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Anatomy of a World-Class Sales Coaching Session

The days of reviewing a sales rep’s pipeline briefly over lunch and calling it coaching are long gone.  Today’s best sales teams have developed methodologies that have transformed coaching and the effect has been seen on the corporate bottom line.  In fact, high-performing firms provide 15 to 20% more coaching compared to other firms (Measuring Sales Management’s Coaching Impact, The Sales Management Association), and according to CEB, coaching can improve sales productivity by a whopping 88%. But, those figures are for sales teams that are following best practices.  Proper coaching requires cadence and adherence to proven processes in order to be effective.

An easy way to think about effective coaching is to remember the 4 Ps—Past, Prioritize, Predict and Plan.

For the Sales Leader


What are the Drivers of Success for your sales organization? Keeping those drivers in mind, review your YTD success.  Do they correlate with your identified drivers? You should pay particular attention to those drivers that have had the biggest effect on success over the previous period. Those are your key drivers.  They deserve the majority of your time and effort.

Remember, outcomes are driven by process and process is driven by activities. Tie your positive outcomes to specific activities and processes that contributed to those outcomes.   

Examine your pipeline. Are there gaps that you can identify that would provide good starting points for coaching?  Are there some stages where performance is lower than other stages? Are some stages taking longer than they should or is there a choke point? These provide good topics for coaching sessions.

Analyze your team.  Coaching really boils down to intentional improvement and it is fairly easy to know who is interested in improving themselves as a salesperson and who is not. Next, identify the areas of opportunity for improvement for each rep.  Are there activities that could be increased? Are there skills that could be improved? These are the things that you can potentially create goals around.  Also, what are your current coaching goals?  Do they need to be reviewed or updated?    

What is the rep’s success trajectory? A rep’s status can be calculated using three points:

  1. Progress to Goal
  2. Process to Requirement
  3. Willingness to Change

If you know these three things about a rep, you know everything you need to know to influence the direction of their career.


Benchmark the performance of your team.  Since your coaching time is best spent with rep’s who are doing well—following processes and being open to coaching—you should stack rank your team and examine their coaching goal history. This will give you an idea of who is doing well and who is willing to work with your coaching to improve.

Next, analyze your team using the following metrics:

  • Opportunity Starts
  • Dollars in Starts
  • Win Rate
  • Velocity

Understand efficiencies by examining:

  • Loss Analysis—To save wasted time and effort, you want your reps to lose early. Loss analysis will let you know when deals go bad and when your reps might be sandbagging.
  • Pipeline Health—Look for opportunities in the pipeline that may be slowing or that just need a little extra attention to close. Focusing on those opportunities will give reps the biggest boost in goal attainment.
  • Sales Stages—Examine your team’s performance in your various sales stages to identify where they might need reinforcement. Stages where they are doing well won’t require much of your time, but if you find stages that are acting as chokepoints, you should focus your coaching efforts on skills and activities that will help ameliorate those situations.

Identify 2-3 monthly priorities that can be used as a basis for new goals. Be careful not to choose too many areas of focus.  Reps respond best to 1 or 2 goals each.


Show your team what success looks like. Model awesome. Make sure everyone is aware of what makes successful reps a success.  If there is a rep that has been able to move deals through the proposal stage more quickly, let everyone know what activities and skill sets allow that rep to be successful in that area. If someone is an all-star closer, make sure his or her routine is known and emulated.

With practice, the relationship between specific skills and activities with desired outcomes becomes apparent. By knowing what processes yield what results, it becomes possible for you to start predicting outcomes.  You will know which skills and activities lead to which results.  Then, you can plan for the effects that improvements in those areas will have.


Collaborate with your team members on setting and achieving goals. You can’t merely dictate behaviors—you have to have buy-in and the best way to get that is by involving the rep in defining his or her own path to improvement.

Your plan should be attainable and measurable. You aren’t going to be able to solve every problem right out of the gate, so set some larger annual or quarterly goals and then break them down into component parts to serve as your monthly goals.  It is much better to move a rep to be incrementally better than to expect world-class performance from the beginning. You want to measure these smaller goals in a timely fashion so that feedback is quick and relevant.

Follow these steps to complete your preparation:

  1. Understand drivers of current performance.
  2. Identify where your rep wants to be.
  3. Prioritize key opportunities for next-level performance.
  4. Dollarize and discuss the impact of each possible change area.
  5. Create “Fork in the Road” moments and identify what the rep is willing to change in order to “level up.”
  6. Set specific goals and measurement plans around activities or skills to drive “next-level” performance.
  7. Create a plan on how you will help your rep achieve their goal and get in the game with them.

For the Sales Rep


Ask yourself, how am I doing? The best way to assess your position is to look at your production, your process and your approach to change.  Are your numbers where you expect them to be and are you hitting your goals? Are you having the kind of success that you expect to have? Is there room for levelling up your skills or to follow processes more exactly? Perhaps more importantly, are you enthusiastic about making changes to enhance your success? A coaching session is the perfect platform for addressing your needs and aspirations.


In order to create your list of priorities, take the time to review your activities to see how efficient and proficient you are with each of them. If you can evaluate your competencies prior to your coaching session, you will be able to participate in an objective manner, giving suggestions and evaluating plans. Your coaching goal history will give an idea of where you have been the strongest in the past and in which areas you have the best chance of succeeding. 

Just like the sales manager, you should think about your performance using these metrics:

  • Opportunity Starts
  • Dollars in Starts
  • Win Rate
  • Velocity

One of the best things you can do to determine priorities is to understand your efficiencies:

  • Loss Analysis—Where are you losing your deals? It’s better to lose early than late, so set your goals accordingly.
  • Pipeline Health—look for areas or opportunities that you can concentrate on that would make the biggest difference
  • Sales Stages—Do you have late-stage opportunities that just need a little extra push? Those types of opportunities are great places to start with your goals.

Once you have established where you can have your largest impact, you can identify 2-3 monthly priorities to concentrate on, knowing that they will have impact.


Your goals for a coaching session should be drawn directly from your past experience modified by your predictors based on your willingness to change.  Where do you want to be?  Visualize your success and the behavior that leads to that success.  Decide now if the results merit the extra work necessary and then you can fine-tune to commitment in your session.

The best way to prepare for a session is to generate “What If” scenarios.  Ask yourself questions like, “If I had x more starts but my deal size and velocity remained the same, what would that do to my performance?” “What if I had slightly bigger deals and closed them quicker? Would that get me to my goal?” Make sure to understand what improvement is worth to you? What is the financial impact of success?   Get those large questions out of the way before your session, leaving you the time to address your needs and functional planning.

Where do you start?  Identify the most desired area to improve. Keep in mind that following process makes your outcomes predictable.


During your coaching session, commit to monthly coaching goals and be sure to record them and track progress. Update your weekly work plan, paying close attention to ensure that all of the parts of your plan will help achieve your goals. Log goal activities in Salesforce so that you can track and measure and check your pipeline health frequently.

Remember that your sales leader is your best resource for achieving your goals.  Make sure to involve him or her in your monthly goal pursuit.

Follow these steps to complete your preparation:

  1. Examine your current performance.
  2. Identify where you want to be.
  3. Make sure you are willing to change in order to “level up.”
  4. Consider possible goals to drive “next-level” performance.

The Perfect Session

Depending on schedules, the perfect session will take between 30-60 minutes. 10% of that time should be used in review (i.e. pipeline review, etc.) and would take 3 to 6 minutes. Then the rep should discuss goals he or she is interested in and ask for any specific help needed. The sales manager should then go over any perceived “level-up” opportunities, discussing the activities and skills that are lacking and improvements that could be made to competencies and efficiencies. The leader should then lead the rep through “what if” scenarios to show what could be accomplished. The sessions should end with the setting of goals based on the issues examined and a follow up session should be scheduled.

Time is a rare resource and the benefits of coaching are too great to squander your resources on lagging indicators or meaningless, sporadic pep talks.  Real sales coaching is about collaboration.  It’s about intentional improvement and when done correctly, it can change companies and change careers.

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