales training?

Sales Events. Local, regional, or national conferences are a great learning resource for sales reps. A lot of these selling events focus on tactics, motivation, new sales tools, and secrets for success. Examples of popular conferences include, RainMaker, and SaaStr, but there are many more high-quality sales conferences.

Local events are also a reliable way to stay up-to-date on sales trends, as well as a way of meeting your peers from other companies. These professional relationships are an experienced sales professional’s greatest resource, in terms of selling opportunities and industry knowledge.

Teach to Learn. A lot of times, the best way to solidify learning is to teach it to others. In order to cover a subject fully —and prepare for potential questions from students, the teacher must fully dive into the content.

For experienced sales reps, they can be assigned a specific subject area from within the business to teach when onboarding new employees. This subject can rotate quarterly between representatives (and all your company’s employees, in fact) and helps keep everyone aware of what’s relevant and changing with the product and business.

Outside Experts. These don’t have to be professional motivational speakers. While everyone loves leaving a presentation feeling like they can tackle the world, the practical value of these pep-talks varies widely. Cultures tend to assimilate, and bringing in outside knowledge can help bring new ideas and best practices into your core sales structure.

Speakers don’t need to be industry all-stars. Draw from your own network of sales managers and top performers. Presentations can be as simple as describing another company’s sales process. What do they do for sales contests? How do they divide their workload? Inspiration can come from anywhere, and a diversity of viewpoints will help this process.

Keeping your sales team motivated

Promotions. Your sales team should be structured in a way that allows for upward mobility. From sales development rep to account executive, but also from junior to senior SDR. Non-title promotions could also take the form of incremental pay increases. The important thing is to let your sales reps know their hard work and achievements will be acknowledged appropriately.

Contests. Sales professionals are competitive by nature. Internal contests provide sales reps with a short term goal which compliments their long term ones (ex. raises, promotions, etc.).

Even better is when these contests promote camaraderie across your team. Tip: Start by creating small groups pairing experienced and new sales professionals. Give each team member an individual target, as well as shared goal. The winner is the team that generates the most qualified leads in a month, and the reward should be something worthy that even promotes sales productivity. (ex. Each member gets a $100 gift card to a local coffee shop.)

Fair Compensation. Sales, when you get down to it, is about money. If your team doesn’t feel they’re being compensated fairly, you’ll have a hard time convincing them to stay with the organization — let alone do their best work.

Fair sales commission will vary according to location, industry, and deal dynamics. To get a good idea of sales industry standards, you can do online salary research, but the best way is to reach out to your close industry contacts (preferably at successful sales-oriented companies) and get a candid idea of how they structure their pay models.

Team Offsites and Outings. Sometimes, a change of scenery will helps sales reps regain momentum. These outings can take educational or celebratory forms, including:

  • A trip to a local sales meetup or networking event

  • A team dinner following a strong performance

  • A training hosted at a cool or unconventional location

Check in with your sales reps

Every sales training strategy starts long before your team is sitting in a room together. To organize and plan an effective training schedule, sales managers need to keep their ears to the ground and find out which aspects of their approach could be improved.

How do you maintain good communication with your sales reps?

A culture of transparency. Pain points and professional weaknesses should be the focus of your sales training, but if your workplace culture antagonizes poor performance, your reps won’t readily admit their flaws. Transparency, in this sense, means your employees aren’t afraid to tell you when they’re struggling to meet quota or perform expected tasks.

This philosophy, of course, starts at the top. Managers who acknowledge the difficulties of the profession and assist, rather than punish, when objectives are not met will receive more constructive feedback — and ultimately better results.

Conduct short, recurring meetings. Transparency can’t be obtained if you’re not talking with your sales reps regularly — reviewing their potential deals and identifying blockers.

It’s important to show your team you’re available and willing to speak, but once the organization grows too large, it’s unfeasible to meet with every individual employee under your guidance.

If your team is structured into smaller pods of representatives, you only need to meet with the pod leader each week. Furthermore, these meetings should be concise, lasting no more than 20-30 minutes. The schedule and agenda are pre-determined, and team leads should come prepared to present relevant information.

If you’re presented with an issue that deserves more time, be sure to schedule an ad hoc meeting for a longer time-period.

To reiterate, sales is a profession based on adaptation — both in-the-moment and in the long-term. The best “technique” sales managers can adopt is to create an environment where teammates want to help one another succeed, and everyone feels comfortable sharing their thoughts with the leadership. When those two main pillars are met, technology-specific training and common best practices become much easier to teach. Investing time in training and coaching will improve your sales performance and help your team achieve its goals.

Published on September 1, 2023.

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