Elevate Sales Enablement with Strategic Thinking

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At the core of any good business’ vision is a disciplined strategy – oftentimes laid out by the most senior leaders in an organization. This visionary leadership is essential at the top-level, but thinking strategically across all levels of the organization should be a welcome endeavor — especially for sales enablement professionals that want to create lasting impact on revenue.

When sales enablement is strategic, it can mean clear-cut alignment to organizational revenue goals. On an individual level, being strategic can mean creating solutions that benefit the long-term success of the team, seller, or customer. Put simply, it’s the difference between a proactive approach to enablement versus a reactive one.

“In sales enablement, [when] we sit down and try to tackle big, hairy problems, we’re able to not only think from the highest level about what matters most, [but also] down to executing all the little things that need to be done to solve that problem,” said Jessica Ryker, sales enablement lead at HelpSystems. “The way I think about it is, ‘How do we want our sales process to work all the way down to a specific individual job aid that will help a rep do their jobs?’”

Unlike most professional skills that have a clear roadmap to development, the pathway to cultivating a more strategic mindset is less defined. In fact, research shows that strategy skills are taught at only 24% of organizations, leaving many professionals uninformed about the big-picture.

However, with established goals and a growth mindset, sales enablement practitioners can strengthen the strategic muscles that will lead to new value for the business, while leading to new opportunities for career advancement in the future. To begin, adhere to four best practices that center on observation, inquiry, alignment, and effective communication.


Gain a holistic view through industry immersion

Making strategic decisions requires a multi-directional understanding of the sales enablement landscape. Without it, ideas about progress and improvement lack the context necessary to identify available opportunities and assess potential risks.

The first step in acquiring the knowledge necessary to make strategic decisions is to routinely immerse oneself in the sales enablement space in order to stay informed about emerging trends, the latest and greatest methodologies, advancing technology, and more. At this stage, it’s important to not only acquire data, but to understand how the data is useful to drive decisions across a multitude of contexts and situations.

In order to begin your strategic thinking journey, engage in these observational behaviors:

  • Blogs, thought leaders, and forums: The internet is a burgeoning resource for anyone affiliated either directly or indirectly with sales enablement. Research and discover which blogs or online forums resonate with you and your organization the most, then maintain a weekly regimen of reading and stay up-to-date with any recent activity. Over time, multi-faceted concepts related to the field will synthesize and incorporate itself into your own strategic thinking.
  • Networking opportunities: Whether it’s with colleagues within your own organization or peers on the outside, initiate and maintain relationships with fellow sales enablement professionals. Use LinkedIn or other membership-based enablement communities — like Sales Enablement PRO — to drive connectivity. Reach out often to peers to hear their perspectives and share your own.
  • Competitive marketplace: Currently, competitive pressure ranks as being the foremost challenge for sellers, and sales enablement can play a key role in alleviating that pressure. Always be informed of the behaviors from direct and indirect competitors in order to gain a broad understanding of industry context. Being able to articulate competitive advantage can be a primary driver of an organization’s sales and revenue strategy.


Stimulate strategic thinking with curiosity

As you accumulate greater industry knowledge, leverage the retention of this information to begin asking questions that broaden your understanding of problems facing the business and potential solutions. Again, the goal is to think about strategy from a multi-dimensional perspective, rather than a linear, sequential one. Instead of looking for direct cause-and-effect relationships, seek out factors or instances that have less-obvious relationships with the issue at hand.

In his book, “Leading with Strategic Thinking,” Aaron K. Olson recommends asking yourself these questions when trying to gain strategic insight that will eventually lead to driving strategic change:

  • What has historically been done?
  • What is the state of the industry, and what’s normally done?
  • What role is personal experience playing today, and what else could it provide?
  • What is the most relevant data, and how do you manage it?
  • What would other relevant stakeholders consider credible?


Adopt a formal approach

Since sales enablement is still a fairly new function for 38% of organizations, the range of maturity can vary greatly from team to team. Less tenured enablement functions may find themselves still navigating the waters with perhaps fewer resources than more tenured organizations, thus resulting in less formalized practices. This can lead sales enablement to become bogged down by tactical or administrative tasks, which can prevent strategic growth and visibility.

With a structured, formal approach to the enablement strategy, practitioners are better positioned to anticipate issues proactively rather than responding reactively.

“There’s always a fire on the floor,” said Adriana Romero, go-to-market enablement manager at Clearbanc. “I had a very interesting director early in my enablement career who said, ‘there’s never emergencies in sales enablement.’ So, if we have a structure, we can try to be more proactive than reactive. Then, we know what we need to do to actually address the gaps on the floor.”

Once sales enablement has determined how to be more structured and proactive within their own teams, there should be an acute focus with developing their strategy in alignment with the greater objectives of the organization. In weekly reviews focused on revenue-facing teams, sales enablement should provide regular updates on how they’ve contributed to outcomes.

“Ultimately, if there is a formal enablement function at the company, then they’re likely going to want to hear from you, what your updates are, and how you’re supporting a lot of big business objectives that the C-suite cares about,” said Vanessa Metcalf, senior manager of revenue enablement at Top Hat.


Demonstrate impact and secure support

Although strategic thinking is the goal, it’s not adequate to just think strategically within a business setting — being able to communicate and verify the depth of strategic ideas is of equal importance. According to the State of Sales Enablement Report 2020, 48% of respondents said sales enablement was either average or below average in their ability to communicate its value to the business.

With this in mind, it’s important not to assume that your audience understands the value of your enablement initiatives. Instead, be sure to emphasize the business impact of your efforts with clarity and precision. In doing so, use data when possible; if there is no data or analytical insight to support your proposal, prepare for critical questioning from your audience.

Then, once you’ve identified your message, secure commitment from cross-functional teams, partners, executives — anyone whose resources you require to design effective solutions. Here’s how to strategically gain support from relevant stakeholders:

  • Create urgency of your proposed initiatives, otherwise they will likely be deprioritized to the back-burner.
  • Share a compelling vision with more than just your words. Ask open-ended questions to draw on stakeholder’s ideas and promote engagement. Use anecdotes and storytelling when possible in order to create an emotional investment.
  • Deliver a hole-in-one pitch. Get agreement from your audience about the current situation, focus on the experience of the desired outcome, describe your proposed solution, and handle any objections. Then, be sure to ask for commitment immediately after.

Operating with a strategic mindset is not only reserved for senior leaders within an organization. By thinking strategically in your role as an enablement professional, regardless of tenure or title, you can lead from any seat and in turn improve enablement’s impact on the business. Through regimented observation, broadened curiosity, a structured sales enablement approach, and elevated communication tactics, sales enablement can be understood as a driver of strategic change for the entire organization.

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