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

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.

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.

Some common frustrations with sales playbooks I've seen over the years...

1. Lack of relevance.

2. Complexity and length.

3. Outdated information.

4. Disconnection from sales process.

5. Insufficient training.

6. Unengaging format.

7. No feedback loop.

8. Limited rep input.

9. Too much content.

10. Lack of interactivity.

To address these, focus on concise, actionable, updated playbooks aligned with sales needs, involving reps in creation, and providing regular training and feedback.

Here are some of the problems I often see with sales playbooks:

1. Too much information/time demand up front – If you're asking reps for 5 hours of study time upfront, you're likely going to see poor adoption. Instead, provide guidance to help them size their opportunity based on data, and then provide just the critical next steps for them to move the opportunity forward. We need to be cognizant of sales teams' bandwidth and not flood them with info about every facet of the problem space.

2. No data-driven opportunity sizing. A rep should be able to use your guidance to figure out a general opportunity size based on their account's current usage or firmographic data.

3. Oversimplification of problem space or pitch – This is contrary to the first point, but if you're over-simplifying a pain point or trying to apply one-size-fits-all thinking in a talk track—you'll lose credibility with customers (and the reps who have to deliver the message). Provide clarity/proof on paths forward for complex problems, but be wary of pitches that overpromise on a really hard problem.

Some tips for creating useful sales plays

1. Be clear on what success looks like - Have you made it clear why we want them to use a certain playbook ? Is it to drive more pipeline ? Improve win rates ? Get to the decision maker ? Improve ASPs ? Defining, and sharing, that success metric is the first step to getting their attention. If reps don't know what you are doing, why would they care ?

2. Get support from sales leadership - You will have to find a way to get the blessings of sales leadership before you roll anything new. Reps are always bombarded with some ask of their time - a new training, a new play, a new webinar, a new certification. The one sure way they know what to prioritize is to listen to their bosses. If you are trying to get sales to adopt something and you don't have their leadership buy-in - you must re-evaluate your entire approach and fix that first

3. Move beyond content - I find that PMMs, particularly in smaller companies, expect that sales playbooks, or any playbook for that matter, is simply a matter of creating high quality content. If you really want that content to move the needle, or even get used, you have to drive some enablement around it. In-person trainings, workshops, Lessonly, 1:many training calls etc. are various forums you can create. Make these sessions memorable. Talk about success stories. Create time for role plays and practice

4. Use social proof - I have a simple rule. Every enablement session i lead must have some 'internal' social proof- where i invite another sales rep to validate my message. This could be a peer who's been given sneak peek into the content, someone who's tested the message/play with customers, ideally someone who's actually seen success with that. Peer validation is extremely important in every aspect of selling- but is particularly useful for convincing sales reps to adopt something new

5. Repeat and reinforce - After you have done everything above, it is time to do it again and again . As reps find success with your newly prescribed plays, share those success stories. Celebrate the wins. Repeat the message. Every all hands. Every team call. Every win-wire

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 :-(