Design your sales playbook

In 1994, one college football coach took his to the extreme. Les Miles’ playbook was, famously, 480 pages. The first 50 were just his philosophy. But verbosity aside, he was on to something:

You can’t just tell people what to do. You also have to explain why.

Your organization’s salespeople will need their own playbook as the team grows. It’s how you document what selling practices work, standardize them, and institutionalize that knowledge. Top performers may not need it and your first salesperson may not touch it. But as you hire, it creates a floor below which no rep can (or should) sink. It makes their effort predictable and measurable.

The only challenge with creating that playbook is in sales, you’re often creating a manual for a machine that … doesn’t yet exist. How exactly does your organization turn activity into revenue? What message most clearly communicates the product’s value? How many touches do you need to book a meeting? Those are still mysteries. Especially at a high-growth startup. You’ll always be operating on the border of what’s known, and guessing—though you’ll still need to build that playbook regardless.

Your job, then, is to fuse what’s worked at other companies with what you see working at yours to craft a living document that you’ll revisit to update. And hopefully, you’ll keep it well under 480 pages.

Sales reps aren’t your customer

The first thing to know when crafting that playbook is who it’s for. And surprise: It’s not for sales reps. It’s for their managers. Your playbook exists to standardize selling and deal management knowledge across the organization so that sales managers can hit their quotas. It should help them onboard reps, save them time coaching, and provide an objective rubric to which they can hold their teams accountable. Especially if that rep isn’t doing well.

Don’t forget: While it’s written to the sales people, it exists to help their managers.

A playbook should pre-answer the most common questions

At minimum, any sales playbook in any industry should answer the following eight questions.

Want to build better buyer personas? Talk to customer success

Salespeople talk to prospects and customers every day, but that doesn’t mean they’re the best source of stories. Salespeople tend to think in terms of their territory and current pipeline, and that limits their view. They also spend most of their time talking to accounts that won’t end up buying. So, instead of asking sales reps who their favorite customers are, ask sales operations people who your company’s (or segment’s) top 50 customers are by revenue. Ask each account owner what those companies and champions have in common.

Rules of customer engagement:

• If you want to talk to a customer, ask the account owner first
• Limit yourself to 4-5 questions (add them to the calendar invite)
• Limit the meeting to 20 minutes
• If it goes well, ask for more time

Questions to ask those customers:

• How would you describe what we do to a peer?
• How do you (or your team) use it?
• How do you measure the impact?
• Why’d we win the deal?
• What advice would you give our sales team?

“The best place I go for insights is to my customer success team. I ask, what are my top 20 customers? And who are those that we’ve built out and are getting insight into? Who’s the champion there? Who’s the one that really sings our praises? Then I get them to share their story with our sales reps.”
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Mark Siciliano, Global VP of Enablement and Productivity at Sprinklr

“You can gamify gathering persona insights with monthly spiffs. Ask for the best story across whatever segment you’re trying to get. Say, ‘I want these three personas. How has it benefited them? How do they use it? What’s it been like over the last three months?’ I’ve done that at Demandbase, Marketo, and Drift. At all three, our numbers jumped because of it.”

‍Mark Siciliano, Global VP of Enablement and Productivity at Sprinklr

Should you store your playbook in a deck, PDF, or software?

The best playbook is the one reps actually use. Some companies prefer a purpose-built software. Others prefer a deck, PDF, or Google Doc. Whatever you choose, pick one. It’s far too confusing for everyone to look in multiple places, and updating two versions will become a nightmare. Remember the lesson from sports playbook: It should be simple enough that anyone can use it under duress, and that includes skimming it while waiting for a prospect to join the call.

When in doubt, use a viewer-only access Google Slides document. Unlike a PDF, you can easily update it and control who has access.

Once you publish the playbook, designate an owner and provide an email alias in case people have questions. Something like, “playbook@company.com.” That way, if they leave the company, there’s no change management. Someone new will assume the email alias. (Alternatively, designate a Slack channel.)

Whoever owns it should create a playbook “fix list” where they can jot down notes of things to add or change, and update the playbook quarterly.

Contents of a playbook:

1. Company purpose
2. Buyer personas
3. Case studies and testimonials
4. Outreach success stories and cadence
5. Demo success stories and deal process
6. Competitive intel and messaging
7. Possibly, win/loss analyses
8. Tools and how to manage them
9. Comp structure

“Personally, we use a PDF because you don’t want to change it too often. If it’s editable, and you leave it in the hands of individual contributors, they might just take what they want and miss context.”

‍Mark Siciliano, Global VP of Enablement and Productivity at Sprinklr

How many playbooks should your company have?

Ideally, one for every segment and sales team. Though before you go making copies, consider the exponential maintenance burden that can create. As a rule of thumb, never have more playbooks than you have people on your enablement team, even if that means combining several sales team’s playbooks into a generalized one.

Store anything extra in an FAQ

To keep the playbook short, store any information that isn’t absolutely necessary somewhere else. Create a frequently asked questions (FAQ) document in your company Wiki or, at minimum, a Google Doc, where you answer common questions and provide links to additional information.

“In my experience, people don’t have time and energy to consume anything longer than four minutes. Create FAQs and cheat sheets they can consume in small bites.”

Sudhakar Jukanti, Director of Business Systems at Confluent

“Survey sales reps who recently onboarded and see what problems they faced. Use their answers to create FAQs to help future hires. And create a cheat sheet on it, like how to create an opportunity or commission works.”

Sudhakar Jukanti, Director of Business Systems at Confluent

How do you know your playbook is working? When you hear your stories repeated

The best compliment on your playbook is that things remain fairly quiet but the right activities happen in the right order. You overhear salespeople repeating key messages on call recordings. Deals are logged with the proper notes. Things just work. It’ll never be quite that perfect, but the areas where things aren’t happening, or you’re getting lots of questions, that’s where you spend your time improving the playbook.

In contrast, you’ll know the playbook is not working when you have a difficult time finding sales reps willing to share publicly about how they’ve used it. If you ask them to speak at the all-hands meeting, and they’re reluctant, something’s missing and people are maybe not telling you.

“You know it’s working when you can see everyone singing from the same songbook. You know it’s not working when you have a hard time finding people to share their success stories. I used to do a monthly all-hands that was solely about successes in the field. I’d highlight all the people following the process and winning. When it’s hard to find people to feature, the process needs work.”

Mark Siciliano, Global VP of Enablement and Productivity at Sprinklr