A Smarter Way to Evaluate Sales Enablement: The What/Who/How Lens

Sales enablement tools are everywhere. Most do what they’re designed to do: track activity, deliver training, organize content. But that doesn’t always translate into better coaching or improved rep performance.

The real challenge? Helping reps apply what they learn. Coaching often falls short, learning fades, and the gap between knowing and doing widens.

If your sales enablement tool isn’t driving the growth you expected, the problem might not be the technology. It could be the fit.

To find a solution that truly supports coaching, reinforces learning, and improves performance in the flow of work, you need a clear way to evaluate your options.

Start by Diagnosing the Gaps That Hold Your Team Back

Before diving into demos, step back and diagnose what’s really getting in the way.

Ask yourself:

• Are skills fading after training, widening the “knowing-doing” gap?
• What prevents managers from coaching consistently or effectively?
• How do reps actually learn day to day? Is learning integrated into their work or siloed in disconnected systems?

Questions like these help you hone in on the real challenges your sales team is facing. This way, you can make sure your sales enablement solution actually helps them grow and achieve more.

A Simple Selection Lens: What, Who & How

When our VP of Training, Jesse Rome, set out to build ASLAN+, he spent a full year in the same boat as many enablement leaders: researching, demoing, and wrestling with what would actually drive lasting change.

 What emerged from that process wasn’t just a tool decision. It was a way of thinking that reshaped how we evaluate enablement solutions altogether:

• What is the solution really offering?
• Who’s driving it?
• And how does it support growth in the real world?

This What/Who/How lens is a way to clearly understand what your team truly needs from enablement to make coaching stick. It’s not a checklist; it’s a decision filter.

Let’s break down how to apply it.

1. Coaching & Development (The "How")

Coaching is the foundation of effective enablement, but only if it’s reinforced, consistent, and easy for managers to lead.

The “how” is about approach, not tools. Jesse’s insight here is simple: If you want to empower front-line managers to coach, you don’t need a tracking tool. You need to make it easier to actually do it. That means supporting flexible styles, prompting conversations, and making reinforcement easy in the flow of work. 

In other words, it’s not about automation; it’s about adoption.

To make sure your new system is actionable, ask yourself:

• Does your system help managers lead better conversations, or just document that one happened?
• Can it flex with your managers’ style and cadence?
• Does it elevate conversations rather than just track them?

2. Sales Content & Resources (The "What")

Too often, content is created, uploaded, and forgotten. The right tool makes sales content feel like part of the conversation, not an archive.

The "what" goes beyond content types or formats. The real question is: What is the enablement system offering to reps, in terms of clarity, consistency, and real sales help? 

“In my research, I looked for solutions that didn’t just store content, but also helped reps focus, absorb, and act,” Jesse says. “The differentiator wasn’t bells and whistles. It was whether reps were better at selling because of what they saw”.

To get to the heart of the “what,” ask yourself:

• Does your content teach reps how to sell, or just tell them what to say?
• Is it integrated into daily work, or just searchable?
• Can managers easily tag and reinforce content in coaching moments?

3. Training & Onboarding (The "Who")

Onboarding is the first test of your sales enablement strategy. If it’s clunky, inconsistent, or hard to manage, you’re already behind.

The "who" matters most onboarding. Jesse emphasized that enablement success hinges on who leads, supports, and reinforces onboarding. If your managers don’t know what they own, or your system doesn’t help them lead through it, it won’t stick.

Ask yourself:

• Does your onboarding create shared ownership between reps and managers?
• Do managers have tools and visibility to coach and guide ramp success?
• Is your system flexible enough to evolve as your org grows?

4. Sales Training Sustainment (Where What, Who, and How Converge)

This is the piece most tools get wrong. They train, but they don’t necessarily help reps synthesize what they learn or use it consistently.

Here’s where the whole model converges. Reinforcement reveals whether your what, who, and how were aligned in the first place. If reps aren’t practicing, reflecting, and improving, daily and naturally, it’s a signal that something’s misaligned.

Jesse’s takeaway: the right sales enablement system will make behavior change visible, coachable, and incremental. Not just measurable.

Ask yourself:

• Does your approach encourage active application and reflection, or just passive review?
• Do managers have a role in guiding reinforcement?
• Is practice embedded into sales activity, not isolated from it?

Quick Assessment: Does Your Sales Enablement Measure Up?

Now that you've explored the What / Who / How lens, use these questions to stress-test whether your current system (platform, practices, and partners) supports the kind of coaching-led growth you're aiming for:

• Does it fit into the natural rhythm of how reps and managers work, or sit outside their daily flow?
• Does it empower managers to coach in real time and improve conversations—not just record them?
• Is learning applied, practiced, and visible? Or does it live in forgotten modules?
• Are the metrics focused on activity, or do they reflect actual progress in skills and behavior?

As your sales org matures, can the platform scale and flex with your evolving needs? If you answered "no" to any of these, it might be time to revisit whether your current enablement setup truly gives your team what they need to improve.

If Your Sales Enablement Platform Doesn’t Help Your Team Grow, It’s in the Way

Enablement platforms don’t drive performance on their own. But the right one clears the path. It makes coaching easier to do. Learning easier to apply. Growth easier to see.

That’s what helps people improve: not more dashboards, but fewer obstacles.

ASLAN+ was built to do exactly that. It reinforces what your managers are already trying to build: real conversations, consistent coaching, and long-term development.

So if your current tool isn’t helping your team get better, don’t settle for “it’s working.” Find a fit that actually fuels progress.

Ready to shift from managing activity to developing people? Let’s talk about what that looks like, and how to make it stick.