If the playbooks are insightful and get used... I'm not frustrated! ;)
Creating sales playbooks is frustrating when we're in a loop of perfection over progress. Oftentimes we forget how powerful a small amount of clear, digestible insight can be over an incredibly robust, in-depth asset. I picked up a mantra from a consultant that I love: "consumable over comprehensive."
Adding depth over time is both more sustainable for you as a PMM and more digestible and actionable for your stakeholders. Get the most important concepts landed, then expand.
There's a lot of reasons sales playbooks might not get used. When that happens, you need to figure out that reason. Some common reasons are:
Great answers from Gregg.
From enterprise B2B marketing experience, I would say types of content you create example sales playbooks - also depends on where you are in the lifecycle journey. If its still in the product-market fit or even when you are building / scaling, you may not know the story well enough for each segment of the market you are addressing. You are still learning as an organization. Unless product marketing is also in a few sales calls and visits customers, you may or may not know first hand - objections received, improvisation needed including customization by segment.
I prefer a more WiKi based format for sales playbook -- I haven't food a generically available tool. So the sales playbook is a living thing that is constantly updated, you can add more details - FAQs, objection handling, segment based nuances, content is searchable.
Yet to see a tool or platform that would make life easier for product marketing and sales :-(