👋 Welcome to another issue of The Enablement Edge newsletter!
Sit back, relax, and get ready for:
- 💻 Key Piece of Tech – 26 Practical Use Cases for AI in Enablement
- ✅ Best Practice – 24 Sales Content Metrics
- ⚠️ Mistakes to Avoid – The SKO Edition
- 💭 Reflective Insight – Doing things solo
Let’s get right into it!
Sponsored by Hyperbound
Scale your winning sales behaviours
Hyperbound turns call data into AI roleplays that accelerate rep growth. Reps gain confidence and skill 5x faster. Managers coach without more calls. Enablement knows where to focus.
It’s the most realistic & versatile AI roleplay tool I’ve implemented – that’s why I partnered with them.
Try a live demo
Affiliate link – I only recommend tools I use and trust.
💻 Key Piece of Tech
AI in enablement is no longer a future trend; it’s already embedded in how teams onboard, train, and coach sellers, organise and distribute content, orchestrate knowledge across the organisation, and draw insights to inform GTM decisions, among much more.
The shift hasn’t happened through big, dramatic rollouts. It has happened gradually, in the workflows we touch every day.
A rep gets call feedback in minutes rather than weeks.
An enabler identifies skill gaps across calls and teams, informing future training interventions with greater precision.
A manager sees which skill areas – both individual and collective – could benefit from focused coaching before the next cycle.
A seller finds the right asset without digging through ten folders.
A buyer receives an executive brief, built with AI and seller oversight, within minutes of a call – closely reflecting the conversation that took place.
When leveraged the right way, AI becomes part of the system – and everything feels lighter.
I believe that the potential for enablement to make a massive impact has never been greater.
Over the past few months, in partnership with GTM Buddy, I mapped the most practical AI use cases in enablement – the areas where work is repetitive, data-heavy, or slowed down by manual effort.
The result is a collection of 26 field-tested use cases, grouped into five categories:
Each use case follows a simple structure:
- Who uses it
- The specific challenge or situation
- How AI addressed the challenge
- The practical outcome
This keeps things grounded and specific, helping you identify the AI applications that can truly make a difference in your context.
I believe AI doesn’t replace enablement; it amplifies it by clearing space for the more valuable work that demands strategic thinking, empathy, and leadership.
👉 Get the full list of 26 enablement-focused AI use cases.
✅ Best Practice
Sales content is one of the most expensive parts of enablement, not always in terms of money, but definitely in terms of time.
Yet in many teams, once content is created and launched… it disappears into the void.
We assume sellers use it.
We hope it influences deals.
But we rarely know.
That’s where content metrics – and the systems and frameworks that enables you to track those – matter.
They’re how you move from “We made good assets” to “This is influencing pipeline, progression, and outcomes.”
Some teams may track basic metircs like downloads, send outs, and views, but those alone don’t tell you much.
You need a more coherent framework of measurament that goes through various levels so that you cen best analyse content performance and prove impact over time.
In my full article, I organise sales content metrics into five layers that build on one another: content management health, seller awareness & usage, buyer engagement, business impact, and operational efficiency.
When you track content this way, it stops being simpe static collateral, and it becomes an operating lever inside your sales motion.
This is because you learn fast which assets:
- Actually help sellers sell
- Support champions and other buyer stakeholders build consensus internally
- And which ones are just… shelfware with pretty formatting
In the full breakdown, you’ll find:
- All 24 content metrics, grouped by the above five layers
- Definitions so there’s no ambiguity in measurement
- Examples to bring every metric to life
- Potential pitfalls to avoid for different metrics
Content can move mountain-sized deals – but only when you identify the assets that truly make the difference. Focus on improving those, not on adding more.
⚠️ Mistakes to Avoid
We’re nearing the end of the year.
Which means one thing: SKO season is coming.
Some teams are already deep into planning.
Others are just beginning to think about beginning to plan.
(If that’s you, consider this your friendly nudge.)
The truth is, SKOs are expensive.
Time, attention, travel, coordination, the whole thing.
And yet… too many end up feeling like a long Zoom call with better lighting.
Luckily, I was able to talk to 16 sales leaders who have led enablement teams at companies like IBM, Salesforce, SAP, Yahoo, and GitLab.
They’ve seen SKOs that inspired teams for quarters and initiated a strong process of change.
And they’ve seen SKOs that were forgotten before the airport Wi-Fi connected.
So I pulled together 26 common mistakes that are made this time around – and how to avoid them.
A few you’ll recognise:
1. Trying to “fit everything in.”
If everything is a priority, nothing is.
Your SKO should have a spine – a single message people remember in March.
2. One-way presentations for two straight days.
SKO is not a lecture.
If reps aren’t talking, practising, or debating… they aren’t learning.
3. Bringing in a keynote speaker with no connection to the actual work.
Inspiration without some level of utility fades fast.
If the speaker’s message doesn’t translate to your reality, it won’t stick.
4. Treating product updates as training content.
Information ≠ enablement.
Reps need clarity, sales-ready messaging, and action, not yet another feature dump or pure marketing jargon.
5. Forgetting the managers.
If frontline managers don’t carry the message forward, SKO momentum evaporates in less than a week.
Manager alignment is the multiplier.
6. No post-SKO reinforcement.
This connects to the previous point on managers.
If the “follow-up plan” is a folder of slides in Google Drive… you don’t have a follow-up plan.
The full list of mistakes covers everything from agenda design and speaker flow, to practice formats, to how to make sure what’s said on stage actually shows up in deals.
If SKO is your biggest moment of enablement all year – treat it that way.
👉 Read the full breakdown and steal the good parts
💭 Reflective Insight
I still remember the first few times I sat alone in a restaurant while travelling.
The waiter would ask, “Table for one?”
And even before sitting down, a quiet tension would creep in.
Not fear exactly. More like a quiet self-consciousness I couldn’t switch off.
The mind would start whispering: “Everyone’s with someone. You’re the only one alone.”
I’d look around – couples, groups, laughter – and suddenly it felt like everyone else belonged more than I did.
It’s strange how deeply that idea runs.
That being on your own somehow means something’s missing.
But over time, I stopped trying to escape it. I leaned in.
I stopped hiding behind my phone. I slowed down. I watched.
And then something shifted.
That discomfort – the one that used to make me rush through dinner – started to fade. It turned into a kind of calm.
I began noticing more: the way the light hit the glasses, the rhythm of conversations, the small smiles from the waiter.
Sometimes I ended up talking to strangers sitting next to me. Sometimes I didn’t.
Either way, it felt full – not empty.
And I realised this: being alone doesn’t disconnect you. It makes you pay attention. It makes you see.
We spend so much time surrounded by people and on our phone that we forget how to actually connect – not just with others, but with ourselves.
Being alone strips that noise away.
And in that space, something honest shows up.
These days, I love eating alone as much as I love eating with others. It feels like the most natural thing in the world.
Funny how the thing that once felt uncomfortable became one of the purest ways to feel present.
---
When was the last time you did something completely alone – not by accident, but by choice?
💭
These are my 3 article picks for this issue from The Enablement Insight:
Know one person who’d find this valuable?
Forward this email or invite them to subscribe here →
Enablement Edge
|
Got 15 seconds? Please share your feedback by hitting the buttons below. Tell me what you liked and how I can make The Enablement Edge newsletter better.
