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5 Deal Coaching Questions Every Sales Manager Should Ask

By Ray Makela

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Deal coaching often gets a bad rap because it is frequently unstructured and often becomes a contentious discussion between  the sales manager and the sales person - with no tangible outcomes or benefit to either party.  Reps keep having to defend their deals, and managers keep wondering why there's so much dead wood in the pipeline. This is unfortunate since (when done correctly) deal coaching can be a mechanism for winning more deals and improving selling skills.

Deal coaching has two key objectives: 

  • Remove stalled deals so the salesperson can focus on better opportunities and help prevent a bloated sales pipeline.
  • Focus on remaining good opportunities, identifying where there are gaps in information and how to improve the strategy for winning.

By addressing these two objectives, the sales manager can have a significant and immediate impact on revenue and productivity. When the sales manager helps a sales rep eliminate poorly qualified deals or stalled deals from the sales pipeline early, the sales manager is helping the rep realign resources (i.e., time) to more productive activities.  Specifically, spending more sales time on better qualified deals.

The foundation of any good Sales Coaching program is on asking great open-ended questions. In this case the focus should be on moving away from "how much is the deal worth and when will it close" to more thought-provoking questions that can help move the deal forward and reinforce key selling skills at the same time.  

There are five key questions that should be in any sales manager's toolkit when embarking on a deal coaching conversation:   

#1 What is the business need?

A key to a successful sale is solving a customer’s business problem in a way that is compelling and differentiating. The question is, can the sales rep succinctly characterize what the organization is trying to accomplish with this initiative and how it will impact their business?  If the rep is simply responding to an inbound lead or RFP, they often miss the opportunity to really understand the business and make a connection to how they’re solution solves the problem. If they can’t articulate the business need (in business terms) how are they going to be able to explain how their solution solves the customer’s problem?

Coaching Point:  Help the sales rep identify great questions to ask the customer to more clearly understand the business need.

#2 What is the unique value you bring?

Once the need is identified and discussed, can the sales rep clearly articulate the unique value their solution provides?  Can they explain why their solution is different and how it will benefit the organization in unique ways?  Again, if they can’t explain it quickly and simply, they probably have more work to do.

Coaching Point:  Help the sales rep develop and practice a “Value Proposition” that explains the unique aspects of your offering and how it brings value to the customer.   

#3 Who is making the decision and what is your relationship with them?

Sales reps often get trapped selling too low in the origination with no clear picture of who will make the ultimate purchase decision and how it will be made.  Suddenly a “mystery decision maker” shows up who has a preference for the competition and the deal is lost.  The goal is to identify and gain access to the real decision maker(s) as early in the deal as possible.  Leveraging our network and “coaches” within the account can help the sales rep identify and potentially gain an introduction to the true decision maker.

Coaching Point:  Help the rep create a plan to identify and access other stakeholders and coaches in the organization who may be able influence the deal and provide access to the decision maker (s).

#4 How will the competition try to beat you?

It’s not enough to know who else is competing on the deal, it’s important to know their strengths and weaknesses of the competition and how they may measure up against you and your offering.  It’s a fair question to ask who else the prospect is talking to and how many firms will be on the short list.  The customer may not answer, but if they do this information can be invaluable in helping you develop a proposal that leverages your unique strengths in context of the competition’s weaknesses. 

Coaching Point:  Help the sales rep develop a matrix of strengths and weaknesses for your solution compared to the competition to identify key messages you want to communication and reinforce with your customer.

#5 Why will you win?

Finally, you must help your sales rep develop compelling reasons why your solution is superior to any other option the customer has on the table, including doing nothing.  These are not generic differentiators, but specific, tangible reasons why the customer would receive the most value from your solution.  If you can’t articulate why you think your solution is the best option for the customer, how do you expect them to choose you over the competition?  Your sales rep needs to believe in the “win themes” and convince you that they have the best option for the customer. Once you’ve identified these themes you should use them in all your communications, presentations and proposals going forward.  If you and your sales rep aren’t excited about your win themes, don’t expect the customer to be.

Coaching Point: Work with the Salesperson to identify and write down tangible reasons why your solution is absolutely the best option for the customer.  Don’t stop until they believe.

The goal of the deal coaching session is to identify where the sales rep has more work to do in terms of research, planning, identifying customer needs or crafting the solution. If there are too many gaps and the sales rep can’t answer key questions here, the discussion should focus on disqualifying the deal or at least moving it back up in the funnel until more information is uncovered.  

Reps will learn quickly that these are the questions you're going to ask for every important deal.  Better yet, provide the rep with these questions in advance in the form of a worksheet that they must complete for each large opportunity in their pipeline.  Imagine how much more productive your deal coaching sessions will be.

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About Ray Makela

Ray Makela
Ray Makela is CEO and Managing Director at Sales Readiness Group (SRG). He oversees all client engagements as well as serves as a senior facilitator on sales management, coaching, negotiation and sales training workshops. Ray has over 20 years of management, consulting, and sales experience and writes frequently on best practices for coaching and developing sales teams.

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