What should sales enablement actually change?

Behaviour in live deals: the questions asked, next steps secured, and risk surfaced—measured via conversion points.

How often should enablement run?

Weekly coaching with 30/60/90-day reinforcement beats one-off quarterly workshops.

How do we measure it?

Track discovery→qualified rate, stage-to-stage conversion, deal velocity, and win rate on coached opportunities.

Do we need a new tool?

Tools help. Change happens through live-deal coaching, role-play, and a shared framework like PROBLEM.

Free Sales Enablement Checklist Template

Matthew Earle
Aug 20
5 min read

Updated: Sep 15

Gap to close this quarter = ______
3 failing conversion points = ______
Coaching cadence (weekly) set? Yes/No
30/60/90 reinforcement plan? Yes/No
Shared language adopted? (PROBLEM) Yes/No
2 enablement plays to run this month = ______

Find more resources here

For a complete guide to our sales enablement strategy, check out our guide to The Revenue Engine ™. Book your free Revenue Diagnostic session to find out more.

Sales Enablement Isn't About Content. It's About Closing Gaps

Let’s get this out of the way. Most sales enablement strategies are just window dressing. What is the account revenue growth strategy? How can there be one when there is no B2B sales account assessment framework?

Throughout my 20+ year career, the default for sales enablement was "more decks, more collateral, more battle-cards". The pipeline generation strategy was simply more of the same!

Why? I assume it was tangible and simple to do.

This is what I thought good sales enablement looked like.

This is what I believed until a number of years ago when I became a certified Richardson sales coach and saw what industry-leading enablement should be.

Your team doesn’t need another deck, cheat sheet, or training portal.

They need to know how to win real deals under pressure when the buyer starts pulling away. They need a sales enablement template.

“Most sales enablement programs fail because they focus on content delivery, not behavioural change.” — CSO Insights, Sales Enablement Report*

Why Most Sales Enablement Strategies Fall Flat

It's Treated Like an Event, Not a Process

One-off enablement efforts are like gym inductions—full of motivation but lacking muscle.

“87% of sales training content is forgotten within a month.” — Gartner, 2024 Sales Enablement Benchmarks*

So if you’re running quarterly sessions without follow-up, you’re building enthusiasm but not skill.

With no B2B sales qualification framework, your pipeline is being filled with rubbish.

It’s Product-First, Not Problem-First

When your enablement focuses on features, case studies, and brand messages before it teaches sellers to understand buyer pain, you get pitch parrots and not problem solvers.

“77% of B2B buyers say their last purchase was complex or difficult.” — Gartner, The B2B Buying Journey*

You don’t solve that with a better slide deck. You solve it by enabling sellers to make the buyer feel understood.

It’s Not Embedded in the Sales Rhythm

Enablement is often siloed from what actually happens on calls.

No coaching.

No reinforcement.

No accountability.

“Teams with a formal coaching process outperform those without by 27% in quota attainment.” — Sales Management Association, 2023*

If there’s no coaching loop, then there’s no enablement. What’s needed is a clear process or framework.

At the risk of a shameless plug, we have built our own value selling framework. You can read more about it here.

What Real Sales Enablement Looks Like

Here’s what the best-performing companies do differently:

Diagnose where deals are getting stuck.
Coach sellers on how to handle those points under pressure.
Reinforce the skills across 30, 60, and 90 days.

That’s not theory. That’s execution.

Get the checklist | Book a free SOLVE session

The PROBLEM Framework: A Real Enablement System

If your sales enablement doesn’t equip sellers to navigate real deal blockers, it’s not enablement; it’s theatre.

Here’s how our PROBLEM framework plugs into enablement strategy:

| Element | What You Should Enable |

|---------|------------------------|

| P — Proponent | Can the rep identify a true champion? Or just someone who’s ‘keen’? |

| R — Resources | Do they know how to surface time, team, and budget constraints early? |

| O — Organisation | Can they map influence and uncover silent blockers? |

| B — Battlefield | Are they prepared for internal politics, ghosting, and competitors? |

| L — Level | Can they elevate pain to priority in the eyes of the business? |

| E — Event | Do they know how to link action to a deadline or trigger? |

| M — Mechanism | Do they understand the real decision process or just hope someone gets back to them? |

This framework doesn’t just teach reps what to look for; it enables them to act on it in the deal, in real time.

“Enablement is about confidence. If your reps aren’t confident asking tough questions, you’ve enabled compliance, not performance.” — Matt Earle, *The Selling Collective

You Don’t Need More Tools; You Need Behaviour Change

“Companies that invest in behavioural-based coaching see up to 33% more revenue growth than those that focus purely on content.” — Forrester, Sales Enablement Trends, 2023*

So stop pouring time into slide decks and digital portals.

Invest in what changes behaviour:

Deal reviews
Real-world role play
Weekly reinforcement
A shared qualification language like PROBLEM

Your Enablement Strategy Should Be Answering One Question:

“What’s stopping my reps from closing?”

If your current strategy isn’t built to solve that, it’s just noise. Clear frameworks using a common language can help you overcome that noise.

A Simple Sales Enablement Strategy That Works

Here’s what we recommend for B2B sales leaders serious about performance:

Step 1: Diagnose the Sales Gaps

Look at conversion points, not content. Where are sellers falling short? Discovery? Qualification? Prioritisation?

Step 2: Align Coaching to Real Scenarios

Forget generic scripts. Coach real opportunities with live call reviews.

Step 3: Reinforce Weekly

Implement 30, 60, and 90-day reinforcement. Every team meeting should link to live deals.

Step 4: Use One Common Language

Introduce a shared deal framework like PROBLEM so everyone is speaking the same language across qualification, forecasting, and pipeline reviews.

Fix the Root, Not the Symptoms

If you're still hoping enablement content will somehow “click” one day, it won’t.

Enablement isn’t about what reps know. It’s about what they do when it matters.

If you want urgency, pipeline, and performance, then stop enabling knowledge and start enabling action.

Want to See How This Works?

Most “strategies” leave reps inspired for a day and ineffective by Monday. Our enablement programmes use the PROBLEM framework to drive sharp execution, better questions, stronger discovery, and real commercial results.