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Enablement at scale: 4 common enablement mistakes—and how to avoid them

April 8, 2024
Stacey Justice

Stacey Justice

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Sales Leadership

“Enablement” is my least favorite word in the corporate dictionary. There, I’ve said it.

Why? Because no one seems to know what it means, and it differs from company to company, leader to leader. As Enablement professionals, it’s our responsibility to set the right expectations and align our initiatives to address the specific needs of the business, and build a team and programs to drive progress that moves the needle on key business metrics.

Yes, you might counter and say, the definition ought to differ based on your company’s specific circumstances—industry, funding stage, business model, business goals, etc. But most organizations take a reactive, one-size-fits-all approach to enablement, and fail to take a proactive approach to drive the right results.

I’ve worked in enablement in some capacity for more than 20 years. In those two-plus decades, I’ve seen the good, the bad, and the ugly across the enablement spectrum, and I apply lessons learned across my work as Gong’s VP of GTM enablement.

Enablement is crucial, particularly as your organization scales. Here, I cover some of the most common pitfalls, and how to sidestep them.

4 of the most common enablement mistakes—and how to avoid them

Mistake #1: Not defining enablement

Sales enablement is probably the most common and best-understood realm of enablement. But the sales team is far from the only team that needs enablement to thrive. It is important to have a clear charter with agreement from leaders and partnerships with cross-functional teams on what makes enablement successful within your organization. 

How to fix it: Remember that everyone involved with the customer journey needs enablement. A healthy revenue organization depends on successful moments of truth across the customer journey. If the sales team is good at getting deals in the door, but the customer success team drops the ball, no amount of sales enablement will solve that problem. You should think of enablement with a holistic, customer lifecycle-centric mindset.

Mistake #2: Taking a reactive, task-focused approach

As a company scales, it introduces new stuff—products, features, online resources, etc.—usually at a rapid rate. Many enablement teams look at the onrush of new stuff and try to enable around all of it, thinking of each new item as a task to check off the enablement list.

How to fix it: Maintain a focus on the overall customer journey. Enablement shouldn’t be reactive, it should be proactive. It shouldn’t be focused around individual tasks; it should stem from an overarching customer journey, with clearly defined steps, teams, and accountability. Challenge every enablement ask with the question: How does this fit into the context of our overarching customer journey?

Mistake #3: Not making the right investments in enablement—or not making them at the right time

A growing company may not understand where to start making investments in enablement.  I’ve seen situations where the loudest leader got the resource, which didn’t help drive scale or programs.  The problem is that this approach doesn’t scale. It leads to information silos, a lack of comprehension between teams, and finally, a blurring of the company’s story and value proposition.

How to fix it: Take a one-to-many approach. My enablement function consists of two core teams, who handle enablements across all different functions:

  1. Customer journey enablement. How do we define the phases of the customer journey, and how do we optimize each phase? This is the heart of the enablement team; anyone with any ties to the customer journey—from sales reps all the way through the customer success team—contributes to and is included in these enablements.
  1. Enablement strategy. Do our sellers understand the product, and can they confidently sell it? Are we partnered effectively with product marketing on GTM launches? This team owns the more cross-functional, programmatic enablements.

Mistake #4: Not aligning to the right business metrics

Like any function within your business, enablement deserves an appropriate level of investment. But it’s particularly challenging to get the enablement investment right because it can be hard to define and measure enablement success.

This is doubly challenging because there’s no one-size-fits-all approach to defining objectives and key results (OKRs) within enablement. At different stages, your company may have issues generating top-of-funnel awareness, middle-of-funnel commitments, and/or bottom-of-funnel conversions. Each issue requires different behavior changes and enablement needs to connect those behavior changes to the overall business result.

How to fix it: Connect enablement strategy with overarching business goals. Derive your enablement OKRs from your company’s overarching objectives. If you’ve got a serious leak in the middle of your funnel, it will likely put a damper on revenue, and you can measure enablement success by tracking your discovery-to-demo conversion rates, for example.

Defining enablement OKRs takes a solid understanding of overarching business goals and a regular reassessment of whether current OKRs are still the most important to prioritize. The better you understand what enablement success looks like, the more you’ll be able to hone your enablement investment.

As with all things under the GTM umbrella, getting enablement right is both an art and a science. There’s no universal plug-and-play approach; it takes good communication across tiers and functions of an organization, and an ongoing effort to translate overarching goals into strategic programs.

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