👋 Welcome to another issue of The Enablement Edge newsletter!
Sit back, relax, and get ready for:
- 🤖 1 Piece of Tech – 32 AI sales prompts you can use today
- 🧱 1 Key Concept – The sales value pyramid
- ✅ 1 Best Practice – Nailing your first 90 days in enablement
- 🧘 1 Reflective Insight – Insignificance is a quiet kind of freedom
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🤖 Piece of Tech
We often talk about enabling reps.
But increasingly, enablement also means enabling AI – designing the systems, prompts, and workflows that let AI support reps in real time.
Over the last few weeks, I’ve partnered with Glyphic to take one of the most practical AI use cases – prompt-triggered insights and actions – and bring it to life.
Rather than relying on broad concepts, I’ve created a tactical resource with 32 AI prompts that I’ve personally tested and implemented inside sales organisations. Prompts that:
⚡ Save reps 5–10 hours/week
⚡ Help managers make better, faster decisions
⚡ Create execution consistency without adding friction
Each prompt includes:
✅ What it does
✅ When to use it
✅ The exact, copy-ready wording
Organised across five high-impact categories:
- Conversation snapshots & insight extraction
- Strategic content generation
- Deal momentum & qualification
- Skill & call coaching
- Follow-up, handovers, & comms
You’ll find prompts like:
- Business case creation,
- Executive brief generation
- Implementation roadmap outline
- Mutual action plan steps
- MEDDPICC deal analysis
- Closing path analysis
- Pain-to-solution alignment
- Pain question missed,
- Pitch and approach improvement
- Stakeholder influence & messaging
- Coachable moments
- Discovery call quality review
- AE-CSM handover summary
- Follow-up email drafter
- Re-engagement plays for stalled deals
Whether you’re deploying a sales copilot, trying to get more value from your CI tool, planning to reduce admin burden, or simply experimenting with GenAI for rep support – this is a smart place to begin.
👉 Check out the full breakdown
🧱 Key Concept
One of the hardest things I’ve found in enablement isn’t getting reps to ask better questions or follow a sales process.
It’s helping them build true business acumen.
Not just understanding pain points or buyer personas, but seeing how a business actually works: how decisions are made, how value is measured, and how different stakeholders shape the outcome.
That kind of thinking changes how reps show up.
But it doesn’t come naturally – especially in fast-paced teams focused on short-term results.
That’s why I was so struck by a deceptively simple model that was introduced to me a while back: the sales value pyramid – a practical tool for seeing your customer’s world the way they do, top to bottom and back up again.
It helps shift the conversation from features to outcomes – and from selling products to building partnerships.
The five levels
The sales value pyramid helps you map out:
- Goals: What’s the big win for the company? (Think mission statements or annual reports.)
- Strategies: How are they planning to get there? (These are the long-range roadmaps.)
- Initiatives: What are they actually working on right now? (Real projects, with budgets, owners, and timelines.)
- Obstacles: What’s getting in their way? (This is where you find pains, not just surface problems.)
- Needs: What do they truly need to clear those obstacles and move forward? (Hint: this is where your solution fits.)
Most sellers barely get past obstacles (pains) and rush into talking about needs.
The best instead work the whole pyramid (up, down, and sideways) until they know exactly how their offer maps to something urgent and funded.
How to level up the sales approach
Never stop at the first answer. If a buyer shares a problem, follow it up: “What’s at risk if this doesn’t get solved?” or “How does this tie back to your company’s bigger plans?”
Link every need to a business driver. Show how your solution clears a key obstacle, unblocks a live initiative, or moves the needle on an organisational strategy.
Map for each stakeholder. Every buying group has their own pyramid or may be focus on a specif level of the pyramid. Tune your message carefully, the CFO cares about high-level goals; operations might focus on obstacles and needs.
Some additional tips:
- Keep your mapping live – update and refine as you uncover more intel.
- Use the pyramid in discovery calls and workshops. Ask the buyer to correct or add to your mapping.
- Don’t try to sell into every box. Focus on where you have a genuine impact; recommend partners for gaps you can’t fill.
Mastering business acumen means moving beyond pitches and learning to see the broader business picture.
The sales value pyramid helps seller become more proficient at doing just that.
👉Check my full sales value pyramid guide
✅ Best Practice
Let’s not sugar-coat it – the first 90 days in a sales enablement role are high-stakes.
You step in with everyone watching: leaders expect results fast, sales want instant support, and, more often than not, the resources are limited to say the least.
It’s your window to earn trust, prove your value, and show you belong at the table.
But there’s another side to that coin. If you focus on the wrong things or fail to manage expectations, it’s hard to recover. First impressions stick. And digging out of a credibility hole is even harder when resources stay scarce.
This shortened 90-day plan pulls from personal experience and conversations with hundreds of enablement practitioners over the years.
1–30 Days: Learn, Listen, Map
- Build trust with reps, frontline managers, marketing, operations, and customer success.
- Shadow sales calls. Observe how reps pitch, handle objections, and follow up.
- Dive into your ICP, market dynamics, buyer personas, and competitive positioning.
- Draft a simple enablement charter: scope, objectives, and what success looks like. You may find this template useful.
- Set initial KPIs tied to revenue levers like ramp time, conversion rates, or time in stage.
31–60 Days: Remove Friction, Build Alignment
- Identify what slows down both reps and buyers – think proposal delays, approval bottlenecks, or tool confusion.
- Shadow a few deals from start to finish to find hidden blockers.
- Set up an executive advisory group or stakeholder council to align on strategic goals.
- Launch a structured intake process for enablement requests; start separating noise from real need.
- Communicate your focus areas clearly and win early sponsorship.
- Prioritise 2–3 initiatives where you can delivery early results.
- Start managing expectations proactively to avoid overcommitment.
61–90 Days: Execute, Measure, Refine
- Deliver those early wins and report results visibly – dashboards, weekly updates, or a short video walkthrough.
- Track relevant leading indicators to evaluate progress and adjust if needed.
- Recalibrate your roadmap based on data and real-world learning.
- Keep iterating. The best plans are built in motion, not in isolation.
You only get one shot at your first 90 days.
So shadow your sellers, remove the biggest blockers, and deliver early value that matters.
Most importantly, manage expectations well – promise what you can own, and then overdeliver.
Your turn:
What worked well during your first 90 days?
Did you have a win – or a setback – that changed how you approach enablement?
Drop your story below or message me. I’d love to hear it.
🧘 Reflective Insight
How would you live if your life was truly…insignificant?
I don’t mean it in a sad way. Not even in a self-pitying way. But in that quiet, cosmic kind of truth that humbles you a little.
And maybe frees you, too.
—
A few months ago, I was sitting by the sea.
No notifications. No distractions. No one needing anything from me.
Just the waves. Coming and going.
As they have for thousands of years. As they will for thousands more.
And I thought:
None of this – my work, my worries, my achievements – changes the tide.
The sea doesn’t care about my to-do list.
The wind doesn’t know my name.
And one day, everything I’ve built will dissolve like footprints in wet sand.
And you know what? I smiled.
Because in that moment, something in me let go.
The pressure to always achieve. To be someone. To prove, to strive, to matter so much.
What if… we didn’t need to?
What if your life — small, fleeting, deeply human — didn’t have to matter to the universe… to still mean the world to you?
To the people you love. To the slow mornings that stay with you. To the work that lights you up from the inside.
Maybe insignificance isn’t something to fear.
Maybe it’s a quiet kind of permission.
To live more lightly. More honestly. More presently.
---
I’m still sitting with this.
Still learning what it means to live from that place.
But I do know this:
The less I try to be important, the more connected I feel – to everything that is.
These are my 4 article picks for this issue from The Enablement Insight:
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