Sales Coaching: The Ultimate Guide

Imagine your sales team performing 19% better month after month.

Sound nice? Of course.

A study from CSO Insights reveals a correlation between quota attainment and coaching. When coaching skills exceed expectations, 94.8% of reps meet quota. When coaching skills need improvement, only 84.5% hit.

In other words, no other productivity investment is nearly as impactful as sales coaching. So, what is sales coaching, and how do you do it well?

Effective sales coaching is iterative, individualized, and inclusive. It’s designed to reinforce positive behavior or correct negative behavior. Typically part of each sales rep’s daily or weekly routine, sales coaching is focused on skills and techniques rather than numbers.

What doesn’t fall under the sales coaching umbrella?

  • Telling salespeople exactly what to do (rather than giving them the end goal and letting them figure out the specifics)
  • Giving the same advice to every single person
  • Ignoring individual motivators, strengths, and weaknesses

Examples of Sales Coaching

To get a better sense of what sales coaching looks like, here are a few examples:

  • Reviewing a call with a sales rep and discussing what went well and where they could improve
  • Offering inside sales training and tips
  • Reviewing remote selling techniques and tools
  • Scheduling weekly check-ins with reps to discuss objectives and areas of the sales process they’re less confident in
  • Shadowing or listening to a rep’s meeting or phone call with a prospect
  • Reviewing a rep’s email conversations with prospects throughout different points in the buyer’s journey

Benefits of Sales Coaching

As highlighted in the introduction, sales coaching has a proven, positive impact on your bottom line. But win rates aren’t the only reason you should coach your sales reps.

1. Sales coaching improves employee retention rates.

Rep turnover is a notorious problem in sales. While burnout or a bigger salary elsewhere will always tempt some, professional development opportunities will motivate many others to stay. 9 in 10 employees say professional development is “important” or “very important,” and 4 in 10 specifically want in-house programs.

2. Sales coaching gives you an opportunity to share best practices.

When you notice one rep is using a strategy to great success, you can immediately teach the rest of your team to do the same thing, similar to how a HubSpot sales rep’s success with video prospecting spread throughout his team. Think of sales coaching as a rising tide that lifts all boats.

3. Sales coaching maximizes your investment in sales training.

Companies spend billions per year on sales training, but research shows most of the curriculum doesn’t stick. Effective sales training relies on consistent, long-term reinforcement — which the sales manager can achieve through sales coaching.

Sales Coaching Models

There are hundreds of different sales coaching models. Many managers are less than enthused about them — and it’s not too difficult to understand why.

Some coaching models are designed for any manager with reports, rather than a sales manager and their reps. But sales is an incredibly distinct profession. It requires a unique coaching model. If you’re considering a generic model, you’ll likely struggle trying to adapt it to your team.

Some models only work with specific methodologies. That can be frustrating if you don’t like the model you’re supposed to use. Luckily, you can always create a hybrid of your prescribed coaching model — one you’re more enthusiastic about.

And remember, some models are overly structured. Look for something flexible that you can use with different sales processes — that way, if you change your strategy, you won’t need a brand-new coaching model.

If you aren’t sure if a coaching model is a good fit, ask your team. Their feedback matters most; after all, they are the ones who should benefit. You might use an employee feedback tool, or conduct an internal survey, to get this information from your team.  

Now that you have a better understanding of what sales coaching is and why it’s important, let’s look at some sales coaching techniques you can implement.

These commonly-used coaching techniques are applicable to all types of sales teams. Don’t be afraid to incorporate some (or all) of them on your team.

1. Use sales data.

It can be overwhelming to figure out what to focus on in terms of sales coaching — both team-wide and among individual reps. That’s where data comes into play. Rather than using your gut to guide you, use your HubSpot CRM and/or sales software to identify where your salespeople could improve.

Wondering what that might look like?

Keep track of conversion metrics on a monthly basis. If you notice deal velocity is increasing but close rates are decreasing, you should dig into your reps’ email-to-meeting, meeting-to-demo, and demo-to-close rates (or the applicable metrics for your sales process) to understand where they’re moving too fast.

You may also see many reps are skipping the discovery call and jumping straight to the demo, which saves time but leads to generic, low-value presentations … and, therefore, decreasing win rates.

In addition, compare each salesperson to their historical performance, the team’s average performance, and/or your top performers’ performances.

For example, let’s suppose your rep’s average deal size is $500. This quarter, their average was $300. Your best salespeople are averaging $600. With this context, it’s clear this rep needs help.

2. Mix up your sales coaching style.

Selling requires a variety of skills and techniques, so make sure your coaching incorporates multiple styles.

Director of Sales Enablement at Brainshark, Mike Kunkle, recommends varying between:

  • Strategic coaching, or big-picture guidance, on topics like selling into a specific market, navigating a complex buying process, working with customer champions, etc.
  • Tactical coaching, or nitty-gritty suggestions on starting a relationship, qualifying, etc.
  • Specific skill coaching, or helping salespeople improve their communication, questioning strategies, rapport-building abilities, remote selling, etc.

3. Get buy-in.

What’s one of the worst ways to try to change a salesperson’s behavior? Tell them what to do.

Most salespeople are fairly independent — that’s why they’ve chosen to work in sales — and don’t respond well to being ordered around.

You’ll have far more success if you involve them in the improvement process. That means asking them how they think they performed, what they can do to get better, and which metrics will help them measure their progress.

4. Leverage your best sales reps.

Salespeople can learn just as much from each other as you. Use that to your advantage — if one person on the team is crushing it, ask them to share their learnings with everyone else.

To give you an idea, imagine two of your reps are getting great results from prospecting on LinkedIn (social selling is a highly-effective tactic, after all). Figure out what they’re doing differently. Are they sending a specific message? Targeting a specific set of users? Answering questions in specific groups?

These reps should give a presentation on their winning strategy — perhaps during your next team meeting. Your other salespeople will be eager to imitate them, and the group will potentially find an even more effective way to execute this play.

Let’s also take a look at the various tools that can help you manage all of these coaching tips and techniques more easily.

There are a number of tools you can use to improve and simplify your sales coaching techniques. These tools include software and educational resources you can use both individually or in combination with each other.

1. provides a simple way for you to use sales enablement practices to coach and empower reps. You can build, implement, and measure the success of your sales coaching tactics to ensure you’re supporting your reps so they’re more likely to hit their goals.

The software’s AI capabilities simplify the creation of your coaching tactics and plans while pulling from real rep conversations, data, and interactions with leads and customers.

2. Gong

Gong provides a unique look into rep interactions with your customers by using the product’s conversation intelligence capabilities. As a sales manager, this feature will make it easy to identify and replicate the actions your best reps are taking as well as assist other reps in the areas they need support. You can review the conversations your reps have with your prospects and customers on the phone, email, or web conference.

3. HubSpot Sales Coaching for Managers

HubSpot Sales Coaching for Managers is a free program for sales managers to learn how to better coach and support reps. The lessons focus on the best ways to coach reps so they can hit their goals and so your team continues to excel and positively impact the business’s bottom line.

4. Showpad Coach

Showpad Coach, formerly known as LearnCore, is a sales coaching and training software. It allows you to organize and manage coaching (as well as onboarding and training) for each rep on your team.

The software offers features that allow you to review analytics related to each of your reps — this way, you identify which people need what type of support and coaching. You can also create and share coaching videos to customize and tailor the support you’re providing your reps with.

5. ExecVision

ExecVision is a conversation intelligence program ideal for coaching large teams of reps. The software makes it easy to assist your reps and focus on their specific areas for improvement by focusing on their behaviors.

The software allows you to easily identify coachable moments in every rep’s processes. It transcribes sales calls and highlights key moments in every rep’s workflow. Then, you can go in and coach the reps in the areas in which they need support.

In addition to sales coaching techniques and tools, here are some all-encompassing tips to keep in mind as well. These tips will help you effectively coach reps to ensure your team is as productive as possible.

1. Focus on the middle 60%.

According to Brent Adamson and Matt Dixon, authors of The Challenger Sale, most sales managers tend to spend most of their energy coaching the “very best and very worst” salespeople on their team.

Managers feel compelled to help the bottom 20% to get their team to quota. They want to help the top 20% because it’s rewarding.

Consequently, the middle 60% gets the least amount of attention. But Adamson and Dixon explain “the real payoff from good coaching lies among … your core performers.”

After all, the worst-performing salespeople (who are consistently underperforming, that is) usually aren’t right for the role. You should replace them, not try to train them up.

And the stars on the team show little to no performance improvement from coaching. So when you’re thinking about which reps to focus your attention on, think of the middle of the pack.

2. Share your vision.

Sales reps want to feel as though they’re contributing to the company’s overall success. This is motivating and provides them with non-monetary fulfillment.

Come up with a mission for your team that goes beyond “Sell X amount of business.” This goal should be specific, actionable, and exciting — think “Break into A market,” “Become known internally for doing B,” or “Break the company record for C.”

Periodically throughout team meetings and one-on-ones, share the overall team’s progress toward this objective. You should also point out the people who have made significant contributions in doing so. For example, you might say, “I want to recognize Joella for landing a huge new corporate account, which will definitely increase our visibility in that market.”

3. Learn each salesperson’s drivers.

Everyone is motivated by different things. Even if the majority of your reps are motivated by making money, their specific financial goals probably vary widely. One salesperson might be paying off their student loans, while another may be saving up for a house. Some salespeople are primarily in sales because they love autonomy.

To identify how you can engage your reps, former HubSpot Sales Director Dan Tyre recommends asking what they want to accomplish in both their personal and professional lives.

“This will not only show you the type of person they are, but also give you insight into what things will motivate them the most,” he explains. Tyre asks these questions:

  • Are you motivated right now?
  • What motivates you long-term?
  • What can you do to motivate yourself?
  • How will I know if you are not motivated?
  • What do you want me to do if you don’t appear motivated?

Having these insights will allow you to tailor your coaching style to each sales rep and their personal visions.

4. Use incentives effectively.

Sales contests and incentives should change behaviors, not reinforce existing ones. That’s why offering $100 to the first rep to make a sale that day probably isn’t helpful.

Figure out what your salespeople aren’t doing that you’d like them to — and design your contest around that action.

To illustrate, maybe your reps are focusing too heavily on product A because it requires less technical knowledge than product B. You might give a bonus to every salesperson who sells more than X units of product B.

5. Give personal rewards.

Individual prizes should be tied to a specific rep’s goals. For example, if a rep is working on increasing their call-to-meetings rate, you might say you’ll take them to a nice lunch once they improve by X%.

Not sure what to offer as a prize? Here’s where knowing every salesperson’s motivators is handy. You can also directly ask them, “What can I give you as a prize for achieving [objective]?”

6. Seek and experiment with new coaching practices and resources.

There are many sales coaching techniques and tools available today — don’t be afraid to experiment with them. Every team and individual are different — meaning, no sales coaching techniques are always going to be one-size-fits-all.

Learn about what’s going to work best for your reps and their needs and ask each rep for their feedback on your coaching style in your one-on-one meetings. Then, stick with these tactics until you reach a point in time when you need to reevaluate their effectiveness and impact.

7. Prepare and practice with multiple coaching scenarios.

As a sales manager, it’s your job to prepare and practice with multiple coaching scenarios. Your team is bound to evolve and the people on it are going to change (in terms of their skillset but also rep turnover).

Stay efficient and effective in regards to coaching by preparing for different scenarios — this way, you’ll be ready to assist and teach reps with different needs and areas for improvement at any point in time.

Additionally, you might notice you have several people who need the same type of coaching in a specific problem area. In this case, you can prepare with training and information around that topic and share it among the group.

Or, if one rep is struggling in a specific area, you may have a prepared outline of a plan you can then tailor towards their needs — then, you can use it again in the future with another rep.

8. Leverage your entire sales team.

Some sales reps learn by example, which is why it may be valuable to leverage other members of your sales team (perhaps to top 20%). Schedule some shadowing sessions during which the reps who you’re coaching can listen in on a few successful sales calls (or sales call recordings). Afterwards, debrief with your reps and break down why the calls were so successful, what could be improved, and how each rep would’ve handled the calls themselves.

Moreover, ask the more successful members of your team what helps them during their calls and consider providing similar resources or encouragement to those reps with room for improvement.

9. Have the hard conversations.

Many sales reps struggle to meet their potential because of the inevitable prospect push-back … and the dreaded word, No. But most reps work their way through this discomfort with practice.

With the sales reps you’re coaching, role play some uncomfortable scenarios and hard conversations, practicing some common objections. Once reps get more comfortable hearing those objections and responding accordingly, they’ll be better equipped to face them on real sales calls.

10. Provide more positive than negative feedback.

For as many pieces of constructive criticism you provide to your sales reps, give twice as much positive reinforcement. Not only does this help maintain morale, but it also allows sales reps to recognize what they’re doing right — and hopefully encourages them to repeat and build on that behavior. 

Put Me In, (Sales) Coach

Sales coaching is both an art and a science. It’s one of — if not the — most important components of sales management. Do it well, and your team’s results will speak for you. So, begin incorporating the various sales coaching techniques, tools, and tips to help your team close more deals, boost revenue, surpass quota, and grow better.

Editor’s note: This post was originally published in August 2017 and has been updated for comprehensiveness.