To what extent are your sales playbooks based on historical data and analytics? How do you allow for the proper amount of creativity?

Sales playbooks should always be based on what you've learned in the past and what the analytics say. 
They give the Sales team guidance in the right direction but then, they need to customize their approach to the customer in the way it is needed. Every playbook or script should allow flexibility and creativity.

IMO historical data and analytics are a good starting point combined with a deep and rich understanding of how buyers buy. They must then be modified and adjusted as new information surfaces.

When in startup mode, you need to be more flexible and adaptable depending on the sales team to learn and adapt to sales opportunities. At the other end if you know the sales formula for your business then you want a standardized, repeatable, consistent (more industrialized) process. In my experience in both cases, there are opportunities to improve, so gathering information on what has worked best and continually updating playbooks is important. Then it is a question of how precisely you expect the sales team to follow the playbook. You will get the best value from your playbook if its content is evidence-based and you are continually gathering feedback from the sales team on their observations with prospects and customers together with their results and keep updating regularly.

Sales playbooks that relate historical data and analytics with the current and future business problem that a client faces works really well. After all, any technology or sales engagement is about solving problems that have been around for some time, in most cases.

Right now, my primary focus is on launching a new SaaS encryption solution. Due to the innovative nature, there isn't any real historical data. This is a crawl, walk, run scenario. That said, with our established solutions, we do utilize historical data and analytics as a foundation to the playbook. The historical data and analytics are critical to building creative approaches to capture realistic growth opportunities. It's also fair to mention that playbooks should not be created in a vacuum. A team approach will improve alignment, creativity, and buy-in.