👋 Welcome to another issue of The Enablement Edge newsletter!
Sit back, relax, and get ready for:
- 1 Key Concept – Bringing structure to deal reviews
- 1 Mistake to Avoid – No lone efforts when implementing software
- 1 Best Practice – Introduce in-the-flow-of-work learning
- 1 Piece of Tech – 31 AI sales roleplay use cases
🔑 Key Concept
For something that can be a truly transformational tool for sales teams, deal reviews are definitely underutilised.
I myself didn’t have a single deal review when I was an individual contributor in sales.
Many teams who decide to do them end up in long, drawn-out discussions where a lot is said but nothing is learnt.
It is a shame considering the fact that properly implemented deal reviews provide immense value – not only by equipping reps to see their deals with fresh perspectives but by driving outcomes for the organisation as a whole.
Disclaimer: I am talking about group-level deal reviews here, not pipeline, account, or forecast reviews.
The key to effective and impactful deal reviews? Structure – as I describe in the image below.
Of course, this is merely scratching the surface of how to approach group deal reviews effectively; after all, this is a newsletter 😄
For a more elaborate exploration, make sure to check out this article.
❌ Mistake to Avoid
Most of us have been there: you’ve identified THE tool that is going to level up your enablement efforts; you managed to get a few people excited about it; you managed to get the budget for it…
…and then…
…you decide to implement it all on your own (optional: with a friendly IT or ops person).
You feel so happy to be able to introduce the tool that you don’t want to rock the boat by asking for help, or you think it will be simpler to be in control of everything.
This is the textbook definition of a single point of failure.
You (and your IT or ops friend) are the definition of a single point of failure.
Simply put, if something happens to either of you, the tool will likely go unused or become unusable – often both.
To avoid this:
- Never take sole responsibility for implementing or maintaining any sales enablement tools.
- Ensure you have more than one ally during the implementation phase.
- Create thorough documentation.
- Gain stakeholders buy-in and support.
- If possible, “recruit” some champion users that can support with driving peer adoption.
You are not doing anyone a favour by doing things mostly on your own.
✅ Best Practice
In-the-flow-of-work learning is one of those ideas that sounds more complex than it really is – and I suspect that perception alone is what holds many enablement teams back from implementing it.
In reality, it’s not a question of complexity, but of mental framing.
It feels “big” because it sits outside the traditional training paradigm. But it’s already happening all around us, just informally and often unintentionally.
For those unfamiliar, in-the-flow learning complements scheduled sessions by delivering real-time, just-in-time support – enabling reps to learn exactly when they need it, without breaking their workflow.
Here’s how it can look in a sales context:
- Microlearning assets: Imagine a sales rep accessing a quick, three-minute video on handling objections right before a customer call. This type of immediate resource can make a significant impact.
- Chatbots and FAQs: Embedding a chatbot or a FAQ section within your CRM allows reps to get quick answers to customer queries while they’re drafting emails or preparing presentations.
- Performance support tools: Tools integrated within your CRM can offer real-time tips on best practices as reps log new customer interactions, providing guidance exactly when they need it in the sales cycle (AI co-pilots are worth taking a look at).
- Peer collaboration: Internal communication platforms can be used to encourage reps to share insights and strategies with each other as they go about their tasks.
The truth is, you probably already have the tools to support this.
Most CRMs today offer some level of integration. Short videos are easier than ever to produce. And you’re almost certainly already using a comms platform that can facilitate peer learning.
So the challenge isn’t technical; it’s habitual.
It’s about building the structure and culture that makes in-the-flow-of-work learning part of how your team operates.
The payoff can range from faster ramp to better retention to a more self-sufficient salesforce.
I want to stress that this isn’t about replacing traditional training; rather, it’s about making learning continuous, contextual, and actionable.
At the very least, give it some thought – because chances are, your competitors already have.
🧑💻 Piece of Tech
In a recent issue of The Enablement Edge, I wrote about AI roleplay software — and one of the most common follow-up questions I’ve received is:
“What can you actually do with these tools beyond the basics?”
Most people assume AI sales roleplay is only useful for things like cold calling practice or pitch refinement.
But that’s just scratching the surface.
To illustrate the full potential, I partnered with Hyperbound, one of the leading AI sales roleplay platforms, to put together a comprehensive breakdown of real, practical use cases.
The result were 31 high-impact AI roleplay use cases, organised into five categories:
✅ Skill development & sales effectiveness
✅ Sales coaching & performance management
✅ Onboarding & training efficiency
✅ Sales messaging optimisation & scalability
✅ Miscellaneous high-impact use cases
You can find the full, in-depth breakdown here.
These are my 4 article picks for this issue from The Enablement Insight:
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