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Transforming Raw Talent Into Sales Success. What Makes Someone Coachable?

“I have great people on my team, but I’m struggling to bridge the gap between raw potential and sales success.”

This sentiment is a common one, especially in the fast paced world of technology where sales leadership often finds themselves recruiting smart and capable people with the intent of developing their raw potential into sales success. Here’s the thing though, the best of intentions don’t always translate to results. Having rock solid on-boarding programs, skills and product training, ramp plans, and mentoring will go a long way towards leveling up your entire team, but they don’t address the individual’s unique motivations and values that will ultimately determine performance.


How do you address individuals to tap into and develop their potential?

Most people would say coaching is one of the best ways to develop individual potential. In the sales world, it’s taken for granted that managers are coaching their reps on a regular basis as one of the pieces of the performance puzzle. While the mechanics of what and how to coach are important, there is a more fundamental question that needs to be explored before devoting time and resource to the actual coaching process.

What makes someone coachable?  

Regardless of the skill of the coach/manager or the potential that could be developed in the coachee/rep, there are fundamental building blocks that need to be present for any coaching to be successful. They might seem basic, but making the assumption the three building blocks outlined below are present is one of the biggest mistakes you can make.


For coaching to be successful, the following must always be present:

Willingness to shine the light in the dark corners

Both the coach and the coachee must be willing to explore the dark corners that are exposed through asking questions that are sometimes hard to ask or would usually be avoided. When you shine the light in the dark corner, you often find things you have forgotten where there, something you had not noticed before, or maybe even a door that leads to an entirely different room. Sometimes this process leads to even more questions or requires us to face some hard truths. Regardless of what we find in the dark corners, our courage and willingness to explore will reveal the information we need before we are able to build strategy and get around roadblocks.

An example of this might be pressing further when a rep consistently has an excuse for why something didn’t happen. It takes a strong manager to confront this and calling it out directly usually results in more excuses and/or blaming. Instead of inviting this behavior by asking why they didn’t deliver on something, the conversation can be expanded by using an approach that is more apt to facilitate exploration and effective problem solving. That expansion might sound something like this:

“There seems to be a place where you tend to get stuck in deals like this. Can you tell me more about the factors that you think create this, and what specifically needs to change so you can get a different result?”


Acceptance that things will get messy in the process of learning

As adults in professional roles, we pride ourselves in our ability to perform and to deliver on expectations. Sometimes we are wildly successful with something new, but more often than not, learning is a non-linear process and the lessons are hard won. Given this context, it is extremely hard to put ourselves in situations where we don’t have all the answers and there is a real potential for failure, or even just coming up short. Here’s the rub though… even at the most senior levels of management or expertise, growth and innovation require us to be willing to expose ourselves to the messy process of learning. To engage in a productive coaching relationship, the coach and coachee must be willing to get messy, draw way outside the lines, try new things, expose themselves to potential failure, figure out how to pick them themselves up when they fall, troubleshoot, and course correct.

Note, if we expect our coachees to engage in this messy process, management must allow time and runway for the coachee to truly be able to practice, fumble, start over, etc. before they ultimately “get it right”.

What does this exploration and learning process really look like in practice for a sales manager and a rep? Let’s use an example where you are selling to a new buyer persona. The marketing team has done a fair bit of research and the new scripting and product positioning has been well received at a few conferences. As you move into an active sales cycle with potential buyers, you have noticed some some variability in responses and conversion rates. The coaching conversation around this might have any combination (or all) of the following questions as starting points to a more creative and interactive brainstorming and strategy building session:

“What are you noticing about the responses you are getting when you use the new first call deck? Where do you think we are on target vs. getting off track? Based on what you have experienced in the past as well as this new opportunity, what do you think we could try to do differently? How might we refine a message that really lands with this new buyer persona?”


Follow through and execution

Unless there are commitments made to take action on the coaching conversation, coaching is just that… a conversation. It might be very resonant and thoughtful, but conversation alone does not create different results. Commitments to follow through and relentless, methodical execution is what produces a different outcome. Sometimes it’s as easy as discussing that execution plan in advance, but often times it requires more exploration around identifying potential challenges. When closing a coaching session, be sure to account for this part of the conversation so the start of the next coaching session doesn’t open with, “I was going to, but…”

The coaching process of supporting follow through and execution might sound something like this:

“It sounds like you’ve arrived at some really good options to try out. Is there anything that could prevent you from moving forward with them? What resources or support do you need to be able to be successful with this effort? How are you planning to manage your time to make this a priority?”

Note on inaction: There are instances where the best course of action is to do nothing at all. This is very different from committing to something, coming up against resistance and then backing down. Intentionally holding off on changing something can be very effective, especially if the timing is not right or additional data points need to be collected, but only with a clear understanding of why and with a timeline of when to return to action.


So there you have it. Certainly not an exhaustive guide to coaching, but some solid starting points to build on. Start building that foundation and asking the hard questions. Explore the darkness and get ready to get messy, but then be ready to do something about it!

Level213 partners with senior management to build the processes, systems and resources that are critical to growing and sustaining performance. We work with sales leadership to build out sales coaching programs, as well as sales coaching training for managers. Contact us here to learn more.


- Amanda Ambrose, Co-Founder & Chief Coaching Officer at Level213

Amanda Ambrose