Free Assessment: How does your sales & marketing measure up?

Get Started

Free Assessment:

How does your sales & marketing measure up?
Take this free, 5-minute assessment and learn what you can start doing today to boost traffic, leads, and sales.
Get Started
Sales & Marketing Alignment  |   Contributor  |   Sales Enablement  |   Inbound Sales

Why most people will fail at sales enablement in 2020

Walter Pollard

By Walter Pollard

Dec 10, 2019

Why most people will fail at sales enablement in 2020

As 2019 draws to a close, many companies are looking to 2020 and thinking about ways to evolve their marketing and sales strategies to drive growth. 

For more and more businesses, this means maturing their existing sales enablement functions or creating new programs that increase pipeline, quota attainment, and deal size, while shortening the sales cycle, accelerating new hire onboarding, and directly and positively impacting other sales metrics.

Whether you need to build a new sales enablement system or you want to improve an existing one in the new year, it’s important to start thinking about it now

Good sales enablement programs are customer-centric and highly strategic, and they work cross-functionally to align marketing and sales, ensuring these two critical divisions understand and communicate with each other well. 

Sales enablement, however, is still an evolving field, and it takes time to create, to implement, and to fine-tune a program that successfully achieves those goals.

Given that, if you want to hit the ground running in 2020, here are 11 common mistakes to avoid when it comes to sales enablement.


11 mistakes that will dramatically affect your sales enablement efforts in 2020

1. Misunderstanding the role of sales enablement

With every passing year, more companies tout the benefits of sales enablement, and 2020 will be no exception. 

Despite its growing popularity, though, sales enablement remains largely misunderstood by many organizations. 

Most companies lack a clear definition of sales enablement and have an even hazier idea of the value it can provide when implemented correctly. (Think dollars and cents.) 

Adding to the confusion? Effective sales enablement is highly personalized to each company, meaning its role and actual implementation can look different from one organization to the next.

If you don’t have a defined role for sales enablement, you run the risk of becoming siloed within your organization. As a sales enablement professional you want to be positioned as a strategic adviser, not an order taker.

When sales enablement does not have a defined role aligned to strategic initiatives and outcomes, though, this is a common occurrence within organizations.

Individuals end up becoming highly tactical and don’t have the opportunity to drive strategic initiatives forward. The role becomes more reactionary and lacks direction.  

Receiving buy-in and financial support from executives allows you to mature your sales enablement function, and management is more likely to take you seriously.

Success with sales enablement in 2020 will start with defining the practice for your company and answering this question: How can sales enablement help you meet your specific goals and objectives?

To answer that question, many companies are turning to a formal sales enablement practitioner

While sales enablement involves many groups (sales, marketing, service, HR, and others), this practitioner should be its own role within the organization. 

Like a good management consultant, a sales enablement practitioner will:

  • guide the sales team through effective communication
  • aid in cross-functional alignment between marketing and sales
  • assess sales reps’ skill gaps, work with the sales training team and sales managers in the creation of new hire onboarding, and evolve everboarding programs for ongoing learning and development for the sales organization
  • emphasize sales content strategy, sales messaging, sales process and methodology, and sales enablement technology
  • have a strong understanding of the company’s foundational strategic mindset to drive growth. 


2. Hiring the wrong person to lead sales enablement

Another common trap to avoid is hiring the wrong person into this role. Avoid individuals who approach the position tactically rather than strategically. (A practitioner shouldn’t just be putting out fires!) 

A good practitioner always approaches the program from a strategic mindset, ensuring every team, including marketing, has a seat at the table to help the reps be more effective.

That’s not to say every company needs a practitioner, however. 

For example, if you’re a smaller organization just getting started in sales enablement and you need to prove the program’s worth with short-term wins, then it’s understandable not to have a dedicated sales enablement practitioner. 

At this stage, you’re simply flying under the radar of management and building a sales enablement initiative to drive toward greater adoption. You might be working in the marketing, sales, or training department and measuring a very specific outcome.      

Your enablement program could live and breathe within a specific division. The important thing is having clarity on where and why that makes sense.

In the best-case scenario, your sales enablement role should live within the sales organization because you need to identify and to evaluate what’s working and what’s not on a daily basis.

Having daily interactions with sales management and sales reps to create credibility and trust is vital to influencing and successfully growing your program.  

3. Skipping the sales enablement assessment

Most organizations won’t spend the time to effectively implement detailed assessments because they don’t understand what’s involved in creating one, or they don’t want to spend the time or money to effectively implement one. 

Without a detailed assessment, though, you will not provide your organization with the sales enablement roadmap and strategy required to be successful in 2020. 

Whether you’re aiming to create a sales enablement program from scratch or you’re building on an existing program, you need to perform a thorough sales enablement assessment. 

(This involves interviewing relevant stakeholders in key areas, including inside sales reps, key account reps, field reps, sales managers, marketing executives, and service executives.)

It should answer these kinds of questions:

  • What are the goals of the sales team, marketing team, and the organization as a whole?
  • What are the KPIs and other metrics?
  • What is the formal sales process?
  • What does the current sales training and coaching program entail?
  • Are you effectively enabling sales managers? How?
  • What are your internal and external content strategies?
  • What are your reps’ knowledge and skill gaps?
  • Where are potential inefficiencies?
  • What are you currently doing to unify marketing and sales?
  • What sales enablement technology are you incorporating? 

A thorough, detailed assessment could take months to create, so if you’re looking to kick off 2020 with your new sales enablement program, it’s best to start this process now. 

Remember, you can never get to where you want to be without knowing where you’re starting from, and an assessment gives you that starting point. 

4. Lacking strategy in sales enablement efforts

It’s tempting to jump straight into a sales enablement program, but real success begins with a company determining what it’s looking to achieve.

What are the KPIs, OKRs, business goals, and sales strategies and objectives? Where is the business going to focus its attention? 

By identifying those goals and objectives first, you can work backward to arrive at implementable, strategically-aligned programs.

Sales enablement without strategy is just reacting to problems as they occur, and if you want to consistently drive the efficiency of your reps to increase revenue, sales enablement must be a strategic function within your organization. 

With that in mind, a strong sales enablement strategy will do the following:

  • Align with your sales process, methodology, and messaging
  • Include a structured framework to build a strategy around and to map training, coaching, messaging, and content.
  • Take a customer-centric approach, including identifying key targets
  • Create content and processes that align with customer needs and roles
  • Integrate with the pillars of sales enablement: structured sales process and methodology, coaching and training (onboarding for new hires, and ongoing learning development), sales messaging, content strategy (internal for reps and external for customers), technology stack, and metrics and data
  • Measure against KPIs, OKRs, and business goals and objectives
  • Detail a go-to-market strategy

Sound a bit overwhelming? Don’t worry. 

Another common mistake is trying to do everything at once. 

Start small. 

Set an achievable goal for your 2020 kickoff, and let short-term wins turn to long-term gains. 

As long as you have the foundational elements in mind/in place, are aligning to outcomes, and are working strategically, the small program you define in 2019 can successfully scale up as 2020 progresses. 

Without a strategy, though, you won’t effectively unify marketing and sales or drive organizational growth in the new year. 

5. Failing to secure executive buy-in

Without a strategic plan of attack in your sales enablement efforts, don’t expect to get executive buy-in, and without executive sponsorship, don’t expect impactful results. 

Your executives must be on board to provide the financial resources to build an effective, successful sales enablement program.  

A good sales enablement program must demonstrate to C-level executives how it will shorten the sales cycle, enhance the effectiveness of the sales team, and increase revenue. 

Executives don’t want one-off tactics; they want thought-out strategy and concrete plans.

When higher-ups are allocating company funds for the fiscal year, you want to ensure you get the money you need to build out your plan for 2020, so only approach executives after your strategy is developed and complete. 


6. Implementing a weak sales enablement content strategy

Every year, content strategy evolves and becomes more comprehensive, so if you want success in 2020, your content game must be strong.

A good content strategy involves both internal content (for reps) and external content (for customers). 

External content must be customer-centric, meaning it’s focused on the people you’re creating the content for. 

When you know your customers’ needs, challenges, and problems, you can set up your reps to provide more relevant, impactful, value-based information. You also empower them to have better, more productive, more insightful sales conversations. 

Your customers have questions and your content must answer them.

Content should also be created with the sales process in mind. 

Because reps often speak to a number of roles in a B2B or B2B business before finalizing a sale, they need content that is relevant and insightful for each of those roles and effectively complements the sales process. 

Content, therefore, needs to be available based on specific roles and specific industries. 

From the initial point of contact up to the CMO or CFO, reps must furnish content that meets the needs of every person they speak to on the journey toward that finalized sale.

For internal content, consider the benefits of on-demand training and microcontent like playbooks and processes. 

It should deliver immediate value to the seller, and be easy to access, share, and retain. 

When content is created strategically and is well-organized, reps can quickly get all the required information before a buyer interaction. 

Also, this content can be aligned to different stages of the sales process and the role and industry of the persona being contacted.

Not sure where to start with all this? 

After you’ve determined where your program will initially focus in 2020 (perhaps a specific product, service, or sales channel), create a strategy with a core focus on internal and external content. 

As an example, if you’re selling a specific SaaS product to commercial real estate developers, you will need to tailor the customer-facing sales content and the sales messaging architecture to address the specific challenges and needs of those developers.

You will also want to tailor the content and messaging based on their roles in the buying decision process. 

Don’t forget to also provide reps with supportive training content based on these roles. Your content training strategy should specifically target industries, personas, and those roles in order to overcome objections, to eliminate skill gaps, and to position value in every sales conversation.

This will help reps close more deals. 


7. Failing to incorporate the pillars of sales enablement

A framework is foundational to your enablement strategy and should incorporate the different pillars of sales enablement. 

These pillars are vitally important, and you must incorporate an integrated approach for training and coaching, content strategy, and a messaging strategy that effectively aligns with your sales process, metrics, and sales enablement technology.

These different pillars of enablement can dramatically affect one another, and without an integrated strategy, the reps’ knowledge and expertise do not typically increase.

Without this integrative approach, reps would not have the enablement support system in place to fully execute this sales messaging strategy.

This integrated system will also drive unification between marketing and sales.

The pillars of sales enablement are:

  • Sales process and methodology
  • Sales messaging
  • Training and coaching (onboarding and everboarding)
  • Content strategy (internal and external)
  • Sales enablement technology stack
  • Metrics and data (how you’re measuring KPIs and OKRs)
  • Go-to-market plan

Incorporating the pillars helps ensure you’re approaching sales enablement with adequate purpose and strategy by creating a highly structured, integrated program that involves all the relevant stakeholders, including sales and marketing.

If you’re kicking off your sales enablement efforts in the new year, you can start small, but ensure you’re thinking about all these pillars from the start. 

Whatever the scope of your 2020 efforts, always ask yourself if you’re shortening the sales cycle, enhancing quota attainment, closing deals more quickly, and providing content that resonates with buyers.

8. Lacking cross-functional alignment and unification between divisions

Alignment and unification across divisions, from marketing to sales to service, is where sales enablement really provides value. 

A strong sales enablement initiative is able to unify departments and  break barriers and silos. 

A good sales enablement strategy and framework includes integrated content, tools, training, technology, and metrics. 

Stakeholders across departments must be aligned to common goals and business objectives that directly affect marketing, sales, and service. Different stakeholders should be required to work together cross-functionally.

A strategic sales enablement program eliminates siloed working environments, allowing everyone to become galvanized around common goals and objectives.

Developing a customer-centric mindset in your organization unifies departments by creating a collaborative working environment. 


9. Underestimating sales manager enablement

Another one of the biggest and most common oversights is forgetting to put sales managers at the forefront of a sales enablement strategy.

Ideally, a sales manager’s role is that of a highly effective coach, but if you don’t have a structured, formal, strategic sales enablement program, how can you hope for those managers to be good coaches? 

At the foundation of your sales enablement program should be sales manager enablement. 

You want your sales managers to have a clear understanding of your sales enablement strategy and framework to effectively coach the reps and to provide them with a clear vision. 

Starting with the sales reps can cause confusion and slow progress because sales managers may not be fully acclimated to the new sales enablement system. 

10. Forgoing a sales enablement playbook

Your sales enablement playbook is a collection of sales strategies, processes, tools, and content designed, structured, and segmented to enhances the effectiveness and productivity of sales reps. 

Due to the evolution of the modern buyer, sales reps today have to be more prepared than ever before, and playbooks give them quick access to details on their targeted industries, buyers, and selling situation.

Playbooks guide reps through what they need to do, know, say, and show to be most effective. 

What should your playbook cover? 

It’s not uncommon to have multiple sales enablement playbooks for an organization. 

You might require documents for each product or service offering, as well as each specific persona and role in a given industry, vertical, or sales stage. 

Individual sales enablement playbooks could be created for:

  • onboarding new reps
  • learning a new sales process and methodology
  • creating a sales messaging strategy
  • utilizing digital and social selling
  • implementing affiliate selling and partner enablement programs
  • learning a new sales technology

You could create a sales messaging playbook incorporating a value-based sales messaging strategy. 

This would train reps not to lead sales conversations with the products but to start from a position of value based on industry trends, valuable insights, and the prospect’s needs. 

This could build credibility, trust, and industry expertise. 

A messaging playbook could also incorporate ideal customer profiles, business challenges and objectives, customer roles, and trends that are driving change.

The specific messages could be organized based on role and industry, which provide reps with the ability to navigate individual role sections and to amass a deep knowledge of the buyer and the messages that are going to best resonate with customers to drive change. 

You might also include video-based training showing reps how to:

  • deliver an effective message through a white-boarding session
  • map messages into other forms of content
  • deliver messages at different stages of the sales cycle 

Sales enablement playbooks should be on-demand and digital in form, making them easy to edit, access, and share. 

Video, short snippets of text, audio, templates, quizzes, and other forms of interactive content are extremely useful to digest and retain information quickly.

It’s best to create these pieces after you develop your sales enablement strategy and framework. 

Without these foundational elements, your playbooks risk being too tactical, not providing the structure necessary to really enhance the effectiveness and efficiency of reps to drive growth.

11. Lacking an integrated sales enablement technology stack

Does this sound familiar? Your marketing team works diligently to create content for the reps, but then the reps never even use it. 

This is frustrating for everyone — the marketers who toiled to create the content and the reps who need it. So, what’s going on? 

It’s usually one of two things: reps can’t find the content or they don’t even know it exists.

Making use of an effective marketing application, sales enablement solution, and CRM can help. These kinds of tools make up a powerful sales enablement technology stack. 

HubSpot (specifically its marketing automation tool), for example, integrates well with Salesforce (a sales software) and effectively provides lead intelligence and bi-directional syncing of contact records and data. 

vPlaybook provides a highly structured system to create sales enablement playbooks with content, tools, training, and coaching to guide sales reps through on-demand, just-in-time learning and coaching. 

Based on the lead intelligence and contact record data from HubSpot and Salesforce, vPlaybook delivers highly segmented dynamic playbook content specific to the opportunity, lead, and stage of the sales cycle. 

This gives reps quick access to information required for each unique selling situation.

Every year, CRMs and other technology collateral become more advanced and more compatible with the evolving field of sales enablement. 

If you’ve been disheartened by tech in the past, 2020 is a great time to revisit your options and to see how things have evolved.

As with many elements of sales enablement, tech is highly customizable to your company.

You want to start by selecting the technology that best aligns with your goals, objectives, and strategy, keeping in mind the most efficient, successful technology stack will differ for every company.

Technology shouldn’t be the starting point of any sales enablement program, but it can make a sound strategic program more effective. 

Start small

Start by creating a strategy and framework that aligns with your organizational goals, objectives, sales KPIs, and individual seller’s outcomes. 

Remember, your sales enablement strategy should be customer-centric and aligned specifically to those customers’ challenges and needs through internal content, external content, and sales messaging. 

This means you will need to have a deep understanding of your customers, specific to their industries and roles. 

This is foundational to getting executive buy-in and, ultimately, achieving success with your sales enablement program.

If you have not implemented a formal sales enablement assessment for your organization, this is a good place to start. 

Do so before creating or evolving your sales enablement strategy, as the assessment will identify your gaps and the areas where you should pay the most attention.. 

Next, focus on integrating the different pillars of sales enablement through your strategy and framework.

Then create a sales enablement program that will align to specific outcomes, such as increasing quota attainment, improving win rates, and shortening the sales cycle in order to enhance sales productivity. 

If you’re looking to get your program off the ground, start small. You don’t have to boil the ocean all at once!  

Focus on specific areas that can improve your reps’ efficiency and effectiveness quickly. 

Remember, a good sales enablement program will unify marketing, sales, and service to ensure these groups are working cross functionally. 

When this happens, you will be able to get more accomplished more quickly with your core marketing and sales team.


Free Assessment:

How does your sales & marketing measure up?
Take this free, 5-minute assessment and learn what you can start doing today to boost traffic, leads, and sales.

Related Articles

The Key to a Better Sales Process? Pretend to Be Your Own Customer

August 23, 2023
Chris Duprey Chris Duprey

How To Create Sales Enablement Content Your Sales Team Will Love

August 17, 2023
John Becker John Becker

Need More Results from Your Marketing Content? Give It To Your Sales Team

August 16, 2023
Zach Basner Zach Basner

Focus on Sales Velocity and Solve the 'Danger Points' in Your Sales Process

March 1, 2023
Nick Bennett Nick Bennett

Check Your Ego and Understand the Metrics that Matter

December 28, 2022
Chris Duprey Chris Duprey

How Does They Ask, You Answer Benefit Sales?

December 7, 2022
John Becker John Becker

How To Align Your Sales And Marketing Teams In 2023

November 12, 2022
John Becker John Becker

How to Convince Your Boss You Need a They Ask, You Answer Workshop

October 18, 2022
John Becker John Becker

Miscommunication is Limiting Your Businesses — Here Are 4 Ways You Can Fix It

October 10, 2022
Marcus Sheridan Marcus Sheridan

Sales and Marketing Friction is Hurting Your Bottom Line – Here’s What to Do About It

August 4, 2022
John Becker John Becker

5 Features of a Sales Enablement Strategy That Actually Works

June 27, 2022
Ramona Sukhraj Ramona Sukhraj

How To Be a Great Subject Matter Expert for Your Content Team

January 13, 2022
John Becker John Becker

IMPACT+ Free vs. IMPACT+ Pro: What's The Difference?

December 25, 2021
Connor DeLaney Connor DeLaney

Sales Enablement Checklist: 5 Questions Marketing Teams Should Regularly Ask Sales Teams

November 30, 2021
Bob Ruffolo Bob Ruffolo

Free Inbound Marketing Courses and Training

November 5, 2021
Paul D. Grant Paul D. Grant

What is the Value of a Digital Marketing Consultant?

November 4, 2021
Chris Marr Chris Marr

4 Signs Your Revenue Team Is Slowly Failing

October 23, 2021
Will Schultz Will Schultz

Sales and Marketing Alignment: How To Shorten Your Sales Cycle

September 17, 2021
Kimberly Marshall Kimberly Marshall

How to Get Great Sales Content from Your Marketing Team

May 3, 2021
Liz Murphy Liz Murphy

What Does Almost Every Business Leader Get Wrong About Sales and Marketing Alignment?

April 7, 2021
Chris Marr Chris Marr

In a Thriving They Ask, You Answer Company, What Role Should the CEO Play?

January 27, 2021
Marcus Sheridan Marcus Sheridan

Marketing and Sales Alignment When Using HubSpot and Salesforce [Infographic]

January 16, 2021
Joe Bachir Joe Bachir

Sales goals: 5 costly ways you're leaving money on the table (+ video)

November 27, 2020
Liz Murphy Liz Murphy

How do I get my old school sales reps to buy in to They Ask, You Answer?

November 18, 2020
Marcus Sheridan Marcus Sheridan

6 most common revenue team meeting problems (and how to fix them)

November 18, 2020
Eric Dunn Eric Dunn