How Smart Is Your Sales Playbook?

smart sales playbook image
Sales Enablement

I read a quote the other day that immediately resonated with me:

“Memorizing a playbook is like memorizing a script. When they change the script at the last minute, it’s like changing a play in the game.”

Never has this been more true than in the art of selling. No two deals are the same, though they likely share common DNA. In fact, with so many variables involved in a deal—from unique buyer objectives, to your timing in a deal relative to your competitors—building playbooks for your sales teams is more like writing a “Choose Your Own Adventure” novel.

In sports, a playbook charts out potential in-game scenarios, containing your team’s strategies and guiding your path from where you are in the “game” to where you want to to end up. In sales, it’s not much different.

A good sales playbook breaks down your sales process—think buyer personas, call scripts, discovery, scoping and negotiation questions, and deal intelligence.

A great playbook tells you when to call an audible in a deal cycle because something fundamental changed or was introduced, helping you to continually adapt to your buyer’s signals.

RELATED: Sales Tools that Actually Matter: Building your Playbook

You were brought on board to make your teams good… here’s how we get them to great:

(Quality) Playbooks Matter

As a sales enablement leader, your first job with new sales members is to successfully ramp them—giving them a map and ensuring they know how to read it. Those critical 3-6 months of ramp are, by far, the greatest expense to your sales org (simple math—a non-producing sales person is very costly). Not giving your team a playbook to follow with their onboarding is like dropping them into the woods blindfolded and hoping they memorized the map well enough to navigate out.

While dress rehearsals, role play and call recordings go a long way to coach and modify behaviour over time, playbooks offer steady reinforcement of your learning process and a killer cheat sheet in the moment.

According to Salesforce via The TAS Group, “Almost half of all sales team don’t have a playbook. For the 60% that do have a well-defined sales process in place, the benefits are clear. Companies that follow a well-defined sales process are 33% MORE likely to be High Performers. The win rate exceeds 50% for two-thirds of companies that have a defined process in place.”

Left to their own devices, sales teams will develop their own content which isn’t entirely bad… as long as it’s good! No guarantees there. You want your teams to be creative, so whatever you do build in your playbooks, ensure that it gives your teams latitude to insert their own personality and flair.

Equally, if team members see continued success with specific messaging or outreach methods from their adaptations of the playbook, use their learning to adjust accordingly. They’re front line in the sales process—ideally they can help you fine tune things based on what’s working and what’s not.

Documenting planned ways to get to your desired outcome as efficiently and effectively as possible will allow you to remove any missteps in your process.

RELATED: Demystifying Sales Enablement: What Is It, Why It Matters, And How To Do It Right

Getting Started

Pretty easy stuff here—figure out who to involve in the process.

Start with the usual suspects—whether this be your VP Sales, Product Marketing or Sales Enablement—you want them in the room with you. Reach out to thought leaders in the space for their insights and subject matter expertise. Most importantly, involve your sales team. Again, your top performing front-line sellers offer a wealth of knowledge and experience… don’t exclude them.

Decide who amongst you owns the playbook building timeline, ensuring that deliverables are, well… delivered.

Be sure to examine and evaluate any existing collateral as your customer-facing teams have likely gone through the trouble of customizing talk tracks, meeting agendas and presentation outlines—don’t let that go to waste. You’ll want to stress test it for effectiveness, but you’ll also improve adoption if you get their buy-in early.

From there, figure out what to measure:

Good: Build a work-back strategy with your team that ties your playbooks back to sales outcomes you need, pain points across the business (pro tip: handover is a huge problem… build a playbook specific to this) and, most importantly, tie your playbooks back to metrics the business cares about.

Great: Derive a sales net promoter scoring (SNPS) system to get feedback from your customer facing teams on the performance of your content contained inside the playbooks. Ensure you validate the subjective feedback from your team against objective, quantifiable measures such as deal velocity, ramp time (cohort metrics) and, of course, good ol’ revenue.

Key Ingredients

In a previous post, I talk about the idea of “Outside-In Selling.” Think of your role in sales enablement as very similar—you don’t start with handling objections and competitive battle cards, you start with telling your sales team why you do what you do, how you do it, what it means to your customer, and who cares. If the team doesn’t understand these fundamentals around your business strategy, the tactical elements of your playbooks end up toothless.

As the “go-to” resource for your team—you want each section of the playbook to serve a purpose.

1. Business overview

Start off by diving into the company’s overall strategy and the reason for its existence: what problem is your organization trying to solve (start with why it’s being solved, first)—and how your sales strategy fits into the bigger picture. Review who leads which teams and what each of them is responsible for, ensuring expectation alignment, and who to go to with their questions. A simple chart outlining who’s who will do the trick!

This is also the spot to go over the organization’s mission and vision so the sales team keeps each top-of-mind. The goal of the overview is to ramp up new hires on the company’s objectives and what it stands for.

2. Sales team roles and responsibilities

Capture each sales team member’s personal responsibilities and have a transparent view on their day-to-day. Laying out the ground rules for activity levels and explaining their quota targets in detail will help your teams prepare a game plan on how they want to hit these goals. According to research conducted by the Aberdeen Group, “Playbook users report 15% more sales reps achieving annual quota, compared to non-adopters.”

3. Ideal customer profile

If you want your teams to focus on the most qualified leads, you’re going to want to drill down on your buyer persona to encapsulate as much detail as possible—from job titles, organizational structure, though to pain points.

Every ICP has similar trace elements, so while it’s good to be thorough, ensure that you also have a top 5 list of criteria. Be sure to note when it makes sense to bring certain people into the buying process—often there isn’t just an ideal customer profile, but an ideal sequencing of those profiles (e.g. “talk to product marketing prior to talking to the VP Marketing because…”).

4. Time management and sequences

Remember—you hired your team for a reason—you believe they possess what it takes to get the job done. Give them the freedom to experiment with their sequence schedule. Just like no two deals are the same, no two sales team members are either.

Some will perform better on the phone, some on email, some face-to-face… so ensure you have alternative paths for each seller type. Test, refine, test, refine. If you have proven guidelines that work to pursue opportunities, lay out best practices but also signals on when to let them go.

5. Messaging

New sales team members require assistance to get up and running. Go into step-by-step detail on each stage of the sales process, including everything from email templates, discovery call scripts, meeting agendas, qualification questions, objection handling—you name it.

To strengthen their comprehension and further accelerate ramp, add call and screen share recordings of live demos. Your team will be able to incorporate key learnings into their own process.

6. Products and pricing

If your sales team doesn’t know your product inside out—how are they supposed to guide prospects in understanding the value it brings to their respective needs and pain points? This section should cover the essentials like pricing, key value propositions, and use cases. If your company has several product offerings, consider building out a selling guide for each one where the buying process drastically differs.

7. CRM tips

Ah, it’s everyone’s favourite part of the job—keeping Salesforce (or equivalent) up-to-date—if only that were true! Use this section to define each stage, which fields are required, how to customize dashboards, etc. Your team should be clear on your expectations of their CRM reporting and when you’ll be reviewing their opportunities.

8. Compensation plan

Put yourself in your team’s shoes—you never want to be kept in the dark of how your pay structure works. Lay it out in clear terms so there’s no confusion surrounding whether their plan is salary only, commission only, or a mix of both. Make it super simple to digest by showing your team what they can expect if they hit 50%, 100%, or more of their targets.

9. Resources

Make close allies with marketing and customer success. These folks are your go-to’s for collecting relevant customer stories, case studies, white papers and testimonials. You want to make sure that this section of your playbook in particular is kept fresh.

It’s important to have content geared towards your ideal customer profiles—after all, they’ll be the ones deciding whether or not to implement your software. Watch your sales teams close rates improve when they have on-demand materials to support their conversations.

Good: Your content library is well curated and tagged for easy discoverability, searchability and, most importantly, learnability.

Great: Your deal-specific playbook components dynamically adapt to buying signals allowing your sales team the ability to anticipate and prepare for buyer questions and concerns, rather than react to them. Your buyers want to know that your sales team understands them, even when your buyer throws an unexpected curve ball.

10. Key performance indicators

Good: Everyone knows metrics are important, but which ones matter most to your sales teams? Which ones make or break whether or not they’ll succeed? Revenue is your obvious North Star metric, but think about other objectives around product mix, time to first opportunity, time to first close, etc. If your team has a clear understanding of how their performance will be measured, you can bet that they’ll do everything they can to hit those goals.

Great: Your sales team also understands how YOU are measured, enabling them to give you feedback to guide improvement to the overall sales process. Ideally, you give them a feedback vehicle to do so.

Once You’re Finished, Break It… Often (i.e. You’re Never Finished)

Building out a sales playbook is a big undertaking—but you’ll thank yourself for putting in the work—especially as your team grows.

Keep in mind, your sales playbook forever evolves. Every time your process changes or your customer profile shifts, reflect those shifts inside your sales playbook. Treat it as a living document that standardizes your sales process for scalability and predictability.

By the time the music starts and your sales team has stepped on the dance floor with your buyer, you’ll know pretty quick if your buyers came to tango. You best ensure they’re ready to respond in kind… don’t let them mess it up by doing the Floss. To truly give your sales team the best chance of success, your playbook needs to not only continue being adapted… it needs to be smart enough to adapt in-the-moment. We’d be happy to show you what that looks like—check us out.


Also published on Medium.

Kris Hartvigsen is the Co-Founder and CEO ofDooly, a real-time sales enablement platform that moves information to and from customer-facing teams in real-time. As a leader in the tech industry with over twenty years of experience, Kris previously consulted on sales process for a series of tech companies and led Vision Critical as their EVP Sales from its early startup days to revenues in excess of $100 million.