Evolving from L&D to Sales Enablement

ISE Season 3 - Enablement History with Erich Starrett

Learning leaders are facing challenges in building a bridge to the lines of business. Some have become partners to the business units, but most feel they don’t have the influence they need to drive strategic learning initiatives.
Take, for example, the gap that exists between learning executives and VPs of Sales. Both groups have a lot of value to the CEO. But, for some reason, that value isn’t being realized – especially within the context of cross-functional teaming to pursue sales objectives.
Here are two fictional letters that distill down what that gap looks like. One letter is from the desk of the VP of Sales and the other is from the desk of the Learning Executive. After the letters, let’s take a look at the suggestions for breaking down these barriers and moving forward in a more collaborative manner.

An open letter to Learning Executives from VP of Sales

  • Dear Learning Executives, I need to talk with you. I have a challenge with my team. I haven’t been able to drive the sales results I need to, and I’m afraid I’m going to get fired because of it. The CEO shared that he counts on you to help improve the human capital of our organization, but so far, we haven’t been able to work together on something specific. Don’t get me wrong, I like you and your team, but it’s hard for me to make major investments in my time if I’m not sure what the outcome is going to be.Our CEO said you were able to get results with that technology we’ve been deploying across the organization. He shared some examples about how you were able to help people get outside their comfort zone to drive our business strategy. I am not sure what to ask for, but I need your help. We both believe people are a critical asset… so how do we get started? – Signed, VP of Sales

An open letter to VPs of Sales from Learning Executives

  • Dear VP of Sales, I would like to talk to you. I have a challenge that I would like to address and get your input on. I haven’t been able to find a way to engage you and your team in an ongoing, continuously improving manner. While I believe you’re my internal customer and I want to make sure you are happy, you’re treating me a lot like an order taker. On one hand, you tell me what you want, and my team delivers. On the other hand, you want me to be more strategic and help you and your teams evolve but won’t help me engage with the field. As a case in point, I have been trying to get on your calendar to talk about some of the projects we could engage with you on, but you’ll only give me 30-minute chunks.I have talked to my peers in other companies and some of them have been able to develop a partnership with their VP of Sales. I would like to do that with you, so how can we get started? – Signed, Learning Executive

We know there are some outliers to these two open letters; however, for most of our clients these letters are reflective of the disconnect I see. So what’s going on? In a nutshell, Sales VPs want to talk about driving sales results and achieving sales objectives, while Learning Executives want to talk about projects and deliverables.

  • If you’re a Learning Executive, what approach do you have in your bag of tricks to pursue business outcomes?
  • If you’re a Sales VP, how clear have you been on the outcome you want your Learning executive to achieve with you?Since the disconnect largely boils down to a communication challenge, and as the self-appointed “marriage counselor” between the two groups, let me offer some advice:


  • Find a small project (like a small team in a region) to give to the learning executive and her team to work on with you.
  • Clarify the outcome(s) you want her to achieve with that small sales group
  • Empower her to drive to the outcome, and then stay engaged by reinforcing her work and helping her report progress on pursuing the outcome.
  • Spend more time telling her sales stories. What wins have their been? What are you hearing from sales managers? What are you seeing on the road?
  • If you feel progress isn’t being made say so. If progress continues to be an issue, then go ahead an let her know you’re moving on and looking for help elsewhere.


  • Work to focus on one group of people to help make them successful first, so you can get traction and build credibility.
  • Make sure you understand the outcome to achieve, and get your Sales VPs point of view on what needs to happen to achieve that outcome
  • Be a leader by gaining more empathy for the salespeople and sales managers who ultimately benefit from your work. If you don’t know their reality and the challenge they have in talking with their buyers, you won’t have credibility.
  • Spend more time architecting an approach to solving the problem before “jumping to the answer.” To sales VPs, leadership isn’t about random activity – it’s about purposeful problem solving
  • If you feel like you have to persuade or educate anyone on why you’re doing what you’re doing, stop.
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