👋 Welcome to another issue of The Enablement Edge newsletter!
In this one, you’ll read about the following:
- ✅ 1 Key Best Practice – Sales training metrics
- ⚠️ 1 Mistake to Avoid – Why sales methodologies fail
- 🧭 1 Key Concept – The winds of sales
- 🧘 Reflective Insight – 31 life lessons
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✅ Key Best Practice
Let’s be real: measuring sales training often ends up as little more than tracking attendance and collecting “happy sheets.”
That’s not enough, especially when budgets are tight and many enablement practitioners are being asked, “What’s actually changing in the field?”
So, what sets modern, strategic teams apart?
They go far beyond completion rates and aim for metrics that answer, “Did this training drive real results?”
Here’s where most teams go wrong:
- Tracking the surface: Counting attendees or quiz scores may show activity, but not meaningful change.
- Ignoring business outcomes: Metrics that don’t link to revenue or performance tend to be overlooked.
- Measuring too much: Tracking everything dilutes focus and leads to weak insights.
To help you avoid these pitfalls, I put together a quick guide to sales training metrics in collaboration with Hyperbound.
They’re organised into six core categories:
1. Reach & Participation
Are you getting learners into your programmes – and keeping them there?
Track how many people sign up, attend, and complete sessions. Spot where and why drop-offs happen (poor communication, low relevance, friction in access), so you can optimise enrollment and engagement across all training initiatives.
2. Engagement & Completion
Did learners go all the way?
Measure how deeply reps interact with training content – from starting modules to finishing on time. Assess how far they get, how long they stay, and where they stall. This helps you fine-tune pacing, structure, and the overall learning experience.
3. Knowledge Acquisition & Retention
Did the training stick?
Move beyond attendance. Track how much learners actually understand, improve, and remember over time. Use assessments, quizzes, and follow-ups to gauge both short-term understanding and long-term, on-the-job recall.
4. Confidence & Satisfaction
How do reps feel about the training?
Gauge whether they found it valuable, are likely to recommend, and feel more confident applying what they learned. These insights, though subjective, help you assess programme credibility and encourage ongoing adoption.
5. Application & Performance Impact
Did behaviour or results change in the real world?
Measure what matters: Are reps applying what they learned? Are managers reinforcing it? Is it contributing to measurable sales outcomes (like better win rates, higher deal velocity, or improved quota attainment)? Use observations, CRM and other tools analytics, and align to real business KPIs.
6. Operational Efficiency
How well is enablement running behind the scenes?
Track how fast you respond to change, how wisely resources are allocated, and how mature your team’s sales training operations are. These “back office” metrics often determine how much more you can do with less, revealing both scalability and hidden bottlenecks.
For each of the 27 individual metrics, you’ll find:
- A clear definition to avoid confusion or poor tracking
- A formula to calculate performance
- A practical example to bring the metric to life
You likely won’t need to track all 27 – and you probably shouldn’t.
Instead, review them.
Pick the ones that will help you measure training success more effectively.
Start small. Build from there. Improve how you train.
👉 Check out the full guide
⚠️ Mistake to Avoid
It happens all the time.
New sales methodology. Big launch, big promises.
But before you know it, it’s gathering dust in the CRM.
Reps fall back into old habits.
Managers grumble that “nothing sticks.”
Deals? No better off than before.
Why does this keep happening? Because the problem isn’t the methodology. It’s the system around it.
—
Here’s where things usually go wrong:
❌ Shaky foundations.
Your sales stages aren’t simple and clear enough. Buyer behaviour barely matches what’s on paper (if at all). Teams can’t track progress accurately, let alone adopt a new way of working.
❌ Managers missing in action.
No deal reviews grounded in the methodology. No coaching, no reinforcement. Behaviour change doesn’t stand a chance.
❌ Death by one-and-done training.
Launch day comes and goes. Little follow-up. No role plays, no integration with real-world workflows. Reps slip back to whatever feels safe.
❌ Leadership turning a blind eye.
Execs say it matters, but don’t model the behaviour. They don’t use the language or drive the discipline needed. The message is clear: “this is just another initiative.”
❌ No plan to adjust.
The team, the market, the tools, they all change – fast. Methodologies that never evolve get left behind, no matter how good they looked in the manual.
So what can you do differently?
✔️ Anchor your process to buyer signals
Redefine sales stages around what the buyer is doing – not just what your team has “done.”
This makes it easier to embed a more buyer-centric methodology and coach against how certain sales actions shaped buyer behaviours.
✔️ Build a real coaching rhythm
Methodologies live or die in deal reviews.
Train managers first. Equip them to inspect deals using the framework weekly; not just at the end of the quarter.
✔️ Train less, reinforce more
Swap one-off workshops for ongoing practice.
Role plays with appropriate scorecards, Slack spotlights, CRM prompts – repetition builds habits when it’s woven into daily workflows.
✔️ Involve leadership from the start
Get your VP and CRO to model the behaviour.
Have them use methodology language in pipeline calls and strategy reviews.
If they don’t, reps won’t either.
✔️ Pilot before you scale
Start small. Prove it works.
Refine based on feedback, then roll it out.
Methodology adoption should feel like a product launch, not a policy memo.
—
The hard truth is that methodologies don’t fail on their own.
They fail when the environment isn’t ready to support them.
So before you invest in a new framework, ask yourself: “Are you fixing the playbook – or preparing the soil?”
🧭 Key Concept
You might recall the sales value pyramid model I shared recently – and how it’s been instrumental in building business acumen across the salespeople I support.
One concept I find especially useful in practice is the idea of headwinds and tailwinds.
Headwinds are obstacles or negative forces slowing your buyer down. These could include economic slowdowns, regulatory shifts, emerging competitors, budget freezes, or internal chaos.
Tailwinds, on the other hand, are positive shifts giving your buyer extra momentum – booming markets, favourable regulation, tech breakthroughs, or strong leadership backing.
How to use them in sales
Headwinds and tailwinds are powerful because they invite discussion. There’s nuance.
And that makes conversations more engaging.
When reps learn to talk about these forces, they move beyond pitching products.
They position themselves as sharp observers of the customer’s world.
Top performers do three things differently:
1. They do the research
They stay plugged into industry news, voices, and trends (and AI can make it easier than ever today).
They listen for anything shifting buyer momentum – positively or negatively.
And they bring that curiosity into conversations.
They ask:
🟠 “What’s making it harder to hit your goals this year?”
🟢 “What’s been giving you an edge lately?”
They listen. Take notes. And only then do they start connecting the dots.
2. They tailor their message
When headwinds hit (e.g., new compliance rules), they lead with how their solution helps overcome friction.
When tailwinds blow (e.g., product demand surges), they show how to ride that wave faster.
It’s never about generic value; it’s about relevant value.
3. They bring it into discovery
They reference real proof:
🔸 “Last quarter, our clients dealing with [headwind] tackled it by…”
🔹 “With [tailwind] in play, here’s how others in your space pulled ahead.”
This builds credibility fast – and keeps the conversation rooted in outcomes, not features.
Quick examples
Headwind:
Regulation tightening → Sales cycles are longer
Your move: Emphasise speed, compliance support, and how you reduce implementation headaches.
Tailwind:
Industry is booming → buyer just got fresh budget.
Your move: Frame how your solution helps scale fast and capture momentum.
A few quick tips
Start every account plan or deal review with this: “What headwinds and tailwinds are shaping this account right now?”
Share insights across your team. If one account is slowed by a headwind, chances are others are too.
Don’t just react. Proactively reposition your offer as the winds shift.
Help your team spot the forces at play, adjust the message, and they’ll win more – no matter which way the wind blows.
🧘 Reflective Insight
A few months ago, I turned 31.
In the weeks leading up to it, I took time to reflect – on the mistakes, the growth, and the quiet lessons that only life experience can teach.
I wrote pages and pages… then distilled them down into 31 punchy insights.
Here they are:
- Measure yourself against your past, not against others.
- Sleep is the foundation of everything you want to build.
- Greatness is a team sport, choose your people wisely.
- You can’t inspire others if you’re not inspired yourself.
- Solving one problem only reveals the next – embrace it.
- True happiness lives in the present, not in milestones.
- Strong intention, clear vision, and action bend reality.
- More possessions bring more complexity, not peace.
- Relationships grow through patience, not shortcuts.
- The faster you move, the faster life fills your plate.
- Success isn’t a sprint; it’s surviving the marathon.
- Your network mirrors your self-worth – nurture it.
- Sitting with yourself is an act of profound sanity.
- Suffering isn’t failure; it’s a step toward clarity.
- Success won’t heal wounds; inner work will.
- When in doubt, stay true to your values.
- Be a giver; the takers eventually lose.
- Build value first – business follows.
- They can take your job, not your skills.
- Fear distorts reality; truth waits behind it.
- Consistency outperforms brilliance over time.
- Relationships are the only real wealth we carry.
- In business, hiring well is your highest leverage.
- Seek truth, even when it breaks your ideas apart.
- Thoughts are not truth; they’re just passing noise.
- Say what matters today – tomorrow isn’t promised.
- Environment shapes you more than discipline alone.
- The best investment is the one you make in yourself.
- Seek what proves you wrong, not what validates you.
- Body, mind, soul – your only true assets. Honour them.
- Protect your focus like your life depends on it; because it does.
Which one resonates most with you?
And what’s one lesson you’ve learnt through your own journey?
I’d love to hear it.
Just hit reply and share it with me – I read every message.
These are my 3 article picks for this issue from The Enablement Insight:
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