Deal coaching has got a bad reputation as it is often unstructured and tends to become a contentious discussion between the sales manager and the salesperson resulting in no tangible outcomes or providing any benefit to either party. It’s a saga where the reps keep defending their deals, and the managers keep wondering why there’s so much deadwood in the pipeline. This is unfortunate since deal coaching, when done correctly, can improve your sellers’ selling skills and help them in winning more deals.

By addressing these two objectives, the sales manager can have a significant and immediate impact on

• The productivity of their sales reps
• Progress of opportunities in the sales pipeline
• And revenue generation

When a sales manager helps a sales rep eliminate poorly qualified deals or stalled deals from the sales pipeline early, she is helping that rep to realign the resources (i.e., time) to more productive activities. Thus enabling the rep to spend more 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.

Below are the 9 key questions that should be in any sales manager’s toolkit when they embark on a deal coaching conversation:

Deal Coaching Questions that sales manager should ask their Sales Reps

Question #1: What are the needs or pain points of the customer?

A successful sale happens when your sales rep addresses a customer’s needs and pain points and solves them in a compelling and differentiating way.

Question #2: What are the business impacts of not solving these issues?

After uncovering the business issues and priorities, knowing the financial impact of not solving them helps to build a business case.
A “back of the napkin” analysis is sufficient to qualify a sales pursuit. Make sure that you bring a significant material impact to the customer’s life through your solution.

Question #3: What compelled the customer to act on the issue and find a solution?

It’s crucial for the sales rep to identify and understand the compelling event that made the customer act to solve the issue

Question #4: What is the unique value you bring?

Once all the needs, pain points, and impacts are identified and discussed, you need to see

• If your reps can clearly articulate the unique value that your solution provides
• Can they explain why your solution is different and how it will benefit the customer in unique ways?
  

Again, if your rep can’t explain it quickly and simply, they probably have more work to do.

Question #5: Who is making the decision and what is your relationship with them?

Often sales reps get trapped trying to sell to the people in an organization without having a clear picture of who will make the ultimate purchase decision. And then suddenly one fine day a “mystery decision-maker” shows up who has a preference for the competition and the deal is lost.

To avoid this, you need to ask this question to get your rep to identify and gain access to the real decision-maker(s) as early in the deal as possible. Leveraging the network within the account can help the sales reps to identify and potentially gain an introduction to the true decision-maker.

Question #6: How will the competition try to beat you?

It’s not enough to know who else is competing on the deal. It’s also important to understand the 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 shortlist. Finding out this information can be invaluable for your sales rep as it helps him to develop a proposal that leverages your unique strengths in the context of the competition’s weaknesses.

Question #7: What are the buyer’s evaluation criteria?

Your sales rep needs to have crystal clear clarity on

• What’s important in their customer’s evaluation?
• And what requirements must be met in order to surface at the top of their shortlisted companies?
  

Question #8: What’s your definitive next step?

When your rep knows that you are going to ask this question, they are going to be thoughtful and prepared with the next action steps involved in moving an opportunity forward. While you can guide your team with the next steps, your coaching will only be effective if you can get your reps to discover the most effective strategies by themselves.

Be sure to follow up on the key activities that were defined as next action steps to see if they had the desired outcome and if any adjustments are needed.

Question #9: Why will this deal not close?

Lastly, it’s important to identify the worst-case scenarios. Because planning for the worst helps you to avoid any unpleasant surprises and overcome hurdles efficiently.

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