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Coaching a sales team: Your guide to high-performance sales coaching

Sales Forecasting Sales Management

great sales coaches quote

Chris. You’re so right.

Coaches live to lift people up and help them succeed. The best ones have a knack for seeing people (their abilities and their flaws) and improving their overall performance.

But coaching sales teams in particular can be tough. I mean, how do you coach someone when you see the results of their work (quota), and not how they work (inside their conversations with customers)? 

Imagine a hockey coach who only saw the final score from games and got weekly or monthly stats. You’d never expect that person to be able to coach their team well.

Unfortunately, that’s often what happens in sales. Managers review a few calls (usually at high speed) and they keep an eye on big numbers, like quota. But they miss the bulk of the work their reps do every single day. 

That’s not how you create a top-shelf sales coaching plan. Good coaches have an eye on the entire sales process, from start to finish, and can spot where sales reps make missteps along the way. 

So what exactly is sales team coaching? 

It’s the ongoing process by which you assess and shape your reps’ skills so they perform effectively as individuals and contribute to a sales organization. It’s how you encourage the right behaviors and correct the wrong ones.

Historically, sales coaching focused on training and hitting quota. It often skipped details about reps’ on-the-ground performance and skill set. Today, technology enables much deeper and more consistent assessments of reps’ work performance. 

It facilitates effective sales coaching.

Need an A-to-Z primer on sales coaching? Master these sales coaching techniques ASAP.

Is Sales Training The Same As Sales Coaching?

Not even.

Training isn’t tailored.

It’s a pre-set curriculum that feeds bulk information into new hires or reps who are retrained on new messaging, initiatives, tools, etc. Training is essential to sales teams, but it’s not focused on helping the individual. It’s about getting everyone on the same page around a given topic. Even when it’s done beautifully, training is prepared in advance to convey specific information to a trainee. 

Coaching, on the other hand, is personalized.

At its best, sales coaching uses overarching goals that are similar for the entire team (hit or surpass quota), but it supports each rep according to their needs, skills, and abilities. What happens in each coaching meeting is different, from the area of focus to the improvement plan. No two reps are the same and no two coaching sessions are the same.

Contrary to training, coaching is also an iterative, consistent, and full-circle process. It’s not one-and-done. 

Coaching allows reps and their managers to review what’s working and what’s not, assess why (that’s so important!), and make a tailored plan to move forward with behavioral changes. And in the next coaching meeting, they start by following up to see whether the right numbers are moving in the right direction. 

Is the rep implementing the plan? If not, what’s getting in the way? And if they are, have the changes moved the needle? 

Coaching is not a train-and-release program for reps. It’s a guided and grounded improvement experience.

Why Is Coaching So Important For Sales Team Performance?

When we describe what good sales team coaching looks like, it seems obvious that it’s worthwhile. But we can’t know that for sure unless we see whether it gets results.

It does. 

The biggest outcomes? Sales performance coaching turns B-players into A-players. Here’s what that means and why it matters:

Whether you know it or not, your sales team has three tiers of reps: high-performers (your top 20%), the middle of the pack  (about 60% of the team), and the lowest performers (your bottom 20%).

Coaching can take your top performers, your A-players, and turn them into Olympian-level salespeople in no time. These folks have a natural gift that deserves to be polished to perfection.

Sadly though, even the best sales coaching is never going to bring your lowest performers up to where you need them to be. Sure, it can help them make improvements, but they’re so far behind the eightball that they’re not where you can have the most impact for your time spent. 

It’s quite possible that your lowest-performers simply aren’t cut out for sales. Give them some coaching and see how they respond — one or two of your reps may surprise you! Just don’t invest the bulk of your coaching time on these folks. 

That energy’s reserved for the middle of the pack.

Those are your B-players. They have natural abilities, are motivated, and usually come close to quota… say 80-90% of it most of the time. They’re reliably decent at their jobs.

But they don’t get the results your A-players get, and they don’t know what to do about it.

You do. You know that coaching can take them from decent to good to great

This sales coaching path has a high ROI because B-player reps have the room to improve (in their quotas) AND the potential to improve (in their skills).

Just be sure that they also have the motivation and desire it takes to receive feedback, work on new skills, track the results, and do it all over again (and again). If they do, you have all the ingredients you need for successful sales team coaching.

Need inspiration?

Try this sales coaching template.

It has everything you need to move past “random acts of coaching” and zero in on high-impact coaching – the kind that motivates your team AND shows up in dashboards.

What Are The 3 Types Of Sales Coaching?

It’s true, there’s more than one. (What, you thought we’d grab a mixed-tape of hype songs and be ready to roll? Nope. We’ll set you up to do this right.) Here’s the background you need on the three main approaches:

Tactical coaching

This is data-backed coaching that’s focused on tactics. You’ll prioritize your coaching efforts based on facts and evidence about what’s really happening inside your reps’ calls.

Unsure of whether problems are happening in discovery, demo, or closing? You likely have your suspicions, but they’re not as good as knowing exactly where the problem is. Turn to the data to see where things go sideways, like when reps are ghosted.

Once you see where problems are, figure out exactly what the issue is. Look for keywords and phrases that may indicate what’s going wrong. Are they having issues with pricing? Are they asking open- or closed-ended questions? Are they talking too much?

Whatever the issue, you can coach on tactics to get them out of the habitual mess they’re in. Focus on sales behaviors that are relevant to that area. That might include improving on poorly executed questions during discovery calls or a lack of follow-up.

Engage in tactical (data-backed) sales team coaching and you’ll win on three fronts:

  1. You’ll have proven facts to address with reps, so you don’t have to rely on anyone’s anecdotes or gut feelings about how things are going.
  2. You’ll spend time actually coaching during meetings, because you’ll know in advance where the biggest issues are.
  3. You’ll know what works when you implement new behaviors and practices. If you watch the data, you’ll see improvements. (And if you have the right software, you’ll even be able to see whether your reps are implementing your suggestions!)

Tactical sales performance coaching gets to the heart of your prime coaching opportunities. It’s where you start.

Strategic coaching

Feeling more adventuresome? Time to dip a toe into strategic coaching, where you’ll play across a deal’s entire path, not just in parts of it.

There are risks hiding inside your reps’ deals. If you know where to look, you can catch them and strategize with your reps to create solutions.

Just like with tactical coaching, you want to look at risk-based data before you go into meetings with reps, so you don’t spend them asking rapid-fire questions to get the lay of the land. Because let’s be clear: Q&A sessions are not coaching. They’re information gathering, nothing more.

Coaching is what happens when you strategize about which solutions you’ll implement and how.

With strategic coaching, you’re going to focus on deal breakers. These risks can send your entire deal off the rails if they’re not caught in time. They include known risk factors, such as a deal not being multi-threaded, reps not getting to power, low email velocity between reps and customers, and several others.

If these risks are present in your deals, take action immediately. Create a de-risking strategy with your rep to smooth the deal pathway and eliminate problems. That often includes teaching reps how to learn more about the customer’s context and use that information to their advantage to address the risks in their deals.

Truly, this type of strategic thinking is where you’re most valuable as a leader. You have years of strategic experience to pass on to reps.

Personal Coaching

Those first two coaching styles are (justifiably) focused on deals. It’s what everyone’s here for. 

But how do you coach the people who are executing those deals? How do you ensure that your team is in it with their heart and soul? Energy-boosted? And motivated? 

You coach your reps, not their deals. The upside is that if you do this well, the positive results will spill over into your tactical and strategic coaching as well.

This is about helping your reps shake off a bad call and get back to that winning streak.

First, you need to know what motivates your reps. They all want to win if they’re truly sales people at heart, but they each have different reasons for that. Ask a few insightful questions and you’ll see the differences come to light:

  • What was the high point of your work week?
  • What was the best call you had this week and why?
  • What’s the toughest part of your sales cycle today?

Once you have a better sense of what’s important to them, you can go a layer deeper to understand what’s really happening in the deal for them.

Often, it takes at least one or two follow-up questions for your reps to understand that you want something more than “To win!” when you ask “What do you want out of your next call?” You might have to throw down a “Fair answer! Now tell me what you really want out of it. I’m genuinely curious about what you want to achieve here.”

Scratch beneath the surface and you’ll see where your reps feel vulnerable and what they value. Both will help you understand how to motivate them.

Why Does Most Coaching Fall Short?

There are four main reasons sales coaching doesn’t succeed:

#1 You don’t have time.

Oh, we know.

It’s the number one complaint from most sales leaders, that they can’t possibly listen to every call happening on their team. And that’s fair. Over-listening is painfully ineffective and woefully inadequate, especially if you need to scale your team.

Not only is it labor-intensive, it’s not helpful in terms of detecting problem areas for reps. You can listen to 50 call recordings in a row from start to finish (but don’t), and you’ll still be making a best guess at what’s going wrong. Don’t waste the bulk of your calendar on something that doesn’t work.

Good coaching doesn’t need more time, it needs to be focused. It needs to zero in on places that are truly problem areas. In other words, good coaching isn’t about spending your time finding problems, it’s about spending your time solving them.

Sure, you have to spend a little time understanding your reps’ challenges before you meet with them, but this should take a fraction of the time that listening to every call takes.

#2 You don’t know where to start.

Fair enough. You’re staring down every deal across every rep on your team. It may be tempting to throw a dart at it all and shout “THIS is where we’ll begin!” But randomness won’t serve you like prioritizing real problems can.

So what’s the issue? Well, it’s figuring out what those ‘real problems’ are. 

That requires intense data assessments. But you can’t possibly replicate the data analytics you’d need to gain useful insights. At best, and with a lot of (painful) background work, you’ll make educated guesses about where to begin. 

The good news is that AI can point you in the right direction. Coaching software can pinpoint the right coaching opportunities. It can tell you that a new hire isn’t ready to demo, that a rep spends too much time talking about features instead of value, or that a rep doesn’t ask clarifying questions after customers provide tidbits of information.

Imagine it, a clear coaching plan emerging from a sea of data. (It happens.)

#3 You can’t measure coaching impact.

And really, what’s the point of investing time and money into solutions if you don’t know whether they work? You won’t know which changes get results, and you won’t be able to roll out what works across the rest of your team. 

Scarier still, you won’t even know if your reps are actually implementing the changes you discuss with them. If you don’t see results after weeks of coaching, is it because the tactics don’t work, or because the rep doesn’t use them?

Focused coaching can and should be measured. That means tracking more than traditional KPIs, like pipeline numbers or bookings or quota. 

You want to track two things: whether your rep is implementing the tactics and strategies you coach them on, and how they do when they implement those new moves.

If you provide focused coaching that addresses one topic at a time to a rep who’s already holding their own, you’ll be able to measure the impact of each behavioral tweak you make together as part of a larger action plan. 

#4 Your team is hard to coach.

Ouff. It’s a tough one.

If there’s no coaching culture on your team, it may take some work to move in that direction. But it’s worth it. 

Staying in a place where you can’t coach effectively is NOT an option at a sales org. Neither is having reps who aren’t coachable. If you have those folks on your team, you need to find them fast. (Yes, so you can replace them with coachable ones.)

The thing about the approaches we’ve discussed so far is that because they’re largely data-based, they’re not subjective. They’re based on objective numbers. And at their core, the top reps love objective numbers. They’re tangible, chasable, and winnable for a salesperson.

And when reps see that you’re coaching based on reality (i.e., data) and not subjective opinions, there’s less push back. They don’t have to prove that their gut instinct is more accurate than yours. Everyone is dealing with the same data, the same deal story.

In this context, they’ll also see exactly how your coaching improves their numbers. That’s going to create a positive feedback loop in which they crave feedback because they know they’ll win more often.

If you show them how data-backed coaching helps them win more often and they still don’t come around to it, you have yourself a problem. (Hint: It’s the rep.)

Use This Five-Step Coaching Framework With Your Team

No more random acts of coaching. We’re well beyond “What is sales coaching” at this point.

You’re here for high-impact sales performance coaching that lights up reps AND your dashboard. 

Elite sales managers use a five-point framework to get their coaching to pay dividends. Here are your Coles notes.

Step 1: Focus on one area per quarter

Pick at the surface of a bunch of issues, and you’ll be left disappointed. Go deep in one place to get clear results. Do that by focusing on sales techniques for calls and strategizing to avoid high-risk deal breakers. Give your reps the confidence to dust themselves off and get back on the horse whenever they have a rough call.

Step 2: Identify coaching opportunities 

Identify your reps’ weak points using data (conversion at deal stage, deal cycle length, etc.). Focus on issues in discovery, objection handling, and low-email velocity. Begin to strategize around larger pipeline issues, like account strategies, pipeline de-risking and more. Bring self-coaching into the picture.

Step 3: Build your team coaching plan

Make sure your reps know what corrective, winning behaviors look like. Get into tactics, like asking too few open-ended questions, steamrolling objections, not following up, and more. Then move into strategies, like getting to power, using compelling events, and risk-mitigation, as well as personal boosters for your rep, like high points from the week and new lessons learned.

And it all starts with a sales onboarding plan.

Step 4: Back it up with data

Measure their progress in very specific areas. Sure, their overall revenue and pipeline numbers should go up, but for now, you’re interested in measuring whether they’re correcting behaviors. What’s their precise talk ratio on calls? Which risks are still present in their deals? And what have they done for themselves lately, like listening to top calls from other reps?

Step 5: Track team progress

Take stock of your entire coaching endeavor. What’s the overall effect of your coaching? Are reps adopting new frameworks? Are other problems preventing them from reaching their goals? 

Craving more detail? The sales coaching template for high-performing teams is up for grabs (for free) here. It has all the deets on the most effective coaching approaches.

EXAMPLE: A Coaching Plan

Let’s take one tactical coaching example and run it through from start to finish. Here’s what the whole thing might look like:

Step 1: Your rep’s customers don’t always make it beyond discovery. Something’s going wrong at that stage. You decide based on the data you’re seeing to focus on discovery and what’s happening there.

Step 2: You look at data from several key areas to see what might be the problem. The keywords and phrases data shows that they’re likely struggling with their line of questioning. They’re doing “light discovery,” so they’re not uncovering the information they really need to move the deal forward.

Step 3: You talk with your rep about implementing potential solutions. These include asking more open-ended questions (which they aren’t doing now), sprinkling questions in throughout a reasonably paced conversation instead of going through a checklist of rapid-fire questions, and talking less and listening more.

Step 4: Together, you track their data. You use coaching-friendly conversation intelligence software to track whether their questions are open-ended, where they ask questions during the conversation (all up front or throughout the call), and their talk ratio. You want them to move from talking 60% of the time to somewhere closer to 40%.

Step 5: Now that you know your rep is implementing your suggestions, you can see how these numbers are affecting their deals overall. What’s working and why? Does anything need to change? At this stage, you can tweak their discovery tactics even further to fine tune them, or if they’re doing well, maintain the use of these tactics and move to the next topic in this rep’s coaching journey.

Want More Types Of Sales Team Coaching?

Can do. 

There are other ways to bring coaching into your team’s culture and they’re incredibly effective, if often overlooked.

The first is peer-to-peer coaching. Salespeople are known for being competitive, but they also like to show off their chops. 

Anyone on the team can share moves that work well for them, or even ones that don’t. Once your team is used to keeping an eye on their data, have them share what’s working. That might include words and phrases that help sell a new offering, or effective ways to handle a familiar objection.

This can be as formal or informal as you like, but sharing info on a Slack channel or through your Call Libraries (lists of curated, top-notch calls) is a great start. You can also play calls during team meetings and encourage reps to discuss their thoughts and opinions before you provide your own feedback. This helps get everyone used to sharing and critiquing with an eye to learning what works.

A slightly tweaked version of this is having coaching mentors

You can ask established reps to share their winning moves directly with newer members of your team. Your older reps will appreciate the recognition they get for knowing their stuff, and they’ll hone their leadership skills as they coach next-gen team members. (That’s something they won’t often get to do, but it’s essential prep if they’re climbing the corporate sales ladder.)

You can also move beyond your own team to encourage mentoring between teams at different stages of the customer journey. AEs can coach new SDRs on the typical concerns customers have when they reach AEs. This will help SDRs anticipate issues in advance and create a silky smooth customer journey. (Enterprise with Commercial, for ex).

There’s a third type of (stealth) coaching that most sales leaders forget to use, and it’s the most effective one of all: self-coaching.

Create a sales athlete. Get them into benchmarking and personal bests by having them watch their past performances. 

Anyone who has ever listened to a recording of themselves knows that what we *think* happened sounds entirely different from what *actually* happened. We notice things during a review that we didn’t notice during the call (or we reframe things in our heads so they match our own narrative).

A nice side-effect is that reps who get used to critiquing their own work become more open to hearing coaching advice from others. Living in a coachable mindset really does matter. Here’s how it happens through self-coaching:

Step 1: The rep identifies an area of improvement.

Step 2: They track their progress week over week.

Step 3: They start craving external coaching advice.

Self-coaching is a win that doesn’t cost you anything. It’s low-touch, so it doesn’t eat up your time or money. Plus, your reps will be better prepared to engage in their improvement plan when you meet for 1:1s. For new reps, it’s also a gentle way to ease into a coaching culture as it’s not intimidating. It’s just the rep and their own call recordings (and accompanying data, if you’re using the right software). 

Sidebar: A Call Library is essential to this type of coaching. Reps must be able to access their past calls any time, anywhere.

Unleash AI. Then Coach To Win.

Well there they are, your new approaches to sales performance coaching: tactical, strategic, personal, peer-to-peer, mentoring, and self-coaching. They’re your ticket to a fully realized coaching operation. 

Here’s a quick recap of three strategies that are key to your own coaching success:

Tactical coaching

This is your foundation. It’s the data-backed approach that’s based on reality, not opinions.  Relying on evidence instead of your gut (or your reps’ rose-colored glasses) means you can uncover risks in your deals, see across your entire pipeline, and use a focused sales team coaching approach that wins. When you know exactly where reps are struggling, you can teach them how to respond.

Strategic coaching

Your reps’ deals are at risk, even the ones that look like they’re going swimmingly. Detect those risks and create strategies to address them. Don’t waste your coaching time figuring out what’s happening. Spend it coming up with solutions and a proactive plan to close more deals. 

Personal coaching

Coaching deals from start to finish is important. So is strengthening your reps along the way. The top teams have healthy, vibrant, and positive coaching cultures. Sales coaching isn’t seen as threatening, it’s viewed as something that improves everyone personally and professionally. Wins beget wins. Boost your people, and your dashboard will light up too.

Want The Sales Leader’s Playbook for High-Impact Coaching? It’s yours for free, here, and it’s a detailed look at everything we’ve talked about here.

Become A Better Coach Without Even Trying

You may have heard… Gong is the #1 sales coaching platform. 

Wondering how it works? Gong’s sales training software tracks every phone call, email, and web meeting between your reps and customers, then analyzes them to get insights about individual deals and your overarching pipeline. 

Take your top-performing reps’ moves and roll them out across your entire team. (You’ve always wanted to clone your top reps, right?) It’s an easy way to coach everyone using a winning playbook. 

Track each rep’s progress (remember, you’re coaching based on data now), and make adjustments based on what’s really happening inside each rep’s deals. 

You’ll also get insights into the risks hiding in your pipeline so you can keep things from going sideways. Here’s what the view looks like:

sales pipeline view screenshot

Once you have insights into risks, you can tailor your coaching to help reps improve their skills and win more deals. Your entire pipeline will become stronger and more reliable. 

It’s the little things that matter, like talk-to-listen ratios, addressing the competition, or involving a decision maker. Those individual skills all add up to major changes in your numbers. 

Won’t it be sweet to watch each rep’s numbers improve week over week?

sales team stats screenshot

Now’s The Time.

Interested in seeing Gong surface the top coaching opportunities for your team? Book your consultation to see Gong in action. You’ll have a winning solution and your leadership team will never have to ask “What is sales coaching” again.

See the magic of Gong in action

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