3 Types of Coaching Sessions You Need to Have With Your Sales Reps

Christian Pieper

April 8, 2024

Today’s sales managers have a lot of their plates. From meetings to administrative work to team leadership, they rarely have a moment to spare.

Yet, when managers were asked what their most important task is, coaching their reps was the most popular response.

Why? Because sales coaching, when it’s done well, empowers sellers to close more deals, faster. In fact, nine out of ten sales managers agree that coaching positively impacts their team’s performance.

But taking an ad hoc approach to coaching won’t cut it. To see real results, a structured coaching strategy is key. You also need to ensure your managers are equipped with the skills and tools needed to effectively lead three essential types of coaching sessions.

So, what types of sales coaching sessions do you need to have with your sales reps? Read on to find out.

Coaching must go beyond deal reviews

Creating a “coaching culture” is often identified as a priority for selling orgs. We define a coaching culture as ongoing, data-driven, and infused into every manager and seller interaction.

When done well, it works.

Research shows that coaching can positively impact the sales metrics that matter most, including win rates and quota attainment.

Unfortunately, many orgs struggle to create this coaching culture and instead take an ad hoc approach focused on short-term fixes. This approach is almost always primarily focused on deal reviews.

Of course, as-needed deal reviews are an important way to improve the outcome of a given sale. But on its own, deal coaching isn’t enough to improve long-term results.

The best sales orgs take a different approach to coaching. Rather than focusing solely on deal coaching, they deliver a blend of coaching types provided delivered at regular intervals to improve long-term success

How the best sales managers are coaching their reps

When athletes ask for coaching, it’s usually to address a specific issue with their game.

The same can be said for sales reps.

However many orgs struggle to identify rep weaknesses, which makes effective coaching a struggle.

According to our 2024 Chief Revenue Officer and Sales Leader Outlook Report, only 40% of C-level executives said they can identify rep strengths and weaknesses.

The first step to effective coaching is to understand rep strengths and weaknesses. To do this, you can take a look at your win/loss reports as well as call recordings to get a better understanding of where reps need improvement. From there, you can equip managers with what they need to “fix” those issues and get your reps back into the field with the skills they need to close more deals,

Let’s take a closer look at the three types of coaching the best sales managers are delivering to reps — and how often they’re doing so.

#1 Opportunity sales coaching

When someone hears the phrase “sales coaching,” their mind might immediately go to opportunity coaching. That’s not surprising, as it’s the most common type of sales coaching. Our research found that 85% of sales reps report being coached on open deals.

Opportunity coaching is an important way to improve the outcome of a deal. For example, a sales manager might identify that something in a deal isn’t going as planned. This might be based on feedback from the rep during a pipeline review meeting. Or, they could get insight by leveraging a conversation intelligence solution that sheds light on how the rep is performing.

In either circumstance, the manager can provide opportunity coaching to help the rep steer the deal back on course. And this will improve the chances of them ultimately closing the deal.

How often are the best managers delivering opportunity coaching? Sometimes, this coaching happens at a regular cadence — for example, during a weekly pipeline review. At these meetings, reps and managers discuss current opportunities and how to move them forward.

Often, though, opportunity coaching is delivered as needed, like when a rep raises a question or concern or meeting intelligence uncovers an issue.

#2 Skills sales coaching

In general, skills coaching is a lot less common. A mere 24% of reps report being coached on skills.

While opportunity coaching improves the outcome of a single deal, skills coaching is required to ensure reps have the skills and behaviors needed to close deals consistently.

The best sales managers recognize the importance of skills coaching on long-term behavior. As such, they aim to deliver at least one skill-based coaching session per month per rep.

What skills do they focus on? The short answer is, it depends. The first step is for organizations to identify the knowledge, skills, and behaviors a rep needs for success by developing an ideal rep profile (IRP).

Then, each rep should be measured against this gold standard. This helps managers identify where there are skills gaps. Armed with this data, sales managers can deliver targeted, personalized skills coaching that addresses the needs of each individual rep.

#3 Targeted sales coaching

If there’s one thing sellers can count on, it’s that things are always changing. New products are released. Pricing or packaging is adjusted. A new competitor enters the marketplace. And those are just a few of the many changes faced by reps.

The best sales managers deliver coaching sessions to address changes and ensure reps are equipped to adapt. Typically, targeted coaching is a single session on a specific, targeted topic — often followed by enablement content such as content, training, or a role-play exercise.

When it comes to sales coaching, follow-up is key

Sales managers are busy. But the best ones know that coaching is worth the time and effort. On average, top managers complete 12 coaching sessions per month.

But coaching isn’t a one-time event. For example, a manager can’t simply deliver a skills coaching session focused on objection handling, check it off the list, and never think about it again — at least not if they expect actual improvement.

The best managers know that proper follow-up and ongoing reinforcement are key to effective coaching. Our analysis found that top managers are three times more likely to assign content, training or a role-play as a follow-up to a coaching session.

This follow-up is paying off. Reps who are assigned follow-up actions post-coaching see an average improvement of 13 points in Sales Readiness Index scores.

How to measure sales coaching effectiveness

The goal of sales coaching is to increase the effectiveness and efficiency of sellers. With the right blend of sales coaching types, you can not only improve the outcomes of individual deals but also drive skill development and lasting behavior changes among your sellers.

But without continuous measurement, it’s difficult to gauge whether your sales coaching is actually driving meaningful results.

That’s why it’s essential to measure the effectiveness of your sales coaching. This allows you to identify what’s working (so you can do more of it) and refine your approach when needed to maximize impact.

But how can you measure sales coaching effectiveness? There are a few factors you’ll need to consider.

Sales performance metrics

One of the most straightforward ways to determine the effectiveness of sales coaching is to track key performance metrics like:

Win rates
Average deal size
Sales cycle length
Quota attainment

If you see improvements to these metrics over time, it may indicate your sales coaching is making an impact. If these sales metrics worsen, there may be opportunities to optimize your sales coaching efforts.

Skills improvement

Every sales rep needs certain skills and competencies to be successful. The purpose of skills coaching is to ensure sellers have mastered these essential skills.

Be sure to track the development of your reps’ skills over time. Improvements in these areas suggest sales coaching is making an impact.

Behavior change

A sales rep may be actively engaged in every sales coaching session. But that doesn’t necessarily mean they’re applying your feedback while in the field.

Be sure to track behaviors over time. For example, if you have a seller who dominates conversations or uses a lot of filler words, track to see how this changes over time. You can do this by observing the seller during calls or using conversation intelligence tools. If you see improvements in behaviors, it’s a sign that your sales coaching is effective.

Sales rep feedback

Ask your sales reps for honest feedback on your sales coaching. Chances are, you’ll get valuable insight into what you’re doing well and what you can do differently to better support and coach each sales reps.

Start closing gaps and optimizing seller performance with coaching

Sales coaching can have a significant impact on the bottom line. With consistent, data-based coaching, you can build an entire team of sellers that’s always ready to engage buyers and close deals.

But deal coaching alone won’t cut it. Instead, sales leaders must use a blend of deal, skills, and targeted coaching to ensure each seller has the support they need to refine their skills and behaviors and close more winnable deals.

Sales coaching doesn’t have to be complicated. With Mindtickle’s AI-powered revenue enablement platform, you can start delivering effective sales coaching at scale.

With Mindtickle’s sales coaching tools, you can pinpoint the strengths and weaknesses of each seller. You can use these insights to deliver both manager-led and AI-powered sales coaching to improve deal outcomes and long-term skills and behaviors. With Mindtickle, you can keep a pulse on sales metrics and skill development to see whether sales coaching is making an impact and where there are opportunities to optimize for greater impact.