π Welcome to another issue of The Enablement Edge newsletter!
In this one, weβre talking about:
- ποΈ 1 Key Resource β Sales playbook template
- β
1 Key Best Practice β Silence as a coaching tool
- π€ 1 Key Piece of Tech β Sales engagement software as an outbound operating layer
- π― 1 Key Challenge β Standing out in enablement interviews
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ποΈ Key Resource
As a practical activation layer of my recent guide on sales playbooks, Iβve put together a sales playbook template for teams that want to build a playbook their salespeople will actually use.
It may sound simple, but we all know thatβs not easy.
The last thing you want is creating a mix of folders, links, notes, decks, and assets that make sense to the people who built them, yet stay too heavy, too scattered, or too far away from the moments where reps need real guidance.
That is the problem this template β alongside the guide I linked above β is meant to solve.
I created it in partnership with Airspeed as a practical way to move from loose sales content to a clearer, stage-based playbook structure, one that helps reps understand what to do, when to do it, and how to apply the guidance in live selling situations.
In other words, it is envisioned as a way to evolve your sales playbook from a static document into something that allows you to:
- Define the scope
- Map your sales stages
- Clarify what strong execution looks like at each stage
- Identify the actual guidance and assets reps need
- Organise those items into a manageable inventory
- Plan how they should appear in the flow of work
- Measure whether the playbook is improving execution over time.
It helps you connect:
Stage β Context β Guidance β Asset β Action
As a result, it becomes an artefact helpful to a variety of teams.
Enablement can use it to turn scattered guidance into a structured playbook.
Sales leaders and managers can use it to clarify what good execution looks like and create a stronger coaching reference.
RevOps can use it to connect process design with the practical support reps need inside each stage.
In my opinion, the strongest value of this template is in its emphasis on focus.
Instead of trying to build the whole playbook at once, you can identify the few parts that matter most, improve those first, and build a version that is easier to maintain and much more likely to be used.
What you get is a genuinely comprehensive, but still practical, workbook.
You can find the template here.
β
Key Best Practice
I recently sat down with Sheevaun Thatcher and Katie Chatterton for a conversation on sales coaching in the age of AI, and one simple, yet powerful, idea was that the silence is a very underrated coaching tool.
In most sales environments, pace wins. A manager asks a question, the rep hesitates, and the instinct is to jump in, rephrase, suggest, or rescue.
That may feel helpful; however, in reality, it often does more harm than good as it cuts the deeper thinking short.
Katie described silence as a superpower.
Sheevaun put it even more directly: βItβs in the pause β¦ where the learning happens.β
That pause gives the rep time to get past the polished first answer and closer to the real issue.
A deal problem can be a confidence problem.
Or a prioritisation problem.
Or a discovery problem.
Or simple fear of asking the harder question.
Without the silence, it is nearly impossible to find the real core of the problem.
What emerged from the conversation is this framework we called βthe listening disciplineβ:
As indicated in the visual, the added value of the sales team adopting the listening discipline is that it can be applied to other conversations, both within the team and, perhaps more importantly, in conversations with buyers.
A seller who learns the importance of pausing from their manager during coaching is more likely to pause in discovery. They hear more, ask better follow-ups, and donβt rush to pitch.
So, one small coaching βupgradeβ Iβd recommend to any manager is this:
Ask the question.
Let it breathe.
Then listen long enough for the better answer to show up.
If you want the full breakdown, the sales coaching briefing covers the wider coaching conversation with Sheevaun and Katie, covering things like the importance of leaving reps with a sense of ownership at the end of coaching conversations, manager enablement, where AI fits in sales coaching, and much more.
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π€ Key Piece of Tech
In researching my recent buyerβs guide to sales engagement software, I found myself needing a better definition of the category before I could even compare the tools properly.
A lot of people still think of sales engagement software as little more than a sequencing tool.
The better way to think about it is as an operating layer for outbound and follow-up execution.
The stronger platforms do not just send emails or queue tasks. They help teams run structured multichannel workflows, capture activity, coordinate work with the CRM, bring data and prioritisation closer to execution, protect deliverability, and create the visibility managers, RevOps, and enablement need to improve the motion over time.
That is the framing I ended up using in the guide.
And it helped me make much more sense of the category.
In practice, most sales engagement platforms now combine five core capability areas:
- Cadences and multichannel workflow
- Activity capture and automation
- Data, targeting, and prioritisation
- Deliverability, governance, and compliance controls
- Analytics and optimisation.
Once these capabilities helped me define the category properly, the buying questions became immediately clearer:
- How does outreach actually run here?
- What needs to be governed?
- Where does the data come from?
- How visible is rep activity?
- How will managers inspect and coach the motion?
- And what exactly are we trying to improve?
As a result, I was able to narrow down my research and go super-deep on the tools that made the shortlist.
If you want the deeper breakdown, the full guide goes into the category boundaries, the adjacent tools I left out, the shortlist itself, and the trade-offs between platforms like Outreach, Salesloft, Reply, lemlist, Apollo, Amplemarket, Regie, Nooks, and Klenty.
π― Key Challenge
Lately, Iβve noticed how many people in my enablement circle have changed companies over the last year or so.
Some teams have been cut back.
Others are building enablement for the first time.
Others again are reshaping the function completely.
Enablement interviews are happening all over the place.
That made me revisit the interview series Iβve built on the Enablement Edge blog, and one thing that stood out is that the strongest candidates tend to separate themselves in three less obvious ways.
First, they stay grounded when the interview stops being βtidyβ.
They are prepared for unexpected questions, awkward scenarios, and incomplete context.
They do not confuse speed with judgement, and they do not rush to sound decisive just because the room has gone a bit ambiguous.
Very often, the better answer in enablement is the one that slows down, asks what is missing, and shows how you would enter a messy system before trying to fix it.
Sometimes that even means showing what you would not do, what you would remove, or what you would deprioritise.
Second, they make their thinking and work visible.
A lot of candidates may sound polished, but they may not sound practical and real.
The stronger ones bring a lightweight point of view on the business, turn that into a rough 30β60β90 plan, and back up their claims with evidence, examples, artefacts, or a small portfolio of work.
They do not hide behind generic enablement language, and they do not speak as if they learned the role from conference panels and LinkedIn posts.
They sound like people who have actually had to make trade-offs, navigate constraints, and connect their work to outcomes.
Third, they treat the interview itself like live enablement work.
They stay curious throughout.
They ask questions that help them understand the business, the motion, the gaps, and the environment they may be stepping into.
They listen properly.
They build on what was said.
And they seem to understand that they are not only being assessed on their answers, but on what it feels like to work with them in a room where priorities are not perfectly aligned and the path is not fully clear.
Iβve gone much deeper on all of this across what is probably one of the most comprehensive enablement interview series on the Enablement Edge blog, including guides on interview preparation, tips from 39 leaders and managers, surprising interview questions, and the biggest interview mistakes candidates make.
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