When does the sales cycle end?

Sellers typically respond: “As soon as you get a firm, verbal agreement.” or “Not until the purchase order is signed.”

But in the buyer’s mind a signed purchase order is the beginning, a tentative step toward promised value realization.

High-growth sales organizations realized this long ago and changed their philosophies to match. In the wake of the COVID-19 crisis and the economic downturn that followed, many organizations attempted to follow suit — adopting a buyer-first approach that focused on building long-term relationships with buyers to enable their success.

Or, so they thought.

Research by LinkedIn revealed that buyers see things differently: While 65% of salespeople (and 72% of top performers) say they always put the buyer first, only 23% of buyers agree.

That’s a serious discrepancy — what’s to blame for the mismatch?

LinkedIn found the single biggest roadblock to implementing a truly buyer-first approach: “Lack of the right skillset among existing sales talent.”

The solution is obvious: Sales training that embodies the five principles of the buyer-first mindset:

Learn, then define

Share, readily

Solve, don’t sell

Deliver value

Earn trust

To do that, you’ll need to implement a value-based approach to sales training that creates customer-obsessed sellers who forge long-term relationships. Luckily, that’s what this guide is all about. In it, we’ll cover the fundamentals of value-based selling and how to build a customized sales training program, drive adoption and measure its impact.

Customized Sales Training

Understanding Your Sales Training Needs

Before implementing a sales training program, it’s vital to understand the differences between a sales methodology and more tactical types of training. This will ensure you identify the most impactful sales development plan for your specific organization.

A sales methodology includes the steps a sales rep would take to move a deal from discovery to “closed-won.” It’s the playbook that teaches sellers how to consistently qualify and close opportunities.

On the other hand, sales skill training is designed to address the specific actions that must be performed in the moment — for example, how to open a sales call by establishing credibility in the first 30 seconds or how to use anxiety questions to shake things up, create urgency and open new dialogues.

When you implement a sales training program where all of these components work together, you’ll have a solution that will enhance skills, create lasting behavioral change and — most importantly — drive results.

In-house vs. Outsourced Sales Training

The 2020 LinkedIn State of Sales Report found that top-performing salespeople are more likely to spend time training with their managers. They’re also more likely to receive training from outside sales experts.

This fits with our experience: When most companies ask themselves, “Which is better, implementing an in-house training program or hiring an external sales training provider?” They quickly come to the conclusion that they don’t want to recreate the wheel.

After all, providing an effective sales training program in-house requires years of near-continual development, piloting, testing and revision — then the inevitable waiting to see if you were able to generate measurable sales results or if another trip to the drawing board is in order.

However, opting for outside experts doesn’t mean you’ll need to outsource control of your sales strategy.

Often, the most effective and sustainable sales transformations involve a flexible and collaborative approach to sales training. In this arrangement, sales and enablement leaders call the shots, and outside trainers bring the expertise needed to implement their vision. Some sales training providers even provide certification workshops for training in-house trainers. This ensures that you’ll be able to maximize your ROI through in-house experts who can train incoming cohorts and offer refresher training for more tenured employees.

At the end of the day, it really comes down to logistics. If you only need to train 20 experienced salespeople, perhaps a small event and an eventual in-house certification is the way to go. By contrast, if you suddenly find yourself needing to train 600 sellers in six languages simultaneously, it’s best to leave this to sales training providers with experience training global teams.

How to Build a Sales Training Plan that Drives Results

For starters, it can’t be cookie-cutter. Nothing causes eyes to glaze over faster than generic training materials that address generic sales situations.

Remember: Your seasoned reps will likely view training initiatives with a degree of skepticism — they’ve seen most “flavors of the week” come and go and, like most of us, are resistant to change. If you don’t provide customized training with real-world examples that immediately demonstrate how they’ll apply it to their next deal, you’re only wasting time and money.

From there, analyze your sales results to identify the roadblocks. Since modern selling is all about identifying the buyer’s process and aligning to it, look for areas where things regularly go out of sync.

Sales process common mistakes typically fall into one of five categories:

1)  Prospecting:

Reliably filling the revenue pipeline is a perpetual challenge for most sales teams, especially in the B2B world.

We get it: No one actually likes to prospect — and that’s okay. However, before you can improve your sales prospecting, you’ll need to identify the issue. 

Are your reps afraid to pick up the phone? It’s easy to think that cold-calling is dead, but there’s a newfound love for the office phone as Zoom fatigue continues to be a problem. 

With a little bit of discipline and a strategically choreographed approach, it’s not uncommon to see results like these: With five full teams working the phones, they conservatively created about $6.5M (USD) in pipeline in their first three days of call blocks. 

For the full guide to creating your prospecting strategy, check out “Your Guide to Powerful Sales Prospecting.”

2) Qualifying:

We see it all the time — sellers tend to think of qualification as a discrete event instead of an ongoing process, and pipelines end up padded with opportunities that will never close.

This can have a huge impact on your win rate. When formulating a strategy to eliminate no-decisions, use these questioning techniques to separate the shoppers from the buyers.

3) Differentiation:

Being different ≠ being differentiated. Many sales teams focus on features here and tend to think of their product or solution in comparison to their competitors — but that’s merely step one.

Top performers know that you must connect your unique capabilities to your prospect’s unique problems. After all, value is always measured in the eyes of the customer.

4) Objection Handling:

Some objections are an attempt to brush you off. Others are perfectly legitimate — and a buying signal.

How can sellers tell the difference? It helps to have a process that can be followed no matter the product, service or situation. For the masterclass on objection handling, watch the webinar below.

5) Closing:

Sales reps often talk about closing like it’s a one-and-done skill, but the reality is more nuanced. When deals stall, it’s because something was missed in the sales cycle — the result of sellers failing to adequately understand the potential customer’s buying process and map to it.

In fact, the problem typically involves some type of qualification, differentiation or timeline error. To pinpoint the specific element you’ll need to address in training, check out this article in Forbes.

Once you’ve identified the problems, it’s time to compose the elements that will enable the solution. To address various learning styles and maximize your investment, your sales training program should be divided into pre-course work, live instructor-led workshops, video reinforcement and microlearning.

Because adult learners acquire skills most effectively by doing, ensure your trainings are activity-based, not lectures. You’ll need to customize workshops and case studies that help learners build skills through simulated sales situations based on credible, real-world stories and expertise.

Structuring Sales Training Initiatives

The fateful day has come! You’ve got the green light, and moves are being made — but before your sales training initiatives can become reality, you should carefully consider the environment and timing.


The setting of your sales training program will vastly impact its structure. Will it happen virtually or on-site?

When choosing a physical location, ensure that the space will support team learning. Here again, it’s about moving away from the lecture-style delivery. Instead of arranging chairs in rows, opt for small tables that comfortably seat three to four participants and leave plenty of space for course materials. In general, it’s best to split your total cohort into groups of 20-22 participants and have a dedicated trainer for each group.

If you’re eyeing a virtual program, carefully consider the logistics. Who will lead the training? Which individuals will act as technical support? How will you ensure that you keep engagement and interaction high?

The divide between traditional classroom and virtual training is wide and characterized by completely different delivery methods. Don’t make the mistake of thinking that a classroom program can make the jump to digital without completely rewriting its DNA.


To pinpoint the optimal time for sales training, ask yourself: How long will it take to address the core principles of our major sales challenges? Do you need two full days? Multiple four-hour sessions throughout the week coupled with follow-up work? Or would a more gradual approach that involves staggered training sessions for individual cohorts within your company be the way to realize the most impactful sales results with the least amount of disruption?

Remember: To ensure retention, you’ll be looking at a program that requires introductory coursework, instructor-led sessions, and reinforcement through coaching and ongoing microlearning. Be sure to carefully align these stages and ensure that they don’t interfere with other company events or hectic times like the end of quarter or year-end.

It’s equally important to understand when you’ll see results. If you’re reading this in April of 2022 and are on the hook to increase revenue by 10% and margins by 2% by 2023, it’s go time! On average, you’ll need at least six months to realize the results.

Delivering Virtual Sales Training

You’ve likely heard it five thousand times by now: Virtual Selling is here to stay — but it bears repeating in this context because when training virtually, you’ll need to model virtual-selling best practices.

Whether you’re the trainer, you’re hiring a sales training company or you’re building an internal corporate university with on-staff trainers, begin with four fundamental principles in mind:

1) Prepare:

You’re entering an inherently distracted training arena where your surroundings will speak volumes — the days of relying upon your laptop’s camera and microphone and the carefully curated bookshelf in the background are over.

You’ll need a dedicated space that allows you to deliver while seamlessly accessing training notes and triggering interactive elements in the virtual environment.

Minimum equipment requirements include: a studio-quality condenser microphone or professional headset, an HD webcam with at least a 1080 pixel resolution, a stand to hold training notes/materials, lighting equipment and a clean background or greenscreen.

2) Practice:

Proper preparation doesn’t stop with the physical environment and tech. If this is your first time training virtually, practice, practice, practice. At a minimum, you’ll need to run through every tech-based action you plan to take during training with the individual who will act as your tech support and a team member acting as a participant. This will ensure you have all perspectives covered and are able to identify any potential glitches before the real deal. 

It’s also important to record these sessions. Sometimes we’re all our own worst critic — use that to your advantage here. Your teammates are there to support you in the practice session, and as a result, they might be tempted to sugarcoat things. When reviewing your recorded sessions, put yourself in the place of workshop participants. Are there too many monologues without interactive elements? Do you struggle to efficiently convey any part of the sales strategy? Find the weak points and rehearse until you’re confident you can deliver an engaging session.

3) Maintain Engagement:

Different learners appreciate different types of learning tools. Some will be comfortable with completely virtual sessions, while others will struggle without physical course materials like workbooks and notepads. Cover all the bases by ensuring that all training materials are delivered to participants ahead of the scheduled workshops. When planning the training sessions themselves, it’s best to keep them to four hours or less. Avoid the lecture-only format at all costs. Schedule breakout sessions every 30 mins so that sellers can run through exercises in smaller groups of three to four — and remember that these exercises must be grounded in real-world situations.

4) Foster Camaraderie:

Bake in opportunities for small talk and other ways for salespeople to connect. Try beginning every session with an icebreaker to get people thinking and talking right off the bat. Another great tactic is to assign homework — that’s right, homework. We promise; it’s not as dismal as it sounds. After day one, assign the team a podcast to listen to or a series of articles to read. This gives them something in common to discuss in the warm-up period on day two. 

More than anything, you’re looking for sales trainers who have a strategy for bringing in the human element to engage learners. At the end of the day, people buy from people. Training should reinforce this concept on every level, including helping sellers connect with one another — but don’t take our word for it. Check out this real-world example of how virtual sales training brought together a remote and geographically distributed team.

Improving Sales After Training

How to Ensure Sales Methodology Adoption

The Most Successful Sales Transformations:
Top-down transformations have the most impact on sales results.

If you’re a sales rep, it’s one thing to be thrown into sales training with your peers. It’s an entirely different experience if your VP of Sales — or one of your C-level executives — is right there too, modeling the behavior and going through the exercises. Not only does this demonstrate how serious your organization is when it comes to training initiatives, but it also ensures that the entire sales organization is speaking the same language. This has a dramatic effect on forecasting. When everyone uses the same criteria and framework for evaluation opportunities, it eliminates confusion and any seller-led “guesswork” that negatively impacts forecast accuracy.

Ensure Buy-in from Sales Managers:
From there, ensure your sales managers are on board with the new program. Sales managers routinely make or break execution. You’ll need them to coach sellers weekly to reinforce key behaviors. Consider instruction dedicated to helping managers understand their new role in reinforcing your sales training curriculum.

Leverage Sales Tech:
If you opt for an outside sales training provider, choose one that provides tech that ensures adoption. Look for a program that includes software tools that easily integrate with any SFA or sales CRM. You’ll also want to consider AI-based conversational intelligence tools that allow you to analyze sales calls, and sales enablement tools to track how sellers are interacting with content and how they’re sharing it with potential buyers.

In the end, sales tech will only get you so far: It’s wise to set up a retainer for ongoing coaching and reinforcement with your training provider to ensure your sales team will have access to expert knowledge when and where they need it.

Implement Targeted Sales Coaching

Sales coaching is a process of developing people to reach their next level of excellence and performance by helping them master skills and overcome obstacles to success — and it’s a critical component of any sales strategy.

Start by making it known that you expect your managers to reinforce training concepts by coaching regularly. Sounds obvious, right? Well, you might be surprised to hear that in a recent webinar, we asked participants, “What gets in the way of your coaching?” Shockingly, 38% said, “I’m not expected to.”

The second hurdle is that managers often conflate managing with coaching, despite the stark differences. Yes, managing will help keep teams on track, but sellers become dependent on their managers. By contrast, coaching begins with the foundational belief that sellers already have the answers to their problems — but they don’t know it yet.

For the full playbook on building a sustainable sales coaching program that mints more top performers, check out: “The Ultimate Guide to Sales Coaching.”

Measuring Sales Training Impact

“If you can’t measure it, you can’t improve it.”

Identifying KPIs:

When managing the effectiveness of your customized sales training, start by establishing a baseline. Choose metrics that your sales training is designed to impact — your KPIs will likely be a close match for the issues you sought to address with training when building your sales development plan.

In general, pay close attention to: win rates, sales cycle length, average deal size, customer acquisition and retention, number of no-decision opportunities and overall revenue.

Remember: Sales training doesn’t happen in a vacuum, which is why it’s best to look at the KPIs you plan to measure against and determine how much they were impacted by extraneous factors. For instance, setting 2020 as your baseline will likely leave you with an overinflated sense of ROI.

Quantifying Behavior Change

While you probably won’t see an immediate lift in KPIs, you should have a plan for analyzing the behavior of your sellers. Significant behavioral change is often a powerful portent of revenue increases to come in the near future.

Let’s say your organization’s product has been commoditized in the past. Now, you’ve adopted a value-based approach to selling and are selling higher up the food chain. As a result, the conversations that your reps are having with buyers have changed drastically. Instead of feature dumping, they’re focused on weaving discovery throughout the sales process — but how can you tell if they’re actually doing it?

Conversational intelligence tools like allow you to quickly analyze the patterns in sales calls. In this instance, you’ll be looking at things like who talked the most, the buyer or seller? What was the length of the longest monologue and by whom? How many questions were asked?

If you see that the majority of your sales force is listening more than talking, keeping their monologues to under 30 seconds and asking more questions throughout the sales call, you’ll know that training was successful and driving behavioral change.

This is merely one example, but you get the idea. You could apply the same principles to notes within your CRM, feedback from customers or sales coaching conversations — the point is to never discount indicators of lasting behavior change because revenue increases are right around the bend.

Setting Expectations

Success looks different for every sales organization. If you’re a large organization with an established market presence and experienced sales team, odds are you’re chasing a specific revenue goal. While a midsize company with a sales team of predominantly first-year sellers will be more interested in behavioral change that lays the groundwork for future sales success.
Whatever your goal, ensure that everyone is on the same page at the start — from the CEO to your newest salesperson.

Conclusion — Increase Your Win Rate with Value-based Sales Training

When you invest in a value-based approach to sales training you create customer-obsessed sellers who solve the most pressing business problems. They engage with intelligence, curiosity and empathy to forge the long-term relationships that are vital to sustainable organizational success.

Today’s buzzword is “buyer first.” If that’s truly what you and your organization are striving for, make sure the sales training you select does just that — puts the buyer first. By definition, value-based sales training focuses on providing value to the buyer.

Sellers and buyers alike win when everyone in the sales organization employs a common language, follows the same methodology and realizes that the deal is never closed until the buyer realizes the value they were promised.