Should Your CRO Coach Frontline Sellers?

Sales coaching is an essential responsibility of frontline sales managers.  In our Sales Management Research Report, we found that sales managers at high-impact organizations (sales organizations where over 75% of sales reps achieve quota) spend significantly more time coaching than sales managers at average (25% - 75% achieve quota) and low (less than 25% achieve quota) performing organizations. 

With such potential benefits, it is no wonder that many sales organizations recommend that their front-line sales managers spend 25% - 40% of their time on sales coaching.

But what about senior management? Should they coach frontline sellers? 

Skip Level Coaching 

The short answer: Yes, even the Chief Revenue Officer. The idea here is “skip-level” coaching. In this coaching relationship, a salesperson receives coaching feedback from a manager several levels above their sales manager, essentially "skipping" a level in the traditional sales organizational hierarchy. This allows for a different perspective and insights from senior leadership. For the CRO, consider the old sales leadership adage: inspect what you expect. 

There are two forms of sales coaching: skill and deal coaching. Skill coaching focuses on selling skills and knowledge. Here, the sales manager observes and analyzes a sales representative’s selling skills or sales knowledge in an actual sales call, discusses what went well and areas for improvement, and then provides constructive feedback.

Deal coaching, however, focuses on how a sales representative approaches an account to acquire new business or sell deeper into existing accounts. It helps sales representatives work through challenges such as account penetration, inability to access economic buyers, competitive issues, and formulating overall account strategies.  Deal coaching typically occurs during pipeline reviews.

Skip-level coaching can be structured as either skills coaching or deal coaching in the form of a pipeline review, but for our purposes, let’s assume that you focus your skip-level coaching time on deal coaching. 

Before engaging in skip-level coaching, a CRO should be able to ask the following questions of the frontline sales managers’ deal coaching and get satisfactory answers:

“When was the last time you set aside 60 minutes with each of your sellers to discuss a maximum of three opportunities in a deal coaching session?”

“Do you have time set aside to do that every month?”

“How do you structure your deal coaching conversation?”

The CRO should ratchet up expectations and lead by example if satisfactory answers aren't given.

5 Critical Deal Coaching Questions 

Here are five impactful deal coaching questions to consider asking the salesperson during your skip-level deal coaching sessions:

1. What is the customer’s business need? In other words, can the salesperson succinctly characterize what the customer is trying to accomplish with a particular initiative and how it will impact their business?  If they can’t articulate the business need (in business terms), how will they 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 understand the business need more clearly.

2. What is the unique value you bring? Once the need is identified and explored, can the sales rep clearly articulate the unique value their solution provides? Can they explain why their solution differs from competitors and how it will benefit the organization uniquely?

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? Salespeople 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 new economic or technical buyer appears who prefers the competition, and the deal is lost.

Coaching Point: Help the salesperson create a plan to identify and access other stakeholders and coaches in the organization who may be able to influence the deal and provide access to the key stakeholders.

4. How will the competition try to beat you? Knowing who the competitors are is not enough; it’s important to know their strengths and weaknesses and how you measure up against them.

Coaching Point: Help the sales rep develop a matrix of your solution's strengths and weaknesses compared to the competition to identify key messages you want to communicate 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 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.

What Should a CRO Expect? 

CROs should be confident in the selling team’s ability to convey the business value that meaningfully progresses customer opportunities and drives customer outcomes. 

What should a CRO do if their teams fall short of those expectations?  Consider rolling out a customized sales training program for the sales team and a sales coaching program for the frontline sales managers.

Another action to consider is reviewing your team’s opportunity plan.  Does your sales team consistently use a simple yet well-crafted opportunity plan to manage sales opportunities?  If your organization doesn’t leverage a standardized opportunity planning tool, that needs to be built and coached immediately.

At SBI, we’ve studied the most effective opportunity plans in complex sales. Those plans always start with a section requiring sellers to hypothesize the metrics and desired outcomes of the customer’s buying decision team. Next, well-crafted opportunity plans ask sellers to be thoughtful about building a powerful narrative that ties those desired customer outcomes back to their solution’s key differentiators.

This amount of thought and advanced preparation on behalf of the seller allows them to show up for the big moments, the big conversations, where they can build customer consensus among stakeholders and meaningfully progress an early-stage sales opportunity.

If you’re concerned about your sales team’s performance, it’s time to jump into action.  CROs and other senior sales leaders should use skip-level coaching sessions to “inspect what you expect.”  That means dropping down in altitude, getting your hands dirty, and leading by example as you coach the frontline sellers.  Then, encourage the frontline sales managers to structure their months in terms of providing one-to-one coaching time for every seller on their team.