What is sales coaching? A complete guide for 2021 & beyond

Until you change the way you look at things, those things will never change.

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In the last ten years, we’ve seen analog “relationship selling” evolve into a new strategy defined by data and powered by algorithms.

Today’s buyers need help finding the right information, on the right channels, so they can arrive at a decision they feel good about. And B2B sellers are expected to build trust and loyalty by delivering relevant, data-driven insights on demand.

A data-first sales coaching program makes things easier on reps and more predictable for the organization. It helps salespeople meet customers where they are right now, enabling them to pivot in real-time when the buyer flips the script.

Below, I’ll explain why every B2B sales team should make sales coaching a top priority, then share some tips for developing a high-impact coaching program that gets results. For some of the finer details about how sales coaching can empower your sales team to meet quota, check out our latest white paper.

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What is sales coaching?

Sales coaching is an ongoing, formal process designed to improve sales performance at both the team and individual level.

Done right, a sales coaching program should do the following:

  • Help sellers focus on the right actions. The best sales coaches help sellers prioritize the activities and accounts most likely to get the desired result. These days, advanced sales tools can help them get the job done by alerting reps to deals at risk before they go south and providing actionable notifications about what to do next.
    What is sales coaching?
  • Teach reps to diagnose problems & improve outcomes. Coaches shouldn’t tell sellers what to do. Instead, they should help them arrive at the right decisions themselves.
  • Provide individualized guidance. A good coach understands each rep’s motivations, strengths, weak points and builds a unique action plan around individual needs.

Why is coaching critical in sales?

According to Gartner, sales coaching is top priority for the highest performing sales managers and they want to provide coaching in the moment when it is most relevant. These days, in-time sales coaching is critical as sales cycles become longer and sales reps frequently do not know which steps to take to reach their goal in their daily work.

That’s where automated and personalized coaching comes in to play, and AI helps push sales training & coaching forward.

Modern sales coaching becomes high-tech

Sales performance coaching isn’t inherently “high-tech.”
However, B2B sales has become too complex for human brains to manage on their own.

With the rapid increase in digital activity, cloud adoption, and the pivot to remote work, reps have more information than ever.

And unfortunately, they’re drowning in data.

What’s more, managers are often the only gatekeepers of best practices. This makes it impossible to scale sales methodologies across large, distributed teams.

According to a concept known as the Dunbar theory, the human brain can keep track of about “150 relationships” before hitting a wall.

Imagine that you’re leading a large, distributed sales team.

You might have 150+ people to worry about.

You’re already maxed out before you can consider the relationships between actions and outcomes. Not to mention the variability between channels and touchpoints.

You’re not going to be able to keep track of every little thing.

Instead, technology fills in the gaps. With AI-powered tools, organizations can design entire coaching programs around strategic goals and known best practices.

Then from there, apply technology to execute & scale the sales coaching strategy.

Revamp your sales coaching

What are the sales coaching benefits?

The best-known benefit of sales coaching is its impact on the revenue engine.

According to RAIN Group data, successful sales coaching programs increased average deal size, sales activity, win rates, and new leads by 25%-40%.

Companies with a formal sales coaching strategy reach 91% quota attainment, on average. By contrast, those using an informal approach average around 85% quota attainment.

For many B2B sales teams, the bottom-line benefits are reason enough to go “all-in” on rep development.

Yet, the magic of AI-powered sales coaching touches every aspect of the sales organization.

  • Coaching helps reps navigate long, nonlinear sales cycles. As nonlinear journeys become the norm, AI-enabled sales coaching is shaping up to be an essential part of the sales stack. Forrester predicts that in 2021, over 60% of B2B sellers will augment their “human strengths with AI and automation tools.
  • Coaching reinforces sales training. Sales training is important, but on its own, knowledge quickly fades. (Per the “forgetting curve” theory, within just 20 minutes). Sales coaching bridges the gap between training and performance using hands-on methods like role-playing and 1:1s.
  • Sales coaching democratizes knowledge. According to HubSpot, more than half of all salespeople rely on peers to get tips for improvement. Sales coaching ensures reps “copy” the right people. Coaches can capture & share best practices from top performers —then use them to lift everyone’s performance.

How much does sales coaching cost?

Sales coaches are often sales managers or directors with proven leadership skills and industry experience.

According to Allego’s State of Sales Coaching report, three-quarters of organizations have a formal sales coaching training program. These programs are very different in costs and depend on the requirements of the organization they are held in and sales coaching techniques covered within the scope of the program.

There are various factors that impact the sales coaching program cost. Public programs can cost from $500 to $5,000. The lower cost programs are generally designed to attract large audiences to whom the organizers can then up-sell other offerings. There are some excellent public programs designed to immerse you into a selling system. If you are a small company and lack a selling system, this can be a very cost-effective approach. By their nature, public programs are “one-size-fits-all.”

Private programs, when done properly, create a foundation of principles, and then hold the participant’s hand from concept through how to apply the concept to your business. Private programs can range from $3,500 per day on the low end, to $25,000 per day on the high end. As you’d imagine, a more experienced facilitator with a track record of results can demand a higher fee than someone who is new to the field.

Researchers found 45% of managers feel like they need more training for diagnosing performance issues, while 42% say they’d like more strategies for motivating reps & getting them to install action plans.

Even though adoption rates for formal programs are relatively high, many managers are ill-prepared to coach.

A great manager isn’t necessarily a great coach. It might be worth hiring a dedicated sales coach to develop internal coaches and grow the program.

What are the different sales coaching types?

Much like sales methodologies, there’s a near-infinite number of coaching models to choose from, each designed to support different strategies, goals, and processes.

While there’s no official consensus, coaching models tend to fall into three main categories:

1. Strategic coaching. Strategic coaching focuses on the big-picture plan and covers market intelligence, emerging trends, and navigating the complexities of buying.

Popular models include GROW, a performance coaching model, OSKAR, a solution-focused framework that emphasizes individual progress, or AOR, a model for aligning sales activities, objectives, and outcomes.

2. Tactical coaching. Tactical sales coaching aims to help sellers develop the tactics sellers use to achieve strategic goals. Essentially, strategic coaching introduces big picture concepts say, social selling and where it fits into your overall strategy.

Tactical coaching is about “the how” so, you might host a workshop on using LinkedIn Groups for prospecting.

Here, you’ll want to provide step-by-step instructions and resources to support the effort.
Brainshark’s model for developing a video coaching strategy is a good example of tactical coaching in action:

sales coaching | Revenue Grid

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3. Skill coaching. Skill coaching is similar to tactical coaching but is more about fine-tuning specific tactics’ execution & delivery. Typically, skill coaching takes on one skill at a time and focuses on practice, repetition, and gradual increases in difficulty.

Sales coaching tips

You’ll want to make sure that your sales coaching strategy keeps that idea in focus—helping your team develop competencies around building trust, personalizing messaging, or surfacing & sharing relevant insights.

While programs vary between organizations, I’ve outlined some sales coaching tips any B2B sales leader can use to guide their team toward predictable wins.

1. Sales coaching begins with good data

For strategic processes like sales coaching, it’s better to work from one unified interface, which typically means the CRM is “home base.”

It should go without saying but before you go any further, you’ll want to make sure you’re working with a complete set of “good” data.

According to Salesforce, 91% of CRM data is incomplete. Incomplete data stands in the way of total pipeline visibility and means you’ll end up making decisions without knowing the full story.

To ensure the best possible results, you’ll need a complete record of all communications, channels, and sales activities.

Then from there, you can start layering AI-enabled tools that can streamline and automate the coaching process.

Another issue is over-reliance on subjective CRM data, which is a major barrier to becoming truly “data-driven.”

CRMs, while essential, function as a centralized database for all sales data. Meaning, they contain a TON of insights but aren’t especially actionable. For example, two-way engagement is a critical data point that can be hard to get from CRM records.

And if you open Salesforce, you’ll see reps having conversations with buyers. The problem is, you’re missing key data points that put those conversations into context and cannot manage your account relationships in the right way.

You’ll want to make sure you’re funnelling all sales data into a centralized location

2. Focus on middle-of-the-road reps

Many companies rely on one or two “star performers” to generate most of the revenue.
Brent Adamson and Matt Dixon, creators of Challenger Sales, say coaches tend to focus on either “A-level” reps or poor performers.

The reason for focusing on one extreme or the other comes down to two key factors:

  • First, working with top performers affirms coaches’ ability to get results. In other words, it’s a nice ego boost.
  • Second, there’s also a sense of obligation to help struggling reps hit quota.

In both cases, what happens is the middle 60% of reps on the “B-squad” must figure things out on their own.

A 2018 report from the Sales Readiness Group said sales coaching is the “greatest point of leverage” in improving team performance. Even the smallest improvements can provide a major boost for your bottom line when multiplied by five, ten reps.

In other words, neglecting your “average Joes” is an expensive mistake.

Rather than coaching top performers, coaches should treat their “in-house” experts as a resource they can use to help the entire team unlock their true potential.

3. Enhance the customer experience

Gartner recommends that reps focus on building customer confidence by making sense of the massive volume of information available.

That sense-making approach involves:

  • Identifying the most important information
  • Determining what questions buyers should ask to access the information they’re looking for
  • Anticipating necessary changes: think responding to new needs or embracing new approaches like social selling, AR product demos, and at a base level, developing an engaging presence on Zoom calls
  • Ensuring that customers arrive at a decision that they feel confident about. In other words, did the buyer achieve their goal by interacting with your company?

According to the Miller Heiman Group, the following three customer engagement practices had the greatest impact on sales performance:

  • Reps effectively communicate value messages that align with individual needs.
  • Consistently positive interactions at each channel & touchpoint.
  • Ability to conduct mutually-beneficial calls/meetings with buyers.

AI-powered coaching eliminates guesswork from the process. This way, reps don’t waste time trying to determine what customers consider a “positive interaction.” They track pipeline changes in real time and get contextual alerts about how to act on the situation immediately.

Programs should focus on transforming reps into “trusted advisors.” Coaches should work on developing skills like identifying decision-makers & the criteria they care about most, and demonstrate how reps can use that information to close.

Sales coaching impact

Effective sales coaching isn’t about giving in-person feedback at random intervals. Instead, sales coaching success hinges on routine. If you’re not sure you can commit to consistent 1:1s and group workshops, eliminate or automate activities eating up valuable coaching time.

Identifying hidden waste centers allows you to optimize workflows by either eliminating or automating tasks that take away from valuable selling time and reinvest that extra time into your coaching program.

As an example, we interviewed sales managers using our Guided Selling platform to gauge its impact on sales productivity. On average, managers estimated that they spent 25% less time chasing down reps for status updates—time that could then be used for 1:1s or developing training content.

Still, figuring out where to focus that time requires some strategic thinking.

Every rep has unique strengths, weaknesses, and learning styles, making it difficult to determine what to focus on to get the biggest returns.

Start by answering the following questions:

  • How much time will it take to coach individuals on specific skills?
  • Which skills are most valuable? Value depends on what you’re trying to achieve increased deal size, shorter sales cycles, more wins, etc.
  • Which skills fail to influence outcomes or worse, sabotage the deal?

You might also use a matrix or scorecard to guide the decision-making process. For example, The Sales Readiness Group (SRG) recommends analyzing individual skill sets using a combination of proficiency and motivation.

From there, you might use a simple table like the one below to start mapping out where you’ll spend your time.

What is sales coaching?

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As you gather more data, you’ll be able to accurately attribute specific actions to successful outcomes and determine sales coaching impact. Long-term, you’ll want to continue to evaluate the data to determine:

  • Which strategies are working?
  • Which reps are getting the best results
  • Who is achieving “predictable wins?”
  • How might your most effective strategies/channels/messaging be used throughout the organization? Or applied toward building a presence in a different market/sector?
  • Which strategies aren’t working and why?

From there, you can use those insights to refine your playbooks and coaching strategy to ensure even better results.

Sales coaching software

Sales coaching software is an expansive category that includes everything from sales enablement and microlearning to conversational intelligence and practice simulations.

Rather than searching for one platform that does it all, focus on building a “sales tech ecosystem” that aligns with business goals and seller needs.

Here are some examples of top-rated sales coaching software you might consider adding to your stack.

Brainshark

Brainshark is a data-driven sales readiness platform designed to provide sales teams with the knowledge and skills they need to engage buyers effectively. Users can generate dynamic content, develop onboarding & training materials, and diagnose performance issues with the platform’s AI-powered analytics tools.

Key features:

  • Controlled practice environment. Brainshark offers video and text-based coaching assessments designed to help managers measure & score performance, provide 1:1 feedback, and share the best performances with the rest of the team.
  • Readiness scorecards. Brainshark’s readiness scorecards provide a 360-degree view of rep skills, making it easy to identify top performers & share winning strategies with the whole team.
  • Design & manage live events. Create course sessions for live events such as instructor-led-training and webinars, right alongside your on-demand training content. Students can select the sessions that best fit their schedules.
  • Create custom learning content. Build a custom learning library to support training, coaching, & onboarding. Reinforce knowledge by delivering learning content to any device, and “certify” rep mastery by sending digital badges when reps hit key milestones.
    You can also use the platform’s analytics tools to track activities featured in the content and their impact on outcomes.

SmartWinnr

SmartWinnr is a systematic sales coaching tool that allows sales coaches to upload core competency frameworks that match their sales strategy and automate content delivery. The platform offers video-based coaching, practice, and assessment features and allows coaches to share individualized feedback.

Key features:

  • Video coaching. Sellers can record and upload video pitches, which are then assessed by the platform’s built-in AI. Coaches & managers can then leave feedback to fine-tune messaging.
  • Product training. Train sellers on new product features & benefits with automated microlearning and quizzes. The platform’s built-in AI reinforces key messages and measures & tracks knowledge retention.
  • Gamification. Smartwinnr also includes gamification features like leaderboards, interactive quizzes, and contests. This way, coaches can track progress while using a sense of healthy competition to motivate reps.
  • In-app chat. Encourage communication & collaboration among team members. The platform’s messaging tool allows reps to share successes & best practices and work together to solve problems.

Qstream

Qstream is a microlearning platform designed to drive behavioral change, reinforce knowledge, and engage learners. with bite-sized, on-the-job lessons.

Key features:

  • Intuitive, graphical dashboards. Real-time, visual reports track sales fluency, improvement trends, performance, and more, based on custom filters.
  • Sales compliance. Qstream is ideal for companies operating in highly-regulated industries like finance or healthcare, offering built-in controls that maintain compliance standards at scale.
  • In-app analytics. Diagnose skills gaps & link skill to outcomes, compare trends across teams, & drill-down to individual reps.

Chorus.ai

Chorus.ai is a conversational analytics platform that captures and analyzes all sales calls, emails, and virtual meetings in real-time.

Key features:

  • Record conversations from all channels. Chorus integrates with dialers, video conferencing apps, and more.
  • Market intelligence. Measure how often your audience mentions key themes, products, or features and their impact on the sales cycle. Insights can be incorporated into the coaching strategy, marketing plan, or product roadmap.
  • Messaging & conversation insights. Conversations can be mapped to the CRM and incorporated into sales reports. Sales coaches can analyze conversations, highlight best practices from recordings, then share time-stamped examples with the team.
  • Analytics. Analyze trends for any conversation topic features, price, competitors, and more. Chorus’ analytics tools allow users to quantify the impact of conversation metrics have on the buying process.

Revenue Grid.

Revenue Grid is a Guided Selling platform that uses the power of AI to support sellers throughout the entire sales process. Sales Leaders can use the platform’s Guided Selling tools to capture winning actions and use them to improve the sales coaching strategy. Revenue Grid’s sales coaching feature helps to correlate the training and performance of your sales teams with revenue results. Using this approach, your sales reps get AI-generated contextual alerts about the actions that will move their deals forward best, right at the moment when they should execute them.

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    Key features:

    • Digital coaching. Replace outdated verbal sales coaching with automated sequences. The platform uses AI-driven insights and sales data to nudge reps toward the right action at the right time based on your pre-defined rules.
    • Conversational intelligence. Conversational intelligence surfaces patterns in calls and meetings that are associated with wins & losses. Coaches can compare rep performance and share real examples of best practices from top performers to help the whole team skill up.
    • Shorter sales cycles. Interactive actionable Revenue Signals moves reps through the sales cycle fast. AI signals point them in the right direction, explaining what actions work best in any sales situation. Reps receive suggestions from internal playbooks and alerts to help them get at-risk deals back on track.
    • Total pipeline visibility. Automatic data capture enables full visibility into all sales activity, deals, accounts, and pipeline. Users can easily see which reps need coaching, in which deals, and with what. Additionally, users can track how individual reps engage with accounts and opportunities to see what has led up to the current situation.

    Final Thoughts

    Using the tools and tips outlined above, you can build a data-driven sales coaching program that delivers real results.

    However, it’s important to note that sales coaching programs are a major commitment, both in terms of money and time.

    While you’re bound to see some initial quick wins, coaching is a long-term collaboration between reps, sales leaders, and the AI-powered tools transforming the sales process.

    Get the insights you need to
    coach for quota in your team

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