An Interview With Anna Talerico: How to Use Sales Playbooks as a Coaching Tool

If anyone knows how to deliver winning sales and marketing strategy, it’s Anna Talerico. After martech SaaS solution ion interactive was acquired, she and the company’s other co-founders became advisors and board members for other SaaS platforms. The experiences she had led to founding her latest venture, Beacon9. The company focuses on sales and marketing alignment, customer success, finance, company culture, and strategy, and it engages with growth-stage SaaS companies with annual recurring revenues between $3M-$10M+ to accelerate growth.

In this conversation, Anna offered invaluable advice for sales leaders about how to prepare and maintain a sales playbook. She also shared specific advice on how a playbook can be used for coaching, and gave several compelling real-life scenarios leaders can repeat with their teams to achieve some of Anna’s success.

How do you define a sales playbook?

Everyone has their own definition of a sales playbook. Some people call it a sales toolkit, others call it a playbook. But Anna views it comprehensively, as the single destination for everything that touches sales:

• Messaging
• Talking points
• Onboarding
• Training materials
• Roles and responsibilities for everyone on the team, including job descriptions
• Tools and processes
• Sales methodology documentation

How should sales playbooks be used throughout the sales process?

For Anna, that depends on the lifecycle of the team, as well as the company and individual salesperson.

“I think about it in different stages,” Anna said. “In a startup environment, you’re going to market with a process you think is going to work, or you’re simply documenting what’s already happening.” In the early days, a sales playbook should be about capturing a living, breathing, evolving process. It won’t yet have a lot of detail, but it will help guide the startup team in their approach.

As an organization matures and scales, its sales playbook should become the go-to for sales team onboarding and training. The sales playbook can also to help seasoned sales professionals by reinforcing steps in the process.

How do you expect sales professionals to incorporate sales playbooks on calls?

Anna believes the playbook should serve as a way to document how sales professionals meet and overcome obstacles throughout the sales process.

“If a team is practicing objection handling and they come up with a great response to a potential objection, they’ll want to document those responses in the playbook and practice them,” she said.

While documenting how different salespeople overcome an objection, it’s still not a word-for-word script – instead, it’s messaging and examples that have proven to be successful. She expects a freshly onboarded sales professional who’s ramping up to make the sales playbook her constant companion. But a more mature salesperson who’s already internalized much of the playbook’s content has more flexibility to use it as a refresher or reminder.

“The sales process is constantly shifting for any team,” Anna said. “They’re going to be tweaking their methodology, processes, and talking points, so their playbook needs to be updated weekly, or at least monthly.” A playbook should remain an organic document, ensuring that salespeople can rely on its up-to-date information. A stale playbook won’t be used by reps, so it needs to always be accurate and current.

Who develops the sales playbook?

Anna provides a lot of personal assistance to her clients, helping companies revise and reorganize outdated playbooks. She also helps companies without existing playbooks, empowering them to add a process to what hasn’t yet been put pen to paper.

Creating a playbook is rarely done from scratch. For some companies, a playbook’s resources may exist in a scattered handful of minds or notebooks. That requires rallying existing resources and getting all information organized into an easy-to-digest format. Lots of content can be leveraged from marketing, but Anna is a firm believer that the bulk of content in the playbook should come from sales.

“Leaders can’t just dump a bunch of marketing personas into their playbook and think, ‘great, we’re done,’” she said. “They have to communicate those personas in a way that builds empathy in their sales team. Even if they’re starting with marketing’s material, leaders have to retool it specifically for sales.”

Where should a sales leader start when developing a sales playbook?

It’s important that leaders don’t get overwhelmed. It’s easiest to start with the basics, completing small sections at a time. Document sales process and then the methodology. From there, move on talking points & messaging. Then, focus on documenting process-oriented tasks like best practices for using CRM and other sales tools.

Anna believes leaders should document what they already know, and sometimes that means locking themselves in a room to get it all together. But the goal isn’t perfection right off the bat. “Get one thing done and share it with the team, then go for another, and so on,” Anna said. “Leaders should keep working on their playbooks and let them grow organically.”

How do you best use the sales playbooks as a coaching tool?

A successful playbook is a friend and a resource, not something used to dictate every move. But it’s an important tool for leaders to guide their teams. If a salesperson comes to Anna with questions about a deal and it’s clear they’ve skipped several steps in the playbook, she doesn’t tell the sales professional they missed something or lecture them about not using the playbook. Instead, she approaches it as a teaching moment, pulling up the playbook as a reference. Rather than saying “You didn’t use the playbook”, it’s “Let’s see if the playbook can help with this deal strategy.”

By gently guiding reps back to the playbook she gets it ingrained in the sales culture from day one. Anna wants reps to think of the playbook as another team member, a trusted advisor they can use to find answers and inspiration. She uses her playbook in pipeline reviews, deal strategy meetings, and opportunity huddles, and always has it on hand.

How do you best coach individual salespeople?

One-on-one meetings between a sales manager and a sales team member should be informal, friendly, and supportive. On the other hand, there should be a formal meeting cadence, so reps know with confidence their time won’t be subject to last minute schedule changes or meeting cancellations.

When it comes to pipeline reviews, Anna believes it’s best to separate them from opportunity huddles. It teaches reps to think about their pipeline specifically and encourages them to ask the following questions:

• What’s my activity been like?
• Is it leading to the results I want?
• How many new opportunities did I open?
• How much have I closed or lost?
• What are the things I did to create my current pipeline?
• What stage are my deals at and how can I move them along?

The goal, Anna said, is encouraging consistency. Helping sales professionals create an aggregate view of pipeline helps them get beyond getting stuck on individual deals. She recommends doing a pipeline review every two weeks with a new rep, and once a month with a tenured sales rep who’s consistently making quota.

How can sales leaders plan these meetings tactically?

Anna believes putting the onus on salespeople to come to opportunity huddles with deals they want to talk about, but sales managers also need to come with opportunities they’ve identified. Managers should ask open-ended questions like, “This deal has been sitting in the pipeline 15 days longer than average for deals in that stage. What’s going on?”

When leaders meet consistently with their team members, they can begin to identify common deals to discuss. This shows the leader has trained the sales rep to think critically and has taught them to spot issues earlier on their own.

Anna expects a sales professional to come to an opportunity huddle prepared. “There should be no deal I ask a rep about that they can’t speak to,” Anna said, adding, “I’ve seen both types: reps that know their every deal intimately and reps who don’t have a handle on that. It’s a lot of work, but the best performers are consistently the reps who intimately know the details of their deals and the specific stages of their deals. When I ask a rep about a deal and they hem and haw, or say they need to look into it, that is usually a red flag.”

How do sales playbooks play a role in strategic account planning?

A sales playbook can help point the way toward the most basic element of sales: knowing your sales process, the desired paths toward a stage in the process, and how to move on from it. Ideally, it’s both methodical and buyer focused.

“It’s still organic in some ways, but a real mastery of the sales process involves understanding what’s happening in every stage for both the seller and the buyer,” Anna said. Following the process for a strategic account could help uncover key information during discovery that leads to helping to close the deal.

How do you think sales playbooks help you as a sales leader?

Anna swears by a playbook’s power to keep a sales team calm, collected, and prepared. “Number one, the playbook can keep you from losing your mind,” Anna said. “Every leader I know has sat in some kind of team meeting where reps are saying, ‘we have this competitive issue, so we need to nail down differentiation.’ A playbook allows you to say, ‘Wait, we have that!’ The playbook keeps you from reinventing the wheel over and over again.”

A playbook can also help streamline a sales leader’s entire process: from training and onboarding to skill development, a playbook can maximize efficiency. Anna keeps videos of presentations, workbooks, supplemental reading, and more in her playbooks so that eventually she develops a robust section on almost any topic she can share with reps in perpetuity.

Anna’s recommended resources for sales leaders:

• Predictable Revenue by Aaron Ross and Marylou Tyler
• Coaching Salespeople into Sales Champions by Keith Rosen
• OpenView Labs’ Blog
• The bombastic advice of Jim Keenan, aka A Sales Guy