Sales Enablement Mistakes That Slow Your Sales Cycle

Optimising your sales enablement strategy can be tricky, but if you avoid common mistakes, it can significantly improve your team’s performance.

Read on to discover the seven biggest sales enablement mistakes and how to fix them.


The 7 Sales Enablement Mistakes You’re Making (and How to Fix Them)

You’re doing all the right things. You’ve trained your sales team, given them access to the latest tools, and made sure your marketing team is working hard to generate leads. But something isn’t quite right. Deals are taking longer to close, or worse, slipping through your fingers.

If this sounds familiar, you might be making some common mistakes in your sales enablement strategy—and it’s not your fault. It’s easy to miss these issues when you’re juggling so much.

The good news? You’re probably already doing a solid job, but with a few tweaks, you can take your team from good to great.

Here are the seven mistakes that could be holding your sales team back—and practical ways to fix them.

1. Sales and Marketing Aren’t Aligned (But They Could Be)

Let’s start with the biggest and most common issue: sales and marketing alignment.

In a perfect world, your marketing team would generate leads that are ready to buy, and your sales team would close those deals seamlessly. But too often, marketing and sales work in silos.

Marketing sends over leads that don’t fit the profile sales needs, or sales doesn’t know how to use the content marketing creates.

Why it’s happening: Both teams are probably working hard, but their goals aren’t always the same.

Marketing is focused on getting as many leads as possible, while sales is focused on closing the best ones. If the two aren’t on the same page, it leads to confusion and inefficiency.

How to fix it: Bring the teams together. Have regular check-ins where marketing and sales agree on shared goals—like the type of leads you’re targeting, the buyer’s journey, and the content needed at each stage.

Consider using a sales enablement platform that integrates both departments so they can work off the same playbook.

2. You’re Not Training Your Sales Team Enough So They’re Making Sales Enablement Mistakes

You might have given your team excellent onboarding when they first joined, but if the training stops there, that’s a problem. The market changes fast, and so do customer expectations.

If your team isn’t continually learning, they’ll be using yesterday’s tactics on today’s buyers.

Why it’s happening: Sales is busy. When the pressure is on to meet targets, training can easily take a backseat.

You might also assume that once someone is trained, they’re good to go for the long haul.

How to fix it: Ongoing training is key. This doesn’t have to be formal classroom sessions—it could be quick, actionable workshops or even peer-to-peer coaching.

The key is consistency. You could implement sales productivity software that offers bite-sized learning modules or weekly sales tips based on current trends.

Keeping it simple ensures training doesn’t feel like a burden.

3. You’re Talking About Products, Not Buyers

It’s easy to focus on your product or service—after all, it’s what you know best. But today’s buyers aren’t interested in a product pitch.

They want to know how you can solve their problem. If your enablement strategy is centered around what you’re selling, instead of who you’re selling to, you’re missing out.

Why it’s happening: We often assume that buyers already know what they want, so we jump straight into pitching features and benefits. But that approach skips a crucial step—understanding the customer’s specific needs.

How to fix it: Shift your focus from product-selling to buyer-centric selling.

Train your salespeople to ask questions and listen to the buyer’s pain points first. Then, tailor your pitch to show how your solution solves their problems.

It’s not about your product; it’s about how your product can help them succeed.

Tools that allow for custom content creation, like customisable proposal generators, can be a game changer here.

4. You’re Not Using Data to Drive Decisions

You probably have access to more data than ever before, but are you using it?

Data can tell you everything from which leads are most likely to convert to how long your sales cycle is. But too often, sales teams are still relying on gut instinct instead of using data to guide their decisions.

Why it’s happening: The data is there, but it can be overwhelming.

Without the right tools to interpret it, it’s hard to turn numbers into actionable insights.

Salespeople are busy, and they may not have the time (or the desire) to dig into complex reports.

How to fix it: You don’t need to become a data scientist, but your team should be using sales analytics tools that make insights easy to understand.

These tools should track key metrics like conversion rates, deal velocity, and content engagement.

Use this data to coach your team and refine your strategies.

Make sure that everyone—from your frontline reps to your sales managers—knows how to access and use the data to their advantage.

5. Your Sales Enablement Tools Are Underutilised

There’s a good chance you’ve already invested in some form of sales enablement software.

But here’s the thing—just having the tools isn’t enough. If your team isn’t using them properly, you’re not getting your money’s worth.

Whether it’s a CRM system, content management tool, or proposal generator, these tools should make your sales process smoother, not more complicated.

Why it’s happening: Sometimes the tools aren’t customised to fit your team’s workflow. Or they’re so complex that your reps avoid using them.

It’s also possible that you’ve outgrown the software you started with.

How to fix it: Don’t assume that the problem is with your team—it might be the tool itself.

Consider customising your sales enablement platform to fit your specific needs.

Work with a tech team to adjust workflows, integrate other software, or tweak the reporting features.

By involving your salespeople in this process, you’ll get better adoption and more value from the tool.

6. Your Frontline Managers Aren’t Equipped to Lead

Frontline managers are crucial to the success of your sales team.

They’re the ones who translate your big-picture strategy into daily actions. But if they don’t have the right tools or training, they’ll struggle to coach their team effectively.

Why it’s happening: Sales directors are often focused on the performance of the whole team, and frontline managers can get overlooked. They’re left to manage with little support, which makes it hard for them to lead with confidence.

How to fix it: Give your managers the coaching tools they need.

This could be data-driven insights that show individual performance or leadership training that helps them manage and motivate their team.

Providing them with actionable data will allow them to guide their team more effectively.

7. You’re Not Centralising Your Sales Content

Salespeople need content—whether it’s case studies, presentations, or white papers—to engage prospects and close deals.

But if that content is scattered across different systems or isn’t easily accessible, your reps are wasting time searching for it.

Worse, they might end up using outdated or irrelevant materials.

Why it’s happening: Content management is often seen as a marketing responsibility, and the sales team might not have a clear system for finding what they need.

In some cases, reps don’t even know what content is available to them.

How to fix it: Centralise your content in one easy-to-access hub.

This could be as simple as a shared folder or a more sophisticated sales enablement platform that organises content by stage of the sales process.

Make sure the content is up-to-date and relevant, and encourage your sales team to give feedback so the materials actually meet their needs.


Sales Enablement Mistakes: You’re Doing Well, But You Can Do Even Better

Sales enablement isn’t easy—it’s a moving target that changes as fast as the market does. But you’ve already got the basics down, and that’s a great start.

Now, by addressing these seven common mistakes, you can take your team’s performance to the next level.

Aligning your sales and marketing teams, training your reps continuously, focusing on the buyer’s journey, using data, customising your tools, supporting frontline managers, and centralising your content will make a world of difference.

It’s all about fine-tuning what you’re already doing well. And with the right adjustments, you’ll see faster deals, happier customers, and a more efficient team.


Read more about Sales Enablement

FAQs

Why isn’t my sales enablement strategy working as well as I expected?

Even with the right tools, issues like misalignment between sales and marketing, lack of ongoing training, and poor tool adoption can slow down your progress.

Small changes can have a big impact.

What’s the benefit of customising sales enablement software?

Custom software lets you adjust workflows, integrations, and features to fit your team’s needs.

This ensures higher adoption rates and better value for your investment.

How can I make sure my team is using data effectively in their sales enablement plan?

Use simple, easy-to-understand analytics tools that show key performance indicators like deal velocity and conversion rates.

Make sure your team knows how to use these insights to improve their performance.

Why is content management important for sales enablement?

Centralised, easy-to-access content saves time and ensures your reps are using the most relevant and up-to-date materials, improving the consistency and quality of their interactions.

How can I improve collaboration between sales and marketing?

Set shared goals, hold regular strategy meetings, and use a sales enablement platform that allows both teams to track progress and collaborate on content creation.

rs your team to work smarter, engage buyers more effectively, and close more deals without needing to hire an army of new salespeople.


Salesdrive: Transforming Your Sales Team with Customised Enablement Solutions

Is your sales team reaching its full potential? At Salesdrive, we specialise in crafting tailored sales enablement strategies that align with your specific business goals. Whether you need seamless CRM integration, advanced training modules, or cutting-edge tools to enhance your team’s productivity, our bespoke solutions are designed to turn your enablement efforts into measurable success.

Discover how Salesdrive can optimise your sales processes and drive significant revenue growth. Schedule a discovery call with one of our sales tech advisors today to unlock the power of customised sales enablement for your business.

Discover how Salesdrive's expert sales enablement tools and training can transform your business, optimise sales processes, and increase revenue.

About the Author

Sophie Carr, Head of Marketing, is an expert in brand building, storytelling, and education. As an experienced writer and growth hacker, she leads the innovative marketing team at Salesdrive.

Written by:

Sophie Carr – Head of Marketing

Sophie is a specialist in corporate content creation, sales technology and education. As an experienced writer and growth hacker, she leads the innovative marketing team at Salesdrive.