👋 Welcome to another issue of The Enablement Edge newsletter!
Sit back, relax, and get ready for:
- ❌ Key Mistake – Treating managers as the final step in an enablement programme
- ✅ Key Best Practice – Ops and enablement working together
- 🎥 This Week’s Video – The missing piece in most sales discovery trainings
- 🤖 Piece of Tech – Do you need forecasting software?
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❌ Key Mistake
I’ve long considered the failure to properly enable sales managers one of the biggest mistakes enablement teams make.
For years, I wanted to write a comprehensive guide on what properly enabling sales managers involves. In collaboration with revenue acceleration partner revlogic, I finally did.
The process helped me clarify where the real mistake lies.
Most organisations involve managers only at the end, after the initiative has already been designed around sellers.
The methodology is announced.
Reps attend the training.
The assets go live.
CRM fields, processes, and reporting expectations change.
Only then does the organisation turn to managers and say: “Now reinforce it.”
The problem goes much deeper than managers missing a briefing or a coaching guide.
Managers aren’t simply another audience that needs to understand the initiative. They are the layer that translates it into daily execution.
They determine what gets inspected, which standards get applied, what gets coached, what behaviour gets tolerated, and which organisational priority survives contact with a crowded week.
Every enablement initiative therefore enters an existing management system.
It has to compete with forecast pressure, pipeline targets, established meeting rhythms, leadership requests, CRM requirements, seller resistance, and everything else managers already need to handle.
When that system hasn’t been designed around the desired change, managers have to reconcile the contradictions themselves.
The training may tell sellers to spend more time diagnosing the buyer’s problem, while pipeline reviews continue to reward speed and next-step progression.
The methodology may introduce a stronger qualification standard, while the CRM captures different information.
Leadership may describe an initiative as a priority, while managers receive no additional time, guidance, or support to reinforce it.
At that point, managers are left to work out for themselves how the initiative should be applied in practice.
Experienced managers may fill the gaps by connecting the initiative to live deals, developing their own coaching questions, and deciding what to inspect.
Others may apply it inconsistently, give it limited attention, or struggle to translate it into practice at all.
The result is uneven execution across teams, despite every seller attending the same programme.
This can mask the underlying design failure. When some managers make the programme work, the organisation may assume the approach is sound and blame those who struggle to achieve the same results.
In reality, these differences often reflect a system that relies too heavily on individual manager judgement and improvisation.
That’s why sales manager enablement needs to be treated as a connected system rather than a manager training programme or reinforcement plan.
The sales manager enablement model I propose brings together the conditions managers need to perform effectively: a clear role, the right capabilities, shared commercial standards, a workable management rhythm, strong coaching practices, useful performance intelligence, and the enablement infrastructure connecting everything together.
So, before rolling out an initiative to sellers, the question shouldn’t simply be, “Have managers seen the programme?”
The better question is, “Have we given managers what they need to lead the change effectively?”
That means deciding:
- which observable seller behaviours managers should reinforce,
- where those behaviours will be inspected during calls, deal reviews, pipeline reviews, and one-to-ones,
- what evidence helps managers distinguish strong execution from weak execution,
- which coaching questions, examples, and methods they can use when gaps appear,
- how the initiative fits into the team’s existing management rhythm,
- what managers should do when sellers resist the change or struggle to apply it,
- what competing work needs to be reduced, changed, or removed,
- and how managers will feed evidence back when the programme doesn’t work as intended.
Managers should also have the opportunity to pressure-test, and sometimes co-author, important parts of the programme before launch.
They can identify where the proposed guidance conflicts with field reality, where standards remain open to interpretation, where the available data won’t support meaningful inspection, and where the reinforcement plan creates more work than the management rhythm can absorb.
These inputs improve the initiative as well as prepare managers to lead it with far more clarity once it reaches their teams.
Manager reinforcement should never be the final line on a rollout plan.
The way managers are enabled determines whether an initiative becomes part of everyday commercial execution, is applied differently across teams, or gradually disappears after launch.
My full sales manager enablement guide explores how to design this as part of a wider system, with each element working together to support consistent execution.
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✅ Key Best Practice
Consider this scenario:
Your Sales Operations team spots a clear drop in post-demo conversion.
The dashboard shows it, and the trend has continued for several months. It is especially pronounced in larger opportunities and appears across more than one region.
The instinctive response is immediate: “We need better demo training.”
It sounds reasonable. The problem appears after the demo, so the demo must be where things are going wrong.
But the data has only shown you where performance is deteriorating. It hasn’t told you why.
The issue could be weak discovery, with reps reaching the demo before properly understanding the buyer’s priorities.
It could be poor stakeholder coverage, with the right people missing from the conversation.
Perhaps the demos are too generic, or sellers are struggling to connect the product to a credible business case.
There may even be a product-fit, pricing, or positioning issue that training cannot solve.
This distinction was central to the pipeline leaks report I developed with enablement expert Lawrence Wayne O’Connor.
We explored how pipeline data, call evidence, CRM notes, and manager feedback can help teams identify where opportunities are losing momentum and investigate why.
But that raised a bigger question:
“Once you’ve located the leak, how do Sales Operations and Enablement work together to improve the underlying performance?”
That question led to further conversations with enablement leader Phil Aaronson and became the starting point for the shared performance loop in my full guide to Sales Enablement and Sales Operations alignment.
The loop starts with a commercial question, rather than an assumed solution.
Sales Operations can locate the gap, quantify it, and show where it is most pronounced.
Enablement can then work with managers and sellers to investigate the causes by reviewing calls, inspecting discovery notes, comparing opportunities, and looking at what stronger performers do differently.
The next step is to translate those factors into something the organisation can inspect.
If the seller’s understanding of the buyer’s problem matters, the visible output might be a discovery summary.
If stakeholder coverage matters, it might be a stakeholder map.
If executive relevance matters, it could appear in an executive brief or the opportunity narrative.
This is more useful than concluding that sellers need “better discovery”.
A manager can inspect whether the seller has clearly defined the problem, established its commercial effect, connected it to a business priority, and confirmed why action is needed now.
As a result, Sales Operations and Enablement have something practical to work with:
- a visible seller output,
- a shared definition of quality,
- evidence that can be captured,
- guidance for improving weak execution,
- and a clearer role for managers.
Only then should the organisation decide what action makes sense.
Maybe sellers need sharper discovery standards.
Maybe managers need a better way to inspect demos and coach against clear criteria.
Maybe the sales process is allowing opportunities to move forward before enough evidence exists.
Or perhaps the original assumption was wrong, and no training is needed at all.
This is why alignment between Sales Operations and Enablement needs to go beyond shared dashboards or occasional collaboration.
It should create a shared performance loop connecting: commercial evidence → performance factors → visible seller outputs → quality standards → operational signals → situational guidance → reinforcement and refinement
A signal in a dashboard shouldn’t simply tell a manager that an opportunity appears to be at risk.
It should help them understand what is missing, why it matters, which questions to ask, and what the seller should consider doing next.
As Phil put it: “If you see this, do this.”
That is the difference between reporting performance and helping the organisation improve it.
My full guide to Sales Enablement and Sales Operations alignment explores this seven-part loop, including how the two functions can move from commercial evidence to clearer execution standards, better seller support, manager reinforcement, and measurable improvement.
🎥 This Week's Video
Most commercial organisations know discovery is a critical sales capability.
Yet when conversion rates connected to discovery drop, the response is often the same: run a workshop, share a question bank, review a few calls, and hope things improve.
The problem is that many discovery programmes start with training content before defining what good discovery should actually produce.
In this video, I explore a different approach: starting with the outputs you expect from discovery, then working backwards to the behaviours, training, reinforcement, and measurement needed to produce them consistently.
🤖 Key Piece of Tech
Sales forecasting is becoming less dependent on who sounds most confident in the forecast call.
For years, teams relied heavily on CRM fields, stage probabilities, rep judgement, manager overrides, and a considerable amount of manual interpretation.
Newer forecasting platforms can draw on a much broader set of signals. These include CRM changes, buyer engagement, customer conversations, qualification evidence, stakeholder coverage, deal velocity, activity patterns, and historical conversion rates.
Together, they provide a clearer picture of what is happening inside each opportunity and how likely it is to close.
I first saw what this could look like while implementing Airspeed (one of my favourite AI tools).
Instead of treating forecasting as a separate exercise layered on top of the CRM, the platform could use conversations, qualification evidence, engagement, and deal activity to strengthen the evidence behind the forecast.
Of course, not every team will need specialist forecasting software.
If your sales motion is straightforward, your CRM data is reliable, managers use forecast categories consistently, and leadership can produce a dependable forecast without hours of manual work, native CRM forecasting may be enough.
Specialist software becomes more relevant when producing and validating the forecast starts consuming significant time.
RevOps rebuilds forecast views in spreadsheets each week.
Forecast calls turn into lengthy deal-by-deal interrogations because nobody trusts the system.
“Commit”, “best case”, and “upside” mean different things across teams.
Close dates slip repeatedly without warning.
Sales, RevOps, and finance arrive with different numbers, then spend the meeting reconciling them.
A specialist platform can bring more structure to forecast submissions, roll-ups, deal inspection, risk detection, forecast changes, and the evidence behind each call. The better tools also help managers see what changed, where confidence is weakening, and which opportunities require closer inspection.
However, more AI does not automatically produce a better forecast.
If CRM data is poor, forecast categories are unclear, or managers apply inconsistent standards, the platform may only produce a more convincing-looking version of an unreliable number.
This is why the buying question should not be: “Which platform has the best AI?”
It should be: “What is weakening our forecast today, and which platform is best equipped to address it?”
I recently evaluated nine specialist forecasting platforms:
- Clari
- Airspeed
- Aviso
- Terret
- Mediafly
- Revenue Grid
- Forecastio
- Weflow
- Xactly Forecast
These platforms tackle different parts of the forecasting problem.
Some focus on enterprise forecast management. Others are stronger in predictive intelligence, deal risk, CRM data quality, conversation evidence, revenue execution, sales performance, or finance alignment.
My full guide compares their positioning, best-fit scenarios, strengths, limitations, CRM fit, implementation effort, and more.
It also helps you decide whether specialist forecasting software is warranted in the first place – which may be the most important part of the buying decision.
Build enablement that changes behaviour and drives business impact
Make better decisions and execute faster with the Enablement Edge Operating System – combining practical tools, proven frameworks, implementation pathways, AI assistance, and a trusted peer network.
SEE WHAT'S INSIDE →
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