11 ways you can coach your sales team to victory

Posted May 25, 2023

By Serena Miller

Editor, Sales Best Practices at Outreach

An influential coach can make a significant difference in an athlete’s life. They have the power to mold players’ mindsets, fine-tune their skills, and motivate them to push themselves. When an athlete succeeds they often attribute at least part of their success to their coach.

A strong sales coach can be equally instrumental in their sellers’ success. Their guidance, support, knowledge, and approval supports salespeople through each stage of the sales process. So why do many sales managers struggle to sufficiently coach their teams.

Effective sales coaching requires meaningful strategies grounded in the most essential—and challenging—parts of being a seller. Here, we’ll explore 11 tips for building your sales teams and championing them to victory. 

A manager and sales rep sit together, taking notes while discussing performance.

11 effective sales coaching tips

A team is only as successful as its weakest player, and sales teams are no exception. To ensure every seller is on top of their game, managers should implement these vital best practices: 

1. Foster trust through authenticity 

Salespeople, by nature, are usually intuitive about people. They are likely to notice if their sales manager has a disingenuous attitude. Some salespeople will distrust their manager’s motives or disregard their feedback. Therefore, managers must project authentic enthusiasm to their teams. Foster an environment of trust and confidence, which will inspire sellers to trust their constructive criticism and advice. 

Sales managers should practice effective listening and build honest, transparent relationships with their reps. Encourage sellers to speak openly during one-on-one meetings and ask how they prefer to be coached. Keep in mind, trust will take some time to build, so managers should build these relationships one step at a time. 

2. Promote self-evaluation

When a seller lands a deal—or screws it up royally—chances are they know exactly what went right or wrong. If the deal went well, they may have invested a little extra time in customer feedback, bonded with that key decision-maker socially, and took a customer-centric approach. If the seller failed, they may have taken too long to follow up after the initial sales pitch or flubbed the negotiation.

Excellent sales managers give their reps space to evaluate their own successes or shortcomings before making any critiques. This empowers sellers to reflect on their own performance and dig deep into what contributed to the outcome. It also demonstrates that their manager trusts their judgment and their ability to learn from their mistakes.

Managers should prompt sellers to conduct a self-evaluation that they’ll discuss during their next one-on-one. This can be an informal, open-ended exercise or a detailed assessment that includes specific questions. Either way, explore what reps believe they handle well, what they’re not, and where they could use help. 

3. Work on one area of improvement at a time

Sales can be overwhelming. Administrative burdens, lengthy meetings, regular travel, and myriad other tasks can make sellers feel like their days slip through their fingers. Some estimate that sales reps only spend about 23% of their time actually selling.  

Inundating your team with ten different coaching exercises will only hinder their productivity and amp up their frustration. Instead, managers should prioritize one area of improvement at a time. Take a close look at team members’ leading indicators (e.g., effort) and lagging indicators (e.g., execution). 

For example, a seller hasn’t created a high-quality pipeline this quarter. While their manager might recognize that this is a lagging indicator that something’s wrong, when they probe they find that the leading indicator is that the seller qualifies every single lead after the first meeting—even when they’re not likely to convert. Armed with this knowledge, instead of  encouraging them to make more cold calls, book more meetings, and send more emails, the manager instructs the seller to qualify deals throughout the sales cycle. This hyper-focused coaching helps the seller build a healthier pipeline moving forward.  

4. Promote accountability through feedback
and challenges

In the current selling climate, managers must help their reps develop the expertise to meet or exceed growing customer expectations

Effective managers use the coaching process as an opportunity to transform sellers’ past mistakes into future wins by cultivating accountability. They’re transparent about the fact that no one is perfect and that true success stems from one’s willingness to take responsibility for what went wrong. They celebrate sellers who recognize their own weaknesses, and avoid pointing fingers when a deal falls through. 

Regular feedback, both formal and informal, helps sellers practice accepting fault and targeted self-improvement. Managers should always include a healthy mix of both positive and negative feedback and communicate both with kindness. They should also offer clear coaching on strategies to remediate any issues and acknowledge when their rep’s performance improves.

5. Provide additional professional development opportunities

According to Outreach’s 2020 report on Recruiting and Retaining Millennials for Your Sales Teams, 75% of millennials believe that changing jobs every couple of years benefits their career development. Sales is notorious for high rep turnover rates, especially B2B sales. Organizations must find ways to enrich employees’ career development to keep their best performers. Rather than limiting their best reps’ growth by only providing their own coaching, managers should encourage sellers to expand their horizons and pursue other development initiatives. Empower sellers by offering additional development opportunities like industry conferences, seminars, workshops, classes, webinars, and networking events. 

Sales reps need their managers and the business as a whole to demonstrate an investment in more than the corporate bottom line. Strengthen your relationship with your sales reps through your commitment to the success of each team member. Inspire them to reciprocate their loyalty by sticking around. 

6. Motivate and celebrate your team members 

According to a recent survey by Achievers, 44% of employees say they will switch jobs if they don’t receive adequate recognition. Coaching isn’t just about course-correcting sub-par behavior and performance; it’s also about applauding hard work and acknowledging wins. 

It's also crucial to recognize a successful rep publicly to motivate and inspire their colleagues. Managers can celebrate team members during internal sales meetings, implement digital or physical recognition boards, host team dinners, or schedule monthly appreciation days. Regardless of the forum, managers should call out the specific actions sellers took to achieve their wins. That way, a moment of recognition can also become an opportunity for sharing best practices among the entire sales team.

7. Allow open communication in regular meetings 

A little friendly competition can sometimes get sellers’ engines revved, but a lack of collaboration, peer-to-peer support, and knowledge-sharing can turn your team dynamic into an environment of combative rivalry. Don’t waste any chances to empower team members to learn from one another and grow their skill sets together.

Since sellers are the ones who are knee-deep in all things sales, inspire them to lend each other a helping hand or offer advice when a coworker is struggling. Encourage open, honest communication among team members during regular meetings. Create an attitude of collaboration by establishing and recognizing mentors within your team. Promote knowledge-sharing and incentivize team problem-solving. 

8. Collect and use sales data in your coaching efforts

Any one manager might have five reps with 20 opportunities each. That manager has to monitor 100 deals at any one time—each with varying sizes, close dates, customer preferences, and more—on top of other daily tasks. Tracking all this manually can waste precious hours on extra deal inspection meetings and cobbling together disparate data sources into spreadsheets. Plus, the resulting information is unlikely to be up-to-date. Therefore the sales team might miss key signals that a deal is coming apart. 

It is crucial to capture and use real-time data for coaching. Technology takes an integrated approach, offering the team complete visibility into what’s going on in every deal. That way, managers always have relevant, timely information and can intervene in problematic negotiations before they fall apart

With the right technology, like tools that offer conversation intelligence, managers can quickly and easily understand what’s happening on calls and in meetings. Some platforms offer total transparency, signaling the health of the deal so managers can assess pipeline health and determine which deals their reps should prioritize. These tools enable teams to capture AI-driven meeting action items, leverage collective intelligence with comprehensive search and notification functions, and seamlessly coach at-scale by sharing best practices and snippets—all while remaining productive and efficient. 

9. Individualize training and goals for each
team member 

Not every rep learns the same way. Some sellers require more hands-on coaching, while others prefer to work autonomously with the support of some timely hits and guidance. Certain team members thrive on constructive criticism, but others require a gentler approach to feedback. 

Avoid creating frustrated, resentful, or checked-out reps by adjusting each coaching element to the individual.

Tailor training methods and goals for each team member. Schedule one-on-one meetings with each rep, and encourage them to discuss how they learn best. After listening closely, structure each individual’s coaching plans and goals based on their work style, personality, and preferred cadence of feedback delivery.

10. Create a consistent and structured process

Your tools, processes, workflows, and techniques shouldn’t be set in stone. Even if you have a consistent style, not every rep is going to know your techniques thoroughly. New reps need onboarding, seasoned reps need refreshers, and everyone needs updating when something changes. But managers shouldn’t treat these interactions as one-off, isolated situations, because that creates inconsistencies, inefficiencies, and—quite frankly—reps who just don’t care. 

Always prioritize documentation to ensure coaching efforts (and, really, every element of the sales process) are scalable, consistent, and fixable. n. Great documentation helps both managers and sellers learn on the job, and empowers sellers to quickly find answers to their most pressing questions. Team members are always on the same page and can continuously learn from best practices that are grounded in proven success.

11. Focus on your team's wellbeing 

Sellers need to be mentally, emotionally, and physically healthy to perform effectively at work. If they’re sleep deprived, malnourished, or overstimulated, they’re at risk for the premature burnout that leads to turnover. Plus, they’re simply not able to soak up any nuggets of wisdom or words of affirmation because they’re not fully present. 

To make sure sellers get the most out of their coaching efforts, prioritize reps’ well-being. Encourage reps to focus on their nutrition, sleep, and exercise, and persuade them to take a break when they need it. Work with organizational leaders to implement health and wellness stipends for employees, make sure there are always nutritious snacks around the office, and connect team members with additional help when needed. 

Remember: healthy sellers are happy sellers, and happy sellers are engaged, productive, and successful. Create a work environment that stresses the importance of a balanced lifestyle instead of incentivizing unhealthy, compulsive work habits, and reap the benefits of a workforce that is able to learn and grow in their jobs.

Streamline your sales coaching process with Outreach 

Quality sales coaching goes far beyond observation and feedback. Effective sales managers leverage coaching strategies, which bolster their ability to push sellers closer to their objectives. Sophisticated tools and processes can enhance coaching—all for a more successful sales team, a better customer experience, and improved win rates.

Outreach’s Sales Execution Platform gives managers access to sales calls they can’t attend in person, allowing them to spot winning strategies, new objections, and competitive threats. Managers can use these observations to guide their sellers to work more efficiently, creating a team that will close more deals and consistently reach their quotas.  
Want to learn more about how to create pipeline that will actually close? Get the complete guide for sales leaders. Or, request a consultation to learn more about Outreach.


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