Book Review: The Sales Leader’s Playbook

The Sales Leader’s Playbook provides an easily digestible and down to earth guide to managing and leading a sales team. 

By Zen Newman, Marketing Analyst at PipelineDeals

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The majority of sales literature focuses on a well-trodden path of good, and sometimes questionable advice and research. It’s focus, though, is almost always on how to help salespeople do their job better. It’s rarer for a book to start out with the explicit intention of focusing on the skills that sales leaders need. This single-mindedness is exactly what the Sales Leader's Playbook provides. The book makes an excellent read for any new sales manager or a review for seasoned managers who want a fresh look at the fundamentals.


Sales managers can find themselves in a challenging position, particularly when they first enter the ranks of management. In most sales organizations, top performers are the one’s that receive first consideration for management opportunities. Most quickly find though that the skills that made them good salespeople don’t necessarily translate into what they need in their new roles.


Sales rely heavily on personal time management, and knowledge of how to move accounts forward through the sales process. Once in management, the needed skill set changes and evolves. Instead of being accountable individual performance, managers need to understand how to build, motivate and train teams.


The Sales Leaders Playbook examines these complicated issues step by step. Where many books will offer a deeper dive into sales theory and organizational management, Jamail provides short and actionable chapters that showcase the challenges and possibilities that present themselves when managing a sales team.


The book starts out with a discussion of what successful leadership entails. With this foundation, Jamail moves on to examine how vision culture and beliefs affect the performance of sales teams. His thoughts on producing a winning culture that operates with drive and vision underpin Jamail’s entire philosophy for managing sales teams.


From its discussion on culture and vision, the author goes on to look at many of the most concrete aspects of running a sales team. From expectations and accountability to business planning and training, the Sales Leader’s Playbook is laid out in such a way that each chapter can form a primer on a topic on its own. What it may lack in subject-matter depth, it makes up for in readability and action-oriented insight.


Perhaps the strongest thing The Sales Leader Playbook has going for it is that it is written for a salesperson turned manager by someone who’s walked that career path. It’s not an MBA textbook, and it’s not a book about how to sell better. Instead, it takes the same action-oriented approach that successful salespeople bring to the job every day and helps apply it to managing the success of others.



Build Trust With A Value Added Discovery

Most salespeople ignore the needs analysis process because they are uncomfortable doing it or don’t understand the full value that it can potentially bring to the sales process. Unlock this part of the sale to start bringing value to your customers. 

By Zen Newman, Marketing Analyst at PipelineDeals

Build trust through the discovery process

Most salespeople are indoctrinated from early on in their sales training to focus on perfecting techniques related to the beginning and end of the sales call. Namely, the opening and the close. After these priorities comes the presentation. Bringing up the rear for most salespeople is the discovery process.


In many successful sales, the discovery is the unsung hero of the deal. Over the course of the sale, the right question got asked in the right way. It gave the salesperson valuable insight into the needs of the account. And it resonated with the customer. The discovery changed the trajectory of the sale and gave the interaction value to the buyer.


The reality is the closes and opens are easy to focus on and refine. The result of always looking at these two parts of the process though are increasingly marginal returns. The key to unlocking ongoing gains and a sustained performance boost to the sales process is to put in the hard effort to master the discovery process.

See better returns from your sales activity with a good needs analysis. 


Done wrong, discovery is a list of questions that a prospect gets drilled with. Many salespeople don’t even get to the point of doing it wrong, instead skipping it all together or moving on after a few cursory questions. The key to digging into the customer’s needs is to make it a value added process.


Conversely, asking the prospect too many questions can be equally damaging. On one hand, you need the information. On the other, it is often perceived as providing value to the sales person, but not to the prospect. This perception needs managing if it's to be successful. Instead of hammering down a list of questions, successful salespeople use the opportunity to engage prospects in a discussion about their situation and its implications. This discussion should be mutually educational.


Many people in the business of selling will read this and roll their eyes. Admittedly, it sounds wishy-washy, and far too easy. The truth is that digging into a value added discovery is immensely challenging. Some customers will want you to cut to the chase. Many won’t see the value of the journey on which they're being led. Still others will distrust you and the information you’re trying to uncover with them.

Engaging in a discovery process means having the courage to start a relationship. 


Sometimes, this can’t be helped, but like everything in sales, the navigating the discovery process is a skill that can be developed. To be successful, salespeople need to plan ahead. Know what information you need to find in advance. In the conversation, control the process and steer its direction. For many sales, this discovery isn’t something that is started and finished in one call. Rather, it unfolds over the course of the sales process. At this point in the call, the salesperson isn’t the expert; they’re the facilitator.


Even for experts on this process, success will never be 100%. When you get an account that is hungry for all the information that you can provide, all the effort becomes worth it. Value unfolds in the conversation long before any discussion of the product begins. Trust deepens, and a relationship starts to develop. These interactions are the bedrock of a sale that measures its success by the value being created and the development of a customer relationship that will last.


What I Learned from Sitting Next to A Prospect Receiving A Cold Call

Receiving cold calls makes it abundantly clear how few salespeople fail to understand what they’re trying to accomplish in the first 30 seconds of the conversation. Don’t run circles around your prospect, make it easy for them to see the value you offer. 

By Zen Newman, Marketing Analyst at PipelineDeals

Receiving a cold call is disruptive, but can hold value. 

For those people in sales who have never had the opportunity to either receive a cold call or listen to one from the receiving end, I’d highly recommend it. All of the techniques that are part of a salesperson's repertoire are just theory until you pick up the phone and start making sales calls. Likewise, these techniques remain abstract for many of us until you get the opportunity to see the effect they have on people who are on their receiving end. By adding this perspective, salespeople can gain a greater appreciation for what their tactics are designed to do and some of the common pitfalls that hamper the efforts of others.


For many salespeople, it can feel like prospective decision makers are completely uninterested until you make them interested. Lack of interested could very well be an indication of something wrong with either the approach or the targeted prospects. In many cases, decision-makers are always on the lookout for new opportunities to move the business forward. Whether in the form of new technology or service offerings, salespeople provide one more channel from which to gain information.


The reality of picking up the phone and cold calling someone is that you are catching them unprepared for a conversation about what you have to offer. In some ways, this can be a benefit as you may be able to get past biases that they may normally have in place. With that said, catching someone by surprise also makes it difficult to have an in-depth conversation about their needs and your product.


While this dynamic can make for challenging conditions to start a conversation, it does not mean that they are uninterested. Instead, what is often the case is that they may in fact be interested in finding out if you can benefit them. The challenge here is to engage them quickly by making it easy for them to make a quick determination about whether what you offer would be of interest.  


Is it going to be 100% successful? Of course not. Simply put, your solution won't be a good fit for everyone. The goal of your first encounter on a cold call is less about qualifying the lead, so much as helping the prospect qualify you. Make it simple for them to make a judgment call on you. Making this determination easy is critical, because the default answer is always “no”.  


It's amazing, having been on the receiving end of cold calls, how many salespeople fail to understand this basic tenant. Instead, their opening pitch is filled with a smoke and mirrors approach that has the effect of hiding what it is they’re after. It’s a shame really because behind their pitch may very well have lurked something that would have been useful.


There isn’t a whole lot to say about opening a sales call that is new or original. Be authentic, be direct and relentlessly focused on their needs. In spite of the conventional wisdom, there are far too many reps who either don’t trust their value proposition, or are too cowardly to approach it directly. Don’t be another speed bump to getting things done. Instead, be the advisor that surprises me with something revolutionary.