👋 Welcome to another issue of The Enablement Edge newsletter!
In this one, we’re talking about:
- ✅ 1 Best Practice – Stakeholder management matrix
- ❌ 1 Key Mistake – Pipeline health as a single metric
- 🎯 1 Key Concept – B2B Sales & marketing alignment as a shared commercial reality
- 💭 1 Reflective Insight – What are you really protecting?
Let’s go!
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✅ Best Practice
Most stakeholder mapping in enablement is too narrow.
We tend to focus first on the obvious people: the senior leader sponsoring the work, the person who made the request, maybe a manager expected to reinforce it.
That gives us part of the picture, but rarely the whole one.
What the stakeholder matrix in my latest guide on stakeholder management skills makes clear is that formal influence is only one dimension. The other is proximity to execution: how closely someone sits to rollout, reinforcement, adoption, and day-to-day behaviour change once the initiative is in motion.
The second dimension makes a huge different because a stakeholder can have relatively low formal authority and still play a major role in whether the work actually sticks.
Likewise, someone can have the power to approve the initiative, yet very little influence on what happens once it reaches the field.
My stakeholder manager matrix helps you avoid one of the most common enablement errors: overinvesting in the people who can approve the work, while underinvesting in the people who will determine whether it lands.
The framework uses two questions:
- How much influence does this person have on direction and priority?
- How close are they to execution?
Once you map stakeholders against those two dimensions, four practical engagement groups emerge:
Shape with – The people who help design the work and strongly influence whether it will land well.
Align closely with – The senior sponsors and backers who give the initiative protection, legitimacy, and air cover.
Equip and support – The execution multipliers, often managers, team leads, field partners, or influential ICs, who may not set direction but heavily affect reinforcement and adoption.
Keep informed and monitor – Stakeholders who matter, but do not need deep involvement from the outset.
What I like about it is that it turns stakeholder management into a set of decisions.
Not “Who should know about this?”
But:
- Who do I need to shape this with?
- Who needs close alignment?
- Who needs support to carry it forward?
- And who just needs enough visibility so they are not surprised later?
From there, it becomes much easier to approach the right people at the right time with the right messaging, to provide materials that will support them throughout the initiative, and to establish accountability.
If you’d like to go deeper, I break the full stakeholder management model down in the article, including the matrix above and the wider set of skills that help enablement work navigate shifting priorities, gain reinforcement, and create real cross-functional impact.
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❌ Key Mistake
Pipeline health is one of the most important measurement layers in sales.
It tells you whether enough of the right pipeline is entering the system, whether it is moving with enough momentum, and whether the current portfolio is strong enough to support future revenue.
One mistake that I see less mature GTM organisations make over and over again is treating pipeline health as if it were just one number.
Usually that number is total pipeline value.
Sometimes it is coverage.
Both matter, of course, but neither is able to tell the full story.
A pipeline can look large on paper and still be weak underneath. Creation can be high, yet the mix can be off-target, low-value, or too dependent on sources that convert badly later.
Movement can look acceptable at a glance, while a large share of the value is silently sitting still.
Coverage can look strong, yet the stage mix may be unbalanced, or too much of the pipeline may depend on a small number of deals.
That is why I find pipeline health much more useful when treated as a portfolio view rather than a headline number.
You need to ask far more questions than just a simple, “How much pipeline do we have?”
Here are just some of the examples:
- Are we creating enough of the right pipeline?
- Is it actually moving?
- Is it slowing down anywhere?
- Is the current portfolio balanced enough to support future targets?
- How much of it depends on only a handful of deals?
The goal is to stop merely reacting only to missed numbers and start looking at the conditions that make those misses more or less likely.
Maybe the issue is not generation volume at all, but ICP fit. Maybe it is not activity, but stage progression. Maybe it is not total coverage, but slippage, ageing, or concentration risk.
The article I wrote in collaboration with Pipedrive breaks pipeline health into two main buckets: pipeline generation metrics and pipeline progression metrics. Then, those are split into categories including creation volume and sufficiency, new pipeline quality and composition, stage conversion, velocity and ageing, and coverage and balance.
Read together, those give you a much more honest picture of whether the pipeline is well-fed, well-shaped, moving with enough momentum, and robust enough to support the target.
If you want the full breakdown, here’s the guide on 22 sales pipeline health metrics, with formulas, examples, and notes on how to use them without collapsing everything into one misleading number.
🎯 Key Concept
I recently brought together original perspectives from 17 leaders across sales, marketing, and sales operations to explore what sales and marketing alignment actually looks like in practice.
What came through most clearly is that alignment becomes tangible when both teams are working from the same commercial reality.
In other words, where they have shared outcomes, shared definitions, shared visibility into the funnel, shared inspection of what is converting or stalling, and shared responsibility for improving it.
That idea becomes much easier to grasp when you look at how some teams actually run.
One of the clearest examples in the piece comes from VP of Sales, Eileen Wiens, who described a weekly funnel review where sales, marketing, finance, and ops all looked at the same pipeline by channel, stage conversion, velocity, and profitability in one shared forum.
If risk showed up in the leading indicators, the expectation was simple: come in with a plan.
Because the discussion happened cross-functionally, issues were diagnosed and solved in real time, instead of being defended from separate corners of the business.
Operating this way has very tangible effects.
It shapes whether teams are building pipeline to the same standard, whether handoffs stay smooth, whether messaging stays coherent from first touch to live deal, and whether problems get solved through shared diagnosis rather than blame.
The full industry article goes much deeper into what effective alignment looks like day to day, where it tends to break, how weak alignment affects behaviour and revenue performance, the role of ops in making alignment real, and how to tell whether alignment is genuinely improving.
Check it out here!
💭 Reflective Insight
Sometimes I notice how often life can feel like something important is at stake.
When you try something new.
When you speak to someone you don’t know.
When you put yourself out there a bit more than usual.
Even simple things… starting a conversation, sharing an opinion, making a call you’ve been postponing.
It can feel like you’re risking something. Your image maybe, your comfort, how people might see you, that small sense of safety we all try to keep around us.
And yet sometimes I stop and ask myself a very simple question: "What am I actually protecting here?"
Because if you really zoom out for a moment, just being here already means we’ve been given something incredibly rare.
A life. A limited experience. A number of years we don’t even know the exact length of. A finite number of chances to try things, to meet people, to change direction, to become slightly different versions of ourselves.
And still, we often move through life as if we are constantly trying not to lose something.
When in reality, we already won something just by being here.
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There’s a Steve Jobs line I’ve always liked because of how simple and honest it is:
“You are already naked. There is no reason not to follow your heart.”
Obviously, not naked in a literal sense, but in the sense that most of the things we think we might “lose” are not really ours in the first place.
Perfect image? Never existed.
Certainty? Mostly something we invent.
Control? Much less than we think.
Most of the time what we are really avoiding is just discomfort. That small moment of exposure where you feel a bit uncertain.
And when you think about it, discomfort is a very small price compared to the regret of not living fully or not trying things that were silently calling you.
---
Fear often feels like a stop sign.
But more and more, I've realised that it’s just a signal that you are close to something that could expand you a little.
Many of the things that later become meaningful in our lives didn’t start as comfortable decisions. They started as slightly awkward ones. Slightly uncertain ones. Moments where we didn’t fully know how things would go.
Maybe the real risk is not doing those things.
Because this experience we’re having… it does end. And none of us really knows when.
And when I look at it from that angle, this is probably the one thought I’d leave you with:
If being alive is already the biggest thing we could have been given… maybe we can afford to be a little less careful and a little more alive while we are here.
💭
See how the Enablement Edge operating system works in practice
Design, execute, and refine enablement initiatives faster using a structured operating system — combining diagnostics, practitioner intelligence, execution-ready assets, and a peer network.
Attendees will also receive a 7-day free access to explore the operating system directly.
🎟️ SIGN UP FOR THE WALKTHROUGH
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