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How To Create a Culture of Coaching With the Right Habits and Coaching Plays

8 min readMay 17, 2022

Coaching is one of the most impactful things you can do for your reps. And when you create a culture of coaching, reps stay longer and hit their quota more frequently, managers are able to provide better coaching and get more out of their teams, and organizations are able to hit their goals. In other words, everybody wins.

In this post, we want to focus on what makes great sales coaches and the things you can do today to create a culture of coaching. We’ll start with four habits of highly effective sales coaches (backed by data in our State of Sales Coaching Report). Then, we’ll dive into five playbooks for creating coaching that drives results. 

4 Habits of Highly Effective Sales Coaches

Habit 1: Coach Based on These 9 Metrics, Not Ad Hoc Requests

performance – as opposed to when reps ask for it – are more likely to have effective outcomes.

The data tells us that it’s not enough to wait around until people ask for help. Coaches must anticipate needs by looking at the data. This reinforces a key principle of good coaching: being proactive.

Our research shows that 38% of companies who coach reps on call performance do so “at random,” while another 31.9% coach reps only on their most recent calls. This means that 70% of coaching is not driven by data. 

Coach Based on These 9 Metrics, Not Ad Hoc Requests

For sales coaches, there are two sets of metrics that we recommend using:

  1. RevOps metrics to track the success of your team and their impact on the business 
    1. Activity on Open Opportunities
    2. Activity by Rep
    3. Lead to Opportunity Ratio
    4. Pipeline Velocity
    5. Net Revenue Retention
  2. Coaching metrics to track how your coaching initiative evolves over time
    1. Calls reviewed and annotations provided
    2. How often coaching sessions occur with the team
    3. How many “coaching events” you have within Revenue.io
    4. How much coaching reps receive per week

Habit 2: Hold Regularly Scheduled Coaching Sessions

Having regularly scheduled coaching sessions leads to both better coaching effectiveness and higher rep satisfaction.

We recently conducted original research and surveyed thousands of Sales teams in the B2B space. In our State of Sales Coaching Report, the data tells us reps who are most satisfied with coaching report that scheduled sessions happen all of the time or most of the time.

In other words, if you want happy, productive and engaged reps, you need to hold regular coaching sessions. 

Hold Regularly Scheduled Coaching Sessions

Habit 3: Provide Reps With an Hour or More of Coaching per Week

The majority of sales reps get less than an hour of coaching per week.

However, when you dive further into the data and segment the respondents into companies where coaching is effective versus companies where coaching is not effective, 61.4% of companies with effective coaching spend more than one hour per rep per week.

Provide Reps With an Hour or More of Coaching per Week

Habit 4: Use a Real-time Coaching Solution To Scale Effectiveness

Our survey revealed that the biggest challenge coaches face is not having enough time to coach. If you’re a sales coach, you’re probably nodding in violent agreement reading that sentence. The good news is that software can help with this by automating some coaching tasks, giving back time to busy coaches.

Companies using a real-time coaching solution reported more sales effectiveness. Real-time coaching with a product like Moments™ by Revenue.io provides analysis and guidance while reps are on calls, helping them to improve the outcome of a conversation in real-time.

Use a Real-time Coaching Solution To Scale Effectiveness

5 Plays for Coaching in Conversation AI to Drive Results

Now that you have the habits that form the foundation of great coaching, we also want to give you some actionable playbooks that you can use with your teams today. Throughout the playbooks, you will see some steps that will require you to utilize parts of the Conversation AI product that may be unfamiliar to new Revenue.io customers (for example, creating a Saved Search around a specific Keyword). But don’t worry, later sections of the eBook will cover how to utilize every part of Conversation AI. 

Here are five proven sales coaching playbooks. 

Playbook 1: Operationalize Positive Reinforcement

Positive reinforcement is one of the most effective forms of coaching because it rewards the desired behavior. Research shows positive reinforcement is much more effective for learning than punishment. Research also shows that praise and appreciation increase oxytocin (aka the “feel-good” hormone), which leads to higher levels of happiness. 

Here is a 4-step coaching workflow you can put into place right now to leverage positive reinforcement: 

  1. Clearly define the successful outcomes you’re looking to achieve. For this example, let’s say you want a rep to book a meeting from a cold call. We recommend you have a dedicated Call Disposition to denote a successful cold call.
  2. Create a Saved Search to automatically surface successful calls. In our example, the search is simply all calls with a disposition of “meeting booked.” Now, turn on notifications to that search so when a call matches the criteria, you automatically get notified in your Conversation AI Inbox.
  3. Review successful calls on a recurring basis. We recommend doing this at least weekly. The shorter the time between the call and the feedback, the more impactful it will be for the rep. 
  4. Leave feedback on the calls. It’s not enough to just review calls – you must annotate, socialize by sharing the call with your team, and curating them into Libraries.

Playbook 2: Encourage Reps To Take Ownership of Their Coaching and Development

In companies with the healthiest coaching cultures, everyone agrees that self-improvement is a core value. Also in these companies, not all coaching is driven from the top-down. In fact, you may be more likely to see coaching that’s rep-driven. When reps ask for feedback, it’s a sign they’re taking responsibility for their own development.

Here is a three-step coaching workflow you can put into place right now to leverage rep-driven coaching:

  1. Ask reps to identify at least one call per week that they’d like their manager to review. This is exactly what the Coach button is for in the RingDNA Dialer, and the Share button is for on video calls. Train your team to use these tools to help them grow.
  2. When reviewing your Conversation AI Inbox as a manager, always prioritize the review of calls and video meetings flagged by your reps. You must reinforce the behavior of asking for feedback. Provide annotations, and make it a point to discuss the call in your 1:1s. 
  3. As with all call reviews, be on the lookout for calls that are helpful examples of certain behaviors, and therefore belong in a call Library for everyone on the team to learn from.

Playbook 3: Create a Culture Where Reps Learn From Their Peers

Reps can get tired of the same coach’s voice in their ear. But don’t worry, coach. Tom Brady didn’t always love hearing Bill Belichick’s or Bruce Arians’ suggestions either. So, turn your reps into peer coaches by occasionally inviting the whole team to review one another’s calls. Not only do you get more feedback, but this also helps create peer bonds. 

Here is a three-step coaching workflow you can put into place right now to leverage peer-driven coaching:

  1. Select a call or meeting that would have particular value for your entire team to review. This will most likely be a challenging situation that was well-navigated or a call that exemplifies a desired behavior.
  2. During a regularly scheduled training, gather the group and give a five-minute overview of the exercise. Ask the entire team to review the recording and provide annotations. It’s critical that reps are required to provide annotations both for the value of the feedback itself and for task tracking purposes. Then, after a five-minute overview, let the group use the rest of the scheduled training session to review the call and leave feedback. 
  3. In your next scheduled team meeting, dedicate fifteen minutes to debrief as a group. Consider coaching the rep whose call or meeting was selected to express gratitude for their peers’ suggestions.

Playbook 4: Reinforce Your Most Critical Training

Most Sales organizations have recurring, weekly training. Yet as we mentioned earlier, Gartner research finds that B2B sales reps forget 70% of the information they learn within a week of training, and 87% will forget it within a month. The solution is reinforcement. Conversation AI is a powerful system to create reinforcement that makes your critical sales training stick.

Here is a three-step coaching workflow you can put into place right now to train your team on a desired behavior:

  1. Choose a desired behavior. For this example, let’s say it’s asking better open-ended questions about a buyer’s pain. Provide reps with a resource that includes a list of those questions. This could be in the form of a deck, PDF, print out, etc. 
  2. In Conversation AI, curate a Keyword Group to ensure that going forward, conversations that include your desired questions will be flagged, identified and tracked. 
  3. Set up a Saved Search to identify calls or meetings where the new Keywords are present. Now, subscribe yourself to daily Notifications, whether that’s in your Conversation AI Inbox or in your email. In the first two weeks after the training, use this to find and socialize examples of reps using the open-ended questions.
  4. At the same time, set up a Saved Search to identify relevant calls where those Keywords are not included. Subscribe yourself to these Notifications, review them regularly, and surface them for reps as missed opportunities to practice the new skill.
  5. In the Reinforce Your Most Critical Training tab, navigate to the Over Time report in the Conversation Topics dashboard, and use the filters to assess the frequency with which reps on the target team are using your new Keywords. Use the date range to easily visualize whether post-training, the team or specific individuals are now more likely to ask your target questions.

Playbook 5: Eliminate Bad Conversational Etiquette

Everyone knows reps shouldn’t dominate conversations, speak uninterrupted for three minutes or constantly interrupt a buyer. But how do you help a rep eliminate this behavior when you can’t be on every call? 

Here is a three-step coaching workflow you can put into place right now to eliminate bad conversational habits:

  1. Use the Insights tab to scan the team for conversation etiquette. Look at Talk Ratio and Monologues, then decide on a threshold. We will target future calls that are above your target threshold for Talk Ratio or Monologues.
  2. Identify the specific reps who need coaching on one of these conversation etiquette behaviors. In your next 1:1, direct them to set up a Saved Search to find their own calls where their Talk Ratio is above the threshold (say, for example, more than 65%). Be sure to narrow it to calls lasting at least five minutes in the Saved Search (or even longer depending on your business). Also, make sure the rep subscribes to immediate Notifications when a call meets this criterion. This will give them timely, automated feedback on all future calls where they found themselves dominating the call (or talking uninterrupted if you’re looking at monologues).
  3. Make it a recurring agenda item in 1:1s with these reps to look at the Insights tab and evaluate their performance change over time in the target Conversation Etiquette category.

The Power of Sales Coaching

The future belongs to the sales leaders who put their teams first and build a real coaching program. It’s time to embrace the next generation of conversation intelligence and use Revenue Science to unlock exponential growth.