Four steps for going deep with Sales Coaching

Four steps for going deep with Sales CoachingOne of the most exciting parts of my role in enablement is coaching, sales coaching to be specific. If you know me, it’s easy to understand why. I was a seller for 8 years before moving into sales enablement, a college athlete, a High D & High I DISC personality type, and I’m Latina…we like to be in the driver’s seat, what can I say? 

In all seriousness though, sales coaching gives me life, that fire, and when a coachable AE makes the necessary changes to their approach, I feel like a proud mother! 

A proud mother who knows her cubs inside and out….

I know who they are as an AE/BDR but I also know them as people. I know what motivates them, what discourages them, what makes them smile, and what makes them scowl in anger or frustration. I know how they like to receive feedback, how they like to learn, and how they like to be coached. I know if they are married, if they have children, if they are in their 20’s trying to live their best life by the seat of their pants…a case of TMI in some cases? Definitely, but I wouldn’t want it any other way! 

This all sounds like rainbows, skittles, and snuggles but the reality is, this type of understanding takes time, a lot of time, and to an enabler, we are always looking for the repeatable, scalable process. This type of knowledge is critical for every sales leader to have though, so how can we go about improving our “ramp time” by obtaining this “insider info”?

You’re so inquisitive! I’m glad you asked!

If my CEO said to me, “Crystal, wave your magic wand and you will be granted with your dream coaching process, including any and all resources!” (I just giggled a bit) After jumping for joy, I would get to work with these 4 steps:

1. Get leadership buy-in that “call coaching” is too shallow and we need to go deeper. 

When I have been coached in the past, whether in sales or as an athlete, my coaches knew what “worked” for me. They knew what their approach needed to be with me, what learning modality got my engine firing on all cylinders, and they knew where I wanted to go next in my career. As an enabler, when I’ve met with our sellers, I worked hard to include all of the “insider info” into their coaching sessions. I will admit, I was lucky enough to have had a solid executive team who valued my insights and understood the importance of my approach. If the buy-in is difficult in your organization, you can still do this! It may take a bit longer because you will have to take baby steps, but as long as you figure out the important KPIs and the revenue impact for each step, there isn’t a CEO who will say no. 

2. Day 1: All sales reps take an in-depth personality assessment and the data is owned by Sales, not HR. 

I bet you are saying, “This is nothing new, my HR team does this!” But let me ask you, what do you do with this data? Do you analyze it? Do you know what motivates your reps from the first day? What about how they best retain information? This is key because once you have this data, it’s time to go Moneyball and create actionable data-driven methods to ramp up the “insider info” of your team. 

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What do I mean by data-driven methods? Well, let’s take the DISC assessment and use my type, for example. As a High D, I want to see the agenda for what I’m about to learn. I have a preconceived mindset about nearly any topic or issue so this means my learning may be more subjective than objective. I can be impatient and want learning and coaching to take place at a fast pace, with little time spent on things I perceive as unimportant and mundane. I will often try to “dominate” the coaching session and my coach needs to reign me in to keep control. I am also a big trial and error learner. 

Now let me ask you, how would you approach me in a coaching session with this data? How would you ensure I retain what you are teaching me? How will you keep me motivated until my next milestone that is ultimately driving toward business outcomes? 

3. Create a culture where coaching sessions are not stand-alone. 

As an Enabler or Sales Leader, we must weave coaching sessions into a “story”, a story about our sales reps. I can’t tell you the number of times I’ve walked into a 1:1/coaching session and I had nothing to build on from the previous week. It created a lack of visibility into forecasted deals, but it also created an employee who would have rather continued going after business than taking the golden opportunity to improve my skill set. 

So, what do I mean by “story”? 

If you take Step #2 above and think about this as the starting point for your relationship with your reps, it becomes easier to envision and execute. In my mind, I have 3 areas I’m hyper-focused on when I coach a seller. 

Improving their skill set to drive revenue

How exactly do I improve their skill set to drive revenue? The devil is in the details. I will pick 1 or 2 calls for review and provide feedback. The feedback I provide is always actionable and focused on one specific competency. They may need to work on 2 or 3, but in my experience, to create expertise and have the knowledge retained, it was best to focus on one competency for that month. In addition to feedback, I come prepared with reinforcement. They will not walk away without a plan for the competency we are focused on. I may even decide to throw in a quick role-play to get their hands dirty if they are trial and error learners. If they are an audible learner, I would have a few calls prepared with what “best” sounds like. You get the picture.  

Improving their skill set to develop and guide their sales path (i.e. BDR wants to be an AE)

Some might argue that I’m developing them with the approach above, and yes, there is some overlap, but the main differentiator and what should be your ultimate goal is helping them to create a strong business acumen. I like to start with having them think about their workflow, is it efficient or do we need to improve? Why or why not? Are they innovating new tactics? Get them thinking about accountability. How interested are they in mentoring? What would their mentor plan look like? What other departments would they like to explore? Side projects? 

Understand how they like to be coached, listen and motivate.

This one is self-explanatory. If I have the data from step #1 above, I will have a good idea from day 1. I think the key for me was to always make sure I motivated them with high energy (if they responded to that), solid data & ACTIONABLE motivators that worked for them specifically based on their assessment.  


In my experience, Steps #1, #2, and #3 can only become a repeatable, scalable process with accurate, focused data and buy-in/alignment from departmental leaders. 

Each coaching session should build on top of one another, weave the story if you will. When we start building the story and tracking performance, we can then see the seller as not just a business asset but as a human being. I understand, however, these concepts can be complex and each step will go deeper, but I believe, when we begin to dedicate our efforts to our sales teams, much in the same we dedicate resources to the customer journey, will we be able to impact not only revenue, but attrition, employee satisfaction, and perhaps the most human metric of all, their mental health and stability. 

Imagine a sales world where we can say, “Isabella is a personality type X. Based on this, we provided X,Y,Z (depending on learning modality) during onboarding and she hit her first milestone 15 days earlier than her peers. In her first 30, 60, 90 days we coached with this approach X (based on personality type & motivators) and she was able to master the skill 10 days faster than her peers. Given her career goals and data, she is 90% more likely to excel as a BDR Manager than an AE.”

I would love to hear the actionable “insider info” that you bring to coaching sessions! What has worked for you? What has not? What suggestions would you add?

“Leadership is lifting a person’s vision to high sights, the raising of a person’s performance to a higher standard, the building of a personality beyond its normal limitations.” —Peter Drucker