Darlene gave this presentation at the Sales Enablement Summit in 2019, when she was Director of Sales Enablement at Yelp.

Download Darlene's deck >

A playbook is defined as a one-stop resource that helps our reps to be more effective and efficient in their jobs, but how do you go about creating one for your salespeople from scratch?

When I started in my role at Yelp I was faced with this challenge, and in this article, I’ll share the seven key lessons I learned along the way.

On October 17, 2017, I walked into the door at Yelp having left Bloomberg after nine years and our CEO said to me, "Darlene, our reps need more structure, accountability and discipline in their days." Sound familiar?

Experience taught me that developing a playbook from scratch was probably what Yelp needed most. But how are we even defining a playbook?

Playbook defined

A playbook is defined as a one-stop resource that helps our reps to be more effective and efficient in their jobs.

playbook defined

But why? Why do we really want to create these playbooks? What's behind all of this?

60% of deals in our current pipelines today never close. Of that 60% of deals that never closed, the question is, what the heck happens to those deals? Where are they going?

Just over half of those are going to indecision, the buyers on the buying team and the cast of characters aren’t even talking about your product or solution. They're doing some internal conversations around where they're even focusing their business.

The other 50% is going to the form of an objection, or the clients or customers saying we don't see value either it actually doesn't solve for something that's going on in my business, or in fact, maybe the rep didn't stitch it together well enough in order to make a difference.

I think the opportunity of creating a playbook can impact that number. It also impacts a whole bunch of other things that you'll define such as better pipeline momentum, greater deal value, conversion of proposals over to contracts faster, and it can also impact the lifetime value of your clients.

The agenda

I've been a little beat up over the course of 15 years creating playbooks and I've learned some lessons along the way. When it came to writing this article, I thought, let's dial it up a notch and let's move beyond the familiar and see what I can provide to you.

7 lessons learned

This is not a perfect formula, step by step, I's dotted and T's crossed or deep dive on content. These are some lessons learned on how to engage with stakeholders and your teams to bring a playbook to life.

To bring a playbook to life, not just that results in really great content, but a playbook that reps access, use, and they actually generate sales results and hopefully make your reps a little bit more money along the way.

One: Everyone’s doing different stuff

Everyone on our sales teams would agree that they're selling and that they're engaging with clients. Everyone on a nightclub dance floor is agreeing that they're dancing around a ballroom dance floor.

everyone's doing different stuff - you need to get alignment

What moves are ‘out there’?

But I guarantee you, even though they're selling or dancing, they've all got different moves. They've all got different plays they think make them unique.

Managers, teams, they make up stuff, based on reps' experience, they walk in the door from other companies or internal movement, and they've got their own song going on in their head, and they go on their merry way and engage, and these playbooks start to intersect.

Very early on one of the lessons I learned is yes, you want to go out and herd the animals in the wild, and figure out what's going on out there. But you're doing this with one specific purpose in mind in addition to bringing in good content.

You want to take very close inventory of what's going on out there because, by the time you come back to position and roll out your playbook, you will have already got and secured some buy-in and support around the concept of the playbook, which is fantastic.

But what you've also done is you know how to communicate it and position it back out. We discovered on two of our teams at Yelp that we had reps going out and they were positioning us with four capabilities. They were talking about Ecommerce, they were talking about delivery, when really, in the end, our playbook was around 'well Yelp drives leads and Yelp drives visits'.

So when we went back to that team, we had to get them to discontinue two of the things they were saying, in order to refine that message.

Change management in disguise

So even though we're creating these assets and these playbooks, it's really change management in disguise, from the very, very start and getting that act of buy-in and support.

When teams have come together, in my experience, they go down this very straight line, one directionally often, they come together and they say,

"Great, let's create a playbook. Let's think about:

  • What are our products?
  • What are our services?
  • What are our benefits?
  • What are our features?
  • What makes us unique?
  • How do we want to position ourselves out there in the market?"
And all of a sudden, we start to get this lopsidedness that starts to be about us, ourselves, and our products or services, whatever words you want to put in there. Very strongly and very quickly, I recommend that we don't go down that path.

Two: It’s not about you... it’s about the customer

I've seen that path happen before. The lesson learned as a sales enablement professional, how can you get in front of the cast of characters that are coming together and say, "Let's start with our clients. Let's start with our customers".

it's not about you, it's about the customer

Goals, challenges, hypotheses

Specifically, we don't need to overcomplicate this. What are our client goals? What are their objectives? What are their KPIs?

When you start to turn that corner a little bit, it's around what are the challenges and the speed bumps that they're experiencing in getting to those goals? That's where the intersection of your product stuff comes down the road but you need to get lockstep in there.

You'll develop a hypothesis that will talk about how you think you can help solve for certain things that challenge in order to help them achieve their goals but get lockstep in that.

View of competition

The other interesting part is a lot of teams get very centric and one-directional around how are we competitive? What makes us unique? I actually don't even recommend you go that far early on in a playbook development.

It would be saying, in the eyes of our customer, relative to how our customers view the competition, what do we need to do?

In fairness at Yelp, it's like how do our clients perceive traditional marketing venues? How do our clients perceive the Google's, the Facebook's, and all of the other options of the world?

We have to get anchored in that as a really good spot.

Three: Identify top priorities

There's a blessing and a curse with all playbooks; this much time, this much content, this much opportunity, where do you start? Here's the recommendation.

identify top priorities

Immediate and long term

Two times now I've worked with teams that have said, "We just need to get going on our playbook." This fundamentally meant we went live with playbooks that were incomplete. They were scrubbed - the parts that we did go out with - but they weren't finished.

One of my clients previous to Yelp, they said one thing "Help. We need more leads into our pipeline and we need our reps having better meetings". We literally patched together a playbook that got more into the pipeline and gave the organization the framework for our reps to go out and have initial discovery calls.

That worked and then we said, "Holy shit, we have all these clients, what do we do with them?" And then we created the rest of the playbook downstream.

Interestingly, at Yelp, we came in the door and we created a little bit more robustness around our products and our solutions because we had to get some clarity there. But my favourite thing is that we went out we said what are the top six verticals we want to start with?

We wanted to start with restaurants and retail and automotive and hotels. Once we pushed that out the door in May guess what we're doing now? Another six playbooks looking at very different industries. We just got it out and the market continues and the reps tell us to continue what to do.

Language is critical

Now here's a pro tip, an insider tip, as you're identifying and starting to put together the components of your playbook, you'll have an agenda, a laundry list, key components, whatever you're going to call it.

Please ensure that you work with the collective people in your groups and come up with the proper naming conventions or language, and the language will stick.

Whether you call them solutions or products, it doesn't matter, pick one. Whether you call them clients or customers, it doesn't matter, pick one. But do it from the outset because the people listening, both internally, need to hear that from day one.

If there's any pause you can bring, bring it there.

Four: Give clear direction

If I told you all to build me a castle, what would it look like? A little bit of the one on the top of the image, or a little bit of the one on the bottom?

give clear direction

Orchestrate & co-ordinate

In the world of pulling together content, it's one of the most fascinating and frustrating experiences. I strongly believe that sales enablement teams are not the owners of the content.

They are the orchestrators, the packagers, the coordinators of ensuring the people that need to use the playbooks and need to follow the step by steps in the plays are actually the ones creating the content.

So as you're going out in your sourcing different people in your organization - could be inside and outside - your ability to be unbelievably clear in what you're looking for in your content, and then tweaking it along the way, will pay off in multiple benefits down the road.

We had seven weeks to create a playbook before we did a big launch at a manager summit in Phoenix. We pulled together four office heads across the country to start to come up with some content.

We went out and we said, "Hey, we need some content on what's going on in this particular industry. What are some of our products and ad tools that actually line up with this industry?" Then we gave them this bucket and we said, "Hey, what kind of nuances do our reps need to be aware of selling into this vertical?"

We were 48 hours out from launching our playbook live to our reps in our entire multi-location org and our content was as varied as those two photos.

Generalities won’t cut it

What we really realized quickly was "Oh, shoot, we should have been more specific in our direction". What do we mean?

Hey, enterprise office head, I want to know the nuances that happen in this playbook. I want to know the nuances that the reps need to know by engaging with clients in this vertical. What did we mean?

We specifically meant:

  • Who are the cast of characters that we want to be reaching out to?
  • What are their roles?
  • What are their responsibilities?
  • What KPIs do they have on their backs?
  • How do they work internally to make decisions?
  • What are they focused on?
  • What do they care about?
  • Who are they connected to?
  • What kinds of objections do we run into when we're trying to do business in those areas?

We totally goofed. Guess what? On another six playbooks that we're developing now, we have got that structure and we learned that lesson early on. The generalities won't cut it and don't leave it to chance and have multiple iterations.

Five: You have a hub

Think of the most functional airport hub in the whole wide world. Your playbook operates as a hub. It is a central - whatever word you want to use - repository and information going in and going out and flowing through.

your playbook operates as a hub

Extreme rep focus

Our current playbook exists, it's about four to six pages, but here's the cool part. I have an extreme paranoia of protecting reps time. That means that the inundation that's going on in reps inboxes and emails drives me bananas.

We've got product sending product updates, leadership giving updates, marketing with their new events and things that are happening, that has to stop.

If you think about this hub in your role as air traffic control is to ensure that the coordination and the sequencing of everything coming in and going out, in fact, is organized in a thoughtful way that the reps actually use it and can access it in the moment that they need it.

It's not like 'Oh, where was that document again?', no, whatever you can do to get the reps' extreme rep focus.

We're actually working right now with our sales and marketing infrastructure to see if as soon as the rep opens a new opportunity in Salesforce, maybe it's in retail, we're going after H&M, boom up comes the retail playbook.

As it navigates along, it'll help the rep at each stage of the sale depending on their experience. Even though we're still evolving there, if you can start to look at your content in this hub, it'll be really helpful.

A, B, C level content

Even though our playbook has four to six pages right now, (please create them in the cloud, please don't ruin trees, please do everything you can, you can do a little laminate on the desk), it's really helpful to start to categorize in whatever way makes sense and matters to you.

How do we want to package this content?

  • A-level content would be non-negotiable, do not pass go, this is your primary offerings. This is about primary information about your clients, what you're offering to them, nuances that go on, and possibly some tools.
  • The B-level content, I start to look at are things that can help a rep, depending on the nuance of the client, or depending on the rep experience. The B-level content for us are things like power maps, we ask that all of our reps create a power map to scope up bigger opportunities so we know what's happening.

We have question repositories in there so as you're navigating through each stage of the sale, we actually have questions that align. Operationally we've stitched in our sales process into our sales playbook.

We have four stages; detect, identify, clarify, execute, that's the type of stuff that sits in the B level and it gets a little bit into A depending on what it looks like.
  • C-level stuff can be articles and additional tools and resources and nice to haves, depending on what the rep is focused on, depending on where the business is headed.

The earlier you can categorize that the better, admittedly, last December, we had some team members working on a playbook, somehow it ballooned to 26 pages. Not cool - not going to work.

We brought a team together, we quickly paired it back, and we have links out of one G-Doc, and they go all over the place. It seems to be working, we just need to make sure, I'm getting incredibly obsessed with where can the reps get this when they need it?

That's what's going to make a difference. The access is key.

Six: They own it

This isn't your playbook and that's hard. Do you technically own it, did you sign out the library book? Maybe.

Leadership leads

Sales enablement doesn't own the playbook per se, so who owns it? Leadership owns it, managers own it, reps own it, different stakeholders own it, you just happen to be the centralized resource that can help pull it together.

Specifically, when you're thinking about executing and rolling it out, I think we did three things really well and we learned these lessons from a few bumps along the way.

When we got our essential playbook together in May, it was all around, "Okay, Darlene, what are you and your team going to do? And how are you going to help roll it out?" I said, "We're going to help roll it out by making sure you're ready to roll it out".

We were the behind the scenes preparers of our CEO, our VP, and our enterprise office head in front of all of our managers in May. We packaged them up and trained them up to design and deliver to all of the managers.

We did a day-long rollout, it was full of information and exercises, but they owned it. We didn't own it at all. One month after May, our CEO and other stakeholders in marketing and product did a roadshow.

Guess what? I was hiding in the corner, we had something to do with it but it was all of the reps came into the room and the Tom's and the Joe's of the world got up and they shared it. They facilitated the exercises with the reps that the managers had already facilitated. We continued to roll this forward.

It was like a really good baton that was being handed off. Now still to this day, my team probably gets bored of me, I don't let them train at all.

I say to them, you know what? What can you package up to put in the hands of managers so that the managers can take this to the teams and or we've got advocates, we've got some reps that are doing really awesome things, we've got a rep that is blowing it out of the water getting more leads than anybody, what's his formula? Let's package that together.


Your role is to see and spot these opportunities and get packaged, so we created these mini scrimmages. At the end of September, what we're doing is we've got these six new playbooks.

I've got Ashley in Phoenix today, what is she doing? She's coming up with this mini scrimmage, "Hey, managers, let's come together. We had the first six playbooks around six different verticals, we've got six more", she's giving them the script, she's giving them the talking points, and she's making it ridiculously easy.

Take 10 minutes in your team meeting this week, roll out this part, take 10 minutes in your following week. She's got these little dotted seeds along the way that are helping the managers to fully own it and the reps to own it.

Sure we show up and help a little bit, but along the way, the managers feel fully involved and I think it's making a big difference along the way.

Seven: Repeat, repeat, repeat

The playbooks are out in the wild, the reps start using them - invariably, there are still going to be some different dance moves to this day.

The fun part is that every day, you walk into a door and I think you have one primary obligation, to put on your playbook headspace, with every meeting and with every interaction.

Performance scorecard

Our VP started having conversations with HR around performance scorecards and metrics and what the reps needed to be held accountable for. We knew we had standards in the playbook, create a multi-tier strategy, create a wider network, move from pilots over to campaigns faster, front-run objections, that was playbook stuff.

Guess what we did? We worked with HR, and now our reps are evaluated on the core standards that sit in the playbooks. And they're not just words - when we say develop a multi-tier strategy, we help them to learn how to do that and we train the managers on how to coach and build skill and capability around that. That starts to come full circle.

Project Simplify

The other thing that we did was we realized we need reps to have a repeatable, consistent approach, time and time again.

It didn't matter if you came into the door at Yelp, and you had been there for three months, or you're a veteran enterprise salesperson with experience out there, we needed to feel confident that baseline was not being eroded. This is tough.

You've got people in your organizations who've been there for a really long time, some people just joined, we needed to get baseline. We created something called Project Simplify.

We worked with our friends in the sales planning marketing world and we started to go to the drawing board, and we literally made decks that were used in discovery calls and some recommendations and pitches down the road.

The reps have access to these linked off of the hub and the playbook so that every time they open up an opportunity, they have to use this consistent deck. Now there's some freedom, and there's some room to breathe, and we position it that way that we're not turning them into puppets that don't have a voice and a mind.

But we show them where they have creative license because we can't afford to goof up any meetings. The complexities of the sales environment are way too high - we can't afford to misfire.

Deal-desk impact

We took it one step further because I'm like, 'you know what, those reps are still going to make up their own stuff', and they did. 'I want to put in this Google stat and I want to put in this because it's cute, and it's fun'.

The answer was, we actually created a deal desk - 48 hours before any rep is going into a meeting (we have exceptions because we'll take meetings anytime) they needed to submit their deck to a deal desk.

There's 10 of us on an alias, and it sent in to pitch review in alias, and one of us picks it up whoever can and it's actually random and it works. We're looking for consistency of message, consistency and proper use of data, proper use of logos - reps do all sorts of fancy creative things.

It's really awesome that we pick these things up. Guess what? My team is also studying all the pitch review all these decks that are coming in and guess what they're doing? They're analyzing it for patterns and themes coming back and saying, 'what else do we need to do?'

I'd love to put the pitch review alias out of business, that would be a goal down the road.

At the end of the day...

How do we tie this all together? This is my sweet baby girl you can see below.


Yes, your approach will work

Mom fail, July 20th, she got accepted into Pre-K3. All that means is she goes from preschool over to Pre-K3. My mom fail was she gets accepted and they have to be potty trained. I'm like, "Oh no, she was the only one in her class that had not been potty trained and I had six weeks to do it.

Like a true sales enablement mother, what do I do? I make up a playbook for how to potty train your daughter who hasn't been potty trained that's also going on a two-week vacation - how is she going to get potty trained by September 5th? What did I do?

I followed some of these seven things. I looked at some of the moves going on out there, I talked to Hillary downstairs, I talked to another friend on the playground. I did it from her vantage point, all of these things, and I just started to cobble something together.

But if all else fails, here's what I did - July 20th I just started. I didn't really have much done I just started. What did that mean? We woke up and every 20 minutes, which turned into every 10 minutes, I have this like diaperless child running around the house for three days and I started to implement a system that I kind of sort of think I had, I knew in my head.

Results will come, stick to it

Within one week's time, she was running accident-free, but I also carry a potty in my backpack.

The point is, just go out and start and trust that any approach will work. Sometimes people say "Darlene, should I put these components into my playbook? Or these? Should we separate by geo, by vertical, by experience?" The answer is yes.

All you need to do is account for the implications of the decisions that you make with your playbook. There's going to be implications downstream, and you just account for those. The thing is results will come. The results will come if you stay the course.

My daughter got potty trained by the time we got on to an aeroplane, maybe I put a pull-up on her, but she got potty trained in time - your teams will get the results in time, but you've got to stay the course.

Reward with M&Ms

If all else fails, M&Ms work, my daughter lived on Goldfish and M&Ms for a very long time as a reward. You want to think about those things along the way too.

This is basic business, but at the end of the day, these are pretty big feats that you're undertaking and you'll do a fantastic job if you reward along the way.

I've covered seven things for you to think about. There's never a perfect order. They'll all work, make up your own version and you'll be perfectly okay.

Thank you

Download Darlene's deck >