Boosting Sales Coaching Creativity: 3 Techniques to Reinforce Basic Selling Skills

By David Szen on Jun 5, 2018

I spend a lot of time with sales leaders and my hat goes off to the hours they work and pressures they accept in their role. Their job is a hard and often thankless one dealing with complex client, employee, organizational, competitive, and financial pressures.

Sales leaders have a great capacity to reinforce essential selling skills in their teams, but all too often, the day-to-day demands get in the way. While dealing with daily pressures and fire drills, many of their reps are stumbling on fundamental selling skills. The ones I hear a lot about are: 1) discovery/questioning skills, 2) navigating and answering the tough questions, and 3) delivering relevant and powerful value messages.

Here are three techniques to put the creativity back into coaching and develop these key selling skills amongst your team.

Sales Leader Dilemma: Infusing Creativity in Sales Coaching

I recently sat with 5 senior sales leaders leading teams of very senior sales professionals.  These leaders were not new to the days of leading teams, but the demands of the job have a tendency to squash creative thinking as it relates to talent development. 

We were discussing how to coach some very important yet basic skills that their teams were just trained on.  Things like: Sales call preparation, listening and questioning skills, asking 2nd and 3rd layer questions, relationship management and development, buyer persona identification, building value, positioning, team selling, and advancing the sales process. 

Where these leaders needed the most help was on how to keep key concepts alive, how to further develop talent, and how to support ongoing skill building in the “real world”.  (I do not like the term the “real-world” when it comes to sales.  Why?  Because it suggests that the world of developing talent and training people is not “real.”  That is not true.  Any time you are coaching or developing talent it’s real, as I assure you, we are not coaching robots.)

Creativity in coaching is how you make the magic that people connect to and learn from while driving the messages and skills you want to develop.  When you are so busy that you don’t have time to think, you end up going through the motions and missing opportunities. 

Applying Creative Methods to 3 Fundamental Selling Skills

Let’s consider the usual forums that sales leaders get to coach in.  They are: Sales team meetings, formal training sessions, 1:1 formal or informal development, or coaching in the field.  Below are creative ideas to maximize coaching time and reinforce three fundamental selling skills.  The suggested forums below are sales team meeting and sales meeting preparation, but I encourage you to think about different situations where you can ask or inspect for these skills.

1. Developing discovery skills for early phase selling.

Part I: Before your next sales meeting, assign this pre-work: Ask each sales professional to be prepared to discuss one client or prospect in an early selling stage (e.g., prospects you are trying to get in front, still qualifying, have had limited meetings/traction, etc.)  In the meeting, ask each seller to share their situation and challenge, then as a team, brainstorm the discovery questions that would allow the seller to establish a foundation around problem definition, needs, product/service fit, and timing.  These can be broad questions -- about the company, industry, market, challenges.  Or targeted questions – about their current provider, top business priorities, decision makers, decision process.  In this process, your team should be taking notes, stealing from each other’s and developing a bank of questions to ask their own clients/prospects that are in an early phase. 

Part II: Have your team go out and ask these questions before the next sales meeting (face to face or by phone) and be prepared to report back what information they have learned and what the next steps are with this clients/prospects.

What are you teaching with this approach?  Questioning skills, listening skills, being prepared, qualifying, following up, asking the harder questions, research, and being naturally curious which is mark of sales excellence. 

2. Developing sellers’ ability to think on their feet and answer tough questions.

Here’s another assignment you can give your team before your next sales meeting.  Have them bring in examples of the toughest questions they received from a client/prospect in the last month/quarter/year, how they responded, and what happened next. They will not be able to participate if they were not listening to the client/prospect and they will not want to come in empty handed in front of their peers.  

In the meeting, list these questions on a white board, select those that are commonly heard and/or particularly challenging, and discuss or role play how to address them.  Discuss techniques such as re-stating the question in their own words to confirm their understanding and asking follow-up questions.  Remind folks not to get rattled or emotional. Encourage them to think about the motivation behind the question based on the buyer’s persona, needs, or biases. As a team, brainstorm answers to questions that highlight competitive differentiation. And most of all, remind them that it is about the buyer, not about you. If they don’t know enough about the client’s needs to answer intelligently, answers such as “I’d like to better understand before answering” or “I don’t know yet” are entirely acceptable and authentic.

What are you teaching with this approach? Listening to the client/prospect, thinking on your feet, and being authentic.  Every outstanding sales professional I have ever met can think on their feet and under pressure.  It is another mark of sales excellence.

3. Developing the ability to deliver value messages that resonate with clients.

In advance of key client meetings, have your people share the following information with you (1:1 or in a small group).  Who are they meeting with? (role/title) What company are they meeting with?  What are we trying to sell?  Who are the likely competitors? (if relevant).  Then have them share the most relevant and compelling value messages your firm will need to position in order to win the business or be well-positioned to win.

Once they share the messages (features, selling points, etc.), ask them this question: “And why should I care if I am the decision maker?”  Keep asking this same question until you hear a true benefit statement that is logical and has a chance to resonate with the intended decision maker.  Caution, they could get frustrated, but it is a healthy frustration that pushes people to form real value statements rather than dropping empty features that do not resonate or position your company or solution well.  You are teaching another mark of sales excellence – clearly stating benefits in a language that addresses they buyer’s needs and interests.

These are three simple, yet effective ways to reinforce fundamental selling skills. The best sales professionals as demonstrated above are naturally curious, think on their feet, and state benefits in a compelling way.

Identify other prevalent skill gaps on your team and find similar, creative ways to ask, probe, and allow your team to learn from you, from their peers, or from their own answers.

Rise up out of day-to-day status reporting

In team meetings, resist the usual sales manager habits of simply talking about status, move dates around on the pipeline, sharing company/product updates, and telling people what the numbers are for everyone to make goal. These are important, but will not move the performance needle or strengthen critical skills. 

Even when you are busy and there doesn’t seem to be enough hours in the day, don’t let your creativity get squashed. Find quick ways to get “in” deals or the buyer's head rather than looking “at” deals with your sellers.  Ask the great questions that your sellers will continue to think about for days, quarters, and years to come. The best sales leaders are creative about how to get the most out of people and find ways to inspire them amidst day-to-day demands.

For more perspectives on sales coaching, see these recent blogs:

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David Szen

Written by David Szen

David Szen is a master facilitator and leadership development expert. As a Principal Consultant at Symmetrics Group, David has designed and delivered custom sales and leadership content for countless clients. He is most comfortable in front of groups or in keynote settings where his high-energy delivery style connects with people and brings content to life. David’s specialties include sales training design, leadership development, coaching performance management, workshop facilitation and strategic account planning. He recently co-authored the book The Multigenerational Sales Team with Symmetrics Group's founder Warren Shiver.

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