4 Questions to Ask Sales Reps to Streamline Deal Coaching

Written by: Lisa Rose
deal coaching

The key is not to prioritize what’s on your schedule, but to schedule your priorities.”
-Steven Covey

Coaching your salespeople through important deals should be a priority, but that doesn’t mean it has to take up a great deal of your time. Deal coaching is frequently unstructured and that unfortunately leads to wasted time with reps updating the current situation—rather than focusing on the things that should be done to strengthen the strategy and compress the sales cycle.

Having a common language in place brings organization and efficiency to deal coaching, and as your reps come to expect the questions you will ask, they will be prepared with the answers. With just a handful of targeted questions you can quickly receive the information you need in order to advise.

Use these 4 questions to streamline deal coaching and free up priceless time on your calendar.

Question 1: Which step of the sales process are you in?

Cut and dry. There is no room for gray area with this question, which is why it’s crucial to have the steps to your sales process clearly outlined and defined. Always including this question is also a good way to reinforce adherence to the sales process—reps understand that an opportunity cannot move into the next stage until they have completed all of the activities in the previous stage.

Coaching Tip: Use this question as a starting point for coaching—find out what phase the opportunity is in to gauge the alignment with the target close date and advise your rep on necessary adjustments.

Question 2: How qualified is the opportunity on a scale of 1-5?

Your reps should be aware of the characteristics that define a legitimate sales opportunity in your selling environment. Establish a clear and concise list of qualifying characteristics used by everyone to consistently and accurately score how qualified an opportunity really is. An accurate qualification score will help you help your rep determine if the lead is worth pursuing, or if it’s just bloating the pipeline.

Coaching Tip: Encourage reps to be really honest with themselves when qualifying an opportunity. It’s better to cut losses early and redirect time and energy elsewhere.

Question 3: Who’s making the decision and what is your relationship with them?

A critical component to deal strategizing is identifying and understanding the buying decision team. Having your reps conditioned to answer this question will help them better analyze the buying criteria for each relevant individual to determine how it will factor into the buying decision, and it will give you the information needed to strategize appropriately.

Coaching Tip: Once you’ve uncovered the answer to this question, advise reps on the differentiators they can emphasize, and which weaknesses they must address with alternative or creative approaches.

Question 4: What’s your definitive next step?

Again, knowing that this question will be asked of them encourages your salespeople to be thoughtful and deliberate with the action steps involved in moving the opportunity forward. While a sales manager is there to guide their people, quality coaching will get your team discovering the most effective strategies themselves. This segment of the meeting should be collaborative, with the sales manager verifying that the action plans make sense with the decision maker’s level of qualification and position within the buying process.

Coaching Tip: 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 what, if any, adjustments are needed.


In the fully-booked, do-more-with-less-time world that a sales leader lives in, there is no time for inefficiency. But being busy isn’t an excuse to deprive your sales reps of the quality coaching they need. Keep your deal coaching lean and highly efficient by nailing down your sales process and the common language that your team uses to communicate. Ask straightforward questions, get straightforward answers, and spend time where it matters—strategizing on the deal.


The Five Qualifying Characteristics of a Legitimate Sales Opportunity

Written By

Lisa Rose

Lisa Rose is a Group Vice President of Sales at The Brooks Group. Lisa has passion for helping managers develop a unique, motivational sales culture in their organizations. She can drive sales managers who merely put out fires day to day to flourish as visionaries who can motivate their team and generate results for their sales organizations.

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