Enablement training: Challenges, expert tips, & learning guide

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Enablement has far-reaching impacts on your company, with research showing that well-established enablement strategies can reduce onboarding time, increase win rates, and boost overall prospect engagement. But to put a successful enablement strategy into effect, customer-facing teams will need effective enablement training.

In Spekit’s webinar, “Enablement Therapy: Lean into Learning,” Angela Romero, Director of Demand Generation, spoke with Shannon Story, Sales Enablement Manager at Mission Cloud Services, and got her expert insights on how to create a productive enablement training program.

This article will share her teachings and how you can create and host effective enablement training.

What is Enablement Training?

Enablement can be a catch-all term that encompasses both revenue enablement, sales enablement, and other efforts. Sales enablement is focused on providing sellers with what they need to make more sales, while revenue enablement focuses more on optimizing revenue at every stage of the buyer’s journey.

Enablement training is a huge part of your company’s overall enablement strategy. Effective enablement training leverages in-person learning, training software, digital content, and virtual instructions to provide the theoretical and hands-on, practical knowledge enablement teams need. 

What’s the Difference Between Enablement and Training?

Training is just one part of enablement. Enablement also encompasses content accessibility and utilization, analytics tracking, and much more.

As Story said: “One thing I think people don’t really think about is that a lot of sales enablement isn’t just the training. It's building relationships; it’s having all those reoccurring syncs and one-on-ones with all different levels of people.”

Challenges Your Enablement Team Might Face 

If you lead an enablement team, you may have experienced some of the challenges Story discusses in the webinar. Here are some ways to manage them so you can support your team and drive organizational success. 

Proving ROI

Story says, “If you’re in sales enablement, the hardest thing is: How do we prove our worth?  “How are we making sure that data is aligned with what enablement is doing behind the scenes?” asks Story. “A lot of what we do is behind the scenes.”

For Story, the answer was to keep track of leading indicators, which is easier when you have insight into your sales enablement metrics. Use enablement tools with content analytics that show you how your content is being used and where your sales professionals may need some additional enablement training.

Lining up with rev ops teams 

“I think that’s the future of enablement: Hand in hand working with rev ops,” says Story. “We have processes and procedures that need to be rolled out—enablement is the tool to get them rolled out efficiently. The ultimate goal is that rev ops goals can be met, and enablement really comes in to support that.”

This alignment is crucial but challenging to build. Without revenue and sales enablement building a bridge between sales and other revenue-generating teams, there can be a lack of communication and sharing of resources and information. When enablement doesn’t line up with rev ops, the rev ops teams can’t fulfill their goal of supporting all go-to-market teams.

Managing cross-team alignment 

“When we look at sales, there are so many different teams that are overlapping with what’s happening with our sellers that, if we can get that cross-team alignment and help solve some of those challenges, some of those bottlenecks, that’s when sales enablement can really shine as that connector,” says Story.

Gartner’s findings support Story’s experience, as their research found that more than 50% of CSOs believe that enablement will support marketing and customer success roles in the next three years.

Cross-team alignment can be difficult to create, as many companies suffer from a lack of cross-team communication and the development of data silos. These silos prevent knowledge and resources from being shared between teams, which is vital for revenue enablement. 

Documentation and communication 

Documentation is vital for future enablement training since it makes it easier to repeat processes that work well. Without the right documentation, procedures become harder to standardize. It also means that multiple teams and team members may end up building their own processes, which opens the door to error and can waste precious time.  

Story notes that documentation also goes back to the necessity of proving your ROI as an enablement professional. When you have detailed reports of what happened in a specific process, stakeholders can start to see the impact. 

“They’re able to recognize patterns, and you’ll start to really build confidence with those stakeholders in enablement’s abilities,” she notes.

Benefits of Effective Enablement Training

Effective enablement training can:

  • Help more sellers reach quota attainment
  • Boost win rates throughout the company
  • Reduce ramp-up time for new hires
  • Establish lines of communication between teams
  • Foster an attitude of excitement for growth and new opportunities

Enablement Training Best Practices (From the Experts!)

Let’s get into the best practices in enablement training with the help of our experts.

1. Determine clear sales goals

It’s essential to determine your sales goals in order to find your ROI, which, as Story discussed, is one of the biggest challenges in enablement.

Determining goals ahead of time helps you track the right metrics to measure your enablement training’s success. You can determine if your team members are getting the help and resources they need for their personalized learning path.

2. Build relationships with stakeholders

“I’m a big proponent of recurring syncs [with stakeholders],” says Story. “One thing I did off the bat was find those stakeholders who would want to see improvements made and set time on their calendar.” 

Stakeholders can become your biggest champions if you build communication with them. If they know your impact, they can help influence your budget and the amount of support your team gets.

“But,” she notes, “the key is not just showing up to that calendar event empty-handed but coming with an agenda.” From there, ask questions about what they want to see. This process ensures you’re “getting their feedback, and then you’re taking that feedback and analyzing it and coming up with some solutions that start to build trust.”

3. Motivate your sales team creatively

Story says that the best way to motivate people is by leaning into the “personal touch.” Story, harkening back to her days as a teacher, gives out handwritten notes with stickers, as well as gold stars. When she sent a note to one of her team members, she also gave him extra stickers as a gift for his three daughters.

“We don’t always have to be doing these big gifts or these big parties,” she says. “Sometimes, just saying ‘thank you’ and recognizing the hard work people are putting in is a great way to motivate people.”

4. Personalize your enablement training

Story also feels that having a personal touch is beneficial in the training itself. She focuses on building relationships, which is why she schedules one-on-one sessions to understand what her team members need. 

“They know that you care about this, that they are still top of mind, and that their need is still on your mind,” says Story. “And it just continues that relationship building.”

They also get learning recommendations based on their sales performance and previous training journey. The top-performing companies in sales are twice as likely as underperforming companies to customize their training to the needs of their employees. 

Just-in-time enablement platforms like Spekit can help create these customized learning paths and offer training recommendations. Spekit’s AI-powered platform unpacks your seller’s performance and previous training to provide them with the resources and knowledge they need—delivering learning directly into the flow of work.

5. Try game sessions

Story has also found that “game sessions” can be highly motivating for enablement training. “It’s a great way to bond with people,” says Story, “but also to learn.” 

Research shows that gamified learning is more engaging and motivational than traditional educational courses. Although Story notes that organizing these game sessions for training can take time, she finds it worth it. 

“No one wants to sit and listen to people talk…they want to engage with the material. They want to be hands-on,” explains Story.

6. Centralize your learning content

More than 70% of sales leaders spend four or more hours per week answering questions related to tools, processes, and methodologies that salespeople need to know to be able to do their job. By creating a centralized location where your sales reps and other customer-facing teams can find the answers and content they need, you’re giving everyone their time back.

While Story uses a Slack channel as the main place where her go-to-market teams can find the information and content that they need, Spekit makes it even easier to ensure your team members can access the information and knowledge they need to succeed. With Spekit’s content management system, it’s easier to access content, monitor content usage, upload and organize content, and more.

7. Schedule enablement training sessions in advance

Story believes that enablement can often get into the habit of being reactive instead of proactive. For example, you might see one of your reps struggling with the negotiation phase. You can wait to address this struggle until they need to go through negotiation with a new buyer–or you can prepare them for this important duty during their sales training and coaching.

The habit of being reactive instead of proactive should really only exist in companies that are just starting to put enablement processes and training in place, as they may not yet have their processes documented. But you can avoid this habit by scheduling training in advance.

Scheduling training in advance gives employees time to plan their work schedule and keeps them from feeling overwhelmed.

8. Focus on retention–not just learning

Sales reps forget 70% of their sales training within just one week, which is why enablement training needs to focus on increasing retention. For Story, that means embracing “drip learning.”

Drip learning refers to making learning available in small doses over time rather than a lot all at once. Story can use platforms like Spekit to provide AI-powered, just-in-time learning. Spekit analyzes your sales rep’s training journey and recommends small, bite-sized bits of learning delivered right to them in their flow of work.

9. Question learning techniques that aren’t working

“One person’s view of what’s happening is not the full picture,” says Story. Talk to your salespeople and stakeholders one-on-one and piece together that full picture by looking at multiple points of view. When you listen to others question learning techniques, you can find more opportunities for optimization.

“Keep that dialogue going, and you can often get to the root of the problem or find another new solution,” says Story.

10. Know how to prioritize training requests  

In Story’s experience, a common misconception on how to address a knowledge gap is to just “slap a training together.”

The result? Lackluster training. Prioritize your training requests and work on the ones that need to be addressed. If multiple employees are coming forward to ask for Salesforce training, which may be a core technology they have to use, but one other employee is asking for a different training on a less-used platform, the Salesforce training must be the one to be prioritized.

Story uses an “advisory board” to determine which training requests are most pressing. Consider meeting with your team leads to form your own advisory board or send out surveys to your go-to-market team members to see what they want to be prioritized in their training.

11. Provide clear action items 

“Who doesn’t like checking things off a checklist,” wonders Story. During her one-on-ones, she pulls up a checklist for each of her team members and they go through it together.

This checklist gives her sales professionals clear action items that help them reach their overall goals—broken down into an easier-to-achieve way. “As soon as people start, they want to start running. I’m helping them run.”

12. Offer group training 

During onboarding, Story utilizes small group sessions to create a safe space for new employees. Since they’re all new together, they feel more comfortable asking questions. 

Using group sessions, Story also encourages cross-team alignment. These groups of new people include from different parts of the company. This process fosters communication between teams and prevents the development of those pesky data silos.

13. Encourage team member growth

Story is always looking for ways to identify future managers and leaders, and one of the most effective ways is through the implementation of Mission’s Peer Ambassador program. 

“The people who are stepping up to be that peer ambassador, those are the people who want to lead,” she says. “So lean into that. Keep note and train those people up.”

A huge part of enablement is training beyond the current role. Enablement professionals need to be looking for how they can cultivate the future leaders of the company.

Improve Your Enablement Training

Enablement training and sales training aren’t synonymous, but sales training is a piece of your overall enablement puzzle. For successful enablement training, your enablement team needs to provide not just what your sales and other customer-facing teams will learn but also how they will learn it. With these tips, courtesy of our expert, Shannon Story, you can build an enablement strategy that unlocks the learning paths your team needs to grow.

To learn more about giving your team the tools they need to succeed through enablement training, check out Spekit’s webinar “Enablement Therapy: Lean into Learning” and get started with Spekit.

About the author

Elle Brayton
Director, Content & Communications
Elle is a boy momma 2x, brand builder, storyteller, growth hacker, and marketing leader with 12+ years of experience scaling SaaS B2B organizations.
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