Ask an Expert: Andrew Gray on Creating Sales Playbooks that Win Deals

sales playbooks

As a sales or enablement professional, there are a few different constant struggles you’re likely seeing:

  1. You want your reps to have everything they need to close deals as fast as possible
  2. At the same time, you want reps to be taking consistent and repeatable actions that can be scaled throughout the team
  3. You want to capture best practices and share them with the team to continually improve your sales velocity

The common industry solution to these paint points is a sales playbook – but… what is a sales playbook? How do you start making sales playbooks?

They’re big questions, and they don’t have simple answers – so we tapped into some expert advice to get the definitive guide on sales plays, kits, playbooks, and everything in between.

Andrew Gray

Name: Andrew Gray

Position: Founder and Managing Director of Gray Scale Consulting 

What’s Your Background? I have a mixed background spanning from quota carrying sales, adult learning, leadership, and business strategy. I have been involved with Sales and Revenue Enablement for 15 years and I view my career as a revenue practitioner as someone who is always trying to advance my ability to execute. 

Fun fact about yourself? I have 3 golden retrievers at home and I spend more time with dogs than I do humans some days. 


Let’s start super basic - what are sales playbooks? Why do reps need them?

To me, a sales playbook is a guiding set of principles for a salesperson to follow. It’s vital for sales reps today, because it provides them with building blocks and helps them understand the sequential steps needed to win a deal, regardless of what they are selling. 

I view Sales Playbooks as a clear and consistent framework for getting the job done when you are selling products or services. It enriches salespeople with step-by-step guidance for engaging with prospects, clients, and customers. These playbooks are critical to a business because they improve sales performance, increase efficiency, ensure consistency, break barriers of institutional knowledge, and improve the lives of your sales force. 

We hire salespeople because they know about relationships and how to work through the complexities of selling in order to get results. What they don’t always know when you hire them is your business vision, your value proposition, or how you are different. A sales playbook is something that brings these things together to give a sales rep an understanding so they are able to go have client-facing conversations on the business’s behalf. So to me that’s a sales playbook. 

There are a ton of terms thrown around when discussing playbooks - could you start out by defining the difference between sales playbooks, sales plays, and anything else we need to know?

So, the sales playbook is a guide that outlines the sales process, sales strategy, best practices, or tactics for your sales reps, kind of gives them all the information they need to go out and sell. Think of the playbook as a collection of resources on a specific topic, like a vertical or solution. 

A sales play is a specific strategy that we’re using to move prospects forward in the sales cycle. It can be a series of steps or a single action, like sending a follow-up email. These plays are typically created based on specific situations or challenges that our sales reps are encountering. 

Additionally, you should keep in mind what a sales methodology could mean to your playbook. Some companies will spend hundreds of thousands of dollars deploying a sales methodology, so it needs to be connected to your playbook. However, your methodology should only inform your plays and their strategic execution, but not define the entire playbook.  

So to summarize, a sales playbook is the guide or the framework for sales, while the sales play is a specific action or strategy used to sell.

A sales play is a specific strategy that we’re using to move prospects forward in the sales cycle. It can be a series of steps or a single action, like sending a follow-up email.

How specific should a playbook get? How do you know when it’s just right?

Here’s the thing, no matter what industry you are in, product you sell, or maturity of your company, the only person that can answer this is you.

Now, there are obviously layers to this. So when you start discussing sales playbooks, you have to think about what you want to achieve, and that will tell you how complex it needs to be. There’s so much knowledge out there on this topic but you have to answer this based on your specific business.

Good questions to ask yourself: What are you trying to achieve? What is your ideal outcome of this thing and ultimately why are you doing it now? Is it to enhance your value proposition statement? Is it to get a more repeatable process? Is it to identify your customer’s pain points better? Is it something you’re trying to create like a closed feedback loop for your team? You’ve got to answer some of these core questions first to understand how specific your playbook needs to be, and this will also tell you if you’ve got all the right stuff in there as well.

What are your must-haves in a sales playbook?

I think about one of my all time favorite debates: “what came first, the chicken or the egg?”

A sales playbook is only as good as the plays you put inside of it, so I’ll focus on what I think is really important here to make the playbook effective. If I said, hey, here’s a sales play for this offering, it’s probably not going to do anybody any good. But if I add some context and pain points along with that, it’s going to be way more useful. 

I believe in structuring a sales play in 3 parts: Discover, Plan, and Act

To ensure that a play makes sense from a sequential and logical flow, the discovery step helps to understand what context your reps need to know before they run the play. Is there info from analyst relations or public relations or competitive intelligence out there, and what do they need to know about it? Then how can they plan to have success? Or are there things that will make this play run more effectively?

This is the really cool thing that a lot of people don’t ultimately take the time to build and it’s actually what your sales people want. I’m pretty sure if you just said, hey, here’s a generic value proposition for each one of our verticals by offer type, they’d say, oh, that’s cool, thanks. 

When you've created your sales play, connect your material as related assets to this so someone does not have to go dig around but rather has everything sequentially laid out in front of them.

But, if you put a sales play in front of your reps that is both dynamic AND linked into the CRM that contains all deal metadata metadata, industry, solution type, and date of last contact… Then it’s basically saying, “here’s a sales play based on where you are at today”. Damn, your sales team would love you. I don’t know about you, but I’ve actually never been able to get to this level of maturity. I’ve wanted to for so long but if you could do this, the impacts this would have on your team would be exponential. 

And the other piece is the act stage. Act should be that solid set of advice, like “here are things that you can go and do right now”. So this would be an outbound sequence, which doesn’t necessarily have to be in the play card. You can hyperlink to an outside source, or wherever you’re keeping it, but a sales play shouldn’t have all of your information inside of it. The play should act as a file of record with context, advice, and information to help your team make an informed decision. Once this piece is done, connect your material as related assets to this so someone doesn’t have to go dig around and has everything sequentially laid out in front of them. 

But, in terms of specificity here, it’s really up to you and what your sales team needs. Don’t build this in an ivory tower, go talk to your field and find your steering committee to help you build out something that makes their lives easier.

Best practices for updating or changing playbooks?

One of the reasons I’m not a fan of creating playbooks in Word documents or PowerPoint slides, or even Excel, is that they just aren’t dynamic. They can be created quickly, but you need to be able to adjust with feedback. It’s not going to be perfect the first time, or maybe even the hundredth time, but if you build it dynamically where people can give feedback on it and you’re taking that feedback and analyzing it on a regular basis, your playbook is going to be way more effective.

I would say depending on how mature your organization is and how large your team is, you should be taking a look at your sales plays at least on a quarterly basis. Take a look at your playbook, and make sure you have metrics mapped up to your sales plays. Pull in sales operations to do that effectively, and get key metrics. Example metrics could be: Sales Play for Pipeline generation, Number of Qualified Accounts added to pipeline, connect ratio, conversion to opportunity ratio, attachment interaction %, etc. Each play needs to have metrics attached to their effectiveness in order to move it into the dynamic category. 

If you’re a small team, take a look at whether or not you’re moving the needle with your current plays and playbook. And if you’re not, adjust accordingly. Again, sit down with your sales ops team to figure out what those metrics are and figure out what moving the needle looks like for your business. 

Building a playbook should not be seen as a destination you are trying to reach or a goal you are trying to obtain, but rather a journey of constant progress and improvement.

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