Ultimate guide to sales coaching: strategies, tips & tools to win

Ultimate guide to sales coaching: strategies, tips & tools to win

Your sales team is in the bottom of the ninth, and you need a home run to win the game. Your best player steps up to bat. As their coach, how confident are you that they’ll knock that ball out of the park?

It’s the sales manager’s job to coach each rep on their team, helping them build their skills and improve their performance. But this has become even more crucial since the world was unexpectedly launched into remote working.

In fact, a study by Gartner in early 2021 found that 93% of reps are struggling with the new challenges of virtual selling. But, more importantly, 66% of those challenges are internal.

In other words, for reps to perform their best, sales managers need to become better coaches. And really, that’s true whether you’re managing a remote sales team or not.

In this guide, you’re going to learn:

  • What is sales coaching?
  • Sales coaching system & process: from onboarding to pro rep status
  • Top 5 sales coaching tips to bring up your team’s batting average
  • Top 5 sales coaching software & tools

By the time you finish this guide, you’ll have the know-how to coach your team so they hit consistent home runs every time they step up to the plate.

What is sales coaching?

Sales coaching is the individual training and assistance that sales managers give to their reps. Coaching involves having 1:1 conversations with reps, reviewing their pipeline and deals, analyzing their calls, and helping them gradually build their skills through practice and collaboration.

Coaching involves one-to-one communication—scheduled meetings between you as the manager and each of your reps separately. This individual coaching time allows you to dig into key motivators for each rep, build their skills as individuals, and help them advance their careers.

In contrast, sales training is the time that you take to build the skills of your team as a whole, practice new scripts or talk tracks, test and measure new methods, or redefine the sales process.

In short, sales training is the time you spend teaching your whole team-specific sales strategies—sales coaching is the time you spend showing each rep how to use those strategies in their day-to-day process.

Why is sales coaching important?

Sales coaching makes the difference between a successful, high-performing sales team and a team that can’t reach quota consistently. Sales managers who coach their reps strategically help them build foundational skills that lead to better productivity, higher performance, and increased win rates and rep retention.

Sales coaching is a way for you to treat each rep individually depending on their unique needs, circumstances, and motivators. This individual treatment is essential if you want to build up your low performers, increase the sales skills of your middle performers, and retain top performers on your team.

Primary objectives of sales coaching

Coaching is more than just telling your reps what to do. Here are some of the main goals good sales coaches focus on:

  • Improve sales skills across the team: Your market, sales process, and pipeline are unique to your business—so, individual coaching helps you build foundational skills across your team based on best practices for your process.
  • Motivate sales reps to perform better: Finding the right motivators for each rep is key, as is building accountability by rewarding them for better performance in the way they prefer.
  • Handle small issues before they become big problems: Coaching on the deals in each rep’s current pipeline allows you to see how each rep performs in different stages and spot weak points or bottlenecks before they negatively impact your bottom line.
  • Enable reps to grow in their sales career: Helping your reps to improve themselves helps them to grow as individuals and build the skills they need to reach their career goals in the future.
  • Reinforce training: 80% of sales training is forgotten in 3 months, which is why it’s essential to use regular, individual coaching to reinforce those ideas and methods.

Benefits of implementing effective sales coaching with your team

It’s no secret that effective coaching takes time and effort. But the more you put into your sales coaching efforts, the more benefit you’ll see.

Here are some of the main benefits that good sales coaches see, plus the data to back them up:

  • Higher close rates: CSO Insights found that structured sales coaching can increase win rates by 28%.
  • Better rep retention: This personal attention makes your reps feel appreciated and challenged in their work, which is probably why 60% of salespeople are likely to quit if their manager sucks at coaching.
  • More satisfied customers: The more effective your sellers are, the better they’ll treat prospects, and the happier those prospects will be.
  • Improved team culture and morale: As your reps improve their own skills and see the results of that effort, they’ll be more motivated to keep working hard for your team.
  • Higher performance across the team: Gartner found that effective sales coaching can increase sales performance by 8%. And according to RAIN Group, companies that implemented a well-designed coaching system saw up to 40% increase in sales activity, leads generated, average deal size, and close ratios.
  • Faster growth across the company: Companies that coach consistently see an average of 16% greater annual revenue growth, and 84% of today’s top sales orgs spend consistent time building each of their reps’ skills.

Convinced yet?

If you’re ready to truly empower your reps, it’s time to build a plan that will lead to more effective sales coaching (and more home runs across your team).

Check out how Director of Sales at Close, Nick Persico, has learned to coach SaaS sales teams successfully over the past decade:

Sales coaching system & process: from onboarding to pro rep status

A structured process is a key to effective sales coaching. So, how do you build a plan that works for your reps and your team?

Here are 6 simple steps to get you started:

Looking for a quick checklist to help you build a better coaching agenda? Download our Sales Coaching Plan Template for a structured agenda you can adapt and follow in your 1:1s.

Step 1. Create foundational sales enablement content

Every good strategy starts with a foundation. Sales enablement content, such as sales scripts, talk tracks, battle cards, comparison charts, email templates, and other everyday sales content is essential to your coaching strategy since it gives you a foundation for your reps to work up from.

It might sound like a lot, but you can get a head start with our Sales Enablement Toolkit, a free download with 8 customizable templates to get you started building this essential foundation.

This foundation should also include a well-structured sales process, with clearly defined pipeline stages that tell your reps the best way to move forward.

You can base a lot of this foundational content on historic sales data. Look back to find key best practices for your team, and build those best practices as the standard to which your reps should aspire.

Step 2. Divide your team into 3 groups

Each rep is an individual and should be treated and coached individually.

That said, you can normally group your reps into three categories, and base your main coaching techniques on which category they fall into:

  • Low performers
  • Middle of the pack
  • Top performers

Low performers may lack those foundational sales skills that every rep needs to succeed. They’re regularly missing quota and can’t seem to figure out why on their own. Coaching low performers takes more patience and empathy, and involves building their own self-awareness so they can effectively identify their main blocks and problem-solve on their own.

Middle performers are where you spend most of your time and energy. This middle 60% of your team aren’t batting foul balls, but they’re not home-run hitters either. Coaching this middle portion of your team helps motivate average performers and can boost their skills and strategies (or motivation) just enough to push them into the top tier of your team.

High performers are the all-stars. They’re hitting home runs all the time, and they’re loving every minute of it. Coaching these top-performing reps will help them maintain that motivation and challenge them to improve, but involves giving them a lot more leeway and accountability within those coaching sessions.

Pro tip: A sales leaderboard can give you a quick view of who’s ahead and who’s behind. Use a sales leaderboard — like the one that’s built into Close — to see which activities reps excel at, and which areas reps are falling behind on.

Step 3. Define key motivators for your team

Incentives run the gamut between luxury vacations, extra PTO, office upgrades, and of course, cold hard cash.

As a manager, it’s your job to find out what motivates your team best.

So, talk to your reps. What kind of sales incentives really get them excited? What motivates them more? Build your coaching around rewards and incentives that motivate your team, and you’ll be more likely to get buy-in from your reps.

Step 4. Create an individual coaching plan and goal for each rep

Now that you have more structure for coaching your team, it’s time to individualize that plan to each rep.

This isn’t something to do on your own and pass on to the rep. For your first few coaching sessions, work collaboratively to build a plan that helps them build the skills they feel they’re lacking, and set long-term goals for their future in sales that you can work together to achieve.

Step 5. Build fundamental skills in each rep and move them to advanced selling tactics

From these long-term goals, work backward to the short-term steps you can take to move each rep forward in their career and their skills.

It’s easy to fall into the trap of making a huge list of things each rep can improve, and working on everything at once. Don’t throw the book at them—work on one skill at a time to help them advance gradually.

Whether working to improve existing reps’ skills or onboarding a new sales hire, start with the basics you set up in your sales enablement content. Once the foundation is established, you can move on to more advanced sales tactics.

Step 6. Review and reiterate as needed

Once a coaching plan is set, that’s not the end of the story. As time goes on, continually review each rep’s progress. Get their feedback on how they feel coaching has affected their everyday sales life. When you see aspects of your strategy that aren’t going as planned, be willing to take that feedback and adjust. When you’re willing to make improvements, you’ll set the right example for your team.


Top 5 sales coaching tips to bring up your team’s batting average

With a basic strategy in place, it’s time to level up your game and increase your own skills as a coach.

Here are just a few tips for better coaching, but be sure to check out our full list of 25 sales tips & techniques to amplify close rates for your team.

1. Perform live call coaching

One of the biggest mistakes a sales coach can make is not listening to their reps on the phone. Sure, analyzing recorded calls is nice, but getting on a live phone call and hearing your reps in the moment is one of the best ways to get a feel for the market, understand your reps’ key abilities, and even coach in-progress calls to save deals that are on the edge.

With the right call coaching software, you can Listen (without being heard by either participant), Whisper (to speak only to your rep), or Barge (to join the conversation as a third party, heard by both the rep and the prospect).

2. Share ownership of your coaching agenda

When your reps are included in the process of building your agenda, they’ll feel more motivated to be there and take full advantage of these sessions.

So, create a shared coaching agenda with a tool like Google Docs or Miro. Allow your rep to add talking points, recorded calls, questions, or ideas they might have. This will help build an atmosphere of accountability on your team, and each rep will have the confidence to come to you with their struggles and their breakthroughs.

3. Encourage peer-to-peer coaching to help reps learn from each other

According to one study, it was found that more than half of sales reps rely on their peers to hone their skills.

While you absolutely want your reps to rely on you first as their coach, peer-to-peer learning can be an effective way to supplement your coaching efforts and reinforce best practices on your team, so you should encourage peer learning sessions that work alongside your individual coaching sessions.

For example, if a rep comes to you with a recorded call that didn’t go well, work with them to pinpoint the skill they need to work on to avoid the same mistake. Then, have them shadow calls with a rep who is proficient in that skill so they can learn from each other.

An ancient proverb says that ‘iron sharpens iron, so one man sharpens another’. Use your reps to sharpen each other’s skills, and you’ll build a culture of collaboration across your sales team.

4. Give reps the ability to approach you for help

Have an open-door policy, either physically in the office or virtually on Slack. Encourage your reps to come to you with their questions or problems. Make sure they’re aware when you’re online so they don’t feel shy to ping you with a question. Give them the opportunity to reach out for help by checking in with your reps outside of your coaching sessions.

In a remote setting, the right tech is essential for this. For example, use Slack status settings to show reps when you’re available to respond right away or let them know you’re in a meeting or busy with other work but you’ll respond later.

Or, show reps how to use the Invite feature in Close to invite their manager or a peer to join an in-progress call, getting help at the exact moment when they need it.

5. Base your coaching goals on real-time data

Data is your friend when it comes to coaching. Using real-time data on sales activities, pipeline, and deal status brings you up to speed before you even step into a coaching session. This allows you to stop wasting precious time talking about ‘what’s up with this deal’, and dive right into the specific steps and strategies reps need to move deals forward.

Top 5 sales coaching software & tools

According to recent research by Gartner, only 39% of sales reps feel that their managers effectively use technology to coach.

Don’t let your company waste money on software that you’re not even using. Instead, do your homework. Find out what kind of sales coaching software and tools you need to really be successful.

To that end, here are 5 top software options, plus why you should consider each one.

Pro tip: Looking for a deeper dive into software for sales managers? Check out our full list of today’s top 15 sales coaching platforms for high-performance teams.

1. Close: Call Coaching

Close is an all-in-one CRM that gives you integrated calling, email, and SMS alongside lead management features, a customizable sales pipeline, and (of course) Call Coaching.

Live Call Coaching in Close allows you to Listen, Whisper, or Barge depending on what the circumstances call for. That means you can silently Listen to the conversation, Whisper to your rep only, or Barge the call so both the rep and the prospect can hear you.

You can see a list of which reps are currently on calls, or join calls directly from the lead page. This allows you to have full context on the deal status and engagement history while listening to the call.

Close also stores call recordings so you can listen back to them later. And, since Close has the best native Zoom integration, you can also set up, run, record, and playback your Zoom sales meetings without leaving your CRM.

You should consider Close if: You want a tool where your sales team can live and breathe, a place where you can perform live call coaching or find the right data for scheduled coaching sessions without having to switch tabs and windows.

2. Chorus.ai

Chorus is a conversational intelligence tool that pulls data from the places your reps are communicating with prospects, such as call recordings, emails, and text messages. Then, it uses AI to give you insights into the conversations that work (as well as the ones that don’t).

You should consider Chorus.ai if: You like AI-based insights such as the best topics to discuss, frequently asked questions, most mentioned competitors, and more.

3. Showpad

Showpad is a sales enablement platform with a product specifically designed for effectively coaching your sales team. This platform also offers conversation intelligence, as well as AI-based transcripts of recorded calls. There are tools to identify weak spots in your reps, perform asynchronous coaching with recorded video practice and role play, as well as a pitch leaderboard.

You should consider Showpad if: You’re looking for a platform that integrates training programs with individual coaching, or if you need an option for asynchronous learning.

4. Ambition

Ambition is a coaching and gamification platform, complete with leaderboards, sales challenges, competitions, and other fun ways to motivate your team. Their coaching features include setting up groups for large sales teams, creating schedules and action plans for 1:1 coaching, rep activity insights, and pre-meeting assessments that your reps can fill out.

You should consider Ambition if: You manage a very large team, and need a place to schedule, organize, plan, and implement your coaching alongside gamification and incentives.

5. MindTickle

This platform is great for asynchronous coaching. Managers can set up missions for their reps to complete based on the skills they want to build, as well as see insights into rep performance. MindTickle also provides pre-made templates for coaching 1:1s.

You should consider MindTickle if: Your team’s schedule and circumstances require you to set up more asynchronous coaching.

Teach your reps to knock more deals out of the park with structured coaching

Whatever time, energy, and money you invest in coaching your reps, it will pay off in serious ROI.

That is, as long as you do it correctly.

Coaching your sales team effectively requires consistency, patience, and a rock-solid strategy to build off of.

These three ingredients start the recipe for an unstoppable sales team.

Ready to build your own plan to boost your reps’ skills and motivation? Download our free sales coaching plan template to get started.

DOWNLOAD OUR FREE SALES COACHING PLAN →