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Best Practices for B2B Sales - Guided Selling

Authored by Ric Ratkowski on August 4, 2020

Guided selling is the process of prescribing optimal sales execution steps to the sales reps to enforce a consistent and efficient sales process. The tasks and process are based on sales patterns of past close-won, and close-lost opportunities.

Dynamic guided selling is the automated collection of prospect interactions and seller activities with the application of artificial intelligence and pattern matching to prescribe optimal buyer role based sales execution steps  and coaching to the sales reps.  The guidance and coaching are in the form of follow up tasks, suggested content to send, scheduling of activities or insights about the opportunity.

Dynamic Guided selling is an adaptive process that uses a wide variety of contextual data to provide recommendations,either for the prospect or to your sales team, for each opportunity.

What Is Not Included in Guided Selling for this Blog

This blog does not include guided selling as it relates to eCommerce or creating configurators to help buyers figure out their needs and the solution fit in a hands-off sales approach.

For this blog, guided selling is being applied to complex sales cycles.  Its scope is to guide the sales rep interactions with the buying team to support their sales process.  In addition to guiding the sales rep on the sales process, it also includes suggested sales enablement tasks to the sales rep to provide “in-the-moment” learning.

Goal of Guided Selling

The first goal of Guided Selling is to manage and facilitate the buyer seller "dance".  Ideally guided selling helps the seller “back lead” the buyer controlled buying process.  Everyone benefits from "back leading" the dance.  The buyers are guided with educational materials to learn what they really need. The buyers are also guided on how to fulfill their needs in a structured, well-considered way that’s appropriate for them. The end result to the buyer makes a better informed decision.  The sellers benefit because they have a more streamlined sales process and provide less “noise” to confuse the buyer.  "Back leading" the dance helps align the buyer lead buying process with the seller's known best sales process.  “Back leading” the dance result in the dance looking better and feels more in-sync. 

Guided selling and the enhanced, dynamic guided selling process results in: 

  • A simplified and accelerated sales process
  • Elimination of friction in the buying process
  • Educating the buyer when they are ready to be educated with content appropriate for their role

The second goal is to create a consistent sales process.  A consistent sales process is a prerequisite for an accurate sales forecast.  A consistent sales process:

  • Keeps everyone on the same page as it relates to deal status
  • Guides the right behaviors of the sales reps
  • Reinforces the sales process and sales methodology
  • Provides a baseline for coaching
  • Helps to identify problems and apply solutions
  • Helps keep the sales pipeline clean and only include deals that are winnable
  • Increase sales rep productivity by focusing on activities to support winning the deal

The most crucial part of B2B Guided Selling is to remove any friction from the buyer’s decision process. Online or offline, buyers need the most straightforward path to satisfying their needs, the seller who gives it to them is often the one that wins the deal.

Components and Tools To Organize the Sales Process

From the seller perspective, the sales process is defined in terms of sales stages. Sales stages organize the activity of the sales team, match it to the needs of the buyer at each major pivot in the buying journey.  It enables your reps to measure opportunity progress.  Sales stages are lines in the sand to measure progress of a sales opportunity through the sales process.  Each stage has a series of defined objectives.  

The measurement of the achievement of sales stage objectives is by measuring sales milestones.  Sales milestones are sub-steps within a sales stage, they represent inflection points within the sales process.  The sales reps must manage through it successfully to move the opportunity forward.  

Below the sales milestones are buyer seller interactions in the form of emails, meeting, and seller provided content to help the buyer make a better informed decision, and buyer provided content to help the seller understand their pain.  Guided selling inserts its alerts and suggestions at the buyer/seller interaction level to guide the sales process.

Guided selling defines actions within each sales milestone.  Those actions depend on the health of the opportunity and activities to date within the sales opportunity.  Each milestone clearly defines the series of actions you need to taken or information obtained to promote the opportunity to the next stage in the buying process.

The foundation of a guided selling, is a well-built sales playbook. It aligns your sales process with the buyer’s journey and it lays out the steps of the sales play. It tells your sales team what to do and what to communicate in a given sales scenario.  Dynamic guided selling automates the playbook and at the same time, increases the segmentation of the playbook by industry and ideal customer profile segmentation.

Related Best Practices From Other Blogs

A previous blog post related to the sales pipeline best practices reviewed two best practices that also support guided selling:  “Proactive Follow up” and “Proactive Delivery of Sales Content.” 

Proactive follow up is system generated reminders, along with the ability to take action on those reminders.  The reminders are compliance based to ensure timely follow up with the prospect and CRM accuracy.  

Proactive delivery of sales content recommends the right sales content and provides insights at the right time.  The right content is a broad term and can include both sales content to the buyer(s) as well as training content/check lists/battle cards to the sales rep.

Both of these best practices are key features of dynamic guided selling.  They provide the sales rep alerts about follow-up and strategic activities with the ability to take action.

Results of Guided Selling

According to SiriusDecisions and our own empirical evidence from our customers,  guided selling increases sales win rates.

Guided selling provides a holistic experience for sales reps.  It allows them to respond to prospects as needed throughout the buying journey and is adaptable enough to allow for the variations for different industries and ideal customer profiles segments.

Guided selling provides a methodology for sales reps to follow so they understand the customers need, can assess product fit and never miss a follow up.  Guided selling can be thought of as a virtual mentor, allowing new reps to benefit from what collectively is the best sales process through guided selling.

Guided selling is also an exceptionally powerful method of building buyer/seller relationships. If done right the seller becomes a trusted advisor and leads the prospect to the right solution quickly while ensuring they are fully informed along the way. This gives buyers the confidence they need before making buying decisions.


Guided Selling


From the Buying Perspective

Gone are the days when the seller held all the cards and could lead the buyer's journey from beginning to end. Sales reps now have to figure out how to sell when the buyer is in the driver’s seat.  Buyers are no longer reliant on sales to educate them on products. Most do a great deal of research before ever engaging with a seller, and as a result, they expect nearly instant responses and personalized communications when they are ready to interact with a sales rep.

Before the average B2B buyer ever actively engages with sales, she/he is 57% of the way through the decision-making process.

From the Seller Perspective

Not too long ago, companies hired sales reps and sales reps did whatever they could to close deals.  They were effectively “on their own”.  

To help increase sales performance and remove some variability in the sales process, companies started to analyze the different sales processes within their company and standardize some of them and provide help to the sales reps.  This help started as some rough sales stages on a PowerPoint slide and evolved to a sales playbook.  Extending the sales playbook concept further, dynamic guided selling automates the sales playbook with AI to guide the sales reps through alerts and insights to help guide the buyer and their buying process.

In Summary

Buyers are more sophisticated than ever and sales reps must adapt. 

Problem/Business Need

The buyer journey is becoming increasingly unpredictable.  Each company is different, their needs are different, problems they are trying to solve may be similar but they have different twists.  The buyer’s needs represent the unique DNA of their company. 

To adapt to this new normal, companies need to perfect a dynamic sales process, incorporating tools and technologies that allow sales teams to quickly adapt to changes in the selling process on a customer by customer basis.

To achieve this, sales leaders must provide tools to support dynamic guided selling to streamline today’s sales complexity and to remain competitive.


SiriusDecisions states dynamic guided selling requires sales organizations to quickly synthesize large amounts of external and internal data, rapidly deliver insights from the data to sales reps and provide dedicated sales coaching. Dynamic guided selling caters to the needs of both buyers and sales reps, by providing personalized guidance to reps and tailored responses for buyers – all throughout the entire selling process. 

The need is to:

The need is to guide the sales reps on actions to take with each sales opportunity and allow them to take that action without leaving the current application. 

Because every buyer and sales conversation is different, guided selling needs to be dynamic and adaptable to unexpected changes in the sales interactions, to shifts in stages or when new buyers to the buying group join the conversation.  It should be an interactive process that gives sales reps the ability to easily find and share what the prospect needs to see in any sales scenario while guiding them through the sales process.

Dynamic guided selling requires clean, real-time data to deliver the desired results





Companies guided selling process consists of a PowerPoint loosely describing criteria for each sales stage

The company has mapped sales stages to sales milestones and has a detailed sales playbook in place.  They have aligned sales stages and milestones to key buyer activity.

Companies have streamlined the processes of recording the achievement of sales milestones within sales stages.  Along with that comes a general increased rigor and consistency around the sales process with the sales playbook.  

Companies have a dynamic guided selling process.  They are capturing all the sales interactions plus milestones and using that information to create a selling process that compliments the buying process.  The system leverages follow up and strategic alerts to help enforce the sales process. 

At the baseline level, companies take a general approach of “let the sales reps sell”.  Minimal guidance is provided in the form of a PowerPoint identifying the key sales stages with minimal definition.  The sales process is characterized by the sales reps “doing their own thing” and the general attitude of sales leadership is “as long as sales reps hit their quota, we are good.”  Forecast accuracy is plagued with inaccuracies caused by an inconsistent sales process, and unchecked “happy ears” and “sandbagging” sales reps.

At the good level, sales leadership takes a more active role in supporting all sales reps to become A-players and achieve their quota..  Sales stages are better defined and their achievement is linked to completing key milestones within each sales stage.  Sales playbooks are used to guide the sales rep to better manage the sales process in line with the buying process.  

At the better level companies have streamlined the process of recording the achievement of sales milestones within sales stages and are tracking it electronically.  This is a required step to move from guided selling to dynamic guided selling.  At this level, achievement of milestones are being recorded and buyer seller interactions can be sequenced to provide the baseline of information needed to move to dynamic guided selling once enough information is collected to recognize sales patterns by ideal customer profiles.

At the best level companies have implemented a dynamic selling process.  They have the systems in place to capture buyer seller interactions and use previous sales patterns to allow their guided selling tasks to adapt to current selling situations.  They have a well defined sales stage/sales milestones sales process and can capture the achievement of sales milestones in their guided selling tool to further feed the guided selling engine.  They have created a virtuous circle where current sales events and guided actions reinforce themselves through a feedback loop to revise the sales processes.

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