15 sales coaching tips for high-performing teams

Posted May 22, 2024

headshot of blog author, woman smiling

By Serena Miller

Editor, Sales Best Practices at Outreach

In sales, like in sports, coaching is the difference-maker. Top performers rarely succeed alone. But for sales leaders, the challenge isn't just finding great coaching techniques – it's figuring out how to replicate them across your entire team. 

How do you scale what works, eliminate what doesn't, and ensure every rep sells like your best? The answer lies in creating a culture of continuous improvement, fueled by data-driven coaching, streamlined workflows, and real-time support.

Here, we’ll explore sales coaching in depth — what it is and what makes it successful — as we share 15 best practices for building your sales teams and championing them to sales success.

Gif of 15 sales coaching tips

What is sales coaching, and what makes it successful?

An effective coaching program is a sales manager's secret weapon for unlocking team performance and driving revenue growth. It empowers managers to go beyond simply setting goals and tracking numbers. Instead, they gain valuable insights into individual rep strengths and weaknesses, so they can provide targeted guidance and support. Sales coaching tools play a role here too, making it easier to detect areas of improvement and offer specific, helpful support. 

With the right coaching, reps become more confident, more effective, and they win faster and more often. What’s more, their success becomes your success. As your high-performing team consistently exceeds targets and drives revenue growth, your reputation as a results-oriented leader grows too. This opens doors to new opportunities, greater responsibilities, and accelerated career advancement.

Why is sales coaching important?

Successful sales coaches empower their teams to do their best work, grow in their careers, and stay motivated. As a result, managers focus on what each team member does best and where they need help, making it easier to meet sales goals. It also builds a culture of ongoing learning and growth, which can improve overall employee engagement and retention. 

How do you coach a struggling sales rep?

When a sales rep is underperforming, not only do their numbers suffer — it can create a ripple effect that impacts the whole team's productivity. As a manager, your challenge is clear: identify the issues, correct the course, and do it quickly.

To coach a struggling rep, ditch the guesswork and get granular. Dive into their activity data for a clear picture of what's really happening: Who are they targeting? What messaging are they using? How persistent are they with follow-up? Compare their activity to top performers to pinpoint where they're falling short. Don’t worry: We’ll show you exactly how we do it at Outreach later on in this article.

What are examples of sales coaching techniques?

Establishing an effective sales coaching program is often difficult because there’s no singular way to go about it. There are numerous models, techniques, and tactics to choose from, each intended to move the sales needle in a different way.

It’s individualized to your team and even down to your reps. But generally, when you think about what sales coaching looks like, it can be broken down into two categories: strategic and tactical.

Image graphic showcasing the difference between strategic sales coaching vs tactical sales coaching tactics.

Strategic sales coaching

This type of coaching looks at higher-level concepts that help sellers have the knowledge and skills to contextualize what’s happening in their sales process to get the desired result.

At an organizational level, this can look like:

  • Sharing examples of best-in-class calls from across the team
  • Diving into trends around competitive threads, mentions of new offerings, and budget discussions from across all meetings

At an even higher level, this includes:

  • Sharing market intelligence and discussing overall shifts in the sales climate
  • Providing coaching on social selling and how it fits into overall strategy

Tactical sales coaching

Sales coaching empowers sellers to take the right actions at the right time. And, if something happens that puts a deal at risk, they have the skills and tools to diagnose the problem. This is where tactical sales coaching comes in. As opposed to strategic coaching taking a high-level approach to sales strategy, tactical dives into the nitty-gritty “how-to.” This can look like:

  • 1:1 weekly coaching check-in around activity, tracking to hit quota, specific prospects in the sales process, etc.
  • Reviewing calls to identify what went right (or wrong) in a conversation with a prospect
  • Evaluating a seller’s follow-ups to ensure time-sensitive actions are taken
  • Practicing specific selling techniques in preparation for a buyer meeting
  • Workshopping how to properly use LinkedIn Group for selling

15 effective sales coaching tips for a high-performing team

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.

Graphic image with sales tip 15: Create a feedback-rich environment
Graphic image with sales tip 1: Foster trust through authenticity
Graphic image with sales tip 2: Encourage self evaluation
Graphic image with sales tip 3: Work on one thing at a time
Graphic image with sales tip 4: Model a culture of accountability
Graphic image with sales tip 5: Offer professional development
Graphic image with sales tip 6: Motivate and celebrate your team
Graphic image with sales tip 7: Encourage open communication
Graphic image with sales tip 8: Collect and use your sales data
Graphic image with sales tip 9:  Individualize training and goals
Graphic image with sales tip 10: Create a consistent structured process
Graphic image with sales tip 11: Focus on your teams wellbeing
Sales coaching tip 12: Reverse engineer your best reps success
Graphic image with sales tip 13: Implement real-time coaching with AI
Graphic image with sales tip 14: Help your team share their expertise
Graphic image with sales tip 15: Create a feedback-rich environment
Graphic image with sales tip 1: Foster trust through authenticity

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 loses one), 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 taken 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 strong 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. Model a culture of accountability

Managers must help their reps develop the expertise to meet or exceed growing customer expectations. That's especially true in the current selling climate.

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 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. 

6. Motivate and celebrate your team members 

According to a recent survey, 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

A single 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. 

These are the metrics sales teams *should* be measuring

Tap into the metrics that stand between you and your revenue goals. Get our checklist of basic and advanced KPIs that best-in-class sales organizations use to measure success. Use these slides as the framework to anchor your sales team meetings, training sessions, strategic planning, forecast calls, or executive briefings.

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. Then, 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 will memorize your techniques. 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. That only 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. Great documentation helps managers and sellers learn on the job. And it empowers sellers to quickly find answers to their most pressing questions. Team members are always on the same page and can learn from best practices grounded in proven success.

11. Focus on your team's wellbeing 

Sellers must be mentally, emotionally, and physically healthy to perform effectively at work. If they’re sleep-deprived, malnourished, or overstimulated, they’re at risk for burnout that leads to turnover. Plus, they’re unable 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, focus on reps’ well-being. Encourage reps to focus on their nutrition, sleep, and exercise, and persuade them to take a break 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 can learn and grow in their jobs.

12.  Reverse-engineer your best reps’ success

Help every rep sell like your best rep by identifying and measuring the successful strategies of top performers. By identifying what works, you can guide the rest of your team to adopt these proven practices. Implement data-driven workflows designed to replicate these successful actions across the team for stronger, more predictable outcomes.  

13. Implement real-time coaching with AI tools

Introducing AI assistants like Outreach Kaia into buyer meetings offers on-demand confidence. As topics are mentioned on the call, Kaia automatically captures action items to follow up on. Reps can also see content cards related to key topics mentioned on the call, like pricing details or recommended responses to objections or competitor comparison questions. The impact is real: Outreach’s data indicates that using Kaia during a call moves deals 19% faster and boosts win rates by 41%.

How AEs use AI to follow up with prospects

Taylor Carthum, Commercial AE at Outreach, shows us how she uses AI to send personalized follow-up emails in just a few minutes.

14. Help your team showcase their expertise 

Encourage your team to look beyond their day-to-day sales skills and dive deeper into their professional development. Support them in attending — or better yet, presenting in — webinars, workshops, and conferences. 

Expanding their knowledge and visibility not only makes them better salespeople but also enriches their understanding of the industry and their clients. Our own sellers frequently appear on and present at industry events, speaking engagements, and sales-related podcasts

15. Create a feedback-rich environment

Make feedback a regular part of your team's routine. Whether it's a quick commendation for a job well done or a sit-down to discuss a recent challenge, keeping the lines of communication open is crucial. Ensure your feedback is specific and actionable so your reps know exactly what they can celebrate and what they need to work on.

Where managers go wrong in 1-on-1 meetings

When done well, regular one-on-one meetings between reps and managers not only help reps grow in their careers and hone their skills but also provide managers with coaching opportunities to help their team read their full potential.

How does coaching develop a sales team?

Coaching is all about bringing out the best in each team member, which in turn elevates the entire team’s performance. Here's a look at the key outcomes to focus on and strategies for achieving them:

  • Faster rep ramp time: Get your new hires up to speed on processes, messaging, and products so they start selling with confidence.
  • Stronger deal qualification: When reps are held accountable to qualification best practices and methodologies, they’re less likely to rely on gut feeling when committing deals.
  • More efficient prospecting: Identify activity metrics and tactics that generate qualified pipeline to ensure your team executes the right top-of-funnel activities to hit their goals.
  • Proactive deal inspection: Understand which deals will close and which are at risk, and provide reps with effective and actionable deal support in meetings.
  • Personalized messaging: Ensure the right message is being delivered to the right buyers in the right way and at the right time to keep qualified opportunities moving forward. 
  • Skills development: Identify your team’s strengths and weaknesses and easily share best-in-class examples of what “good” looks like to close any skill gaps on your team. 

How to measure sales coaching effectiveness 

Sales leaders often struggle to track and measure rep performance beyond the volume of activities, meetings, and pipeline coverage. To improve performance, it’s rarely enough to ask reps to just do more of what they’re already doing. Instead, consider how to measure the quality of their activities, conversations, and deals. 

Within Outreach, sales leaders can review daily activity reports to measure team performance by observing how teams engage in emails and calls. For example, our head of business development Angela also looks at sequence performance to understand the sentiment of the responses reps are receiving, especially objections, to give her team specific, actionable feedback on their prospecting strategies.

Managers can also review conversation intelligence data to see how reps are performing live in meetings. Metrics like talk time percentage and monologue length suggest potential areas for coaching — and spotlight reps who are consistently following best practices.

As a senior sales leader, Angela needs to understand how to provide feedback to her team, but she can’t be everywhere at once. Here’s how she uses Outreach to make sure her reps are reaching the right buyers with the right message at the right time.

Common sales coaching challenges and how to overcome them

1. Personalized coaching is difficult to scale 

As teams grow, your approach to coaching and enablement needs to shift, too. Sales teams often fall into one of two categories: some rely too much on personal observations and not enough data, while others lean on data alone without really knowing what their reps are doing. Effective coaching mixes clear goals with timely feedback. It’s important for reps at all stages — whether they’re just starting, chasing leads, managing deals, or growing their skills.

2. Can’t identify or replicate what makes other reps successful

It's tough to clone your best sellers if you're not sure what makes them stand out. There’s a widely accepted idea in sales called the 80/20 rule, where 20% of your team generates 80% of the revenue. Managers may know who is successful but struggle to replicate that success across the team. But we shouldn’t be satisfied with the status quo, especially when teams are struggling to hit their goals. 

The key lies in pinpointing the exact actions these top-performing reps take. It's equally important for managers to understand the individual strengths and weaknesses of each team member to provide tailored guidance that really resonates.

3. Limited time and attention

When managers have to split their attention between multiple reps, deal reviews and status updates can easily sidetrack any one-on-one coaching time. 

This is where technology can help save significant time. Instead of having to ask for updates and feedback, managers should be able to open up their rep’s active deals, see next steps, current blockers, and recent engagement.

This helps managers understand the big picture and drill down into specific opportunities to identify where and how reps can improve. 

The saved view Outreach sales leaders use to help their teams crush quota

Outreach’s engagement data helps you understand the quality of your engagements, not just the quantity. These insights are indispensable to sales managers; they make it much easier to improve deal performance and identify timely coaching opportunities.

Tools and technology for modern sales coaching

Talent management is the make-or-break factor for successful revenue organizations. From ramping new reps to continuous skills development, it’s exceedingly difficult to decipher what’s right and determine how to scale those best practices across your entire team. 

That’s where AI comes into play. These tools and features help managers get immediate visibility into what’s working well or what needs improvement across their teams — and what specific feedback they can offer their reps to improve performance. 

As a sales manager, Sydney is focused on the most effective ways to coach and improve her reps' skills. Here’s how she uses Outreach’s conversational AI to get the data and insights she needs to give her team actionable feedback.

Today’s sales managers have more visibility into the specific actions that reps can take to be successful, which also means that reps are facing a new level of accountability. 

In his article, “It’s Time To Track Sellers Like Athletes,” Seth Marrs, Principal Analyst at Forrester, likens the new reality to the way that professional athletes track and optimize every aspect of their performance: “Sales teams are not used to having all their interactions tracked and analyzed, but neither were the athletes they are so often compared to. Nowadays, there is very little that isn’t tracked on a playing field. Insights from tracking are taking athlete performance to new heights. Today’s athletes are bigger, stronger, and faster. The same performance improvement is going to happen in sales.ⁱ”

How to build a sales coaching culture

It’s no secret that sales team culture can make or break performance, team morale, and overall company success. Plenty of leaders talk the talk, but low rep attainment and high rep attrition within an organization points to a less sunny reality: sales has gotten progressively harder in the last couple of years, many reps are feeling burn-out, and team culture has stagnated. The good news is that it is possible to improve, but it takes deliberate, consistent effort. 

When so much of the culture conversation gets weighed down with perks, it’s easy to forget that the foundation of any culture will always be making sure your team has what they actually need to do their jobs — and that includes the right knowledge, training, and coaching.
Kevin Bognar, SVP of Sales at Outreach

Create actionable onboarding and training programs with clear and deliberate goals to support and guide your sellers. Communicate your expectations, run predictable and defined meetings that measure progress, problem-solve issues, and reward and share great work. 

While sales leaders are tasked with taking the lead and setting the example, it’s not all on them. Consider the sellers within your team who consistently crush it and reverse-engineer their successes. In other words, what are they doing that other sellers are not? 

Top sellers are more important than ever, as they are the model that companies will use to improve the performance of the entire sales team. This means that the best-performing sellers will need to evolve, as middle-level sellers constantly improve based on what they learn from those at the top.ⁱ
Seth Marrs, Principal Analyst at Forrester

Successful sales coaching implementations

Coaching at the enterprise level presents its own unique challenges, but with the right technology implementation and enablement, teams can drive significant improvements. Take this recent success story from Cisco

“We didn't have a lot of global consistency. With a team of over 1200 sellers, there were a lot of pockets of different processes and different habits,” said Donna Sanborn, Senior Leader, Global Sales Effectiveness. 

Outreach served as the foundation for a uniform, programmatic sales process across the organization. According to Donna, “Our sellers can evaluate their entire territory, create plans, and then immediately take action within Outreach.” Today, there’s a clear blueprint for teams to identify and repeat their most successful sales motions. 

The results speak volumes: Sellers using Outreach were notably more active — 85% more than non-adopters — leading to a 9% increase in pipeline and a 5% higher closing rate. Deals influenced by Outreach also closed 50% faster

Outreach is helping us deliver the science while we give our sales team the time and space to really master the art.
Donna Sanborn, Senior Leader, Global Sales Effectiveness

Improve the way you coach your sellers with Outreach 

Quality sales coaching goes far beyond observation and feedback. Effective sales managers leverage coaching strategies that push sellers closer to their objectives. This results in an overall more successful sales team, a better customer experience, and improved win rates.

Outreach’s Sales Execution Platform gives managers more visibility — and actionable data — to scale what works and change what doesn't through targeted coaching, best practice workflows, and real-time support.

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Additional sales coaching FAQs

Can sales coaching be effective for remote teams?

Yes, sales coaching can still be effective for remote teams. Consider the tools and processes your team uses to stay connected to communicate expectations, offer support, and monitor performance. 

What is the difference between sales coaching and sales training?

Sales training and coaching are two unique concepts. Training is structured and imparts fundamental skills to all participants equally. Coaching is personalized and ongoing, focusing on individual development and strategic advice tailored to each rep's needs.

How often should you offer coaching sessions?

Sales coaching sessions should ideally be weekly or bi-weekly so managers can keep pace with their team's needs and provide timely feedback. Consider making coaching a regular part of team meetings or rep 1-on-1s. The frequency of your coaching will vary based on a rep’s experience and performance.

How do you tailor sales coaching for different sales roles or levels?

Coaching should be customized to the specific challenges and goals of each sales role and level. Beginners might focus on basic skills, while experienced reps might concentrate on strategic insights and leadership development. A data-driven approach ensures coaching is specific, relevant, and effective for reps at every level.

ⁱ Seth Marrs Principal Analyst, “It’s Time To Track Sellers Like Athletes,” Forrester Blog, Jan 16, 2023


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