September 6, 2021

Sales Coaching Guide: Tips to Boost Your Team’s Win Rates
Sales Coaching Guide: Tips to Boost Your Team’s Win Rates

Table of Contents

When we think about what a world-class coach looks like, it’s easy to picture an athletic coach with a clipboard shouting instructions to players on the field. While sales coaching can take a lot of inspiration and lessons from the great coaches of sports teams, we must find the techniques that work best for sales teams.

In this article, we discuss the importance of coaching in the context of a sales team and feature tips to find the right coaching protocol for your team.

What is Sales Coaching?  

Sales coaching is the process of building, teaching, and refining the skills and techniques of a sales rep or team through the active involvement of a manager, leader, or dedicated sales coach. Sales coaching is not the same as the rep onboarding and ramp period when most of the actual sales training will occur. Instead, sales coaching is an ongoing process towards continuous improvement, even after the rep is fully ramped. The modern sales coach, much like a modern athletic coach, is heavily reliant on data to guide their strategies, such as identifying the team’s strengths and weaknesses, understanding when to pivot a sales play, and more.

Why Coaching Sales Reps is Beneficial

Sales coaching is beneficial for a number of reasons, the most obvious being the boost in performance from the reps being coached. Just like in sports, a sales coach is typically a former expert practitioner or top performer in their field, which gives them the unique perspective to see things through the lens of their experiences and expertise. 

Working with a coach can also help reps become more accountable to their sales metrics because, in the process of discussing a shift in strategy or new strategy entirely, they are more likely to follow through with it if directly tied to their KPI. 

1. Increases Win Rate

If we had to choose only one indicator (besides top-line revenue) of how a sales rep is performing, we believe win rate would be that metric. A coach might not always be able to increase the number of total opportunities, but a good sales coach will certainly be tracking rep win rate as their KPI, which is also the case in sports coaching. 

Coaches help reps focus on the mechanics of the sales process — the things that can be done repeatedly and consistently to get predictable results — which directly correlates with win rate. The sales coach can explain why a tactic works and give examples of how it’s worked in the past.

2. Strengthens Sales Team Culture

A sales coach can strengthen and reinforce the company’s culture and adherence to values. Since the rep faces a regular feedback loop about how their actions measure up within the context of the broader sales team, they can continually iterate on their process which propagates throughout the sales force. 

Reps will mirror what their colleagues or sales coaches do, not what is discussed or written as the SOP. Perhaps your sales team is highly competitive which supports a win-at-all-costs approach, leading to a toxic sales culture that is difficult to change once in place. If your team is collaborative and additive, coaching on culture will be as easy as looking in the mirror.  

3. Reduces Rep Ramp and Churn Rate 

Establishing a sales coaching culture for new hires is essential to getting them onboarded and productive quickly. Some organizations expect absolute autonomy as a rep gets ramped, which might work well for autodidacts (the self-taught), but most people learn more effectively when actively taught. 

There’s an old Chinese proverb that was later adapted by Ben Franklin and now perfectly supports the power of dynamic sales coaching, “Tell me and I'll forget; show me and I may remember; involve me and I'll understand.” 

Best Practices of World-Class Sales Coaching

Sales coaching is like an iceberg — 90% of it lives under the surface, behind the scenes … you get it. Although a coach is still vital on game day (throughout the sales process), it’s important to understand that the coach’s job is more about proactively setting the team up to perform under pressure.  


One of the most important aspects of sales coaching is preparation. As a coach, you must be able to assess each team member’s strengths and weaknesses and understand how to leverage those strengths while improving on weak areas. 

This could mean dedicating some time each day, week, or month to review sales activity data, communication, results, and more to bring actionable insights to your coaching sessions. Alternatively, you could utilize a tool like to surface those insights for you, while you focus on implementing and coaching on the sales playbook. 

Focus on Fundamentals

Many of the best coaches in the world are known for — besides their win rates — their meticulous focus on fundamentals. John Wooden, the legendary UCLA coach, would even dedicate time to methodically teach players how to properly put socks on. At first, you might question coach Wooden’s sanity or how socks can influence basketball games, but socks that are put on incorrectly can cause blisters, and blisters can cost games. 

When coaching your sales reps, think about the small things that can have negative impacts on performance, and coach your team towards a solution. Communication cadence and number of meetings, for example, are still vitally important in sales, so be sure you are coaching reps on how often to follow up and when to push for more meetings.


Practice makes processes permanent and discipline makes practice permanent. Sales coaching is an ongoing process, not a one-time thing, and must be practiced on a regular basis. Having discipline in the practice of coaching is in itself a lesson to be taught to reps.

Tom Coughlin, the former coach for the NY Giants, famously fined his players for being on time to practice, because he believed that being five minutes early is being disciplined while being just on time is disrespectful. 

As you coach your team, be regimented but also be conscious of your rep’s time and schedule. If you establish a daily, weekly, bi-weekly, or other cadence of sales coaching, keep it consistent and keep it contained to the allotted time. 

Sales Coaching Tips and Techniques of Winning Teams

Below are some of the common themes and trends we see coming out of the top sales organizations. These tips are not specific to any industry or organization but should be applicable to your sales team. 

1. Rely on Activity Data 

Similar to sales forecasting, sales coaching was traditionally reliant on the coach’s gut feeling. Using anecdotal evidence from one person’s perspective can get you only so far, which is why the modern sales coach leans on accurate and up-to-date activity data to make plays and recommendations.

Katie Sowers, the 49ers offensive assistant coach, talks about how tracking technology is used to monitor activity data which helps coaches make data-driven decisions that impact actual performance. 

When a strategy needs to be pivoted based on real-time feedback, this activity data can help the sales coach call an audible. 

For example, you’ve long been advocating for reps to leverage multi-threading to incorporate more personas and departments, increasing buy-in from the customer’s company. Now, you show data on reps who have multi-threaded deals and how it increases their win rate.  

2. Use a Sales Playbook

Having a sales playbook simply means being prepared for any and all scenarios that your sales team could encounter. It’s remarkable how similar the sales process can become even in industries, categories, or roles that require a great deal of situational awareness to close deals. 

Even if your organization has a handful of reps (or even just one) a sales playbook can help perfect the sales cycle and win more deals. Even having a well-thought-out elevator pitch for your product or service that can be rehearsed, refined, and recited naturally will help project confidence during the initial sales call. 

3. Actively Coach On KPIs

Active or Hands-on coaching doesn’t mean you need to physically hold your rep’s hand through the sale, but being available in real-time to brainstorm strategy and make helpful suggestions can be hugely beneficial for driving results. 

There’s a common process in software development of pairing two programmers together to work through a problem, reinforcing the old saying, “Two heads are better than one.” A sales coach paired with a rep can really focus on moving the needle towards the individual- and company-wide KPIs. 

For example, if your rep has a goal this quarter to increase their win rate by 5%, actively coaching on the revelation uncovered earlier that multi-threading has been shown to increase win rate and reviewing upcoming calendars to suggest strategies for including more stakeholders can help the rep achieve their goal. 

4. Coach Everyone 

We say it pretty regularly but it’s worth bringing up again, the goal of any sales coaching strategy is not to close the gap between top and bottom performers, it’s to move the entire range of performance up. This means you shouldn’t exclusively coach the underperforming reps and leave the top performers to their own devices. 

Not only will coaching top performers help you more effectively coach the bottom performers, but it’s also possible (and probable) the best of the best can get even better. 

Coach everyone, especially your top players. 

5. Be Proactive, Not Reactive

Don’t wait until the game is over to coach on how to improve — if you see a problem, offer solutions in real-time. This is the power of leading indicators, those metrics that are causal to a future outcome. Symptoms are lagging indicators, condition and conduct are leading indicators. 

If it means having weekly or even daily standup meetings with reps to understand the condition of their deals and how they are conducting themselves, so be it. 

Be a leader, not a laggard. 

Sales Coaching in Practice

Consider a coach that has a full data analysis of each player at their fingertips during practice. This coach can effectively predict the scoreboard and what the ultimate outcome of the game will be. 

Sales coaching should be no different. Having predictive AI at your fingertips with can help you win more deals and achieve more predictable revenue. Not only can automate and aggregate rep activity data, but can even surface areas of opportunity for coaching.

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