“For the last five years, sales coaching has had the greatest impact on win rates and quota attainment.” – CSO Insights Study
You read that right; sales coaching is the number one way to improve your sales win rates and quota attainment.
But much has changed in the past few years.
The speed of technological and sociological advances is ever-increasing and iterating.
From iPhones to artificial intelligence (AI), the coaching methods available to remote sales coaches are racing into the future.
In this comprehensive guide we’ll cover:
- How to coach individuals and teams remotely
- Types of sales coaching
- How to choose the right technologies for remote coaching
- Advanced remote coaching tips
- Much more!
So if you want to improve remote coaching for your teams and win more deals, you’ll love this guide.
Let’s get started.
Table of Contents.
- Remote sales coaching defined
- Why remote coaching is important for sales
- The key tools in the remote coaching arsenal
- Remote sales coaching tactics
- How to coach individuals remotely
- Remote sales coaching through role-playing
- Thoughts and insights from around the globe
Remote sales coaching is a process that provides individualized feedback and support that enables all sellers to achieve their selling goals.
This process is accomplished by identifying limiting behaviors and correcting them through repeated feedback/practice loops – remotely.
Remotely – meaning from a different location!
Thus the coach has the disadvantage of not being in close contact with the person being coached, making direct observation much more difficult than in person.
With that said, sales coaches need to take advantage of a wide variety of tools and techniques to make sure they can provide the right coaching for individual sellers and teams.
Despite this limitation, a huge variety of sales skills can be coached remotely with proper planning and strategies in place.
We’ve met sales coaches that are coaching as many as 100 reps per month sometimes across oceans in multiple languages. So it can be done!
A word of caution…
There’s a dark side to this as well.
The majority of research shows a disconnect between sellers and sales managers in terms of the effectiveness of current sales coaching.
Not surprisingly, sales managers consider themselves far better coaches than the sellers they are coaching do.
One can imagine that this effect is amplified when the coach can’t actually see what the seller is doing.
Remote Sales Coaching is not the same as Remote Sales Training
Sales coaching is not the same thing as sales training. However, these two concepts are often used interchangeably leading to lots of confusion.
Sales training provides education to sellers on products, skills, methodologies to help sellers succeed in difficult sales situations. It typically occurs in a team-based manner, so that everyone is on the same page.
Remote sales training might include:
- Knowledge transfer on things such as sales processes, products, and personas.
- Measurement tools like quizzes to validate team understanding.
- Broad team-based skills like objection handling, problem identification, and listening skills.
- Technical skills like pitching and using CRM.
Want to improve your Sales Training? Read about The 7 Most Important Sales Training Techniques.
On the other hand, sales coaching is working with individuals one-on-one to help them correct weaknesses in their sales game and improve their results. Coaching requires coaches to personalize and custom-tailor knowledge to the specific seller and situation they are working through.
For a sports analogy, Tiger Woods has a putting coach and swing coach that helps him improve as an individual in very specific parts of his game.
Remote video coaching sessions are not status meetings
This isn’t the time to play Monday morning quarterback and second-guess the work that has come before the meeting as we’ve observed so many times.
Rather, the goal of each remote coaching session is to improve an individual’s actions and approaches to increase the likelihood of closing deals, delivering value to your customers, and ultimately maximizing revenue for your business.
In its Fifth Annual Sales Enablement Study, CSO Insights found that “For the last five years, sales coaching has had the greatest impact on win rates and quota attainment.”
This means that organizations spread across large geographic regions must develop remote sales coaching strategies, processes, and KPIs in order to realize this benefit.
They simply can’t coach in person at scale.
Sure you can occasionally sit shotgun with sellers on Zoom calls, but keeping a coaching regimen up without a remote video coaching plan will simply not get you the results you’re looking for.
But don’t just take our word for it.
In the same CSO study cited above, they also found out that…
“As vital as sales coaching is, the majority of organizations (62.9%) said they follow a random (coaching is left up to managers) or informal (coaching guidelines may exist, but no formal implementation) approach.”
Digging deeper, companies that performed “random sales coaching” (entirely led by the sales managers), had lower win rates than the study average.
Take a second to read that again.
Random sales coaching = lower win rates.
What’s more, the more formal sales coaching approaches had significantly higher win rates, nearly 9 percentage points higher than the average compared to random coaching which came in at 5 points below the average.
The lesson for companies doing remote sales coaching?
We have to be even more formal with our coaching activities to overcome the inherent barriers to being physically separated from our sellers.
Still not convinced of the importance of sales coaching? Dave Kurlan provided an analysis in 2018 that demonstrated:
Sales managers who devote at least 50% of their time to coaching have salespeople who score 13% better in Qualifying and 24% better in closing than the salespeople whose sales managers rarely coach.
The shift to remote selling
Selling by definition has long been a remote profession.
According to an article published by CNBC in October of 2019:
- U.S. Census data indicates that “5.2% of U.S. workers completely worked at home in 2017” — that’s about 8 million people.
- One Gallup survey found that 43% of Americans work from home occasionally. That’s up from 39% of those who did in 2012.
However, the global pandemic that began in late 2019 has forced thousands of organizations to shift to strictly remote sales.
While no one can predict the long-term impact of the pandemic, it is likely that the number of people working at home, either part-time or full, will continue to rise as a result.
Luckily for those left stranded, technological breakthroughs make remote sales coaching much easier and feasible than ever before.
“High-performing organizations invest 27% more in sales training and coaching.” – Sirius Decisions 2019
The top-performing businesses are investing in technology and talent to ensure they succeed.
Remote coaching tools are plentiful, ranging from virtually “free” (i.e., smartphones), to extremely powerful Enterprise tools that have AI-like capabilities for assessing seller strengths and weaknesses.
Below we’ve put together a list of remote sales coaching technology in 3 distinct categories for your consideration.
Just-in-time remote coaching tools
Let’s get back to basics for a moment. While we won’t go back to the telegraph, smoke signals, or naval flags, the phone remains a viable and valuable tool for remote coaching.
Sales coaches can build programs to directly coach individual sellers before and after prospect calls/meetings.
Think of it as “Just-in-time coaching”. Because sometimes a little reminder is all people need to succeed.
Coaches can use mobile video call software like FaceTime to see sellers’ reactions in real-time, so it’s not just a voice.
Pro-Tip – Try not to dictate the next steps to take over the phone. Coach them on the situation with scenarios that force them to come up with their own answers. Sometimes they might surprise you!
Chat tools (Slack, Microsoft Teams, Salesforce Chatter)
These modalities are most useful when you only have a small amount crucial in-the-moment coaching feedback to provide.
For example, let’s say you and the seller are on a conference call with a potential customer.
As you are listening, you observe an area for the seller to correct to improve the call outcome.
If you were in the same room, you can easily catch their attention and point that out to them without making the prospect aware of your support.
However, when you are both sitting in your own space, away from each other, a chat message bridges that divide in a non-obtrusive and direct manner while not impacting the prospect’s perception of your seller.
Pro-Tip – Practice using Chat tools in advance with your sellers. Many sellers are using live video feeds with prospects and their reaction to your chat message can make them appear distracted on the video feed.
Pro-Tip – Turn off sound and notifications during a live presentation. Those beeps and boops are highly distracting and virtually all prospects know what they indicate. And you surely don’t want to the prospect seeing your note!
Coaching suggestions for CRM
Sellers spend countless hours inside your CRM system.
Coaches can provide pre-recorded just-in-time coaching at the Account or Opportunity level that could mean the difference between a closed-won and closed-lost deal.
Pro-Tip – Many modern learning platforms offer “smart” capabilities that can automatically associate a suggested coaching session or best-case video suggestion for sellers based on content or tags in CRM removing the time needed to coach at scale for every possible scenario.
Live remote video sales coaching tools
Meetings (Zoom, WebEx, etc…)
These tools are the workhorse for remote sales coaches for one-on-one sessions.
They are as close to “in-person” as you can get with remote video coaching because the video sales coach can hear and see the seller.
In addition, sessions can be recorded for later review by both coach and seller.
Pro-Tip – Live meeting software etiquette is often poorly observed and network delays result in awkward silences. Coaches should be cautious and not “talk over” sellers before they finish thoughts and sentences as this can be very distracting/annoying. Zoom published a very helpful blog post, titled Five Tips for Successfully Managing Your Remote Team, which is worth reviewing.
Remote sales coaching software
A growing number of SaaS-based remote sales coaching tools have entered the marketplace to help coaches scale as well as to measure the impact of their activities. Here are a few of the key features that facilitate remote coaching.
Remote video Coaching
Remote video coaching provides an asynchronous method to coach sellers at scale.
Asynchronous, meaning one-on-one coaching can still occur but the coach and seller interact via the software at the time of their choosing.
Remote sales video coaching platforms give coaches the ability to develop assignments for individuals and teams and push them to remote sellers.
Sellers can then record themselves and upload recordings for coaches to review and provide feedback.
Best-in-class platforms provide a wide range of tools for coaches to give specific feedback on seller’s video recordings.
Pro-Tip – Perhaps you want your sellers to demonstrate their whiteboarding skills as they provide an overview of your product to the prospect’s security team.
The easiest solution? Have your sellers set their tablets in front of the whiteboard and videotape themselves practicing.
Most video coaching solutions support this type of activity. From here, sellers can then submit these video coaching sessions directly to their managers/coaches for detailed review and feedback.
AI Assessments and Behavior Scoring
Let’s face it – not all sales coaches are perfect. On good days we may catch subtle cues that can help sellers improve, while sometimes you just miss things.
Al-Assessments and Behavior Scoring provides a computational based way for coaches to take the guesswork out of assessing sellers’ video-based responses. These programs can easily detect inflections, facial expressions, and a variety of other “human” communication points beyond normal perception.
Remote sales coaches can utilize these tools to score a batch of video submissions from sellers and check their internal reactions to sellers against a gold standard.
Pro-Tip – Make sure to let sellers know you will be utilizing AI and Behaviour Scoring as many are uncomfortable with this type of technology. Take time to show them what the computers “caught” and why they may have been flagged as positive or negative by the machine.
Knowing where to start with remote sales coaching can be tricky.
First, we recommend thinking through what type of sales coaching you need to focus on with your sellers. Here are a few general categories to get you started:
Sellers are human, and like all humans, they forget things. Many of them are embarrassed to admit they forgot fundamental facts and information. A portion of any remote coaching effort needs to focus on coaching the fundamentals
Examples might include:
- Facts about your organization
- Listening skills
- Objection handling
Making foundational coaching consistent and providing just-in-time best examples via videos should be a part of any remote coaching plan.
Review the 10 Essential Selling Skills Every Sales Rep Needs in 2021 by HubSpot.
With remote situational coaching, you’ll be getting down to the nitty-gritty of working through conversations that a seller might find themselves in.
What happens when a prospect clams up?
How do you react when a prospect asks difficult questions?
Situational coaching should be custom-tailored to every seller’s job and customer base. Role-playing with a coach can fit under this category as well, and sellers don’t hate it as much as you might think!
The real beauty of sales coaching technology is using asynchronous coaching to provide “just-in-time” always ready coaching for special moments. This gives sellers the ability to work with coaches to brush up on a sales play or test a transition when they need it, not when coaches want to coach it.
That’s a critical distinction for coaches – when sellers need coaching and when they will “annoyed” by it.
Who to coach first – A vs B vs C players
You have a finite amount of time available to train, coach, and improve your organization. To maximize this investment, where should you focus?
Do you focus on making your top sellers even stronger?
Do you focus on your underperforming C players?
Do you focus on those middle-of-the-road B players?
While your A players could improve slightly, they are already your top performers, and the amount of improvement they will make doesn’t justify the hours required to make the improvements.
Your C players are underperforming. While we would all like to see them improve to the A-level status, the reality is that this will not happen the majority of the time. This fact does not mean they can’t be successful in another role or another business. It merely means they will likely remain underperformers in this role; don’t waste your limited time trying to change this.
Your B players are where you need to invest.
Your B players are often motivated and very capable, but lack some of the skills required to reach that next tier. B players who believe in your products and solutions, who believe in your mission, who are willing to work hard and apply what they learn, and are the ones who are capable of becoming A players. These sellers need your focus to coach and guide them forward to the next tier of performance.
Assessing gaps for individual sellers
What do you coach? You coach the gap. Build a bridge that takes your people from where they are today to where they want or need to be. – Keith Rosen, Bestselling author, and Executive Coach
Here are a few things to consider when trying to decide where to start coaching an individual seller. Again we’ve tried to make some distinction between remote and in-person coaching.
Observational – live calls with customers
Sales coaches should spend a portion of their time watching/listening to their sellers having real conversations. These observations are critical for identifying opportunities for additional improvement. Live meeting software is the obvious tool for this.
After each observation, schedule time to provide the seller with feedback and determine if they really need additional coaching. When giving feedback, include either a plan or next steps to create a plan to correct these areas of opportunity.
Surveying/asking sellers where they need help
Most of us are not nearly as self-aware as we would like to believe. We are not the best judges of our strengths and weaknesses.
However, we are often capable of identifying areas where the entire team can benefit from coaching.
Ask the teams for their feedback on areas where the entire team could benefit from more practice. Also, ask for feedback on areas where coaching can be improved.
Sometimes, understanding where salespeople need coaching is apparent. You may have observed their product demo and found it lacking. You may have reviewed a sales call and have immediate feedback for improvement.
However, there is often a lot that you will be unable to observe – this is where data can guide coaching efforts. While the actual information you collect and analyze must be your guide, here are a few ideas to get you started thinking about using data in your coaching efforts.
- Identify where specific sellers have significantly lower transition rates across sales stages as compared to similar sellers. Why are they struggling?
- Identify where sellers have lower cross-sell opportunities as compared to similar sellers. Are they failing to include other products in their sales when they should be?
- Are customers churning at a higher rate than average for specific sellers? Why? Did they misrepresent the solutions? Did they fail to do a proper internal hand-off?
Data is a powerful tool; use it with caution. It can support incorrect assumptions if not handled carefully. Use it without having preconceived notions, and you are far more likely to learn from it and improve individual, and team performance, in the process.
The level of support provided by your sales enablement team for coaching activities should be clearly covered by your sales enablement charter. Don’t have one yet?
Download our Sales Enablement Charter Template to get started.
Never before has the pace of technological change been this rapid. As a result, different generations are being exposed to different learning approaches, leading to changing preferences across generations.
Some sellers will do better with face-to-face, in-person interactions. Others will prefer the use of video-based feedback tools.
Regardless of the approach used, here are essential guidelines for you to implement as part of your coaching program.
Create a safe environment
Regardless of the technology used, the environment within which the remote coaching occurs must be a safe space. Coaching sessions must follow these rules:
- They can never be personal – personal attacks never accomplish performance improvement.
- They should lead sellers to solutions, not provide them with solutions.
Create a plan
The coach and the seller should have an agreed-upon plan of action. This mutually agreed upon plan should:
- Cover what is being coached.
- Discuss how the coaching will be performed.
- Identify how progress will be measured.
Jointly creating this plan will lead to better buy-in from all parties and increase the level of success obtained by following the coaching program.
Customize to the individual
Use assessments – Everyone has different strengths and weaknesses, identify the gaps, and coach to individual needs.
Schedule remote coaching sessions
Remote video coaching requires ongoing focus. Sessions should be frequent enough to reinforce the necessary changes to reach skill proficiency.
Sessions should be as frequent as possible, weekly, or bi-monthly is acceptable.
Focus on one thing
Coaching sessions should answer the What, Why, and How questions for the sellers.
- What? What is the focus of this coaching session?
- Why? Why is it important to focus on this change? How will this change improve their outcomes?
- How? How will successful improvement be measured?
Both the coach and seller need to come prepared. This is critical. Sellers and coaches should agree on what is being coached and ensure both parties enter the conversation prepared to begin.
Take detailed notes.
The seller, not the coach, should take detailed notes from the session.
These notes should be in a shared location where both parties access.
Review planned next steps
Leave time at the end of the coaching session to review lessons learned, as well as to discuss the next steps and follow-up required from the meeting.
Coaching is a journey, not a single meeting. Coaching sessions should build on each other and validate that progress occurs.
Review this helpful article from Deloitte on how to create a continuous learning environment.
Role-playing sessions are good candidates for virtual meetings. We’ll dive deeper into role-playing in the next section.
Exceptions to the rules
Although we’ve made a clear distinction between coaching individuals and training sales teams, there are some overlaps that sales coaches can take advantage of using remote selling tactics.
Here are a few examples to add to your coaching arsenal.
Role-playing with team members
Role-playing sessions are valuable learning opportunities. They can be accomplished during individual coaching sessions, but there are times when role plays can be most effective by bringing in more teammates.
Complex B2B sales can involve multiple individuals from different parts of the organization into which you are selling. You may be performing a discovery call with representatives from marketing, sales, IT, and finance, each with very different concerns. Practice these calls by having members of the team play each role. These conversations are high-stakes and complex, and it is incredibly challenging to cover the needs of each person in the meeting.
How do you perform effective role-playing sessions remotely?
The most natural solution is to leverage live meeting capabilities.
Pro-Tip – Most of the live meeting solutions allow meeting participants to change their names in the session. Have each participant take the name of the actual person or persona they are playing.
Pro-Tip – Always leave video cameras turned on. We all must get comfortable with this. Even if we cannot be physically together, you must always seek to add humanity and personality to your interactions, showing your face helps with this.
Pro-Tip – Record every session. Just as pro athletes watch the tape to learn what worked and where they can improve, sellers and coaches can and must do the same.
Pro-Tip – It can be helpful to role-play critical opportunities before big meetings. Consider adding this as a suggestion to your Sales Playbooks.
If you need assistance with Sales Playbooks, download our Definitive Guide to Sales Playbooks.
Choose the best examples and create a competitive environment
Those role-playing sessions which you recorded are pure gold for the participants and all sellers in your organization.
Curate the best videos and publish them, along with detailed feedback, someplace that your teams can watch, review, and learn.
Additionally, record all sales conversations (with the appropriate permission granted of course), and share the best examples of excellent sales calls during remote coaching sessions.
Videos are an excellent tool for learning, but, when passively consumed, you are wasting the opportunity to raise team performance. Follow these tips to maximize the value of your videos:
- Include videos as part of a learning experience.
- At the end of the video, require sellers to answer a few questions to validate that they learned the key lessons.
- At the end of the video, have users record themselves performing the critical action from the video. These recordings should be submitted back to their coach for review and feedback.
Remember, not every video is worth sharing. Your sellers need to be actively selling, not watching videos. However, the best videos, those that provide real lessons for the team, should be leveraged in these ways to enable the organization to improve continuously.
Smart Groups – Agoge Teams
Sam Nelson is one of the most recognized and respected thought leaders on the role of the SDR.
In August of 2018, Sam wrote an excellent post titled “The Agoge Tribe: An SDR Onboarding Revolution.” In this article, he shares a history lesson from Ancient Greece and an approach to learning and onboarding that is worth understanding. Since this guide focuses on coaching, not training, we will review this approach purely from a coaching perspective.
The concept of the Agoge tribe is, at its core, about bringing together a set of people under a shared system of training to ensure consistent approaches, methods, and beliefs, to deliver consistently excellent outcomes.
How does the Agoge tribe approach fit with remote sales coaching?
Ask yourself, is the behavior I am coaching unique to this individual, or is it a skill needed by teams of sellers? If not, consider using the Agoge method to coach a group of sellers on the changed behavior. By taking the team-based coaching approach for shared areas of improvement, you gain:
- Coaching efficiencies. Instead of coaching one seller, you can coach many at once.
- Peer level reinforcement. The cohort of sellers coached on a specific skill or behavior change can support and coach each other without the coach being present. Peer coaching, support, and pressure further reinforce the desired changes.
- Team building and collaboration. Often your B-players do not have the network of team support your A-players have established. Agoge teams support the creation of these networks.
Agoge teams do not have to report to the same sales manager. In fact, in organizations with multiple sales teams, there is tremendous value created when bringing sellers from different groups together to learn and support each other and their teams.
A lot of insight has gone into the creation of this article, and we hope you receive tremendous value from it. We wanted to go beyond our experiences. With that in mind, we have been reaching out to many others who have their thoughts on this topic.
We are adding, as we receive their feedback, their insights below.
Walter Pollard, President and Founder at Brand Fuzion, shared these insights on incorporating a New Game Plan, Strategy, and Framework for Coaching.
“Having a customer-centric approach in sales is more critical than ever before. Leading from a position of value, as opposed to product or service, is essential in conversations with customers today.
In many cases, customers’ worlds are dramatically shifting. Their clients yesterday might not be their clients today. Their business models might require transformation. Their products and services might have to evolve quickly, and roles within their organizations might have changed.
With such disruption in the customer’s market, we must think of new, innovative approaches that provide real value for our clients. In many cases, this requires translation through sales coaching and the creation of a sustainable coaching program that can evolve through the COVID-19 pandemic.
To effectively deploy the skill sets, guidance, and empathy required of sales reps and sales managers, developing and updating sales coaching strategies and frameworks is essential for many organizations.
How will you structure your coaching conversations to align your coaches with specific strategies? As an example, if you’re using the GROW sales coaching model, make sure you identify, adopt, and evaluate updated approaches to your strategy and framework.
Seller goals will likely need to be redefined, along with customers’ goals.
What is the new reality today for customers and sellers, and how can they find innovative approaches to navigate and to overcome these barriers effectively?
Options and Obstacles
Options and obstacles might have dramatically shifted for sellers and customers. Outline and incorporate new approaches that can drive successful, value-based conversations and outcomes.
Prioritize the steps and guidance necessary for the reps to be successful in moving forward with innovative customer sales initiatives.
Taking a step back and reevaluating your sales coaching strategy to enable your customers effectively and sellers can be pivotal at this time.”
Enablement teams must partner with sales managers and individual sellers to ensure they are delivering the right value to the organization. Use our Sales Enablement Survey to determine the questions to ask them to ensure you are meeting their needs.
Imogen McCourt, Co-Founder & Chief Executive AndGrow.io
“I agree about quick ‘course correction’ coaching in the moment, and the opportunity to use a coaching approach in pipeline review meetings, or Strategic planning sessions. I also love that you call out scheduled sessions for coaching. For me, they are key moments to think about higher-level goals or longer-term development – a positive outcome that frames and motivates the ‘fixes’ that either or both parties may have identified. Coaching to a positive outcome creates real ownership and determination to own and fix the issues from the coachee. This level of internalisation means sales managers can trust that something is going to be done between sessions, and not put off once the individual has ended the call or zoom.
With the opportunity to create scheduled, expected coaching sessions with salespeople, I find it is exponentially more impactful if the ‘coachee’ feels proactively involved in the process. In those types of coaching conversations, the salesperson is given an opportunity to uncover for themselves the areas that perhaps they need to focus on or improve because they are hindering their longer-term goal of ‘Be a VP in 2 years’ or ‘Go to president’s club this year’ or whatever the initial goal was that they co-created with their Manager.
If one is providing Sales Managers with training on coaching models and thinking frameworks, share that with the salesperson too. The salesperson can lean into these conversations, and do a lot of the ‘anticipatory’ thinking in the moment.
Here’s the rub for Sales manager: In most selling organisations the career path for our best salespeople; the ones that demonstrate the skills, behaviours (and results) that are valued from a seller; is to pick up a team and try and get them to replicate what they have done that made them successful. Then we tell that newly promoted person – “Oh but you must coach, not tell” Immediately asking them to do something that they haven’t demonstrated and probably don’t know how to do well, yet. The fix: A culture of coaching has to start top-down, so those successful sales individuals know and recognise coaching opportunities from their own field experience, and because some of their accelerated success came from great coaching too. It never surprises me when I find that there is a bias in the number of people who get promoted up the ranks from one sales department or group – at the top is a great coach.”
Remote sales coaching offers a brave new world to scale and improve your seller’s individual contribution to topline revenue.
However, by definition, remote coaching is inherently more difficult than in-person coaching.
Look at your favorite sport, and it is apparent which individual players have the best coaches.
Their form is perfect.
They rarely commit unforced errors.
They win more of the time.
In Sales, the best coaches will be the ones with the most significant percentage of sellers achieving quota.
Great remote sales coaches are great collaborators and communicators. They partner closely with sales managers and other sales leaders to ensure that sales teams are achieving their goals.
The best sales teams in the world are investing in great remote sales coaching, are you one of them?