Learning in the age of AI
AI IN ENABLEMENT: MOVING BEYOND ADOPTION TO FOCUS ON ADAPTATION
These days, it’s hard to open an email, click on a website, scroll through your LinkedIn feed, or tune into a podcast without encountering a discussion about AI. And this makes sense, given the amazing capabilities provided by AI and the lightning speed at which AI is evolving. In the context of sales enablement, that narrative is all about the need to adopt AI, the effective ways it’s enhancing our work, and areas we need to be mindful of regarding our overall AI strategy. But amidst this whirlwind of enthusiasm, there's a critical conversation that's not being discussed enough: it's not just about bringing AI into our world; it's about transforming our world because of AI.
THE MISSING PIECE IN THE AI DIALOGUE
Adopting AI isn't the endgame—it's the starting point of a much deeper shift. We're so focused on acquiring the latest AI tools that we're overlooking a fundamental question: How do we change the way we work, think, and enable, once AI is part of the equation? In short, we need to avoid simply "adding AI capabilities to an existing thing" without rethinking how we enable our teams holistically.
A PARALLEL EXAMPLE
Let me offer a parallel that illustrates this point: When I was an elementary student, rote memorization was common. For example, we had to memorize all 50 U.S. state capitals and then get tested on them. Fast forward many years, no students today do this kind of memorization because tools like Google have made this practice obsolete. Educators recognized that new tools meant abandoning outdated practices and adapting their teaching methods. For example, many shifted their focus to teaching students how to critically evaluate online sources—a skill that became essential with the rise of search engines—while reducing the need for rote memorization.
THREE EXAMPLES WHERE ENABLEMENT SHOULD ADAPT
This leads me to the critical question: In what ways are we asking our GTM teams to do the equivalent of “memorizing state capitals”, despite the availability of new AI capabilities? I’d like to explore three example areas where I see the need for enablement to evolve beyond traditional approaches, with the hope of beginning a much larger discussion about how we can adapt across all aspects of sales enablement.
EXAMPLE 1: TESTING & CERTIFICATIONS
Raise your hand if you've ever created a course in your LMS, quizzed your GTM teams, and marked them complete once they achieved a passing score. I’m guessing most of you have done this to some extent. While I’m not saying this approach is wrong, I do think it represents an opportunity to revisit and evolve our methods.
Let's also challenge our approach to certifications. The traditional way might involve having teams complete certain LMS courses, perform an action to become certified (take an exam, upload a pre-recorded video, or go through a mock, in-person version with their manager) and then we move on to the next thing once the individual is ‘done’.
When we zoom out to what we're ultimately trying to achieve with testing and certifications – upskilling our GTM teams – we can see the limitations here. I believe in a simple formula: for knowledge to become a skill, you need practice and feedback. Traditional approaches to testing and certification often lack these critical elements, resulting in knowledge that doesn't translate to actual skills. But it doesn’t have to be this way, if we adapt with (and not just adopt) AI.
With new AI tools now available, we can reimagine these processes. Consider the existence of AI-Powered Knowledge Assistants based on a company's proprietary knowledge base. With these tools, individuals can interact directly with company documentation, reducing the burden of learning every piece of content about the company. This allows us to shift away from testing individuals on information that AI can readily provide, and instead focus on creating opportunities for practice and feedback. A solid way to do this is with the growing array of AI sales coaching tools available, which is a much more effective way for an individual to turn their knowledge into skills.
As for certifications, traditional practices emerged before tools like Conversational Intelligence (even more powerful with AI these days) existed. Rather than creating artificial certification scenarios that may or may not be implemented in real-life customer conversations, use Conversational Intelligence+AI to have GTM teams implement skills in real customer conversations (with practice happening beforehand with the aforementioned AI Coaching). Certify them only when they've demonstrably and successfully showcased these skills with actual customers, using AI to evaluate their performance in real-world situations. This ensures that certification truly represents skill mastery and is happening out in the wild.
GUIDING QUESTIONS - TESTING & CERTIFICATIONS
To begin adapting your testing and certifications approach, consider these guiding questions:
Assessment Approach: When was the last time you evaluated your testing approach? Which of your current assessments are still measuring memorization rather than application?
AI Tool Integration: What AI-powered knowledge tools are available in your organization that could reduce the memorization burden for your GTM teams?
Practice Opportunities: Where in your current certification process could you incorporate more structured practice opportunities with AI-driven feedback?
Real-world Application: How might you leverage your existing conversation intelligence tools + AI to measure skill application in actual customer interactions?
Certification Redesign: Which of your current certifications could be transformed from knowledge-based assessments to (AI powered) skill demonstrations?
EXAMPLE 2: CHANGING BUYER EXPERIENCE AND IMPACT ON SALES ENABLEMENT
The second area requiring adaptation is how AI is impacting the buyer experience. We all recognize the growing demand for self-service journeys, where buyers conduct extensive research before engaging with sales representatives. AI tools available to buyers continue to proliferate, fundamentally changing what individuals need to do when meeting customers. Tools that replicate parts of the traditional sales motion are increasingly available directly to buyers.
Given these shifts, we need to evaluate where we should redirect our enablement focus to meet buyers where they are, rather than continuing to enable based on outdated buying journey models. Consider a simple example: enabling GTM teams on a first-call deck or pitch. How realistic is it, given today's buyer expectations, that a prospect will enter a conversation without having researched your company? If this scenario is increasingly rare, why are we still investing heavily in enabling GTM teams to present introductory materials?
Instead, we should focus on enabling individuals to engage effectively with customers who are already informed and further along in their journey. The skills required for these deeper engagements will continue to evolve, requiring greater attention from enablement teams to keep pace with the changing buying landscape. This shift is closely connected to customers' increasing expectations for hyper-personalized interactions, which we’ll consider in our next area of focus.
GUIDING QUESTIONS - CHANGING BUYER EXPECTATIONS
To start evolving your sales enablement for this example, consider these guiding questions:
Buying Process Mapping: When was the last time you mapped your customers' actual buying journey rather than your ideal sales process?
AI-Informed Buyers: What evidence do you see that your buyers are using AI tools before engaging with your sales team?
Content Strategy: How are you adapting your sales content strategy to support buyers who are further along in their journey?
Value Demonstration: If buyers already understand your basic value proposition, what advanced value demonstrations should your sellers be equipped to deliver?
Differentiating Questions: What questions can your sales team ask that AI tools can't answer for prospects, creating genuine engagement opportunities?
Enablement Priorities: Which traditional "early-stage" enablement programs could you scale back to invest more in "mid-to-late stage" sales capabilities?
EXAMPLE 3: PERSONALIZATION
A third example where adaptation is essential involves the personalization of content provided to GTM teams, whether it’s learning materials, sales assets or job aids. Depending on an organization’s maturity, the default approach often involves publishing a single or selective subset of learning courses or assets for diverse GTM segments. This is perhaps the area with the greatest potential for AI-driven transformation.
We should leverage AI to tailor learning courses and sales assets for each segment across customer-facing teams (SMB vs. MidMarket vs. Enterprise AEs vs. CSMs vs. Solution Engineers). Publishing an LMS course on a new product release? Use AI to customize it for Sales, CSMs, and Customer Support roles. Have a one-hour recorded training to upload to your CMS? Before making it available, use AI to tailor that content for different audience segments.
This customization might involve adapting the core content itself or creating supplemental materials addressing the unique needs of each segment, such as specialized FAQ documents, role-specific summaries, or customized job aids. While a one-size-fits-all approach occasionally works, customer facing teams generally benefit from tailored content, which aligns with the buyer expectation of hyper-personalized interactions. Since AI can integrate multiple inputs to create cohesive outputs, providing personalized content to customer-facing teams should become standard practice for enablement teams. The last thing to state here is that more and more we’re seeing tools give GTM team members the option to personalize content themselves. This is a huge opportunity to let GTM teams embrace their craft, freeing up Enablement to focus on other areas of critical support. Consider finding those opportunities (and tools) for GTM teams to proactively create their own learning and content using AI, which is a win-win for Enablement, customer facing teams, and ultimately, customers.
GUIDING QUESTIONS - GETTING PERSONAL
To explore how you can incorporate AI for more personalization, consider these guiding questions:
Content Audit: Which of your current enablement materials could benefit most from AI-driven personalization across different GTM segments?
Personalization Criteria: What are the key differentiators in how various teams (SMB vs. Enterprise, Sales vs. CSM) need to consume and apply the same information? (This should inform your AI prompting!)
Scalability Planning: How might you create a scalable framework for personalization that doesn't require manual customization for every piece of content?
Self-Service Enablement: Which content creation or customization tasks could you empower GTM teams to handle themselves using AI tools?
Organizational Readiness: What cultural or process changes would need to happen in your organization to fully embrace personalized enablement?
Prioritization Strategy: If you can't personalize everything at once, what criteria would you use to decide which content to personalize first?
WHERE DO WE GO FROM HERE?
My intent with this post is to start a conversation about moving beyond AI adoption to meaningful adaptation. I've outlined three examples where enablement is still asking GTM teams to "memorize all 50 state capitals" when such approaches no longer make sense in an AI-enhanced world. By transforming our testing and certification processes, reimagining our approach to the evolving buyer journey, and leveraging AI to deliver truly personalized enablement content, we can begin to adapt in meaningful ways. But this is just the beginning.
Where have you evolved your enablement practices in response to AI? What areas do you see needing change given access to AI tools? What questions do you have on this topic? As a community, we can support each other through this evolution. While staying current with new AI technologies is important, the true transformation comes from adapting our practices to reflect the new realities facing our customer-facing teams.
Written by Tyler Luiten for The Enablement Squad
