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Definitive Guide Sales Playbooks
Definitive Guide Sales Playbooks
Definitive Guide Sales Playbooks
to Sales Playbooks
2020
The Definitive Guide to Sales Playbooks — 2020
We have also seen how hard it is to drive adoption for anything new, including Sales Playbooks. Our results from the
Experience Room we ran at the Sales Enablement Society National Conference provided us with additional insights
on this topic. Adoption is critical if you want to see results from your efforts. We will share with you what we learned.
This guide is for anyone tasked with spearheading Sales Playbook initiatives in their B2B company. B2C is different,
and this guide does not cover these use cases.
In the next few pages, we’ll share a complete approach to create, deliver, and maintain Sales Playbooks. Our goal is
to demystify Sales Playbooks and provide a structure that you can adapt to a wide variety of sales methodologies
and business development goals.
A Playbook in American Football defines specific plays that have high success rates in gaining yards and scoring
touchdowns. Similarly, a great Sales Playbook will equip sales teams with approaches and knowledge to help buyers
identify pain points, jointly develop solutions, and navigate the path to deal close.
As we think about creating resources like sales Playbooks, however, we should recognize that we are rapidly moving
from a mindset where the consumption of learning is moving from the screen on a laptop to the iPad or phone.
The last three years have seen a significant shift in learning habits in the workplace, and this includes salespeople.
It’s getting harder and harder to get people to read conventional eLearning courses and documents. The move is
to consume information in bite-sized pieces—often on the phone. We have to adapt our thinking on the way we
construct and deliver sales Playbooks to meet this radical shift.
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The Definitive Guide to Sales Playbooks — 2020
As you consider your metrics, work backward from the business outcome, back down the line to the individual experience.
If you are unable to define these outcomes, you will likely deliver an incomplete Playbook, and, as a result, your Playbook
adoption will be low.
The following sections cover the revenue-based metrics we see being influenced by delivering great sales Playbooks.
Each of these metrics directly ties back to revenue earned, cost saved, or both.
Deal Stalls
The reality is that some deals linger in your pipeline.
They enter with assurances by the team that the opportunity is fully qualified. Just do your sales thing, and let’s start
counting the revenue. Unfortunately, sometimes the deal gets stuck at a specific point.
There are countless reasons for a stall, some are avoidable, and some are not. However, your Sales Playbook should
ensure the avoidable situations are not problems, and the unavoidable solutions are discovered sooner, reducing time
spent on unwinnable deals.
The result of better managing deals and avoiding stalls is that you will have the opportunity to win some percentage of
these opportunities, and that is money in the bank.
Lost Deals
Guess what? Some percentage of those deals that you lost should have been won.
Many of the reasons that lead to deals stalling also lead to deal losses. Maybe you failed to educate your buyer as to the
reasons why your product solved their problem. Perhaps a competitor did a better job personalizing their messaging for
the buyer.
Your Sales Playbook needs to help you overcome these challenges and more.
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The Definitive Guide to Sales Playbooks — 2020
Your Sales Playbook tackles this problem head-on, and you should measure the increase in ASP, as well as the discount
percentage on deals, per deal per sales rep.
A Point On Measurement
Before you begin a Sales Playbook project, make sure that you can measure “If you can’t measure it,
and baseline the metrics you expect to influence. These metrics will be one
you can’t improve it.”
of the indicators of your success or failure with a Sales Playbook.
– Peter Drucker
Measure twice. Cut once.
It would help if you were realistic about how quickly your Playbook will begin impacting these metrics. The goals identified in
this guide are trailing indicators that may, depending on the length of your average deal cycle, take months to understand fully.
What can you do? Measure leading indicators that can be measured quickly, at the moment, and provide a level of guidance
as you march forward. What leading indicators should you use?
Playbook Adoption
If they are not using it, it will not impact your deal outcomes.
Work with your Sales Managers and internal sales influencers to ensure they are promoting the Playbook and requiring its use.
During deal reviews have the team discuss how they are using the Playbook.
End-User Feedback
Your Sales Pslaybook is not perfect. While you may know about some of the areas for improvements, odds are you are
blind to many others.
You want to create feedback loops that allow end-users to provide candid feedback. What do they like? What needs
improvement?
It is essential to recognize that receiving a lot of feedback is a good thing. If you receive little feedback on what can be
improved, it is likely that either:
> Few people are using your Playbook.
> There is a cultural problem in your organization, preventing feedback.
Either of these situations are severe problems and need to be investigated, understood, and corrected.
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The Definitive Guide to Sales Playbooks — 2020
A Case Study
We delivered a Playbook solution for a Global Business Information Solutions Vendor. The company provides a leading
research and analysis platform and serves law firms, accounting firms, corporations, and others.
2. New deal closed within 6 weeks of roll-out, as a result of an insight found in the Sales Playbook
3. 50% increase in average deal value since Playbook roll-out
As you can see by the third bullet, when a Sales Playbook is well designed, containing great information, and adopted
by the sales teams, magic happens.
Increased Positive
Adoption Outcomes
The Continuous
Cycle of
Positive Benefits
Increased Satisfied
Revenue Customers
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The Definitive Guide to Sales Playbooks — 2020
If you work in a straightforward environment with a small number of products, a buying community you know well, and
with low seller turnover, your Playbook may be very straightforward to create. However, for many, creating a great Sales
Playbook is not a trivial effort. Depending on the number of solutions you sell, the vertical you sell into, the buyer personas,
this could be a few pages to a few hundred pages in length.
It’s always been hard to grab the attention of salespeople with new tools and materials. In today’s world, where we are
awash with information, and attention spans appear to be getting shorter, it’s becoming even more laborious.
Creating a new tool or resource for salespeople without input from them, then loading it to the company intranet and
directly sending an email doesn’t cut it anymore! The following paragraphs below give guidance and tips on what to do
to achieve adoption and ensure the best chance of success.
Executive Sponsorship
You will need cross-functional support to create a Playbook, and you will want an executive sponsor to ensure this happens.
You may already have the processes in place to support this, if not, follow this simple guidance:
Do an Informal Survey of Your Sellers, Marketers, Finance, and Customer Care Teams
Your goal here is to establish an understanding of existing pain points in their roles, which a Playbook could potentially mitigate.
Instead of creating a digital survey, sit down with each individual, and walk through the entire buyer journey with them.
For each phase of the trip, ask them:
> Are they currently involved in this part of the process? If not, should they be?
> Are the processes they use, or that they are part of, documented?
The goal of this is to dig deep, documenting everything. You want to gain a complete understanding of the buyer journey
and be clear as to where pain/friction exists for internal staff as well as for your customers.
Your initial focus will be upon the sales portions of the process, but take the time to interview this broader set of people to
ensure you build a 360-degree view. You will gain a deeper understanding of the business, and your Playbook will benefit
as a result.
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Sit Down with the Head of Sales, Marketing, Finance, Customer Success, and Product
You will use this meeting to discuss why a Sales Playbook is needed. Your goal is to get permission to run an initial project to
understand the level of effort, potential project timeline further, and what resources are required initially and ongoing.
If you can, tie the conversation to the goals of individual executives and use this conversation to identify which executive
will most benefit from your success. Are they willing to lend their leadership to these efforts and become the sponsor?
> What current information is in place and its current level of quality?
> What teammates are needed for the creation of the initial Playbook?
> Processes and tasks to be worked through as part of the Playbook build-out. For example:
> What training is needed for the sellers and those maintaining the Playbook?
> What are the business impacts of documenting best practices and ensuring everyone is using the right
processes, messaging, and approaches, everytime?
You will want to use all of the information you are gathering to create a draft project plan, project schedule, cost esti-
mates, and the expected benefits.
It is now up to you, in partnership with your executive sponsor, to make your case, get approval, and get moving.
Good luck!
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Create a Team
The group you have been working with up to this point may, or may not, be the correct team to complete the work.
You need a team around you:
> That will be able to execute under pressure. This project represents a significant investment by your business,
and they will expect to receive a return on this investment on this effort.
> Who can effectively communicate across various business functions (sales, marketing, customer success,
product, finance, IT, etc…)
This team must be able to refine and manage a complicated schedule with participants and stakeholders across
multiple organizations.
This team must be able to either execute upon or bring resources to assist with the initiatives taken on by this team.
This team was likely formed with executive buy-in, and with an executive sponsor who expects your efforts to help them
achieve their business goals. The pressure to execute is guaranteed.
> Does the team have any concerns around the goals?
You do not want to go back to your executive team with significant changes to the metrics and related targets at this
point. However, you also do not want to march forward towards goals the group does not support.
Take time to be specific about the impacts and the timeline for these changes. It is critical for you to be conservative
on this front and to focus on achieving a few early wins. This will create confidence inside and outside of your team
and offer you the opportunity to get the team working together well.
However, people’s information consumption habits have changed since then. Think of the Google effect: people are far
more likely to forget information that they can readily find online — a side effect of having worlds of knowledge at their
fingertips as long as they have an Internet connection.
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PDF Playbooks no longer cut it because they don’t really take into account the way people learn, use and retain information.
1. PDF Playbooks are too inaccessible and bulky to help with real-time selling situations. Sales reps don’t have the time
to hunt through different repositories to find the most recent version, much less wade through 20, 30, even 70 pages
of content to find the bits they need.
2. The long, static format makes PDF Playbooks ineffective reference and support material. Large chunks of information
don’t play well with human attention spans, or with our limited capacities for storing and retrieving information.
3. PDF Playbooks don’t offer the interactivity needed to engage sellers and give them the reinforcement they need to
retain information for the long haul.
Your Playbooks should be living documents, updated regularly to address new lessons, best practices, and any other
new information. It is for this reason that we recommend a digital, cloud-based and interactive, Playbook. This will
simplify maintenance and ensure sellers always have the latest information.
Solution
Don’t bury the salesperson with information and don’t try to provide everything to everyone.
Choose a focus area for your Playbook and break into a few, shorter versions if needed
(e.g., vertical, global region or product). Make it short and engaging. Use technology
to make them web-based and more dynamic. Again, think about how people seek
information in their daily lives; quick searches for short, snackable information.
Once you’ve determined the target customer segments and personas you’re looking to sell into; you’ll need to put
together a project stream to look at gathering and/or creating the content for your Playbook.
Start by reaching out to key stakeholders in product, sales, and marketing who may have worked on marketing and sales
tools for the solution(s) in the Playbooks. If you have a Learning team, they may also have materials with insights that can
be extracted and used in the Playbook.
Use a Sales Playbook Template (see an example in this Guide, below) to understand the type of insight you are looking
to gather. Typically, there will be content articulating what the product does and the value it delivers. Still, it may be more
challenging to find industry trends that are relevant to your solution, customer pain points, workflows to target, and
information about personas.
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The key is putting in place a structured process to get input from the people you need, testing it with customers or
prospects, and aligning it with your proposition. It is essential to be clear to everyone involved what the steps are, how
you will capture their input, and how the final content in the Playbook gets signed off.
The following provides some practical steps for developing new content:
> Map your company’s capabilities to customer challenges and articulate value delivered
> Produce a Selling Knowledge document and get sign off from stakeholders
> Develop content elements (e.g. conversation openers, qualifying questions) for the Playbook based on insights
developed (or gathered from existing materials)
We’ve found the best sales Playbooks have the following characteristics:
Easy to Reference
Include interactive links to each section in the table of contents so sellers can locate the right resources at the right time.
Even better, break up your Sales Playbook into concise modules. ATD notes that breaking up content into bite-sized
pieces makes the transfer of information 17% more efficient.
Engaging
If all you do is break up a text-heavy Playbook into chapters, it won’t improve seller engagement.
Research has shown that our brains process visuals 60,000 times faster than text. This makes videos an excellent option
for demonstrating sales best practices. These can be anything from examples of top sellers negotiating to the marketing
team explaining the benefits of a new product.
In Context, On-Demand
According to IDC research, 33% of all unsuccessful client deals could have been won if the salesperson had been better
informed and had acted more client-oriented. Even experienced salespeople with mastery of their subject occasionally
need support, especially with new products, or opportunities to upsell.
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To best enable your sellers in situations like these, ensure your Playbook can serve up the most relevant and up-to-date
information during crucial, time-sensitive moments.
What causes it? Reviewing the same piece of information again and again
isn’t good for encoding, but we convince ourselves that we know all of the
information we’ve read and won’t learn more.
Why should I care? Reading and re-reading static playbooks facilitates this
illusion. Combine this brain glitch with hubris and sales ego, and you have a
recipe for under-performing sales reps.
What can I do about it? On-the-job retrieval practice — lots of it. Build in retrieval
practice into your playbooks using tools such as knowledge checks, flashcard
decks, and self-testing modules. Some solutions even allow you to automate
retrieval practice by scheduling assigned content at per-determined intervals.
> Is it in a format that supports using it when the sellers are looking for information?
> Does it contain the information required to guide buyers through the sales process?
Who should be part of the pilot? Consumers and creators of Sales Playbook content need to be involved.
At a minimum, include:
Be clear about what changes you can sign up to make during the pilot testing. Will you make cosmetic changes?
Are you open to a full redesign?
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> Enlist managers and top-performing reps to champion the new Playbook.
> Develop quick guides to help the team understand how to use and where to find information in the guide.
> Create a training program that you can deploy through your LMS or another learning system.
> Train your sales managers on how to leverage the Playbook as part of their coaching sessions.
> Set up ongoing office hours and training sessions to reinforce how to use the content in pre-meeting planning,
during a sales meeting, and as part of the post-meeting follow-up.
As part of this roll-out, ensure that there are clear channels available to the broader team to use to provide feedback
as they begin using the content. This should be in addition to the regular office hours mentioned above.
> Report on lagging indicators quarterly. This will not shift rapidly enough
for anything more frequent.
Your business is changing at the speed of the internet, and your Playbook must keep up.
You first need an ongoing plan to revisit your business outcome and enact change management to commit to the
team revenue goal in the business issue you are solving together.
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> Approved changes should result in updates being made to the Playbook.
> Rejected changes should be followed up on based upon the reason for rejection.
> Set up a meeting with all sales managers to give them a preview of changes being made in this monthly update.
> Share the why and how it impacts them and their teams.
> The new Playbook should be updated along with documentation explaining what changes have been made, why,
and how they impact sales managers and sales reps.
?
Who should be part of this review committee? Include all sales managers, your executive sponsor, leads for marketing,
customer success, and any other team creating content for, or consuming content within, the Sales Playbook.
Rarely: Some information such as, the company story, will stay the same for years.
Drive Adoption
Adoption will not happen as a result of a big kickoff meeting and a few quick guides. While important, you are working to
change behaviors, and this takes time and focused effort.
As mentioned in the KPIs and Metrics section, you should report all of the leading and lagging indicators regularly. Monthly,
as part of your standard committee review, include a readout of all metrics.
Make adoption a vital aspect of all monthly committee meetings. If it is not being adopted, why?
As noted by the Hubspot Ultimate Guide to Sales Playbooks, “Some companies create one sales Playbook per product;
take this route if your products are fairly different, require radically separate buying processes, and/or are sold by different
members of your sales team.”
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If the customer insights, questions to ask, value propositions and sales messages vary markedly by segment, then you
will either have to produce separate Playbooks or organize content broken down by market in tables on the pages.
What you say to a customer should always vary depending on the buyer role (i.e. persona), so you will also need to set
out insights and messages by persona.
If you want your Sales Playbook to be the ‘go to resource’ for sales people as they work deals, structure the sections of
the Playbook around the main stages in the sales process followed at your company.
This makes it easy for a sales person to dive into the Playbook and immediately find the relevant insights, guidance and
messages for the point in the sales process they are at, for the opportunity they are currently pursuing.
In spite of the name, Sales Playbooks aren’t actually ‘books’ that sales people read, and all too often they end up sitting
on a document server, unread and unloved! In this age of information on demand, people want to find the relevant right
slice of information when they need it.
If a sales person can’t navigate or search a Sales Playbook quickly and find the right insight, guidance or message for
their next customer interaction, they will very quickly stop using it. The paragraphs below provide ideas for structuring
Playbooks that encourage usage and adoption, based on experience.
Section Structure
If you want your Sales Playbook to be the ‘go to resource’ for sales people as they work deals, structure the sections of
the Playbook around the main stages in the sales process followed at your company
This makes it easy for a sales person to dive into the Playbook and immediately find the relevant insights, guidance and
messages for the point in the sales process they are at, for the opportunity they are currently pursuing.
If you have sales teams organized around market segments, then the answer will undoubtedly be yes.
If the customer insights, questions to ask, value propositions and sales messages vary markedly by segment, then you
will either have to produce separate Playbooks or organize content broken down by market in tables on the pages.
What you say to a customer should always vary depending on the buyer role (i.e. persona), so you will also need to set
out insights and messages by persona.
Content Elements
What you actually present on the pages of the Playbook will obviously vary widely depending on the type of products and
services you sell and the markets you serve.
Nevertheless, for selling solutions B2B there are some common elements you’ll want to consider for inclusion at the
relevant stage in the sales process, as outlined on the next page.
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4 Market context and drivers (insights into what’s going on in customer markets that could drive good
initial sales conversations)
4 Segments (descriptions of the companies the proposition targets and the characteristics of a good prospect)
4 Personas (descriptions of the personas sales people need to engage with to sell the proposition)
4 Pre-call preparation checklist
4 Conversation openers
4 Questions for initial probe
4 Elevator pitch(es)
4 Pillars of the proposition
4 Links to relevant tools (for this step in the sales process)
4 Discovery checklist
4 Customer research ideas (tips on where to look to find out customer goals, strategy, etc.)
4 Business issues and impacts (typical challenges / opportunities different types of companies and personas face)
4 Needs discovery questions
4 Links to relevant tools
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Closing Thoughts
As you have seen throughout this guide, developing a great Playbook requires a significant investment in resources
and time. However, doing so can result in improvements in seller performance, predictability in forecasting, and more
productive sales managers.
If you are unprepared to invest the time and resources, you probably should not begin the process at all. Creating a partial
Playbook, or one that will quickly fall out of date is simply a waste of money for your business and a frustrating situation
for all those involved.
Some will suggest that your Playbook should cover every possible policy, selling scenario, and more. Be careful not to go
too far beyond this guide. Doing so will require more resources, more maintenance, and likely yield little incremental value.
Stay focused. Gain executive support. Create a fantastic team. Build an amazing and maintainable Playbook. Build
a governance committee. Set up a maintenance schedule. Do all of these things, and your business will benefit from
your efforts.
Why Bigtincan?
Our software modernizes the way sellers work by delivering just in time sales enablement to customer-facing sellers. Sales Technology
overload leaves sales reps unable to find content to share with prospects. Leading companies use Bigtincan to create, automate, structure,
deliver, and analyze content, skills training and coaching in a single digital platform that works online or offline, across any device your
sellers are using. Sales enablement automation is the evolution of customer engagement into an enterprise-wide discipline.