👋 Welcome to another issue of The Enablement Edge newsletter!
Sit back, relax, and get ready for:
- 🚀 Key Concept – How do you build a winning sales culture?
- ⚠️ Mistake to Avoid – Making product training myopic
- ✅ Best Practice – Effective sales coaching prep
- 💰 Key Idea – Overpaying for sales talent
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🚀 Key Concept
I spent much of this summer diving into books, research papers, and conversations with fellow enablers and sales leaders.
The topic was sales culture.
Among other things, here’s what I found:
- There are about 8.7 trillion definitions of it.
- It’s maddeningly hard to explain in writing.
- It’s deeply multifaceted.
- Building or changing it is complex, because every component influences the rest.
That said, after plenty of digging and discussion, I distilled an actionable 7-step playbook for building a high-performing sales culture:
1. Psychological safety first
A culture of candour lets people share early, admit mistakes, and challenge ideas without fear of backlash. This speeds up learning and problem-solving while deepening trust.
2. Align on purpose and values
Make sure everyone knows not just what you’re trying to achieve, but why. Reinforce purpose and values consistently so they become lived standards, not just a slide in onboarding.
3. Translate purpose into goals and ways of working.
Turn values into specific behaviours, team rituals, and measurable goals. This clarity removes ambiguity and ensures everyone pulls in the same direction.
4) Measure what matters
Go beyond revenue to track the inputs and behaviours that lead to results. Use fair, transparent measurement to guide coaching and course correction.
5) Celebrate effort and wins
Recognise achievements regularly – both the visible milestones and the behind-the-scenes work. Done well, this fuels motivation and reinforces positive behaviours.
6) Encourage innovation
Give teams the space to experiment and voice fresh ideas, even if they challenge the status quo. Innovation thrives when people feel their contributions are valued.
7) Weave connection and fun into the work
A culture that balances performance with enjoyment strengthens team bonds and resilience. Make room for moments of levity alongside the serious work.
👉For a (much, much, much) deeper dive, check out the full playbook here!
Since sales culture sparks a wide range of perspectives, I’d love to hear yours. If you have questions, ideas, or constructive critique, feel free to share – I’m always keen to learn from the conversation.
⚠️ Mistake to Avoid
One of the fastest ways to create irrelevant, forgettable product training?
Letting a single department build it in isolation. (This applies to most training types, not just product.)
Product training for sales should never sit solely with enablement, product, marketing, or any one team.
No single function has the full picture of how the product is used, where customers struggle, or which features actually matter in different sales conversations.
To avoid this, bring in experts from across the organisation:
- Sales teams can flag common objections and competitor comparisons they face in the field.
- Customer success and account management can share pain points addressed post-sale and the features that drive long-term adoption.
- Product teams can provide the “why” behind the roadmap and upcoming releases.
- Solution engineering or IT can highlight frequent implementation challenges that should never be overlooked.
By weaving these perspectives into your training, you make it far more relevant, practical, and reflective of real-world conditions.
As, Head of Enablement, Devon McDermott shared with me:
The added bonus is that this kind of cross-functional collaboration builds alignment and ownership, meaning your teams are more likely to use and reinforce the training once it’s live.
How do you handle product training? And who do you involve?
If you’d like to go deeper, here’s a full guide to product training best practices.
✅ Best Practice
Thinking of launching a coaching programme for your sales team (or revamping an existing one)?
Here’s a tip: don’t just grab a few resources, schedule some “coaching sessions,” and hope magic happens.
That’s like launching a spaceship without oxygen, food, seatbelts, or a plan for what to do when (if) you take off.
But hey, at least the playlist’s good.
Now, I don’t know how to prep a rocket for a launch, but I do know how to do a checklist before you launch a coaching programme:
1. Assess your coaching maturity
Are you in “random acts of coaching” mode, or is there already a formal process in place? Knowing whether you’re starting from scratch or levelling up makes all the difference.
2. Take inventory of what you’ve got
List every coaching resource, official and unofficial. That killer call-review template a veteran manager uses? That’s gold. Catalogue it alongside your formal programmes and tools.
3. Gather feedback and data
Talk to reps about the support that’s actually helped them. Peek at exit interview notes. Ask sales ops where deals most often get stuck. Those bottlenecks are coaching opportunities in disguise.
4. Identify the gaps.
Keep what works, toss what doesn’t, and make a wish list for what’s missing. You might discover you’re drowning in e-learning but starving for live role-play practice.
5. Prioritise for impact.
Don’t try to fix everything at once. Start with the gaps that will move the needle fastest, ideally where a small improvement could unblock a big chunk of revenue.
If you follow these steps, your coaching programme won’t just limp into orbit and hope for the best.
It’ll have a flight plan, a capable crew, and enough fuel to keep going.
And trust me, your sellers will feel the difference long before you hit “cruise control.”
PS: Did you know there are 6 main types of sales coaching? You can find them here.
💰 Key Idea
Have you ever wondered why so many companies overpay for sales talent? I did a few months back.
Here’s the (simplified) pattern that I see over and over again in organisations:
1. Hire 10 reps
2. Hope for the best
3. Cross fingers that the A-players stay
Because there’s no real enablement system, the company pays a premium for ready-made stars, then watches them walk out the door.
I believe companies should flip the script.
Hire solid B-players, turn them into A-players, and keep them longer.
That’s what enablement systems are for.
- Dynamic playbooks
- Regular feedback loops
- Targeted, timely coaching
- Modern, fit-for-purpose tools
- Just-in-time content in the flow of work
- Clarity on job expectations and standards
- Clear career progression and growth opportunities
- Peer mentoring and knowledge sharing
- Data-driven insights to tailor support
- Personalised learning paths
- Continuous development
- Structured onboarding
These are the elements that help develop talent, beyond simply managing it.
And the gap between what a company pays and what they produce is simply profit.
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More and more organisations should understand that enablement, executed well, reduces cost, increases retention, and turns development into a competitive edge.
The best companies don’t just hire A-players; they create them – with enablement.
These are my 4 article picks for this issue from The Enablement Insight:
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