5 Strategies to Align Learning and Sales

Not too long ago, the sales execs were the jocks of the office cafeteria and learning professionals were the nerds. And if you’ve worked with sales for any length of time, you may have encountered the stereotypical BMW-driving, fancy-watch-collecting, golf-game-talking, pretty boy that would convince you to do his homework for him—whether it’s a proposal, a presentation, a demo, a tough consultation, etc. Why were we convinced? Well, we were charmed by the same charisma as the client prospects, right?  Or maybe we just accepted the fact that salespeople were different creatures worthy of significantly higher salaries because they had that X factor we lacked.

Of course, most industries and most sales teams have experienced significant disruption of late. We have new personas and many different expectations both for our sales teams and for the learning professionals that support them. The dirty, not-so-secret of charisma selling, which hid ever so successfully underneath an alphabet soup of handy acronyms, is giving way to new approaches. Forget that faux jock persona. The new achiever is the valedictorian of the organization, and she’s equipped not only with her own ideas and experience but she’s eager for information, metrics, and insights. And, while she’s certainly capable of doing her own homework, she’s ready to embrace the learning opportunities that the last generation took for granted.

Suddenly, we as learning leaders find ourselves in exactly the situation that we’ve always craved—one of relevance. Perhaps in no other part of the organization is the visibility to results quite as obvious or as immediate as it is in sales. And never have we been more in demand and for the right reasons. The much-touted and possibly exaggerated death of solution selling has created a different kind of gap and need on the sales team. Sales leaders are facing:

1. What does sales look like in a world where “enabled” buyers have access to so much information?
2. How do we outfit the sales team with the insights and expertise to succeed in this new marketplace?

Those are some hefty questions and it isn’t necessarily our job to help them with those questions, right? Wait, we’re talking sales and of course, their challenges are our challenges. Do you know how to navigate the myriad offerings of sales training vendors? Do you know your SPIN selling, your Challenger Sale, your MEDDIC? What about your inbound sales strategy? Do you have a different track for the inbound sales team? Shouldn’t you? Here is the corresponding set of challenges for learning leaders:

1. How do I curate the right content for the sales team or teams that I’m supporting?
2. What is the right learning cadence for the sales team? How can I become a long-term partner for success?

That second question assumes that at least part of the answer to the sales need for insight and expertise in continuous improvement. We must get beyond whatever packaged or canned sales methodology we’re embracing—beyond theory to practice. The goal for learning leaders is to become a vital part of the sales process—perhaps as vital and as indispensable as the CRM. That goal is going to require some innovation. We need to sell our value at each step in the sales cycle and at each step in the development of the sales expert.

Here are five strategies for bringing your learning strategy into alignment with sales:

Strategies to Align Learning and Sales

1) Go Macro and Micro

Yes, your yearly boot camp, your sales summit, & your quarterly sales meetings are excellent opportunities for learning, but, to target continuous improvement, you need a macro-plan for developing the tiny habits that will keep the same team engaged in everyday learning. And it can’t be separate from the account goals and the client targets or it will get deprioritized. Create relevance by sequencing and timing the learning activities around internal and client-focused milestones.

What’s the toolkit for this strategy? Learner journeys, microlearning, curated and push learning, etc.

2) On-the-Job (& On-the-Deal)

Sales is an ideal lab for learning because of the cyclical nature of the sales cycle. Over and over, we have new opportunities to practice qualifying an opportunity, for example. Each time we loop back around is a chance for on-the-job learning. In sales, I like to call it on-the-deal learning because it creates a connection between an idea and a real sales advantage on a live opportunity. Because sales learners are highly motivated to tip the scales in their favor, they are especially open to learning in these moments.

What’s the toolkit for this strategy? Simulation, role play, live practice, coaching, etc.

3) Let’s Huddle

Sales can be solitary, particularly during the pursuit phases. A huddle strategy can be an excellent opportunity not only for camaraderie but for idea-sharing and learning. The right mix of mutual accountability—what are we doing today—with a reminder of key goals—where we want to go tomorrow—keeps the development of expertise front of mind.

What’s the toolkit for this strategy? Prompts, flashcards, critical thinking questions, etc.

4) Stretch Assignments

Of course, the biggest champion for learning on the sales team needs to be sales management. We must have the right partnership with sales management if we really want to bring learning into the sales workflow. A key part of that workflow is going to be the interactions of the sales learning with the representative.

What’s the toolkit for this strategy? 1-on-1 prompts, coaching guides, evaluation matrices, co-selling, etc.

5) Storytelling

How does one become a sales legend? It’s more than just the numbers—it’s the full story of going from an unlikely start to a surprising result. Stories are important both internally, building up the net experience of the group, and externally, giving client prospects a glimpse of what the brighter and better future state really looks like. Learning leaders can help to vet and curate these stories, aligning them with specific objectives and helping sales representatives select the right story for the right opportunity. Stories help to motivate and create belief—belief in the company, the product, the sales methodology, or even in the available training resources.

What’s the toolkit for this strategy? Video stories, scenarios, case studies, plot frameworks, etc.

Each of these five approaches will help you increase the relevance of your sales training efforts. And, although a systematic integration of learning with the sales workflow may be required to maximize results, even an incremental change will help to build momentum and win over any detractors. By leading out on sales enablement training, learning leaders can establish themselves as willing partners with practical ideas that can scale from the everyday huddle to the global sales summit.