Sales coaching: How to coach reps to succeed in 2023

High-impact sales companies rank at the top of the list for many reasons, but one of their most enviable traits is that over 75 percent of their reps achieve quota. Meanwhile, companies in the mid- or low-impact range may be struggling to reach even 25 percent quota attainment.

If you’re one of the hundreds of businesses striving to boost your reps’ sales numbers, your first question has to be: How do these high-impact companies do it?

The short answer? Comprehensive sales coaching.

But coaching isn’t intuitive. Many people either don’t want to do it or don’t know how. According to sales expert Norman Behar, many sales managers:

• Don’t feel they have the time to coach

• Don’t understand the benefits of coaching

• Are concerned about putting reps down with criticism

• Have no idea how to begin coaching

We can’t give you more time in your day. But we are here to provide solutions to the last three issues. In this piece, we’ll take you through the ultimate guide to sales coaching so that you can direct, motivate, and train your team to become sales superstars.

Sales coaching vs. sales mentoring

Sales coaching, sales mentoring, and sales training are all meant to enhance sales rep performance. But each method approaches this goal from a slightly different angle, so it’s essential to know the variances.

Sales training involves more generalized teaching of universal sales strategies to multiple reps. These strategies aren’t geared toward individuals, and they’re usually practiced in hypothetical situations rather than with actual prospects. Sales training is all about opening reps’ eyes to new tactics that they can use to increase their success.

Sales coaching adopts a more personalized approach but remains focused on multiple sales reps. Sales coaches look at company data and sales team KPIs to pinpoint specific strengths and weaknesses. They then work with the sales team on identifying new strategies to actively use on the floor.

Sales mentoring takes the personalized approach a step further. Sales mentors meet with sales reps one-on-one to evaluate their overall career trajectory and the support they need to achieve their goals. Some sales mentoring can overlap with coaching if the rep is struggling in certain areas. But for the most part, mentoring is about crafting a long-term vision, while coaching and training focus on day-to-day improvements.

Why is sales coaching important?

The sales industry is always evolving. Whether it’s market demographics, societal impacts, economic fluctuations, or simply a change in the weather, something is always there to shake up a sales rep’s day. With that much variety, it’s hard for even your best reps to be experts in every aspect of sales.

Sales mentoring and coaching bring an outside perspective: reassuring your sales reps when they’re right and guiding them when they’re wrong. So, it’s not surprising that companies with a dynamic coaching program average at least 28 percent higher win rates than their competitors.

It’s not surprising that companies with a dynamic coaching program average at least 28% higher win rates than their competitors.

Additionally, sales coaching can reduce employee churn, increase company performance, and raise sales rep morale. Data shows that no other productivity investment improves rep performance better than coaching.

But beware: You don’t want to jump into any type of coaching without doing your research and ensuring you have the best possible coach for your needs.

What makes a killer sales coach?

Many sales organizations and sales leaders waste precious resources on random and ineffective coaching approaches. This tells us that most organizations understand the importance of sales coaches but not how to go about finding an impactful one.

So, what separates an excellent sales coach from a bad one?

It’s all about the approach.

Essentially, a great sales coach—like any great teacher—comes from a place of empathetic listening. They assess where the work needs to happen and then come up with specific strategies to address weak spots. A sales coach isn’t a boss; they’re a counselor.

Effective sales coaching tips

While a good sales coach will adapt to a particular company culture, there are a few strategies that are effective in any coaching situation. Let’s look at a few universal tips to help you become a successful sales coach. Then, we’ll dive into coaching tactics for specific types of sales and sales issues.

1. Vary your coaching style

   Sales itself uses a wide array of techniques and styles, so why shouldn’t sales coaching? Depending on what your team needs, you can try different approaches, including:

   • Tactical coaching: very detailed suggestions about certain situations
     
     Specific skill coaching: looking at individual skills (like question strategies)
     
     Strategic coaching: big-picture coaching

   All these coaching styles may be useful for various circumstances, and all provide diverse benefits to the team. Incorporating each of them when appropriate will give your coaching more layers. Plus, your trainees will be able to see that you’re not just giving them cookie-cutter training.

   As Birst CEO Jay Larson puts it, “Today, top sales reps want to work with leaders who are invested in their success and will help them develop both their sales skills and general business skills.” Staying flexible while offering both big-picture and situationally tactical coaching is the key to success.

2. Let your reps own their process

   Sales reps can be a tough breed to coach because so many of them embrace an independent state of mind. Someone who works independently and on commission doesn’t love being told what to do.

   So, how do you coach without being overly instructive?

   You enable your reps to help themselves.

   According to Ray Makela, managing director of Sales Readiness Group, “People are very aware and often extremely critical of their own performance…the one or two points they make are right on target if we give them a chance to analyze their own performance instead of telling them what to do. Not only will they be more likely to ‘own’ the solution, but they will often surprise you with the suggestions and insights they bring.”

   As stated above, great coaching works from open-ended questions and self-directed learning.

3. Focus on the reps with the most to gain

   Sales coaching benefits the entire team, but there are always going to be top performers and low performers for whom coaching won’t have as significant an impact.

   That’s why it’s necessary to direct your focus on the middle—your average sales reps. It might sound like you’re leaving others behind, but this is often the most effective strategy for the overall company. Take it from Shelley Cernel, VP of Marketing at Thirty Capital:

   “Rather than focusing on the leaders and the laggards, coach the middle two-thirds of reps who have both the room for improvement and the incentive to be top performers. A study from HBR showed that coaching has a marginal impact on either the weakest or the strongest performers in the sales organization.”

   By focusing on the sales reps for whom coaching can make a real difference, you’re maximizing your impact (and ROI).

4. Use sales data to your advantage

   When you’re coaching, chances are the sales managers already have data reports ready to go. Even if they don’t, nervous reps are frequently obsessive about their numbers. Take a look at sales data to determine where the problems lie so you know what to address. For instance, if reps are turning leads into prospects but aren’t able to close, then that’s where you need to direct your efforts. Divide and conquer the trouble spots in the sales funnel—don’t take on the whole thing at once.

SaaS sales coaching

SaaS (software as a service) sales can be deceptively difficult. It’s usually simple to get a prospect to try a free demo but hard to convince them to buy your full-price versions. SaaS coaching is all about focusing on the problems unique to SaaS sales and the particular buyer’s journey of SaaS clients.

The most challenging aspect of SaaS sales is staying engaged with prospects who are actively using demos. Some demos extend as long as 60 days. During that time, it’s easy for sales reps to forget about their demo prospects amid all their other communications.

This means sales coaches should focus on that part of the sales pipeline: the journey between persuading the prospect to start the demo and closing the sale. Ask reps to create follow-up schedules that involve gathering specific feedback about the demo. If a prospect loves particular aspects of the demo, those are great selling points and potential opportunities for cross-selling or upselling.

Consultative sales coaching

Consultative sales coaching refers to any coaching done by a third-party sales coach, not an in-house sales manager. This type of coaching is very common, but it does come with challenges.

Most notably, consultative sales coaches have to play fast catch-up on company policy, history, and culture. It’s not their company, and despite their expertise, they need to become familiar with the practices and culture to help their trainees.

Our best tip? Start with listening. Talk to workers at all levels of management to get a full picture of how things work at the company before you start instructing. Your sales reps will be more likely to listen if they know you took the time to learn about them.

One important note: Consultative sales coaching is not the same thing as consultative sales. Consultative selling is a sales style where reps act as advisors, while consultative sales coaching refers to the practice described above.

Coaching closing sales

No matter how good a sales rep may be, closing sales is never easy. Coaching closing sales requires a delicate balance between finding the style that works for a rep and getting that rep comfortable with multiple strategies. Ideally, every rep should be able to close in different ways—it all depends on the client.

Michael Gorman notes, “As a coach, it’s important to take techniques for closing the sale seriously because they can make or break the business. They define the final decision determining if your efforts will amount to a profit or nothing, meaning that mastering various techniques is critical to your reps’ success.”

That said, not every rep is going to excel at every technique. If you have a rep who’s struggling, focus on finding them one solid strategy—it’s still going to go a long way.

How to ask sales questions

Asking the right sales questions is as important as knowing how to sell. Powerful sales questions are the secret to getting prospects to talk themselves into a sale. They’re one of the most effective tools in a salesperson’s arsenal, and not enough sales reps know how to use them.

When you’re coaching sales questions, make sure reps have a purpose and a throughline for their questioning. It’s not enough to ask yes or no questions—honest, friendly, and open dialogue is the goal. Reps should be pulling from their skills in personal selling and relationship selling to build rapport and dive deep into their prospect’s needs.

While coaching soft skills (like charisma and empathy) can be tricky, if you ensure every sales question has a natural follow-up, your coaching will be effective.

Dealing with objections

The majority of sales is about thorough preparation to avoid obstacles before they occur. It’s no different with sales objections. Many reps get deflated by objections and don’t know how to work around them. That’s what a good sales coach is there for.

In addition to running objection practice scenarios, a sales coach’s job in this situation is to diffuse the importance of objections. The more a sales rep can understand how common they are, the more they will internalize a critical sales rule: the objections are not about them—they’re about the prospect.

This type of sales psychology works just as well on reps as it does on prospects. When sales objections are no longer huge barricades, reps can make creative choices and keep moving.

How do you know if coaching is working?

With so many external factors affecting your sales, it can be hard to know if your sales coaching is having an impact. So, we’ve made a list of things to look for. When your coaching is working, you’ll see the results in two main areas: sales metrics and sales rep behavior.

Sales coaching and sales metrics

The first place you’ll spot success is in your quotas, KPIs, and sales goals. Ideally, if your team is learning from your sales coach, you’ll see improvement in these numbers across the board. If you want to get more specific, work with your sales coach to zero in on the metrics they focused on.

Ensure you’re evaluating all metrics in comparison to where they were, not in comparison to what the goals might be. If your company goal is a 95 percent quota attainment per month and your reps pull 90 percent, that looks like a failure. However, if they were at 80 percent before you started coaching and now they’re at 90 percent, that’s a huge success.

Some of the metrics you might want to consider assessing include:

• Deal size

• Deal profit

• Quota attainment

• Quota exceeding

• Frequency of upsells and cross-sells

• Client retention rate

• Number of prospect conversations and sales calls

• Number of leads contacted

• Overall sales team revenue generated in each sales cycle

Sales coaching and sales rep behavior

The next place you’ll want to look for success is in your reps’ sales performance and experience. Sales is a highly competitive and fast-paced business, and sales reps are likely to feel frustrated with companies that don’t provide them with the resources and tools they need to thrive.

Great sales coaching can turn that feeling of resentment around. When reps receive reassurance and guidance, they perform better and are more likely to see a path to promotion and satisfaction.

Once your coaching sessions finish, send out an employee survey. Find out how your reps feel about their job satisfaction and the company at large; this will help you gauge whether reps are headed for the door or inspired to stay. You should also look at the promotion rate within your team. If it goes up, chances are your coaching was a wild success.

Impress your sales coach with a quality CRM

Your sales coach can only improve your team as far as your technical assets allow. If you don’t have the necessary organizational sales funnel software, your sales coach can’t help your reps speed up their communications. If you don’t have sales pipeline software, your sales coach can’t fully help your reps increase their conversion rate.

Before you bring in your sales coach, make sure your team is set up for success with a high-powered CRM like Zendesk Sell.

Zendesk Sell is a user-friendly, high-functioning sales CRM designed to maximize productivity, pipeline visibility, and revenue for sales teams. With Zendesk, your sales reps can take their coach’s advice and easily put it into practice with their prospects. Additionally, you can use Zendesk’s fast tracking and reporting abilities to follow your most valuable metrics and make the most of your sales coaching.

Request a demo today and ensure your sales coaching makes the maximum impact.