How to Create a Sales Playbook Your Team Will Actually Use

If sales leaders want their reps to engage with a sales playbook, they should let employees play a role in creating and maintaining it.

This was the advice we heard time and again from sales leaders across LA who have years of combined experience managing sales teams. 

Kaulana Shum, a sales manager at Redgate Software, said he’s seen “adoption soar” when everyone plays a hand in building and updating the playbook.

“It becomes ‘their’ playbook, not ‘their boss’s’ playbook,” Shum said. 

Shum said he’s seen success in spreading the burden across team members, inviting them to contribute to the playbook on topics they’re most knowledgeable about, like “LinkedIn prospecting” or “running demos.” This practice not only encourages reps to utilize playbooks in their day to day but also builds up reps’ confidence.

Contribution shouldn’t be limited to adding content to a physical playbook, either.

Feedback from the team indicates where reps struggle in their sales strategy and need training and support. According to the three sales managers we spoke with, adding interactive tools and events to the playbook process, such as informational town halls, product demonstrations and video courses, also help with adoption and engagement.  

 

Sales Manager Kaulana Shum believes in the power of sales playbooks to help reps reach their targets, but stressed that building them is a collaborative and ongoing process. While writing a playbook for Redgate Software, a company that develops tools for Microsoft Data Platform, he asked his team what they specifically wanted to see in the process to help them win. 

 

How do you format and deliver your sales playbook to the team?

I’ve experimented heavily with playbooks and found that it’s important to determine beforehand what you want to accomplish. For some, it’s best practices and messaging for their sales reps. For others, the goal is to help new hires get up and running as fast as possible. For me, I believe that if a rep reads through the playbook and uses it to learn and execute, then they will hit their target.  

I now save playbooks as Google docs so I can update them as often as I want, and the reps can always access the latest versions.

 

How do you keep playbooks up to date, and when do you know it’s time to change?

At some point, you’ll feel like the playbook is complete, so you push it aside and let it sit. I recommend fighting against this tendency because the playbook should be a living document that is constantly updated. If a sales team doesn’t adapt and optimize, then they’re getting outclassed by their competition. With that said, my teams have always been very proactive in running tests to see if we can improve our success rate on the phone or via email, and we’ll record the results in the playbook.

With help from sales ops, I also track conversion rates from stage to stage, and see how we can tweak the sales process. For example, if we have a low conversion rate from the point-of-contact stage to the closed or won stage, we spend some time examining and updating the strategy and methodology in the playbook.

 

How do you include your salespeople in the process of developing your playbook?

One of the best tactics I’ve used in creating a playbook is to spread the burden to my team and invite them to contribute on a topic they’re knowledgeable about. Sales reps then associate that skill as part of their identity and self-image. The message they get is that they are a great LinkedIn sales prospector, or they run great demos. When writing about the topic, they tend to deconstruct every step in their process, making them even more deliberate in this skill.

The hardest lesson I learned after rolling out a playbook to a team occurred when I asked for feedback and only got silence. It reminded me that adoption is a process and sales reps aren’t exactly clamoring for things to read in between emails, demos and dealing with legal. Instead, I now ask, “What do you want to see in this playbook that will help you win?” Then we work together to get their recommendations into the playbook.

Adoption soars when everybody participates. It becomes “their” playbook, not “their boss’s” playbook.

 

 

National Director Paul Cohen said his sales team’s main focus is getting their broker clients to start using the company’s product, real estate platform CREXi. Though the objective may sound simple, Cohen said the sales team uses several specialized playbooks to help close every kind of deal. Outside of the playbooks, video courses and product demonstrations keep the team informed, engaged and ready to provide feedback on the process. 

  

How do you format and deliver your sales playbook to the team?

We actually have several playbooks for our sales team: a BDR playbook, an SDR playbook, an AE playbook, a territory manager playbook, a regional director playbook, a conferences playbook, and so on. We don’t hire salespeople; we hire consultants. We don’t sell CREXi. Instead, we show our commercial real estate broker clients how to use CREXi to sell and lease their listings. This subtle shift in thinking makes all the difference in our strategy. We simply need to show our clients how to use the tools we provide. From there, we get them on a demo.

Many on our sales team come from a commercial real estate (CRE) background, so their working expertise plays into our conversations with brokers and how we address their real-world pain points. On the other side of the coin, much of our personnel come from the SaaS world who recognize CREXi’s unique position in the CRE market. To train our non-real estate employees, we give them a crash course in CRE. This video course is led by dynamic in-house instructors who break down everything CRE into simple, bite-sized chunks.

 

How do you keep playbooks up to date, and when do you know it’s time to change?

Our playbooks are living documents that grow and morph as new processes and product features are developed. Since our platform is evolving on a biweekly basis, keeping the team up to date on new tools is vital. We hold weekly Zoom product meetings led by our product development team. The product is unveiled, feedback is sought and changes make their way into the corresponding sales playbook.

It’s a very open and collaborative process with the sales team providing feedback from the field and our engineering team making it possible. 

 

How do you include your salespeople in the process of developing your playbook? 

We maintain our playbooks in SharePoint, where any member of the sales team can make a recommendation. In a recent sales call, several sales team members shared that they didn’t think their product suggestions were being heard or prioritized appropriately. 

As a result, the playbook was modified to include a monthly sales and product “town hall,” where the territory manager shared survey results from the entire sales team, which prioritized the most impactful upgrades of our platform based upon client feedback. Many of these changes were quick yet impactful, such as adding new search filters for property types on the platform, like “cannabis” and “religious facilities.”

The open dialogue between product and sales is essential to equipping our broker clients with the best CRE tools possible.

 

SVP of Sales Tom Straszewski said a sales playbook’s purpose is to ensure reps have the tools they need to offer excellent customer service to their clients at crowdsourced shopping platform Slickdeals. His team continually analyzes internal activity data and updates the playbook from there.  

 

How do you format and deliver your sales playbook to the team? 

Sales playbooks are important tools to help educate our team and are designed to assure our team is offering best-in-class customer service to our clients. At Slickdeals, we host ongoing internal meetings and training sessions to ensure that all members of our team are aligned on advertising solution presentations and sales processes. These meetings also allow space and time for team members to ask questions and workshop conversations they may be having with clients. 

Additionally, we use different sales pipelines that are precisely mapped for each type of revenue-generating initiative across several categories, and we enable automation to assign tasks and route business. This guides the entire sales process for our team.

 

How do you keep playbooks up to date, and when do you know it’s time to change?

We are continually analyzing our sales efforts and make regular updates to optimize our playbooks based on internal activity data. We have found that a powerful, automated and user-friendly sales CRM that can also integrate with marketing efforts provides a holistic and accessible view into real-time performance. We use HubSpot for our sales CRM and B2B marketing efforts. 

Typically, we elect to make changes when we see drastic swings or differences in performance between various content or tactics. Our approach would probably be best described as “continual A/B testing” with a lot of trial and error.

 

How do you include your salespeople in the process of developing your playbook? 

Our salespeople play an essential role in helping define our sales processes and playbooks. For most of Slickdeals’ history, we did not use any kind of CRM tool, so the experiences of our salespeople and account managers were foundational in the initial integration. Likewise, we continue to solicit feedback from our clients.

Recently, we’ve invested in specialized case studies and abbreviated collateral conducive to quickly sharing information with peers, per the team’s request. Another recent example would be an adjustment to the hand-off process between the sales team and the account managers, which streamlines the onboarding process based on client persona and lead score.