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3 Questions Every Sales Leader Should Answer

Sales leaders know that in order to have successful teams, they need to coach. But where do you start? And how do you measure success? There are three questions that sales leaders should ask themselves:

  1. How do I prioritize my limited coaching time?
  2. How do I optimize my coaching efforts?
  3. How do I dollarize coaching impact?

Answering these questions can provide the basis of establishing and maintaining a strong coaching culture.

How Do I Prioritize My Limited Coaching Time?

Time is a finite resource and without careful planning, it can be wasted and/or squandered on activities that at best don’t impact the bottom line and at worst, hurt it. One of the biggest culprits is a lack of cadence when coaching.  First, you should avoid ad-hoc coaching sessions.  They are reactionary and de-legitimize coaching goals with backward-looking, lagging indicators.  Coaching sessions take on real meaning when they focus on forward-looking analysis of potential areas of improvement. Second, you should establish a regular schedule and stick to it. Constant re-scheduling sends the wrong message about your commitment level. In the end, consistancy will save time for you and your reps.

Coaching time should be dependent on the reps willingness to change.  Coaching falls on deaf ears when reps aren’t willing to share a vision of intentional improvement. Sessions need to be focused on potential improvement, not just on missed quotas—they need to be forward-looking, not backward-looking. Those reps who are engaged see an opportunity to level-up and improve their performance and career. Spend your time with those reps, no matter where they fall in the success spectrum because they are where you can achieve the most lift.

You should also spend time with reps who have responded best to coaching in the past. You know that they are willing to put in the time and effort and your time won’t be wasted with them. Take advantage of their enthusiasm and make sure you convey the positive effects of achieving the goals you establish.

How Do I Optimize My Coaching Efforts?

What are the best things to coach on? What are the structures and workflows to make coaching an operational strength?  If outcomes are tied to activities, coaching should always center around adding or improving activities that are known to yield success.  You should coach on the skills associated with those activities. Increasing skill always trumps adding numbers, or to put it another way, you are better off pressing the “how” button than simply pressing the “more” button. Once you know what skills have opportunities for improvement, you can address the activities they influence.

Is your plan simple enough to be scalable? Remember, you have an entire team to coach, not just under-performers. You have a finite amount of time to dedicate to coaching sessions, limited funds and team members with assorted needs, so making the most of your resources is extremely important. Best practices suggest that a cadence of one-hour coaching sessions, once per month is the most effective.  If you have 10 reps, that’s an investment of just 10 hours a month.

Is your coaching stack capable of supporting your goals? The last thing you want to do is try to introduce analysis-based coaching without the technology and tools to automate the process. Remember, you must keep track of goals, scheduling and rep needs.  And you need to have a way of monitoring skills, activities and willingness to change.  Your technology should remove the tedium of creating and endlessly updating spreadsheets. Good sales coaching software will tell you who needs to be coached, when you need to coach them and what they need to be coached on.

How Do I Dollarize Coaching Impact?

Are you tracking and illustrating the impact of coaching on deal capture, sales velocity, revenue attainment, rep engagement and response to coaching goals? Once you put a coaching plan in place, tracking the changes in these areas will allow you to see an accurate dollar figure for your efforts.

There are three primary metrics to evaluate pipeline viability, and sustainability provided by coaching. The analysis of these metrics at the individual rep level also forms the basis for determining coaching priorities.

  1. Dollar Value of New Opportunities—Goal / Win Rate determines the total pipeline value required to hit goal.
  2. Number of New Deals—Starts$/Ave Deal Size determines the total number of deals required to hit goal.
  3. Sales Velocity—Tracking total sales cycle by stage determines the timing of quota attainment.

There is a simple formula to calculate the overall lift provided by coaching:

$ = Opportunities * Deal Size * Win Rate
                Length of Sales Cycle

Knowing how to dollarize the impact of your coaching will prove invaluable in getting rep buy in to coaching goals. It’s easy to be an enthusiastic participant when you can see the end result of your efforts.


Consistent coaching focused on high-value skills and activities is critical to developing a sales rep’s ability to add customer value, yet most companies struggle to implement sales coaching at scale or to track and measure coaching’s execution, cadence and impact. Answering these three questions can help you create a robust coaching program that will change companies and careers. It will also help you sell the program to the exec team, become more predictive in your reporting and use your time prudently for the best possible result

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