Need to Create a Sales Playbook? I Feel Your Pain.

A rocky start for my first sales playbook

Many years ago when I took over running one of our sales teams directly, one of the most pressing things I needed to do was to scale from 5 people to at least 15 overnight. And I also knew that running a team of that size would be exponentially different than running a smaller team. We’d need to get better at recruiting, onboarding, training and supporting reps in order to scale.

So, I set my sights on creating a sales toolkit. Or was it a playbook? And really what was the difference? I wasn’t sure, but I knew I needed it. Whatever it was. I knew this both because every sales management blog and article I read told me I needed one. But also, because I actually was feeling the pain of not having a collective place for all things sales—our knowledge, our approach, our buyer, our responsibilities, our processes.

On top of that, I really love organization, processes, and documentation. Like, for real, I do. And without a playbook, I didn’t feel organized when it came to our resources. I didn’t have a consistent place to point reps to when they needed something. It was always, “Our ideal customer profile? Oh sure, that’s documented, let me find it and send it over to you….” or, “What do you mean you don’t know the criteria for the opportunity stages? Of course, they are documented…where is it documented? Oh, well, you know, it’s on the drive….”

So, I set out to create a sales toolkit. Or was it a playbook? I still wasn’t sure. I used the term interchangeably back then, and no google search in the world was helpful in defining the difference between the two.

And once I did understand the difference (it’s pretty negligible really, and I am not a purist, so I think you can safely interchange the terms), I was left confused about what should actually be included. Some things were self-evident—a document describing our ideal target account. Other things weren’t evident at all—like defining our sales process or documenting best practices for objection handling. Sure, I knew what these things were, but I didn’t really know how to go about getting them created and in what format they should be.

I wanted examples of what a real-life sales playbook looked like, and I found nothing. I went through some frustrating fits and starts with sales consultants who said they could help with this but ended up being no help at all. Some of my reps were kind enough to share old playbooks from their previous companies…they were underwhelming, mostly comprised of a few printouts in a three-ring binder. My vision was bigger—my vision was a resource that would actually help ramp reps faster, help reps sell more and help us all be more consistent in our processes and usage of tools.

First incarnation: pretty awful

So, here’s the truth. My first sales playbook was pretty lackluster, made up mostly of content that I cobbled together from a variety of sources. I don’t even know what was in that first incarnation. I didn’t spend too much time on it and it showed. Worse, once we took it live, I don’t think we ever looked at it or touched it again. It sat collecting dust on our virtual bookshelf. It was one of those things that always nagged at me —knowing that the sales playbook could be an important resource for us, and also knowing I didn’t hit the nail on the head in my first attempt.

Second incarnation: slightly better

Later, when I hired my first sales operations manager, a revamp of our sales playbook was at the top of my list. By then, a year or so had passed and I had more experience and knowledge under my belt. Once again, some content we needed was self-evident, like conversation guides around key concepts the reps were stumbling on. But my overall vision was still vague.

My sales ops manager and I set off to create new content and update the old, and we largely accomplished this by locking ourselves in a room and writing on a whiteboard. She would take feverish notes, get everything organized and get it into the playbook. We were highly efficient and we got a lot accomplished.

When we were “done” the content was…eh…fairly good. Not terrible, not great. Somewhat useful. We referred to it once in awhile and endeavored to keep it up-to-date. Mostly, I used it to point out when reps weren’t following our process (UGH—Why did I do that!? Note, that is not what a playbook is for because then everyone just ends up resenting it. Think of the playbook like a supportive best friend who always has an answer, not a dictator who rules with fear).

Anyway, reps complained the playbook format wasn’t as useful as they would like (we had it in an internal wiki tool, which were basically web pages you could surf around with a tree navigation), so we moved everything over to Google Drive in sheets and presentations and documents. That proved less useful, but by then, I didn’t have the time or inclination to move it. It felt like we’d spent a lot of time, for something moderately useful and I had other things to focus on. I put the playbook on ice for awhile.

The third incarnation: nailed it

After a lull, and some turnover on the team (including my amazing sales ops manager who left me to live in another state with her fiancé), it was time for a significant refresh. And I was ready. I wanted to launch something that would become our bible. Something useful, that we would reference often and would keep up to date as things changed. The Google drive thing from incarnation two wasn’t working. I had wanted it in Drive so it would be accessible and easy to update. But it was confusing and hard to find things, and you had to open a document to get to any content. I wanted to sales playbook to be navigable and searchable, like a website.

So…back to the wiki we went, the same tool I used for my earlier attempts at a playbook. To be fair, I spent a good deal of time searching for some kind of solution that would be perfect. I figured there would have to be a handful of SaaS products on the market specifically made for creating and managing sales playbook. But nothing really suited our content or was just what I was hoping for. (Of course, today there are so many sales enablement tools to help with this.)

By now, I had a director of sales who was focused on the day-to-day management of the team. This left me with a bit of breathing room to really focus on the content in our playbook. Everything finally fell into place with my third attempt. I worked on the content (sometimes on my own and sometimes collaborating with the team) over a period of about a month. By the time I launched it, we finally we had a robust collection of resources and content that would be useful to our reps.

Of course, a playbook is never final and it gets updated frequently, but I found through my various attempts that it really needs a big push to get the meat of it outlined and fully flushed out. I couldn’t estimate how much time went into the playbook, because we had so many iterations of it and sometimes I would just update older content, often I would start from scratch. But, I can say on that 3rd incarnation, the one I was really happy with, I probably spent 50 hours over the course of that month. Rewriting older content, writing all new content, refining it, editing it, organizing it, etc.

And finally…. is it a playbook or a toolkit?

How about both? I never really figured out a definitive answer to this. I ended up calling the entire collection of content our sales toolkit, and within that had a section called our playbook, which had some of the meatiest content about our buyer and our sales process.

Back to the toolkit versus playbook debate though, I have a couple of definitions I really like:

“A sales playbook is a collection of tactics or methods that characterize the roles and responsibilities for you (and your sales team), lays out clear objectives, identifies metrics for measurement, and provides a common framework and approach for closing sales.” Laura Patterson

“A Sales Toolkit is a collection of assets useful to the sales team in closing business. The “tools” in such a “kit” obviously differ by industry.”  Michael Trioano, Actifio CMO

See what I mean? The terms are pretty interchangeable. Today, I usually refer to the comprehensive collection of resources a sales playbook.

The real truth about creating a sales playbook

It’s a big undertaking. And once you have it launched, it doesn’t guarantee adoption. And it needs to be updated very regularly. And reviewed for accuracy. It’s just a lot of freaking work to get the ball rolling and keep it in motion. But it’s so worth it.

Once we had our playbook in an ideal state I found we referenced it all the time, used it as a jumping off point for many coaching sessions, used it to onboard and ramp reps faster, developed educational workshops for the team from it, etc. The playbook just became a central part of our sales team culture and I loved that we all had a common point of reference. It was a unifying part of our interactions.

Bottom line: Sales playbooks are important and worth the time & energy.

I’ve written a bunch of articles on the who, how, what and why of sales playbooks, you can check them all out here!

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