Sales Enablement Lessons from the Trenches

01 Apr Sales Enablement Lessons from the Trenches

Many client-facing, revenue-generating employees in sales and service organizations are continuing to struggle communicating the value of their products and services to their customers. In many of our client companies, sales leaders and their managers often face an ongoing struggle to help their sales people increase their impact and achieve their sales quotas.  Without belaboring the point, there are a lot contributing factors to this challenge.  For example, products are getting more complex, and buyers are becoming more sophisticated.

Since the challenge of communicating value to customers is a very real one, many executives continue to invest in developing the skills or their sales team.  They have to respond (in other words, they have to do something), or they risk eroding market share, or competitive losses.   For example, many of our clients are investing in negotiation and questioning skills or looking to develop programs to connect with and educate executive level clients on industry trends and insights.

Against this backdrop of increased business challenges on one hand and increased investments in skills training on the other hand, you would think sales enablement leaders within organization are expanding their influence and taking more direct control over expenditures.  Surely, if the problem is in the “wheel-house” of the sales enablement team, and the need is so great, the influence of the sales enablement function will continue evolve, right?

Nope, that’s not happening in most of the organizations we talk to.

The reality is, many sales enablement professionals are struggling to reach out to the sales leadership team and create a truly effective partnership that drives lasting business results. This is perplexing because the sales leadership team runs a specific functional area that a) needs the help of “skill developers”, and also b) falls within the potential scope of a “performance challenges that need to be addressed”.  In the view of one VP of Sales, “I hate to say it, but I think I need too much help. The challenge I have is figuring out where to start.”

So, what’s up?  Why are sales leaders not engaging their enablement and training function more collaboratively?  Why aren’t training leaders able earn the trust of the sales leadership team in order to truly take a more proactive stance?

Tough Question: Tough Answers

When it comes to addressing this reality, it’s a two-sided coin.  Clearly the sales function and the learning function should, and could, become partners.  Getting there requires meeting in the middle.

If you are a sales enablement leader, it’s likely you have a sales problem.  Your challenge has to do with helping sales leaders understand the help you can provide, and more importantly the value you can create with the sales teams you support. I will share more about this below.

If you are a sales leader, it’s likely you have a creativity problem. Your challenge has to do with making a decision to create “white-space” around a specific team or group and boldly experiment to find out what will really truly work to communicate value differently within your sales environment.  Creating that white space requires bringing the right cross-functional team of training, marketing, technology, and content providers together with the sales team to work together. More importantly, it means allowing the cross-functional team to test, learn, and deploy in an iterative and adaptive manner that is equivalent to “failing forward” (more details on this forthcoming in another blog post).

In both cases, business as usual is the equivalent of putting your head in the sand.

Closing the Sales Enablement Disconnect:

As we work with sales leaders, we often ask;“What is the business purpose of your sales enablement/training function?” Their answers provide a dose of reality.  Some current perspectives that Sales Leaders have about the training function include;

  • “That’s the group that does HR training”
  • “That’s the group that does training (and manages the course catalog”
  • “That’s the group that runs our kickoff events”
  • “I’m not sure what they do.  They do their stuff, we do ours”
  •  “They help me shift the behavior in our sales team to sell to executives more consistently” (this is very infrequent..  1 out of 50)


So, where does that perspective come from?  As we said, as a sales enablement leader, you have a sales challenge.  So, what are you selling to sales VPs?  If you were to write an email to a VP of Sales, what would you be “selling” him or her?

Hello VP of Sales:

  •  “We need to make sure every salesperson attends information security training”
  •  “We would like to talk to you about the courses you would like us to offer next year”
  • “We are hosting several lunch and learns on the technical aspect of product X”
  •  “We would like to conduct a needs-analysis”


All of these =”not good” from the VP of Sales perspective.

So, in sales the way you engage your customer (the sales leadership team) often dictates the expectations you create.  In working with sales leaders, it’s important to take stock of the expectations they likely have of you and your group and confront reality.  To some in the space, this is equivalent to more design thinking, or thinking more like an architect.  I think Steve Jobs summarized the challenge the best when he said:

“A lot of people in our industry haven’t had very diverse experiences. So they don’t have enough dots to connect, and they end up with very linear solutions without a broad perspective on the problem. The broader one’s understanding of the human experience, the better design we will have.”

— Steve Jobs


So, what experiences have you had?  How are you at connecting the dots for your sales leaders?  Are your answers linear (are you always recommending the same solution to a problem?)

To help, let’s take a step back and take a look at the questions that sales leaders are likely asking with regard to their sales enablement teams.

  1. What’s in it for me?
    •  Translation: What are you selling me?  A course? A needs analysis? An approach?
  2.  Why should I work with you?
    • Translation: How are you going to work with me?  Are you going to put the burden on me to figure out things, or are you going to offer me your thoughtful point of view, so we can co-problem solve? What are you bringing to the table?
  3. Why should I care?
    • Translation: What problems do you really solve?  What are you going to take ownership of?  What are you willing to get fired over (because that’s my reality – it’s likely I won’t be in this job more than 2 years)

These would seem like fairly reasonable questions to ask, especially if you’re responsible for a multi-million dollar sales quota, and you are getting questions from executives, board members, and customers on a daily basis.

An Aspirational Charter for Sales Enablement Leaders

So, as we enter into a new calendar year, perhaps it’s time to take a moment and step back.  It’s definitely a good time to take stock of what you are doing well, and what you might need to work on going into a new year.  And it’s probably a good time to think deeply about how you’ll evolve as a Sales Enablement leader responsible for partnering with the sales executive team. Here are some things to think about:

  • How will you increase productivity of workers across sales, marketing, and service organizations in order to increase your company’s return on human capital assets?  What small initiative can you start that tries to move the needle?
  •  How will you help the executive team bridge the gap between strategy and execution by helping workers align work accomplishments to the forward-leaning business strategy and changing human capital strategy?  What likely initiatives are coming down from the executive team?  How can you get in front of them?
  • How will you decrease the friction between groups within the organization who need to work together on important business initiatives and produce new outputs that are valuable to customers?  Where do teams need to learn and how can you help them?
  • How will you help workers increase their value contribution by learning new skills and acquiring expertise they need to drive our company’s business strategy forward?  Do you know the future-state definition of the roles you support?  What are they moving away from, and what are they moving towards?

A word of caution:

Make sure you can deliver on the expectation you’re setting.  Take the time to ask yourself the 3 questions from above.  You have to be able to explain what you’re really selling, how you work with sales leaders, and the problems you solve for them.


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