What are your biggest frustrations with creating insightful sales playbooks that get used?

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:

• It's too detailed or prescriptive: Sales requires a certain degree of improvisation based on customer discovery and what's needed to establish trust with a given customer. When playbooks are too detailed or prescriptive, it gets in the way of reps' ability to customize their approach to meet the needs of the customer.
• The story is wrong: Sometimes we deliver a playbook or pitch that just doesn't resonate with customers. Usually it's a result of insufficient testing -- both getting the feedback from your sales team during the development process and piloting it with customers with the help of a small number of customers.
• The training/launch was wrong: If sales reps don't (a) understand the value and how to communicate it and (b) have faith that it will WORK as evidenced by successful peers promoting it as part of the launch, you won't see much adoption.

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 :-(