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Definitive Guide to Sales Coaching

We've coached thousands of IT staffing sales professionals and IT recruiters and hundreds of sales managers.  We've made a career out of providing sales coaching.   Now we're going to share with you our definitive guide to sales coaching including a whole host of sales coaching strategies and tactics that you can test out for yourself to improve the performance of your sales team.


Today’s sales manager is expected to be part sales superstar who still carries a bag and his or her own personal sales quota, part CFO, part trainer, part CRM, part ATS expert, part “chief problem solver,” and most likely parts of a half-dozen other roles. Sales managers are responsible for territory management, compensation and commission plans, customer segmentation, sales strategy, revenue forecasting, goal setting, and generating reports among many other tasks and responsibilities. Suffice it to say, the role of today’s sales manager is diverse and complex.

Prevailing wisdom has always told us that if you want to improve sales performance you need to train your front line salespeople. They are the ones who are engaging in customer facing activity. As it turns out sales coaching represents one of the biggest opportunities for improving sales performance and sales effectiveness. According to research conducted by the Corporate Executive Board, core sales performers could see a performance boost of 19% given a significant improvement in the coaching they receive. Sales coaching, however, is one of the most misunderstood management tools.

Think about it, how many sales managers tell their sales reps they need them to get more weekly meetings with new prospects and open more accounts? Most, if not all of them. Sales managers as it turns out are pretty good at telling their people what to do (get more meetings, make more placements, close larger deals, expand account wallet share). However, most sales managers tend to struggle with empowering their salespeople for solving their own problems and coming up with solutions on their own. That is sales coaching. Sales coaching is about empowering people.

The remainder of this article is designed to provide you with an overview of sales coaching, how it differs from managing and the benefits of sales coaching. We will discuss the essential sales coaching skills, how sales managers can transition from being a sales manager to being a sales coach and how sales managers can create a coaching culture amongst their sales team.  We also share how by leading with open-ended questions, sales managers can engage in effective coaching dialog. We provide a guideline for sales managers to use in establishing a coaching framework with their direct reports. This article also explains how sales managers can communicate to their direct reports-how and why they are changing their leadership style to reflect that of a coach-and ultimately change their existing sales culture. Finally, by applying these sales coaching tips and suggestions, sales managers will not only see the path for creating a culture of self-accountability based on employee empowerment but create a coaching culture.

Managing vs. Coaching

Managing is simply the process of communicating vision and strategy. It includes setting objectives, assessing performance and managing and facilitating the administration of those objectives. Managing is more about “telling” others which tasks to execute and focus on and ensuring people are following processes. Traditional managers tend to focus on exerting control, “hoarding” information and maintaining structure to ensure departments are functioning properly.

Traditional sales managers often want to focus on sales objectives or sales outcomes (number of weekly sales meetings) rather than on driving desired behaviors. These traditional sales managers often say things like “your pipeline is looking dry this month,” or “you need to get your weekly face to face meetings up. What seems to be the problem?” This really isn’t what sales managers should be after or talking about because it is focused on business results rather than on behaviors. This behavior is simply not helpful for the sale rep. Being told what to do vs. how to do it are two very different things.

Sales coaching on the other hand represents one of the biggest opportunities for improving sales performance. Coaching is about tapping into the DNA of an individual and seeking to understand their viewpoint, motivation, goals, aspirations, skill sets and way of thinking through the use of open-ended questions. Coaching is ongoing and highly customized to the individual and is about challenging,encouraging, supporting and empowering people to achieve higher levels of performance while allowing them to bring out the best in themselves.  For the coach it is about leading their people to places they have never been, which often require pushing them outside of their comfort zone. Coaching and good coaching questions focus on opening people’s minds to the “what if” possibilities and getting them to believe in themselves.

Sales coaching is best thought of as a behavior, not a task, where the  manager is focused on helping team members self-assess, self-diagnose and self-discover ways to improve performance and achieve break-through results. Common objectives of sales coaching are to:

  • Assess strengths and identify areas/opportunities for optimizing performance
  • Provide ongoing feedback
  • Develop knowledge and skills
  • Change behaviors

In the end, coaching is about making people more valuable. Sales coaching is not just a huge driver for improving sales performance, it also plays a major role in retaining employees. People (sales people in particular) don’t leave their company; they leave their manager. Good coaches however make people want to stay.

Sales Coaching Skills

A study conducted by the American Management Association found that firms that provide optimal sales coaching achieve 17% greater annual revenue growth than those that don't.  Another study conducted by CSO Insights found that organizations that have a formal coaching program achieve 28% higher win rates. Those are some pretty gaudy numbers, and the numbers don't lie. But you might be wondering, what makes a good coach and what skills do I need to possess to be a good sales coach?  

Presence simply refers to the manager's ability to convey interest in their subordinate including their goals, aspirations, challenges and way of thinking.

Relating is a skill that refers to the manager's ability to connect with his or her people including the ability to build rapport and empathize.

Leading with Questions
Arguably the most important sales coaching skill is the manager's ability to stop telling, and instead start leading with questions.

Leading with Questions,The Vehicle to Effective Coaching and Empowering Your People

As mentioned above, the key to coaching and tapping into one’s individuality is through the use of well thought out, open ended questions. When leaders lead with questions they will not only uncover root because issues but they will challenge assumptions and require people to think and uncover new ideas and possibilities that they would not have come up with otherwise. More importantly, people like the feeling that they have when they discover the answers on their own. When people come up with their own ideas or solutions, they own it and when people own an idea or  solution they are far more likely to apply it. This level of ownership breeds a deeper level of accountability compared to simply exerting control out of authority. It also builds their self-confidence to solve problems and generate solutions on their own. Coaching is what is needed to both cultivate and sustain these behavioral changes. This in essence, is what sales leaders are supposed to do. Leading with questions is the vehicle to make it happen.

Avoid Telling Dependency

Many managers think that as the “leader” they’re supposed to have all of the answers. This simply is not true nor is it even possible. Leaders who never learn to abandon the role of “chief problem solver” end up creating a culture built on “telling dependency.” Telling dependency is when team members rely entirely on what the leader tells them to do. In a culture of “yes men” or “head bobbers” where team members rely on the leader to tell them what to do, the leader robs his or her people of their creative thinking, decision making ability and the ability to solve problems and create solutions because they have become dependent upon the leader to always answer their questions and tell them what to do. Ironically, the leader has also robbed people of self-accountability, the very behavior all leaders want their employees to own and embrace. When team members can’t solve their own problems or come up with solutions on their own, the leader is required to step in. The leader thus becomes the bottleneck for fiscal growth and scalability as well as people development because all solutions run through the leader. Perhaps the biggest problem with telling dependency is it is exhausting for the leader because it requires him or her to do all of the work.

Road Map to Results

Sales managers can break this cycle by changing their leadership style to reflect one that is indicative of leading with questions.

When sales managers lead with questions they:

  • Are able to more effectively connect with team members
  • Create freedom for themselves (as the leader or sales manager
  • Build self confidence and self-esteem among team members
  • Create a culture of shared responsibility in which team members take responsibility for their own actions and results
  • Drive self accountability
  • Empower people to solve their own problems and come up with their own ideas
  • Gain a competitive edge

Listening Skills
The listening skills I'm referring to is the manager's ability to concentrate and focus on the sales person’s point of view without thinking about their own.  Far too many managers get caught up in their perceptions (of the salesperson) and focused on telling that they can't block out the noise and truly listen, hear and understand their salesperson's point of view.

Positioning refers to the sales manager's ability to present information persuasively including their ability to use specific examples when discussing the sales reps performance or selling behaviors. 

Checking is the act of the sales manager asking the salesperson for feedback on something the salesperson has said or on something they have said.  Checking lets manager's test for understanding and ensures the manager and seller are in agreement on what has been discussed.

For those who want to excel at sales coaching, demonstrating empathy means that you are able to put yourself inside the shoes of your salesperson or recruiter and see the world through their eyes.  Possessing the skill of empathy is important for sales managers not just because it shows that you understand your employee, but more importantly because of the way it makes your employee feel. 

Setting Expectations for Changing Your Leadership Style

You can’t just flip on the switch and expect to change your leadership style overnight. And you certainly can’t expect people to follow you without first communicating the change and reasons for the change. The first step is to set new expectations of your team members so that they understand what your intentions are and what is in it for them. Remember, people don’t care how much you know until they know how much you care. If you don’t communicate your intentions and what you’re changing and why and what is in it for them then people will automatically respond with fear. Setting expectations is absolutely critical.

How should you introduce this change in your leadership style? Some leaders communicate this change in a team meeting while others communicate it in one-on-one meetings. There is no right or wrong way just as long as you communicate your intentions, why you are making the change and what they (your team) can expect. Clear communication is important to avoid collateral damage later when your team is left to analyze and interpret your personal agenda. When communicating the reasons for changing your leadership style, you can share with your team members that you recognize that the role of being a leader has evolved and that you are trying to evolve with it. As such you can simply share with your team members that you are trying to change your style to be more of a coach. Explain to them why you’re making this transition and how it will benefit them. Also explain to them how it will impact your relationship with them. You want to set the tone and expectations for how your interactions with team members as a “coach” will differ from what it has been like as a “manager.” This prepares them for change. If you don’t do this it will catch team members off guard and confuse them and/or send a mixed message.

Gain Alignment with Your Direct Reports
The goal is to get buy-in and alignment between you and your team members around this change in your leadership style. Start by scheduling a time and place to meet with each team member individually. This is not a five a minute “on the fly” conversation. You want them engaged in the meeting. Expecting them to drop what they were doing or to adapt to your schedule on the fly often results in them resisting your message or simply appeasing you rather than being genuinely open, interested and willing to engage in meaningful dialogue.

The purpose of the meeting is for you and subordinates to have a conversation about

  • Why you are changing your leadership style to reflect that of a coach
  • What coaching is; You want to establish a common definition or framework with your subordinates on the definition of coaching
  • What their perceptions are of coaching
  • What experiences they have had being coached (personally or professionally)
  • What concerns they have about being coached 

Engaging Your Team in Sales Coaching Dialogue

You will want to craft your message on how you’re going to open the conversation and get your direct report to engage in dialog about coaching. Here you will want to set expectations about what both you and your direct reports can expect as well as use questions to help drive the dialog around how they want to be coached in a way that will be most valuable to them.
You might say something like this:

“My intention and goal is for you to achieve your career goals and aspirations. But I recognize that as the leader I need to change my leadership style so that I can do a better job of developing and maximizing your full potential. To use a sports analogy, the coach is always there pushing, motivating, encouraging and supporting their players to be at the top of their game. I have come to the realization that to be a better leader I need to play the role of a coach so that I can develop you in a way that will enable you to achieve even greater success. This change is new to me and it will be new to you which means we’re going to experience a learning curve. Keep in mind that it probably will not be perfect the first time. What is most important is that you understand my intentions which are to support you, encourage you and help you achieve the level of success you’re striving for.  I wanted to take some time to talk about coaching and your perception of coaching so that you and I can come up with mutually agreed upon definition and framework for our coaching. From there we can set some measurable (SMART) goals and parameters around our coaching that will be most valuable for you. How do you feel about discussing this?”

Questions to Establish a Coaching Framework

  • How would you define my job as your supervisor?
  • How would you define the role of a coach?
  • Have you ever been coached before? What did you like? Dislike?
  • What would you expect from me as your coach?
  • What would you like to cover or accomplish during our coaching sessions that would be most
    important to you?
  • How would you feel about scheduling coach calls on a weekly basis to strategize on your accounts, contacts and opportunities?
  • Is there anything I shouldn’t do when coaching you? Anything you mind demotivating?

Finally ask you subordinate, “can I share with you how I envision our coaching sessions so you can understand my style and know what to expect from me to ensure it is in alignment with your expectations?”

Your First Coaching Session

Now that you have met with each of your direct reports in a one-on-one meeting to establish your coaching framework, expectations and measurable goals, it is time to schedule your first coaching session. Scheduled coaching sessions are always 100% about your direct report. Do NOT come with a predetermined or underlying agenda. Coaching sessions are always for your people to come with their own agenda, whether it be to discuss their personal goals, their career or what they need to do or learn to become more effective and valuable. It is their time to express how they feel. Remember, developing a coaching relationship with your direct reports is built from trust. If your direct report feels as if you have a hidden agenda you will fail to establish trust and the process will feel awkward and superficial. Your direct report will most likely give you lip service and simply tell you what they think you want to hear.
When asking questions it is important to come from a “learning mindset” versus a “judging mindset.”

Leaders with the learning mindset tend to be optimistic and presuppose new possibilities, a hopeful future and sufficient resources. They exude possibilities and hope. The judging mindset on the other hand is reactive and tends to focus on the past, not as a means of learning but to apportion praise or, more likely, blame.

Learning Questions Judgement Questions
What is good or useful about this? Why is this a failure?
What possibilities does this open up? What is wrong with you?
What can we do about this? Who's fault is this?
How can we stay on track? Why can't you get this right?
What can we learn from this? Why don't you start doing it my way for now on?


How Much Time Should I Spend on Sales Coaching?

At this point you might be thinking, “Wow, I have seven direct reports, when in the heck am I going to find time to schedule these coaching sessions with my reps? I have no time as it is!” Remember, leading with questions is going to give you freedom. When you empower people to make decisions on their own you no longer have to get into the details of every situation and solve every problem. Imagine how much free time you would have if you didn’t have to solve every little problem in your office? The frequency or cadence of your coaching sessions will vary from rep to rep. Again, coaching is highly customized to each individual. If you have a sales rep who is really struggling then you may need to schedule coaching sessions with him or her daily. On the other hand you may have a consistently strong performer who needs coaching once or twice a month. For core (average) performers however, you
should be facilitating, on average one, one hour coaching session per week per individual. As you get going you will get a feel for how frequently your coaching sessions should take place with your direct reports.

The Power of Sales Coaching Through Observation

Keep in mind that up to this point I have been talking about coaching in the context of one-on-one meetings. Sales managers must also engage in active coaching and observation. Active coaching and observation is where the coach is observing the sale rep in live, active sales calls (on the phone and in client facing meetings). Let me use a sports analogy to illustrate. During a game, say football or basketball for example, coaches stand on the sidelines bent over watching the game. Why do they do this? So they can watch and observe how their players perform. If I’m a football coach I’m looking at my player’s stance, their pad level, how they get out on their blocks, foot work, and so forth. This is observation. In the sports world players need their coach to observe how they’re performing because players can’t see their weaknesses or blind spots when they’re engaged in a game. When players run off the field to the sidelines you always see the coach running up to the player to share a few words. Combined with observation, this is active coaching. Sales people need this same kind of coaching because like players on a football team, sales people can’t see their blind spots. Actively coaching through observation answers the question “why is my player performing
the way they’re performing?” This insight is far more valuable to improving sales performance and sales effectiveness than the data that comes from your CRM or ATS application. Data from your CRM or ATS simply tells you what is happening. When sales managers engage in active coaching they learn why what is happening, is happening.


At this stage you now understand the difference between managing and coaching and that leading with well thought out, open-ended questions is the vehicle to effective coaching. You have gained alignment with each member of your sales team and have communicated the reasons for why you are changing your leadership style and what your subordinates stand to gain from that change. Lastly, you have engaged all of your team members in your initial coaching dialog. Now it is absolutely critical that you and your subordinates commit to a coaching schedule and that you stick with it. If you skip a meeting or show up late your reps will start to assume this is just another “flavor of the month” management gimmick. Sticking to a schedule requires careful planning and preparation on your behalf. Just like sales people must prepare for sales calls by planning out how they will open and close a meeting and plan what they will say and questions they will ask, sales managers must do the same. This doesn’t mean that you come with a pre-determined agenda but you do need to be
prepared to ask open ended questions to guide the conversation and empower your reps to come up with solutions on their own.

Next Steps

Finally, in an ideal world your direct supervisor would serve as your coach for personal development and holding you accountable to not only consistently coaching your direct reports but also to help keep you at the top of your game. Unfortunately this is not always possible. If you really believe in coaching and are truly committed to coaching your direct reports and bringing out the best in them then it only makes sense that you also have a personal coach. Heck, look at any professional athlete, they all have personal coaches to maximize their potential and hold themselves accountable. Remember, if you’re not continuously learning and pushing yourself you’re not growing, and if you’re not growing you’re dying.