Why Sales Coaching Fails—And How to Do It Better

Often, the most critical assistance a sales manager can provide a seller is to demonstrate what “great” looks like.

Stop for a moment and remember an early experience of doing something you had never done before. Remember the feeling of doing something you really wanted to be great at as quickly as you could. Odds are it took someone who had been there before to help you understand the rules, avoid common mistakes, and make the most of your natural abilities. It doesn’t matter whether your memory was from playing a sport, being on the debate team, or tying your shoes for the first time. The person who helped you was your coach.

The idea of using traditional coaching methods to help develop people on the job surged in popularity during the early 1990s. Over the last few decades, “coaching” has become both a signifier of the desirable way to manage people and a catchall term used haphazardly to group almost all manager-to-rep interactions. Most sales leaders (and virtually all sales training professionals) believe that if sales managers would just “coach” more frequently and effectively, then sales performance would improve.

The coaching that is used every day in sales organizations means conversations that involve some or all of the following:

  • Encouraging self-discovery
  • Assessing performance
  • Providing feedback
  • Setting goals
  • Driving behavior change
  • Having difficult conversations
  • Building confidence
  • Reinforcing training

Frequently, the term “coaching” is employed when leaders want sales managers to change some aspect of salesperson behavior without coming across as being too directive or controlling. Their hope is that through some magic bag of coaching skills, the salesperson can be skillfully and subtly manipulated into discovering the new approach on his or her own. Occasionally that can work, but in our experience it’s the exception, not the rule. Far more frequently, coaching conversations turn into a game where the salesperson knows exactly what the manager is trying to drive and just plays along.

The most frequent application of sales coaching follows a pattern:

1. The manager accompanies the salesperson to a visit with a customer (or listens in on a call).

2. Sometimes the manager has an observation checklist of behaviors to look for, but frequently does not.

3. After the customer interaction, the manager asks the rep to self-assess, “How do you think that went?”

4. The salesperson offers a few observations (“I could have done a better job of . . .”) and then quickly shifts to discussing the customer or the opportunity.

5. The sales manager explains where he or she agrees and disagrees with the manager’s self-assessment.

6. Together, the manager and rep agree on what the salesperson will do differently the next time.

7. In rare cases, the manager actually follows up afterward to ensure the committed actions are done.

Here are the problems with that approach. First, there are plenty of good models available for leading a traditional coaching interaction. However, few of them help managers diagnose the core issues, and even fewer drive the discipline required to form new habits. So coaching builds awareness of potential issues but not the pathways to results. Second, these conversations are only rarely guided by a larger development plan. In fact, from one coaching interaction to the next, it is likely the salesperson will be hearing about completely different areas to focus on. There is rarely any tieback to a previous conversation or a focus on one set of behaviors over a continuous period of time.

Demonstrating What “Great” Looks Like

We find that the term, “coaching,” is used so broadly today that it has ceased to be useful. In our own work, we try to avoid the term, and instead we drill deeper to get at what each sales leader is trying to drive. Is it feedback? Is it expectation setting? Performance management? Assessment? We then focus on exactly that need, rather than the generalized world of coaching. Often, the most critical assistance a sales manager can provide a seller is to demonstrate what “great” looks like. There are three ways a manager can offer this assistance.

1. Modeling: In today’s world, people need to see what a behavior looks like in order to replicate it. You can tell them what is involved in, say, asking questions of a C-level executive, but most people need to see it in order to get it. The seller and the manager can agree before a call on what skills the manager will model and what the seller should expect to see. (See the next tip, “Co-Selling,” for how to manage that customer meeting.) After the call, the seller should give the manager feedback and ask questions. The two then can have an open discussion about how the manager can be even better and how the salesperson can adopt the behaviors she saw. To some extent, modeling is the opposite of the salesperson practicing and receiving feedback.

2. Co-Selling: Here’s another tip that contradicts conventional wisdom. It’s widely believed that sales managers should play a passive, observational role when they accompany salespeople to a customer meeting. The fear is that the manager will “take over” the meeting. As a result, managers often sit relatively quietly. Yet salespeople actually learn best when they can watch someone demonstrate a new behavior. The answer to this dilemma is simple: Managers and reps should decide before the meeting who will be responsible for each element of the conversation. The manager can take just one element of the meeting, such as asking discovery questions, white boarding a co-created solution, or advancing the customer to the next stage of the buying process. The salesperson can lead the remainder. The sales manager, of course, must refrain from taking over the sale.

This approach reinforces the idea of the salesperson and sales manager selling together, jointly responsible for the outcome of the meeting. It replaces the pressure of “being observed and judged” with a partnership in which both people are working together toward a collective goal. The follow-up discussion, after the meeting, then can delve into what was going on in each person’s mind during the meeting. Sharing the underlying thought process is as important as getting the talk track right. After the meeting, there are typically further opportunities for the manager and salesperson to collaborate. They can work together on any deliverables where the salesperson is still developing capability.

3. Practice: Oddly, while the world of sales lifted one element of behavior change from sports, coaching, it forgot the other much more powerful one: practice. Yes, we know salespeople hate practicing. But it works. In other occupations that require constant high performance, from performing arts to the military, repeated practice is the foundation of success. Embedding a culture of practice (before critical customer meetings and presentations) is a safe way to achieve big gains. How many customer visits have you been on where you winced as the salesperson did something that easily could have been corrected in a prior practice session? Practice sessions are also an easy way to leverage the power of peer feedback. Once a rigorous practice model has been established, the manager need not even be present.

Lou Schachter and Rick Cheatham lead the sales practice at BTS, a global professional services firm supporting world-leading businesses. They are the co-authors of “SELLING VISION: The X→XY→Y Formula for Driving Results by Selling Change” (McGraw-Hill; March 2015).