![[Thumbnail] 13 Out-of-the-Box Sales Enablement Ideas to Try](https://federicopresicci.com/wp-content/uploads/2026/01/Thumbnail-13-Out-of-the-Box-Sales-Enablement-Ideas-to-Try.webp)
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Introduction
“No two sales enablement teams are alike.”
This is a recurring theme I’ve encountered from the incredible contributors who have shared their stories and insights since the inception of The Enablement Insight.
Each enablement team, along with the individuals who drive it, operates within its own unique environment, facing distinct challenges, responsibilities, and goals.
Some teams prioritise training and coaching, while others focus on creating sales content, optimising processes, or managing sales enablement technology.
Factors such as the maturity of the enablement discipline within the organisation, the reporting structure, and the size of the company further compound these differences.
Despite those, one thing remains consistent across all sales enablement teams: their unwavering commitment to continuously improving and better supporting their go-to-market teams.
In enablement, it’s never about following a standardised, one-size-fits-all approach; it’s about innovating and discovering new ways to drive results that are contextual to the organisation.
In this article, we’ll explore a variety of innovative ideas that sales enablement professionals can use to elevate their efforts.
Whether you’re refining your current practices or experimenting with something entirely new, you’ll find inspiration here to help you and your team make a meaningful impact.
#1 Implement pre-boarding and ever-boarding
One of the most common responsibilities for sales enablement teams is onboarding new sales reps.
However, instead of viewing it as a one-time event that concludes after a few days or weeks, many of our contributors – and my own experience – suggest treating onboarding as an ongoing journey that begins the moment a new hire accepts their offer and continues throughout their entire tenure with the company.
This approach involves what we can think of as two key phases: pre-boarding and ever-boarding.
Pre-boarding starts before the new hire’s first day, allowing you to harness the excitement and energy they feel after accepting the job offer.
By providing them with resources, introducing them to team members, and familiarising them with company culture and products early on, you lay the groundwork for a smoother transition when they officially start.
Of course, this should be done in moderation, as it’s important to recognise that new hires may still be off-boarding from their current employer and could feel overwhelmed if you overdo it.
Once they’ve officially joined, onboarding shouldn’t stop after the initial training period.
The concept of “ever-boarding” involves providing continuous support and development opportunities as new sales reps settle into their roles and progress within the company.
This approach allows new hires to steadily build their skills, align with the company’s strategy, and fully integrate into the organisational culture through regular milestones and check-ins during the first 90 days and beyond.
Ongoing training and coaching is what makes ever-boarding possible, yet these aspects are often neglected by organisations.
In my recent investigation of sales enablement statistics, I found some concerning points:
More likely than not, this is a consequence of limited resources, but enablement teams should strive to address these gaps if they want to run an effective sales enablement department.
Check out my sales onboarding guide for a deeper exploration of pre-boarding and ever-boarding.
#2 Get involved or expand into partner enablement
For many companies, sales partnerships are playing an increasingly vital role in their revenue streams. These partnerships may include:
Managed service providers (MSPs)
Channel partners
Ecosystem partners
Technology partners
Affiliate and/or referral partners
Regardless of whether partnerships are managed by a specialised team, sales, or the broader revenue unit, the sales enablement department can be a valuable asset by supporting or even spearheading partner enablement efforts.
Partner enablement is still a relatively new concept, focused on building stronger relationships with various partners by offering training and certification when necessary, creating co-marketing content, and ensuring alignment between your company’s goals and those of your partners, both business and personal.
There are notable differences between partner enablement and sales enablement, most significantly in their external versus internal focus, as well as the limited influence over certain aspects of your partners’ selling strategies and practices.
However, there are also several similarities, and sales enablement departments can undoubtedly contribute to partner enablement.
In companies where partnerships are often signed and then left to chance, one could argue that sales enablement could provide significant business value by initiating effective partner enablement.
#3 Introduce AI sales roleplays
It is no secret that practical training, coaching, and roleplaying are among the most effective ways to enable sellers. Among other benefits, they provide the following:
Increased confidence in handling objections and concerns
Enhanced communication and presentation skills
Accelerated improvement through gap identification and timely feedback
Reinforced product knowledge and positioning
Sharpened problem-solving abilities and adaptability
Improved active listening and empathy skills
Opportunities to simulate and prepare for diverse customer scenarios
Until relatively recently, there were three main ways to conduct roleplaying sessions for salespeople: investing a significant amount of time from the enablement team and sales managers, bringing in outside trainers and coaches to facilitate practice, or having salespeople practice peer-to-peer.
Fortunately, AI roleplaying tools have now reached a level of maturity where they feel natural and intuitive, almost as realistic as real conversations.
These sales enablement tools are now more than capable of allowing salespeople to practice, master the basics, and experiment with new approaches on AI personas that closely reflect your real buyer personas.
Beyond providing a risk-free environment for reps to refine their sales conversation skills, these tools also offer valuable insights into common mistakes and support the development of personalised training and coaching.
Over the past year, I’ve had the opportunity to leverage what I consider one of the best AI roleplaying and upskilling platforms available, Hyperbound, in my role as Director of Sales Enablement.
I’ve built 9 AI roleplay scenarios for sales you can find here, if you want to see how good they can be.
The conversation quality of their practice bots is outstanding, and the AI coaching suggestions, paired with customisable call scorecards, have significantly enhanced the effectiveness of my training programmes, particularly in terms of stickiness and driving desired behaviour in collaboration with sales managers.
I’ve specifically integrated Hyperbound into our strategic outbound prospecting and sales discovery training programmes.
Turn sales call insights into revenue-driving action
#4 Conduct workflow audits
Regardless of how mature the enablement function is at your company, even the most established sales enablement strategies must be continuously analysed for efficiency and effectiveness by reviewing metrics, gathering feedback, and making adjustments based on those insights.
In other words, a successful sales enablement team is always committed to continuous improvement.
However, gathering feedback and examining metrics can only reveal so much.
Feedback, while valuable, can often be subjective, and metrics alone may not fully capture how salespeople are engaging with training materials, utilising sales materials, or adhering to the established sales process.
The solution to this is relatively simple: conducting workflow audits.
I say “relatively” because, while it may seem like a straightforward practice, it can often backfire.
As a sales enablement professional, your intention is to objectively and holistically observe a salesperson’s workflow to gain insight into how they are benefiting from your enablement efforts and/or what other areas for improvement exist.
However, the salesperson may perceive this as an invasion of their professional privacy, a sign of distrust, or an additional layer of evaluation.
This is why it’s essential to make it clear that you’re not there to criticise their methods, but rather to observe and understand how to enhance their experience. Approaching it this way will give you valuable insights into how things truly work and whether your coaching, training, or content is making the desired impact.
Moreover, it offers a great opportunity to identify what “good” looks like for processes and workflows.
As is often the case in enablement, building trust is essential before conducting workflow audits. Once that trust is established, the information you gather will be far more representative of how much salespeople are benefiting from enablement.
Additionally, these insights will provide you with a wealth of ideas on how to improve your enablement efforts and better support your sales force.
#5 Manage sellers’ cognitive load
The business world has become almost obsessively infatuated with information.
Everywhere you turn, someone is advocating for more data, more insights, more details, more opinions, and more options.
And yes, in many cases, having access to more information is beneficial, as it leads to more informed decision-making.
However, in our quest to provide everyone with more information, companies sometimes overdo it.
With the best of intentions, various stakeholders end up inundating sales personnel with an overwhelming amount of information daily.
The product team sends a 20-page, tech-heavy document on a new feature that could easily be summarised in a single sentence.
The marketing team floods them with a thousand new leads that are barely qualified, if at all.
The AI-savvy CRO spends a day on G2 and decides to implement six new AI sales tools within 24 hours.
The HR/communications team blasts out 15 corporate updates per day, none of which have anything to do with sales.
The VP of sales adds 13 new qualification criteria for advancing leads through the 72 stages in the pipeline, 17 of which were just introduced.
The sales managers insist that the documentation for every deal in the pipeline be as detailed as the assembly instructions for flat-pack furniture.
The sales enablement team introduces one new sales enablement platform and at least two new training programmes that require an additional five hours every week.
These examples may be exaggerated for effect, but situations like this do happen.
The end result is an overwhelming information overload, leaving salespeople with only a small portion of their workday to actually focus on selling.
Sales enablement can and should be the function that helps manage the cognitive load of frontline sellers and their managers.
The first step is to build a clear communications plan that extends beyond just the sales team.
This involves prioritising communications, standardising formats, and consolidating communication channels into a single, unified platform.
While company stakeholders should be able to contribute to this channel, they must always adhere to the agreed-upon formats and prioritisation guidelines.
As Head of Sales Training & Enablement, Edurne Rodríguez, put it succinctly in my sales enablement best practices article:
In larger organisations, this may require significant effort and some political manoeuvring, but the benefits far outweigh the challenges.
Every company ultimately wants its salespeople to focus on selling, and if you clearly explain the reasons behind this initiative, you’ll find that getting people on board is easier than you might expect.
#6 Build relationships beyond the professional space
Tackling the matter of building relationships with co-workers beyond the professional setting can be tricky.
Some people prefer to keep their professional and personal lives completely separate, and they have every right to do so.
However, engaging with colleagues beyond the confines of work can offer significant benefits in most roles.
Building personal connections helps foster trust, improve communication, and create a more collaborative and supportive work environment.
In the field of sales enablement, this is even more true due to its intrinsic cross-functional nature.
Over the years, I’ve noticed this myself, and many of my peers agree.
Chris MacDonald, one of the contributors to my enablement best practices article, even highlighted it as crucial to his role as the Director of Sales Optimisation, emphasising the importance of building relationships beyond the professional space.
The reason so many enablement professionals value the interplay between the professional and personal is that, at its core, sales enablement is about building trust and fostering relationships.
If you limit yourself to building relationships only during your 9-to-5 workday, you’re missing out on countless opportunities to do your job better and to connect with some truly fantastic people.
Without the trust of various stakeholders at your company – sales and marketing teams, the C-suite, or managers – it becomes much more difficult to secure the buy-in needed for any enablement initiative to reach its full potential.
Moreover, when trust is lacking, your efforts to support and assist can easily be misinterpreted as merely adding more work to their plates.
Chris described what to focus on when building these relationships:
He acknowledged that while this can be a significant time investment, the feedback, openness, and buy-in you receive in return can be transformational in the long run.
Interestingly, in my article on a day in the life of a sales enablement manager, contributors shared their views on the most important skills for enablement professionals. The most frequently mentioned skills were variations of empathy, personability, active listening, patience, and emotional intelligence.
#7 Stop being THE expert
While we’re on the subject of building personal relationships that strengthen your professional ones, there’s an insightful idea shared by Jonathan Kvarfordt in the sales enablement best practices article:
Allowing others to contribute and showcase their expertise is an excellent way to build relationships that go beyond mere professional courtesy.
Jonathan added:
“It helps showcase others’ strengths and makes the speed of enablement faster because I am no longer the bottleneck of the expertise. Too many times we put so much pressure on ourselves to be the expert, but the more I let go, the more I am able to do a better job with enablement.”
At first glance, this might seem like common sense – something most of us already do, or at least something we believe should be easy in the field of enablement.
However, when you delve deeper into what Jonathan said, it becomes clear that this is much more than just giving credit where it’s due. It represents a complete shift in mindset, one that demands a great deal from an individual.
Firstly, it requires a significant relinquishment of ego, which, as most would agree, is one of the hardest things to do, whether in a professional or personal context.
For many, even keeping their ego in check is a herculean task – let alone taking a metaphorical stick of dynamite to it and igniting the fuse.
Beyond this deeply personal process of dismantling one’s ego, there’s also the concern that some may struggle with the idea of seemingly diminishing their role and contributions by stepping back from being the expert in every situation.
They might fear that their standing within the company could suffer or that their outward projection of expertise will weaken.
However, as Jonathan made clear, this act of alleviating pressure on oneself and letting go can (and almost always does) lead to us performing our roles as sales enablement professionals more effectively and serving our companies better.
If this idea appeals to you, the first step is to have an honest, in-depth conversation with yourself.
It’s crucial to ensure that you’re not doing this just for appearances but because you genuinely see it as a step in your self-improvement.
If you find that self-improvement is your primary motivation, then by all means, give it a try. It may be challenging at first, but it could also become a transformational step for you – not just professionally, but personally as well.
#8 Make your enablement charter dynamic
In my article on sales enablement strategy, I mentioned (among other things) that a 2019 CSO Insights Sales Optimization Study found that organisations which had a formalised enablement charter saw win rates 8.7 percentage points higher than the study’s average.
Personally, I find it crucial to position sales enablement as a strategic function – an approach many of our contributors have also endorsed over time.
For those unfamiliar with it, a sales enablement charter is a document that outlines the mission, duties, objectives, and priorities of the enablement team. It serves as both an accountability tool and a means to communicate essential information internally, as well as to marketing and sales teams, other departments, and the GTM leadership.
Unfortunately, many enablement teams still adhere to an outdated view of their charter, treating it as a static document – something defined at a single point in time and left unchanged thereafter.
In most cases, the charter remains unaltered because many enablement teams spend the majority of their time putting out fires or acting as order-takers, operating almost exclusively in a reactive mode.
This creates a sort of enablement Catch-22: the static nature of their charter prevents them from positioning their function as strategic, and the lack of a strategic role hinders them from making their charter a dynamic document.
To break this difficult cycle, it’s crucial to define your enablement charter as a dynamic, evolving document from the very beginning.
A dynamic charter ensures enablement stays aligned with shifting business priorities, particularly go-to-market strategies.
Rather than operating in isolation, enablement becomes an active, strategic partner – not just reacting to other departments’ demands but proactively shaping outcomes.
A dynamic charter also means being more transparent about the current state of enablement, including its existing sales enablement process, as well as the most pressing challenges and limitations.
By incorporating up-to-date data, you can clearly demonstrate what enablement is achieving and assess whether it’s equipped to meet new challenges.
Additionally, embracing a dynamic approach acknowledges that different stakeholders within your organisation have varied interests when it comes to enablement.
For example, the CFO may be focused on how funds are being utilised, while the VP of Product might be concerned with how much capacity enablement has to support new features or product releases.
In essence, you’re adapting your enablement charter to serve as a business case for various internal stakeholders.
#9 Improve your data maturity
The next sales enablement idea shifts focus from more subjective approaches, such as intuition and personal judgment, to a data-driven, objective method.
This particular concept is all about leveraging data to amplify the impact of enablement efforts and build a strong sales enablement strategy.
As Vanessa Metcalf put it in my enablement best practices article:
She emphasised the need for sales enablement teams to operate with the most up-to-date, well-managed, and comprehensive data.
Moreover, she highlighted the importance of being able “…to link enablement efforts to success metrics and to examine those metrics collectively to assess the overall effectiveness of the enablement function”.
While even the most intuition-driven enablement teams track some data to guide their decisions, few truly embody the level of data maturity Vanessa describes.
In smaller companies, this is often due to limited resources within enablement teams and the fact that data is tracked haphazardly and in a disorganised manner.
Frequently, less mature enablement teams in smaller companies also lack the expertise needed to effectively collect and manage data.
In larger companies, enablement teams face different challenges when it comes to the data they want to track and use:
Vast amounts of data, making it difficult to extract the insights they need
Heterogeneous and mismanaged data from numerous tools
Limited access to, or collaboration with, teams primarily responsible for data management – such as IT, SalesOps, or RevOps
Your journey toward improved data maturity will depend on several factors: the size of your company and GTM unit, the existing data infrastructure, and the individuals, teams, or departments responsible for managing data in your organisation.
The quickest way to advance your data maturity is by fostering strong relationships with the individuals and teams responsible for data management, such as IT, SalesOps, or RevOps.
By collaborating closely with them, you’ll gain access to the specific data your enablement efforts require and receive valuable assistance in linking outcomes to your initiatives.
If you’re handling data collection, management, and reporting on your own, you may face limitations based on the capabilities of the sales enablement software you use.
In that case, it’s worth reaching out to your company’s IT or tech team to see if someone with data management experience can offer guidance and support.
#10 Measure enablement holistically
In the previous section, we didn’t dive into the specific metrics sales enablement teams should track to measure their performance or the impact of their efforts on the broader revenue organisation.
That was intentional.
The challenge isn’t just about which metrics to track – plenty of resources exist for that – but about how to track them effectively and manage your data in a way that provides real value.
This isn’t merely a matter of listing the right metrics; it’s a more complex issue that requires deeper thought.
If you aren’t careful, personal biases or past experiences can easily skew your approach, causing you to miss valuable insights.
Sure, we could have given you a standard rundown of metrics commonly tracked by enablement teams, but that’s already been covered in countless articles.
Repeating that here wouldn’t add much value.
Instead, Jocelle Sarenpa, a contributor to my enablement best practices article, introduced an idea that fits perfectly in this context: tracking more holistic enablement metrics.
As a seasoned leader, Jocelle observed that enablement teams often develop tunnel vision when it comes to metrics, focusing heavily on quantitative data while neglecting valuable qualitative insights.
Interestingly, some might argue the opposite – that enablement leaders are too focused on qualitative aspects, such as training feedback or team dynamics, while struggling to capture hard, quantitative data.
This is especially true in the current landscape, where there’s an increasing focus on measuring ROI and quantifying the impact of sales enablement efforts.
While it’s true that quantitative metrics are crucial for demonstrating ROI, Jocelle stressed the importance of not losing sight of the broader picture.
Qualitative metrics can offer a deeper, richer understanding of the overall effectiveness of enablement.
By focusing solely on numbers, there’s a risk of overlooking essential elements like time management, the development of positive habits, fostering a growth mindset, and even personality assessments, which help reps better understand themselves.
By incorporating these holistic elements, sales enablement can go beyond simply improving sales skills. It can create psychological safety, foster a sense of belonging within the team, encourage openness to different perspectives, and support reps as whole individuals, not just sellers.
If this holistic approach is new to you, a good starting point is to align your enablement programmes with your company’s core values.
Define how you expect reps to embody these values and build a system to measure this alignment.
Examples include developing an Ideal Employee Profile (IEP), conducting 360-degree reviews focusing on core values, and encouraging personal reflection among reps.
#11 Incorporate in-the-flow-of-work learning
Sales training is one of the key responsibilities of sales enablement teams, starting with onboarding (and, after reading this article, hopefully from pre-boarding) and continuing throughout sales professionals’ time with the company.
With the rapid advancement of sales training software, this practice is constantly evolving, introducing new ideas at an accelerated pace.
We’ve already touched on one of these innovations earlier in the article – AI sales roleplaying software.
Another valuable approach to consider is in-the-flow-of-work learning, which I’ve personally seen do wonders for the majority of salespeople.
This method complements traditional, scheduled training sessions by offering real-time resources that sales reps can access while working, enabling them to learn exactly when they need it.
Here’s how it might look in a sales context:
Microlearning assets: Imagine a sales rep accessing a quick, three-minute video on handling objections right before a customer call. This type of immediate resource can make a significant impact.
Chatbots and FAQs: Embedding a chatbot or a FAQ section within your CRM allows reps to get quick answers to customer queries while they’re drafting emails or preparing presentations.
Performance support tools: Tools integrated within your CRM can offer real-time tips on best practices as reps log new customer interactions, providing guidance exactly when they need it in the sales cycle.
Peer collaboration: Internal communication platforms can be used to encourage reps to share insights and strategies with each other as they go about their tasks.
Incorporating in-the-flow-of-work learning into your sales enablement strategy keeps learning continuous and relevant, without disrupting the team’s workflow.
Also, it is much more in tune with adult learning principles as it is more hands-on and relevant for the learners.
#12 Start the evolution towards buyer enablement
Of all the sales enablement ideas shared in this article, this one is arguably the most ambitious, complex, disruptive, and potentially transformative.
There are several reasons why evolving from sales enablement to buyer enablement is particularly challenging.
First, most sales enablement teams remain focused on sales processes, with their efforts primarily aimed at supporting those processes from an internal perspective – without fully accounting for how buyers’ behaviors and expectations have drastically changed in just the past five years.
In essence, this represents the classic limiting belief of, “This is how we’ve always done it,” and as any sales enablement professional knows, it’s one of the toughest barriers to overcome.
To truly embrace buyer enablement, both sales teams and sales enablement professionals must shift toward a buyer-centric approach – one that requires a complete transformation in how enablement is designed and delivered.
Traditionally, onboarding, training, sales methodologies, and sales enablement content have all been structured with the seller in mind.
But in a buyer-centric model, these elements must be reframed through the lens of the buyer’s journey – ensuring that every aspect of enablement supports the way buyers research, evaluate, and make purchasing decisions.
This is a massive undertaking.
To be completely honest, another major reason why seller-focused enablement persists is because it’s easier to control. Data is more readily available, and the connection between actions and outcomes is more straightforward to observe and influence.
Illustrating just how difficult the transition from seller-focused to buyer enablement can be, Woody Walker, Global Sales Practice Lead at one of the world’s largest IT advisory companies (with over 60,000 employees), identified it as one of her team’s greatest challenges:
While it might seem daunting to hear that even large companies with substantial enablement budgets face this challenge, it’s essential to recognise that is a gradual step to move towards, given how B2B markets are evolving.
As I’ve mentioned earlier and discussed at length in my article on buyer enablement, there are several steps you can and should take to ignite this evolution.
1. Align the sales process with the buyer journey and start making buyer jobs simpler and easier.
2. Build buyer-based sales collateral.
3. Implement buyer-centric sales training and coaching – prioritising understanding the buyer’s perspective, personalising solutions, and fostering long-term relationships, rather than simply pushing products or meeting sales quotas.
As you can see, even the foundational steps in shifting from sales to buyer enablement are ambitious undertakings.
However, as selling becomes increasingly complex – particularly in industries like software, tech, consulting, and services – this is a transition best made sooner rather than later.
# 13. Own and run win/loss analysis
Many enablement teams spend their time reacting to symptoms or underwhelming results, such as a low win rate in a segment, poor messaging adoption, or inconsistent deal execution.
It is time for enablement to get ahead and start looking at the causes.
This is where the win/loss analysis becomes a powerful (usually) underused idea for enablement teams.
Traditionally, win/loss has lived in ad-hoc conversations, biased CRM fields, or one-off projects owned elsewhere. As a result, insights stay shallow, anecdotal, or disconnected from real decisions.
Enablement is particularly well-positioned to change that, sitting in between departments where action happens and having access to data from sources beyond just the sales team.
2026 feels like the perfect year to start doing it, with a growing number of useful tools like modern AI sales copilots and conversational intelligence platforms making it possible to analyse hundreds of calls automatically, track recurring themes like competitor mentions, typical objections, or decision criteria, and correlate those signals directly with deal outcomes.
What was once slow, manual, and subjective can now be continuous and data-driven.
In practice, enablement can:
- define the questions the business needs answers to (e.g., “Why are we losing enterprise deals late?”),
- work with RevOps and Sales to segment the right deal sets,
- use AI insights and targeted buyer feedback to uncover root causes, and
- translate those findings into concrete actions.
By taking ownership of win/loss analysis, enablement can move upstream — from supporting sales execution to informing go-to-market strategy. Namely, it gives enablement credible evidence to challenge assumptions around ICP, personas, vertical focus, and sales motion – something that used to be “reserved” only for sales leadership.
As an additional bonus, when you can explain exactly why certain initiatives work, where they break down, and which strategic assumptions need revisiting, it becomes easier to engage in conversations about additional budget or headcount for the department.
For teams looking to become more strategic in 2026, owning win/loss analysis is one of the most direct ways to earn that seat at the table. If you decide to do it, make sure to check out my full guide to strategic win/loss analysis.
Conclusion
The sales enablement ideas discussed in this article are drawn from a blend of insights shared by my contributors in various collaborative pieces on The Enablement Insight, as well as my own observations on what’s effective but less commonly implemented by enablement teams.
These ideas strike a balance between those that require only a bit of extra effort from enablement professionals and those that are more systemic, requiring deeper changes and investment.
They offer a path for both quick wins and long-term, transformational shifts.
I’ve also written an article on quicker, less demanding interventions, outlining some useful sales enablement tips!
At the very least, I hope these concepts serve as a springboard for brainstorming with your team or engaging in valuable discussions with your peers.
By exploring these approaches, we can continue to push the boundaries of what sales enablement can achieve.
After all, we are all in this together, driving sales and enablement forward.
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