14 Costly Sales Enablement Mistakes and How to Avoid Them

Introduction

Mistakes are an inevitable part of any job.

In a field as relatively new as sales enablement, it could be argued that they could even be more common due to the lack of standardisation and established industry-wide processes and best practices.

Additionally, people enter sales enablement from various backgrounds, often without a comprehensive understanding of the discipline (let alone adequate sales enablement training), increasing the likelihood of mistakes being made.

In this article, I aim to highlight some of the most significant mistakes you might want to avoid as an enablement professional to prevent costly consequences. 

Drawing from my own past experiences in sales enablement, as well as those of my peers, colleagues, and acquaintances, I will provide insights into common pitfalls as well as proven ways to avoid or mitigate these, making your sales enablement efforts more effective and successful.

To make this investigation as comprehensive as possible, I will also incorporate insights from conversations I had with leaders about their sales enablement best practices and the sales enablement challenges they face.

Let’s get right into it.

1. Not establishing sales enablement as a strategic function

Not establishing sales enablement as a strategic function is likely one of the most significant mistakes you can make, with consequences that can negatively influence every programme, initiative, and activity.

But what defines enablement as a strategic function?

Simply put, sales enablement needs a seat at the table.

The person who owns sales enablement (depending on the company size – a Sales Enablement Manager, Director, or even a VP) must have a direct line to revenue leadership and, ideally, plenty of exposure to executive levels of other GTM units.

They must have a voice.

Sales enablement should be seen as a strategic partner to sales leadership and other revenue functions, focusing on process improvement, scalable upskilling, and cross-functional orchestration, among other goals.

In some companies, sales enablement often grows out of sales, marketing, or sales operations teams, which is why it is not automatically given a seat at the table.

In many cases, it remains at least one level removed from strategic decision-makers.

As a result, sales enablement becomes a reactive, tactical department assigned short-term tasks that yield only limited and usually short-term results.

This is the same scenario when sales enablement is equated solely with sales training, onboarding, or other parts of a much bigger whole.

This is a waste of resources.

Sales enablement can reach its full potential only when it delivers far-reaching, all-encompassing value for the entire GTM organisation (in which case, we can start talking more about revenue enablement).

In the next few sections (particularly number 2, 3, 4, 5, and 6), I will cover the “sub-mistakes” that may be contributing to this overarching mistake of not positioning sales enablement as a strategic function and provide you with some simple tips on what to do to avoid or correct them.

2. Focusing on the wrong metrics

Many enablement teams make one very specific mistake that prevents them from becoming a strategic function in their company’s revenue machine.

Namely, they focus on surface-level metrics such as course completion, content engagement, training attendance, and onboarding satisfaction.

And while these metrics may be useful for internal assessment, the business doesn’t care about these, as enablement leader Rosi Young shared with me for the sales enablement best practices article.

Instead, sales enablement should focus on their contributions to improving the metrics that affect the revenue outcomes, such as average deal size, sales cycle length, time in stage, conversion rates by stage, and ramp time for new sales reps. 

In other words, as a function, sales enablement should tie every programme or initiative to a clearly defined business OKR, with enablement metrics that illustrate the impact.

From there on, you should identify the key performance indicators that you will use to show that it’s the sales enablement programmes, initiatives or activities that are contributing to those OKRs. 

This will require you to become data-literate and to understand where to look for data and how to interpret it.

Enablement expert Vanessa Metcalf suggested building a strong relationship with the operations teams, who can be of huge help with this.

Finally, you have to make sure to provide regular updates, such as QBRs, to key executives in order to keep them engaged and informed about the impact of enablement efforts.

3. Underestimating the “quick wins”

As I mentioned earlier, sales enablement works best as a strategic function.

That being said, many sales enablers make the mistake of underestimating the value of “quick wins” – demonstrably valuable short-term initiatives which provide a taste of what enablement is capable of when given enough resources and room to operate.

I would like to reiterate the importance of those quick wins being demonstrably valuable in the sense of boosting revenue-related metrics.

A great example of a quick, short-term win would be a programme aimed at improving the onboarding process.

By revising onboarding materials and optimising the initial training of new reps, a sales enablement team can dramatically shorten ramp times, which has a direct effect on the bottom line. 

Namely, if a sales rep starts hitting their quota within three months on average instead of six because of the new sales enablement-led onboarding process, it doesn’t take a data wizard to demonstrate the value to the executive level.

Depending on your company, the sales process, the current state-of-the-field, and the performance of the sales force, quick wins can be found in improving metrics such as:

• Conversion rates by stage – e.g., running custom-tailored training to address a stage in the sales process which has a drastically high fall-off rate.

• Sales cycle length – e.g., implementing a new effective sales enablement technology such as digital sales room software or conversational intelligence.

• Time in stage – e.g., increasing the speed at which marketing-qualified leads become (or don’t become) sales-qualified leads through enhanced cross-functional collaboration between marketing and sales teams (common qualification criteria, quicker hand-offs, etc.).

• Salespeople confidence index – e.g., building new or improving existing sales collaterals for scenarios where salespeople had previously shown low levels of confidence.

Once you clearly demonstrate the value of sales enablement by undoubtedly improving revenue-related metrics, it becomes far easier to position sales enablement as a strategic function and gain support and resources for long-term initiatives such as implementing MEDDPICC (or another sales methodology), sales leadership development programmes, or changing the sales culture to become more buyer-centric.

4. Not setting boundaries

The surest way to lose the strategic footing as a sales enablement function, or fail to gain one in the first place, is to indiscriminately accept requests without clear boundaries and prioritisation criteria.

For one, this way you relinquish control over which (if any) OKRs you will align your initiative with, making it more likely that even the best-executed initiatives will result in underwhelming effects on the bottom line. 

Furthermore, acquiescing to such an arrangement will turn the sales enablement function into an order-taking, task-fulfilling reactive department that has little to no say in what they are doing, why they are doing it, and how they are contributing to the GTM organisation.

In such a constellation of things, it is extremely difficult to prove the real worth of the function, which can only perpetuate the negative cycle. 

4.1. Not establishing and vocalising an enablement charter

In the majority of cases in which the aforementioned enablement-as-reactive-function arrangement becomes the norm, one of the main contributing factors is the absence of a comprehensive sales enablement charter or a failure to vocalise it explicitly to other stakeholders, especially revenue leadership and executives. 

Your sales enablement charter is essential for outlining the mission, vision, goals, and strategies of the enablement team.

It also needs to define how you’re gauging success and identify the mainstays of your enablement efforts, such as onboarding, methodologies, skill enhancement, and leadership enablement.

Last but not least, it should contain a roadmap with a timeline for the agreed-upon initiatives achievable with current and/or expected resources.

In short, your sales enablement charter informs the rest of the company (and the enablement team) about what enablement does and what it doesn’t do.

It’s a critical component at the basis of your sales enablement strategy

However, it’s not enough just to be in possession of a charter.

It is essential that other relevant stakeholders in your company are aware of it and reminded of it as appropriate. This ensures that any and all new requests are reviewed in relation to the charter, enabling you to clearly state how they would affect your roadmap and whether they would require additional resources. 

4.2. Lack of a structured enablement request process

Another extremely useful tool that is often mistakenly ignored or neglected is a structured enablement request intake process, which would be mandatory for departments and individuals who wish to ask for specific enablement interventions.

As enablement leader Jocelle Sarenpa pointed out so adroitly in my enablement best practices article, without a formal request process, you end up executing enablement initiatives for “issues” that could’ve been solved with an email.

The easiest way to go about bringing it to life is as an intake form, which helps with inbound requests for ideas or needs that require the involvement of the enablement team. 

You can offer fields like:

• The description of the need/idea

• OKRs and KPIs tied to this request

• A strategic initiative that will be positively impacted by this request

• The timeline

• The audience

The purpose of the enablement request process is not to discourage people from approaching your team.

The main purpose is to make sure the requested initiatives are truly needed at that particular point in time. 

It is also the perfect starting point for the discussion of what your sales enablement team can commit to with its present resources in the proposed time frame. 

By comparing the request against your charter, you can easily demonstrate why a certain initiative can or can’t be done in the proposed time frame and with the available resources. 

Maintaining a strategic enablement request process also ensures that enablement efforts are directed where they can have the most significant impact.

Routine tasks should not monopolise time without a clear strategic purpose.

Aligning objectives with the sales team and focusing on measurable outcomes is crucial.

For instance, if a product launch is an initiative, defining targets like pipeline activation or competitive win rates ensures that enablement efforts are outcome-driven.

Setting boundaries of what sales enablement does and doesn’t do protects your team from being overworked and also ensures the resources invested in it are not squandered on activities that do not contribute to the company’s strategic priorities. 

5. Skipping needs analysis

A critical mistake in sales enablement is rushing through, or altogether skipping, a thorough needs analysis.

Put differently, assuming that past strategies will work for any company can only result in misaligned, ineffective approaches. 

Each company presents unique challenges that require tailored strategies. 

Conducting a needs analysis or a “state-of-the-field report” helps understand the gap between the current state and desired outcomes.

In order to analyse the current state, you have to balance quantitative insights (data) with qualitative ones (e.g., feedback from sellers, sales managers, and sales leaders), thereby informing better decision-making.

Defining problems accurately by examining how different data points interrelate allows for solving issues on a larger scale.

Failing to do so sets the enablement function up for failure by not addressing the true needs while considering the history of the front-line teams.

However, an in-depth needs analysis should involve more than just collecting and analysing data; it requires understanding the unique context of the organisation, industry-specific challenges, the various nuances of the sales organisation and its relationship with other GTM departments. 

6. Neglecting executive alignment and support

If you manage to avoid or mitigate the mistakes I’ve covered so far, you should have no problem with this one either.

If you have a portfolio of successful initiatives that have resulted in better business results, and you have established enablement as a strategic function in your company, your department should already be more than just a blip on the executive radar. 

However, this doesn’t mean you should stop being proactive in your relationships with the executive level. 

That would be a big mistake.

As enablement leader Ashton Williams mentioned, it’s crucial to have a dedicated executive sponsor for each major initiative and to keep them engaged through regular updates, such as QBRs.

Without the support and involvement of executives, projects easily lose momentum and direction.

The best way to gain this kind of support is to align enablement with their goals and pains.

Building relationships beyond professional interactions, understanding individual motivations, and addressing even the smallest challenges will greatly help you build trust among the executives.

Without trust, gaining buy-in and achieving long-term objectives becomes exceedingly difficult, as sales excellence expert Chris MacDonald shared.

A huge mistake in trying to build this trust and securing executive buy-in is failing to understand and communicate in terms that resonate with them.

Just as AEs need to speak the language of their key stakeholders, enablement professionals must be fluent in pipeline health metrics, deal velocity, time in stage, conversion rates by stage, ARR, MRR, and many other revenue-related metrics.

7. Overlooking sales managers

Building trust and securing buy-in doesn’t stop at executives.

While they will ultimately make “life-or-death” decisions that affect your department, the success of the vast majority of enablement initiatives will depend on how well you enable sales managers. 

In fact, most successful sales enablement leaders will tell you that overlooking sales managers is among the absolute biggest mistakes you can make as an enablement professional.

For one, managers’ involvement will reinforce every initiative aimed at improving the results of the teams they are managing.

They can boost overall engagement by tracking whether the salespeople are doing their part. In addition, they are the first to notice whether improvements might be occurring. 

Enablement should create a dynamic by which managers provide regular feedback about the effects of specific initiatives, signalling if something isn’t working and might need modification. 

Furthermore, it’s worth highlighting that sales managers often naturally engage in enablement-like activities, whether they realise it or not.

They are constantly analysing sales performance, sales messaging, tracking the key metrics in sales enablement tools, and providing (more or less structured) coaching to sales reps. Sales enablement can provide support in all of these areas, helping build field training and sales coaching skills in managers.

In order to be able to count on sales managers to provide support to enablement efforts, there are a number of things you can do.

For instance, get them involved in the process of creating training materials and other collaterals that will have an effect on their team. Their insights are invaluable and co-creating enablement initiatives with them is really a no-brainer.

Another good idea is to illustrate how the initiatives will benefit them personally. 

Let’s say you are planning an initiative to shorten the sales cycle by improving sales personnel’s discovery skills. What manager wouldn’t want to lead a team that shortens its sales cycle by 15-20% in a single quarter? 

When it comes to supporting them in the enablement efforts they are already putting in, there is really no need for any convincing. All you need to do is make sure that they feel that the time spent with you or your team is time well spent.

Manager-led enablement should be a priority.

As enablement leader Sarah Gross mentioned, sales managers should take enablement materials before front-line teams, help kick off sessions, and provide input on team needs and success metrics.

They are the critical change agents for post-rollout activities, ensuring sufficient comprehension and sustained adoption across the field.

Do. Not. Overlook. Sales. Managers.

8. “Unleashing” initiatives on sales reps

Even though they might not possess the decision-making authority of executives and managers, the majority of sales enablement initiatives will focus on sales reps and their day-to-day work life.

Introducing yet another enablement initiative without proper reasoning and planning can be a significant oversight and can be seen as disrespectful, to say the least.

As Chris MacDonald pointed out in my article on enablement challenges, it is perfectly natural for salespeople to respond with the following questions upon learning about a sales enablement initiative:

Why should I make this change? Why should I do more admin work (perceived)? How is it going to help me sell more?

This is a perfectly understandable reaction, especially in the case of more long-term initiatives where positive outcomes take time to become obvious. 

This is why it is always ill-advised to simply “unleash” an enablement initiative on an unsuspecting sales team.

Instead, try to involve them from the very start.

Ask them how they feel about a specific area that you may want to address with enablement efforts.

Ask what they would like to gain from it.

Ask them if they think it would help them become better at their jobs beyond this particular initiative. 

More often than not, you will encounter sales reps who might even be interested in co-creating sales enablement content with your team and you should always welcome such participation.

This will provide you with valuable insights from the front lines and also help create enablement champions within the organisation. 

These champions provide insights into the real-world application of strategies and serve as peer-driven educators, which is often the most effective form of training.

Engaging successful peers in the enablement process makes the content more relevant and encourages broader participation, driving greater impact.

As enablement leader Ross McLean pointed out in my best practices article:

“People want to learn from peers who are successful.”

Another great way to improve the participation of salespeople is to create an environment where they feel safe not knowing everything, failing and improving gradually. 

 As enablement leader George Campbell said in that same article:

“…help sellers to understand that you defend their permission to get good at a reasonable pace.”

Engaging sales reps through in-person workshops focused on personal development, team building, and open discussions can create a supportive environment. These sessions allow reps to share feedback on existing initiatives, voice concerns and feel heard, helping them see the genuine care behind enablement initiatives.

Finally, making sure to align new operational procedures with sales reps’ goals and demonstrating long-term benefits is one of the surest ways to overcome resistance. 

9. Focusing solely on “obvious” allies

As we’ve mentioned on a number of occasions, the sales enablement function is unique in its need to engage stakeholders across both the vertical (hierarchy) and horizontal (cross-functional) vectors. 

One mistake that sales enablers often make is looking only to the GTM teams when looking for allies (e.g., marketing, customer success).

In all honesty, this is perfectly understandable – in the majority of cases, these will be the departments you collaborate with the most.

However, you shouldn’t ignore other business groups in your organisation. People from departments such as HR, IT, Data, and Engineering often have unique expertise that can be of massive help in achieving enablement success.

You’d be surprised how much people are willing to lend a helping hand, especially if you make them understand how enablement supports the business.

For instance, there might be a data analyst you build a relationship with who is always ready to put together some data points for you in a way that is easily digestible.

Or there might be someone in HR with leadership development expertise who could help with sales managers’ enablement.

In short, it pays off to make connections outside the GTM unit.

10. Failing to include early

A critical mistake in enablement is not involving stakeholders and business partners as early in the process as possible. 

Bringing these key players into the journey from the start is essential.

Co-creating programmes with input from sales leadership, managers, reps, and other GTM units ensures that initiatives are well-rounded and supported.

Before you even start building an initiative, make sure to present them with the current state of affairs, data points, and proposed solutions to gather their insights and feedback.

By doing this, you will unearth a treasure trove of insights and suggestions that you would never uncover without their help. Not to mention that it will show an enormous amount of respect for them personally and what they do.

Regularly checking in with stakeholders during the development phase keeps the process iterative and responsive to feedback.

Although this approach can be more time-consuming, it pays off in a number of ways.

For one, incorporating various viewpoints and drawing from different areas of expertise maximises the potential of your initiatives and ensures that they are aligned with your organisation’s needs.

Equally as importantly, it also helps foster a sense of ownership and partnership.

This will result in enhanced support for the initiatives, as well as better engagement from everyone involved.

11. Not tearing down the silos

One of the most common complications that prevent new sales enablement teams from maximising their effectiveness are siloed GTM departments – sales, marketing, customer success, and product.

Allowing departments to keep operating in silos leads to inefficiency and misalignment caused by a lack of effective communication and collaboration. 

Enablement is uniquely positioned to act as a go-between for the various GTM departments and failing to utilise this potential is among the gravest mistakes you can make.

A good starting point is setting the expectation that enablement is a core part of the business engine.

You can do this by attending critical meetings such as leadership sessions, deal reviews, customer rehearsals, pipeline reviews, weekly sales meetings, sales operations meetings, and QBRs. 

The next step is to build a consolidated partner roadmap that aligns different teams with shared objectives and where every department becomes accountable for their contributions. 

Remember to also make clear how they can expect to see benefits from supporting enablement initiatives. 

True sales acceleration only happens when sales enablement finds a way to utilise the collective knowledge and expertise of the entire GTM organisation.

Without this, the enablement process becomes fragmented and less effective.

12. Introducing too much enablement and change at once

Change management is an integral part of sales enablement. The discipline fundamentally revolves around facilitating change, which can often be challenging.

Sales enablement efforts frequently involve helping sales teams, leaders, and other departments adapt to new processes, mindsets, and behaviours. This makes it easy to make mistakes, particularly when finding the right tempo for introducing changes.

One common mistake is overwhelming the sales team with too many changes at once, leading to change fatigue.

Sales teams, already under pressure to meet quotas and juggling more tasks than the average air traffic controller, can become disengaged when faced with excessive changes.

Conversely, rushing into changes without proper structure and measurement can waste resources. Setting timelines for new initiatives and evaluating their effectiveness is crucial.

Seeking feedback from involved teams ensures that only the most effective strategies are adopted.

In the article on sales enablement best practices, Nate Vogel suggested that no more than 5% of reps’ time should be dedicated to enablement activities. He also advised limiting the number of enablement topics to three per quarter.

Balancing the pace of change with adequate support and clear communication is essential to maintaining morale and productivity.

When it comes to change management, shifting mindsets, especially across the sales organisation, GTM departments, and company leadership, is perhaps one of the most challenging things to do.

It requires tact, incremental steps, and substantial data to support the change.

13. Viewing sales onboarding as a one-off event

One of the critical sales enablement mistakes is not establishing a comprehensive sales onboarding programme which will extend past the first two weeks.

When new sales hires aren’t thoroughly familiarised and practised with the company’s culture, target markets, customers, products, and sales processes and techniques, they can quickly become disoriented, leading to slow ramp times or even high turnover. 

Missing out on detailed training, mentorship programmes, and regular check-ins during the first 90 days often results in sales reps who are poorly integrated and less effective.

Another prevalent error is neglecting the onboarding programme after its initial setup.

This neglect can lead to enablement debt, where gaps in skills, operational excellence, and product knowledge emerge, necessitating reactive programmes later down the line. 

Without continuous updates, sales reps may be inadequately prepared, creating long-term inefficiencies and inconsistencies within the team.

14. Neglecting self-improvement

The final mistake I’d like to point out is somewhat paradoxical, considering that sales enablement is all about continuous improvement of the sales organisation.

Namely, at times, enablement professionals can get complacent and start thinking there is no room for them to improve. 

Sometimes it is not even that.

Sometimes we get so swept up in our responsibilities that we fail to find the time to focus on our self-improvement. 

This is not only detrimental to our personal betterment but also professionally irresponsible.

We should always strive to get better at what we do and that includes working on ourselves.

A good place to start is to reframe your self-image from an expert-at-everything to a facilitator of other people’s expertise, a great point made by enablement expert Jonathan Kvarfordt.

By focusing on celebrating others and leveraging their strengths, enablement efforts become more effective, inclusive and natural. Putting others in the spotlight for training, coaching, and content creation speeds up the enablement process and prevents you from becoming a bottleneck.

Another area for self-improvement is learning how to relinquish control.

This doesn’t mean that you should neglect your responsibilities or refuse ownership of enablement initiatives. This is about recognising that certain things are out of your control and that obsessing over them can only cause harm. 

For example, while you may not have control over which direction your organisation wants to take, you can control your participation in supporting new strategic initiatives.

Making such distinctions will help reduce stress and enable you to focus on things you can control.

There is also an endless list of sales enablement skills we can work on, but the one I’d like to emphasise here is familiarising yourself with adult learning principles.

Understanding how adults learn and retain information is essential for creating engaging and impactful training, coaching, and even sales content.

You don’t need a master’s degree in adult learning, but perhaps pick up a book or talk to someone who is an expert. 

Conclusion

Initially, I planned this article to feature over 35 sales enablement mistakes that I’ve seen people make. In the end, I decided to prune the number down to 14.

Why?

Well, listing 35 possible mistakes may come across as intimidating and overwhelming, not just in terms of word count.

Moreover, I realised that many of those mistakes are minor ones that typically don’t have significant consequences or are merely symptoms of more serious errors, which I decided to include in these fourteen.

These fourteen mistakes are the ones you should avoid at all costs, but which can sneak up on you without you even noticing them.

Hopefully, this article will help you spot them early and prevent them from jeopardising your enablement efforts.

I certainly wish I had come across an article like this when I was starting out in enablement.