Boosting Sales Coaching: 3 Techniques to Reinforce Selling Skills

We spend a lot of time with sales leaders, fully understanding the hours they work and pressures they face in their roles. 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, 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 fundamental selling skill gaps we observe most often are:

• Conducting effective discovery (questioning skills)
• Navigating and answering tough questions
• Delivering relevant and powerful value messages

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

Sales Leader Dilemma: Infusing Creativity in Sales Coaching

We 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 tend 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. We discussed topics such as: sales call preparation, listening and questioning skills, relationship management and development, buyer persona identification, building value, positioning, team selling, and advancing the sales process.

Where these leaders needed the most help involved keeping key concepts alive, how to further develop talent, and steps to support ongoing skill building in the “real world”.

Creativity in coaching is how you create the magic that connects people and helps them learn – all while driving the messages and skills you’re developing. When you are so busy and don’t have time to think, you end up going through the motions and missing valuable opportunities.

Applying Creative Methods to 3 Fundamental Selling Skills
Let’s consider the usual forums that sales leaders get to coach in (including 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 we encourage you to explore different situations where you can inspect for these skills.

1. Developing discovery skills for early phase selling:

Before your next sales meeting, assign this as pre-work:

• Ask each sales professional to be prepared to discuss one client or prospect in an early selling stage
• 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 (e.g., about the company, industry, market, challenges) or targeted questions (e.g., about current providers, top business priorities, decision makers, decision process)
• In this process, your team should be taking notes, sharing insights, and developing a bank of questions to ask their own early phase clients/prospects

Also, have your team ask these questions during the next sales meeting (virtually or in-person). Ask them to be prepared to report back what information they’ve learned and next steps.

What are you teaching with this approach? This approach teaches questioning skills, listening skills, preparation, qualifying knowledge, follow up knowledge, the ability to ask hard questions, research skills, and a natural curiosity. These behaviors show a knack for sales excellence.

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

Here’s an additional assignment you can give your team before the next sales meeting: have them bring in examples of the toughest questions they received from a client/prospect in the last month/quarter/year. They can prepare a summary of how they responded and what happened next. They will not want to come in empty handed in front of their peers.

In the meeting:

• List these questions, 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 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, and/or biases
• As a team, brainstorm answers to questions that highlight competitive differentiation
• 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 productively, 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? You’re establishing how to listen to the client/prospect, the steps for thinking on your feet, and how to showcase authenticity. Every outstanding sales professional we’ve met can think on their feet and under pressure. These qualities are 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 team share the following information with you (1:1 or in a small group):

• Who are they meeting with (e.g., role/title)?
• What company are they meeting with?
• What are we trying to sell?
• Who are the likely competitors?

Then, have them share the most relevant and compelling value messages your firm will need to position to win the business or be well-positioned to win.

Once they share the messages (e.g., features, selling points, etc.), ask them: “And why should I care if I am the decision maker?” Keep asking this 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 value statements rather than dropping empty features that don’t position your company/solution well.  

You are teaching another mark of sales excellence – clearly stating benefits in a language that addresses the customer’s needs and interests.  

Putting It All Together

These are three simple, yet effective ways to reinforce fundamental selling skills. The best sales professionals (as demonstrated above) are:

• Naturally curious
• Able to think on their feet
• Able to 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, their peers, or their own insights/answers.

In team meetings, resist the usual sales manager habits (e.g., talking about status, moving dates around the pipeline, sharing company/product updates, sharing sales numbers to hit goal, etc.). These are important updates but will not particularly 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 heads rather than just looking “at” deals with your sellers. Ask questions that your sellers will continuously think about for days, quarters, and years to come.

The best sales leaders are creative about getting the most out of people and finding ways to inspire them amidst day-to-day demands. Contact us for ways to effectively lead sales teams or other ways to strengthen your sales organization(s).