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An Interview With Doug Davidoff Part II: The Art of Optimizing Sales Playbooks

By: Teresa Weirich

December 26, 2018

Doug Davidoff, Founder & CEO, Imagine Business Development

Sometimes, succeeding in business comes down to a basic understanding of how things work. For Doug Davidoff, the Founder and CEO of Imagine Business Development, a playbook-focused customer acquisition platform, understanding how sales works on a fundamental level is the lifeblood of the company. This understanding has helped Doug become one of the foremost thought leaders in sales playbook strategy and optimization, but he still does what he can to keep the ‘fun’ in sales.

“They’re called playbooks for a reason – there is a clear parallel between sales and sports,” Doug explained. “We try to keep our reps at Imagine Business Development competitive, at the top of their game, and well-versed in how to win with strategy, which are all features shared with top professional athletes.

In the second part of our conversation with Doug, he talked at length about how sales playbooks are properly used in winning sales teams. With so many incredible insights to share, we had to split the conversation into two parts. Enjoy the rest of our conversation with Doug!

How do you work with clients to develop a ‘custom’ playbook that meets their specific needs?

One thing I come across a lot, especially on the advisory side, is that sales playbooks often follow a one-size-fits-all approach. If a sales leader has success doing something somewhere, they often bring that same approach to their new team. But, this is the same as in sports where a team is successful and, when the coach moves to a new organization, they’re typically not as good because they haven’t adapted the playbook.

For my team personally, we look at six specific criteria to determine the game a customer is playing so that we can design the right playbook for their sales process:

  1. The relative sale value of the deal
  2. The perceived risk of the purchase decision
  3. The pre-existing demand in the market for their product/service
  4. The existing awareness of the issue or problem in the marketplace
  5. The brand awareness of the company
  6. And the overall natural buying cycle

With this background information, we can actually get to the bottom of the industry, the customer, and the solution, and build a targeted playbook off of that data, so they play their game and increase their likelihood of winning.

Can you give a real-world example of your playbook creation thought process?

Across the customer journey, we have around seven different cohorts of game plans at our disposal, all developed after years of studying and implementing like-wise sales organizations. We work hard to determine the ‘game’ our customer is playing, look at their overall demand generation and customer activation approach, and analyze the actual team that will be working with us. Once we know the game – and the why behind it – it’s easier to customize the playbook for that specific situation. You’re not rewriting anything from scratch, you’re working with the tools that are already in your arsenal.

How do you help clients iterate and update playbooks as they’re being used?

So, to answer this question I just want to give a quick disclaimer: I hate the New England Patriots! But, even I have to admit that they continuously improve from one game to the next, and they have done so for the last five or so years. And, of course, this is because they are constantly updating and adjusting their playbooks. And so are we.

My team doesn’t have scheduled review cycles for playbooks because it is a constant, ever-evolving process. Sales is a participation sport. Every single playbook has metrics, analytics, and more built in so we know exactly what to look for in a review. We know what’s working and what’s not so that when we come up against a situation that we haven’t seen before, we’re prepared. A strong playbook process requires that the playbook is continuously improved.

How have you been able to optimize this playbook update process?

On a tactical level, our playbooks are a series of objects. Each one of these objects can be moved and manipulated, but they’re all the same across different plays, depending on the customer need. For a while, we struggled with adjusting plays even slightly, since it meant going through a whole new training process. After partnering with Costello, reps can avoid any chance of falling back into old habits. We can easily remove the objects that aren’t relevant and allow reps to focus on the key principles at hand.

Additionally, whereas before we spent so much time teaching technique and methodology, we can now focus on things that need to involve training, such as conversation. We’re training our reps on the objects of a play, and then organize them differently to get to the same result, so they can quickly move from one situation to the next.

How do you add a sense of fun to your sales team?

Working with playbooks can become tedious, but we aim to keep it fun and unique. When a rep faces a new situation or conversation, we’ll name the play after them. After a while, just looking at the naming structure gives you a good idea of what the play is about. For example, we have six or seven variations on the Question of the Month play. But running this play early in a customer lifecycle is much different than running it at a later stage, which is where our gasified naming process comes in.

What is the hardest part of implementing playbook with a sales team?

Ego, without a question. I recently had a conversation with some advisors where I was showing them a new playbook, and one of the questions they asked me was if, after diagramming all of these plays and situations, I was worried that my reps would feel constrained. And my response was to ask how Tom Brady feels after Bill Belichick calls a play. He feels empowered and ready to do his job.

Salespeople often come into the industry with a lone wolf mentality where they want to do it their way and showcase their unique skills. For this reason, there is this idea that playbooks are only for ‘bad’ salespeople. The best reps, however, are often the ones that benefit the most from great playbooks. Playbooks give them a measurable, repeatable recipe for success.

What measurable success has your team seen with playbooks?

They’re just a great way to stay on task without thinking or worrying. It’s amazing how much of our brain is spent on process and how much is spent on being in the moment. We are so used to 70% of our brain being process-oriented, but once we get past ego and look at actual claim management the way other departments do, everything runs a little smoother.

In our case, sales rep productivity actually increased 5 – 15 points. Playbooks helped reps to recapture time by identifying both good and bad prospects earlier in the cycle. They are able to accelerate good opportunities and end bad deals faster so they’re not wasting time.

Do you have any advice for a sales team just starting to use playbooks?

Never think of a playbook as being complete. There is always somewhere to grow and become better. When starting out, the best place to start is to just create a play. Start with the place you think need the biggest impact, which doesn’t have to be the cold call. It can be at the close, or the end of a deal – wherever some structure is most needed. It’s like they say, the best time to build a playbook is five years ago. The second best time is right now.

Did you miss Part I of our conversation with Doug? Check it out here


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    Teresa Weirich

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