How to create a sales playbook

For you if you want to develop a playbook, but don’t know where to start. See what one looks like, what to include, and how to get it adopted. 

Now that we’ve talked about why you need one, it’s time to talk about how to create a sales playbook. Exciting! Done right, it’ll give your team a single source for the tips, tactics, and techniques they need to be successful. Of course, it takes a lot of work to get there. And you might be surprised to hear that writing a great B2B sales playbook doesn’t actually start with writing at all.

How to create a sales playbook: Start by talking to sales

Last year, we surveyed 341 sales and marketing pros about sales enablement. And we found some things that really surprised us. Here are two of many:

• 71% of respondents said they have challenges ensuring that sales adopts the materials they’re given.
• The top challenge — reported by 27% — was the inability to understand salespeople’s needs, experiences, and concerns.

Before you write a single page of your sales enablement playbook, you must make sure you understand your sales team — including their struggles and strengths. The best way to do that is by talking to them. Seems simple. But you’d be surprised how often it doesn’t happen before marketing creates materials.

Tips for fruitful sales conversations

• Talk to the right people: Collaborate with sales managers to identify key reps to interview.
• Prioritize strategically: Focus on top performers or those in critical market segments.
• Make it manageable: Even a short interview or survey shows sales their voices matter.
• Get input early: Ask reps what they need to succeed. Their challenges, stories, and goals shape the foundation of the content.
• Give recognition: Highlight reps in examples or success stories to reinforce ownership and motivate peers.

How to interview sales for your customized sales playbook

To have the most fruitful conversation, you need to ask lots of questions. (Note: I practice what I preach. Just ask our team. I’m practically the Riddler. Proof: This hat I was awarded at last year’s company party. Flattering, no?)

Anyway, back to your interview. Start by asking your reps what types of materials they’d like to see in a custom sales playbook. But if they don’t have a clear answer, don’t be surprised — and don’t be discouraged, either.

Odds are, they know what they want to achieve, even if they can’t articulate which tools and materials would help them get there.

For example, a rep probably won’t say, “I need value props and messaging tailored to specific decision-makers.” But! They can tell you they struggle to convey the business value of your product to the C-suite — even though they’re closing deals left and right with facilities managers.

That’s your signal: They know the friction. They just don’t know the fix. Your job is to listen, probe, and connect the dots. It can take a little detective work to find out what tools will help.

Here’s a sample question list. You don’t have to ask all these, of course. But it’s a good starting place.

Ask what tools and materials actually help

• • Which tools are working for you in the field? Which ones are gathering dust?
  • What materials do you wish you had?
  • What have you already built for yourself — and why did you need to?
  • How do you prefer to absorb new information — reading, watching, listening, quick reference?
  • Which of our products/services are you most confident talking about? Which ones do you struggle with?

Use their answers to: Find out what’s working, what’s not, and what sales needs next. And focus your efforts where they’ll make the biggest impact. When you’re figuring out how to create a sales playbook that truly works, this is the groundwork — real input from the people who will use it every day.

Dig into their goals and how they prep

• • What are your biggest goals this quarter? What’s standing in the way?
  • How do you prepare before a meeting? What resources do you rely on regularly?
  • How do you define a successful conversation with a prospect?

Use their answers to: Create resources that fit into their real workflow and sales process — not ones designed in a marketing vacuum.

Unpack how they talk with prospects

• • When you’re meeting a prospect for the first time, how do you start the conversation? How do you get them talking about their business?
  • What story or example do you tell most often to help a prospect “get it”? What analogies seem to land best when explaining the product?
  • Which competitors come up most often in your conversations? What do prospects believe those competitors do better than you, and how do you position against them?
  • What kind of follow-up or post-call content helps move deals forward?

Use their answers to: Discover what moves buyers, and shape messaging that mirrors real conversations.

Find their potential pain points

• • What questions do prospects ask you most often?
  • Where do deals tend to stall for you?
  • What moments in your calls or demos feel the most natural? Which feel forced?
  • What problems do you commonly see when you’re on-site with a prospect? How do you bring them up, and how do prospects typically respond?

Use their answers to: Pinpoint coaching and content opportunities.

Tap your veterans for hidden wisdom

• • What skill and knowledge gaps do you see in our less experienced reps?
  • What questions do newer reps ask you most often?
  • If you could go back and give advice to your younger self when you first started this job, what would you say? What techniques have you learned in your time here that you wish you had known earlier on?

Use their answers to: Capture proven strategies, stories, and shortcuts from your most seasoned reps. Their perspective shows what really works in the field. That’s insight you can turn into onboarding content, coaching tools, and examples to help newer reps ramp faster.

Note: You won’t get all this from a single conversation

Your immediate goal is to create a sales playbook, so your initial conversations should be geared toward accomplishing that. But even when the playbook is done, don’t stop the communication. Create a cadence of ongoing collaboration. It’s one of the most fundamental sales playbook best practices. When you’re regularly checking in and getting feedback, you develop a culture of trust. They feel a sense of ownership. And that’s where adoption thrives.

Keys to a good interview

1. 1. 1. Don’t be handcuffed to the interview questions. If your rep goes off on a tangent, go with them. That’s often where you’ll learn the most.
      2. Don’t forget to record the meeting! It keeps you from having to write down every little thing. Most meeting software programs support this, so just hit record if you’re meeting online. If you’re in person, take a voice memo on your phone and have it transcribed later.

Remember: These conversations are the foundation for creating a sales playbook that gets adopted. Read more interview tips.

How do I turn all this into a sales playbook template?  

In my next post, I’ll walk you through the process of sifting, sorting, and shaping what you’ve learned from your reps into a powerful sales playbook. So stay tuned! In the meantime, see a few sales playbook example sections. And if you want to delegate playbook duty to the experts, get yourself a counterpart for that.

Related:
What is a sales playbook?
Onboarding sales reps? Help them ramp faster.