Inspiring and developing an environment for continuous sales improvement

How are companies creating a culture of continuous sales improvement?

Sales Improvement conversation at the Boston Chapter of SESThat’s what the Boston Chapter of the Sales Enablement Society recently set down to explore — and what we wanted to share with you here.

In this article, we’ll take you through a few key points:

  • Background on tech vs. sales improvement
  • Thoughts on building a culture of sales coaching that leads to continuous sales improvement
  • Best practices for sales improvement

While we primarily focused on sales coaching throughout our conversation, I’ve taken the liberty to add additional thoughts where they make sense.

By the way:  If you are looking for inspiration about the power of sales coaching on life and business, check out this great conversation.

Background of investment in tech vs. sales improvement

SmartSellingTools Founder, Nancy Nardin, keeps up with sales technology and yearly posts the Sales Technology Landscape. It’s an eye chart.

And, there is a tool for everything, so we must be improving, right?

SmartSellingTools SalesTech Landscape

Well, maybe not.

Our conversation noted the exponential growth in sales enablement technology vendors to over 400, yet sales productivity has steadily decreased over the same period.

  • 68% of organizations plan to increase sales headcount
  • 425+ Sales Enablement Technologies, $5B in Investment
  • 53% of Sellers Make Quota & 55% of Forecasted Deals Close

The current investments in technology are not leading to a corresponding increase in sales improvement and productivity.

So — what gives?

Investing in sales technology without investing in the people and the processes will fail.

In this article, we will stay focused on sales coaching as the tool for sales improvement, not instead of investing in technology and people, but in addition to those investments.

Note:  There are no silver bullets for improving sales performance; it requires multiple approaches working in harmony. Remember the foundational elements of building a robust sales engine:

  • A well-defined sales process.
  • Mapped buyer and customer journeys.
  • Onboarding programs.
  • Compensation plans.
  • Other core components.

Continous sales improvement supported by sales coaching

You should review this article on building a culture of sales coaching in addition to these insights.

Our group began the conversation by ensuring everyone understood the distinction between training and coaching. Sales training broadly delivers information and insights to a group, whereas sales coaching personalizes the knowledge transfer to the individual based upon their needs.

For sales coaching to affect sales improvement positively, you must weave it deeply into your culture.


Executives must lead the way

Your executive cannot sit back and mandate coaching; they must demonstrate its importance.

  • Executives should regularly speak about the importance of coaching
  • Executives should have coaches and talk publicly about how their coaches help them be successful

Enablement must be trained, coached, and empowered

Coaching, like any other skill, must be learned first and practiced second.

Ensure your Enablement team receives regular training and coaching on being a great coach and has the skills to coach your sales managers to coach.

Sales leaders must also empower the Enablement team to work directly with the sales managers and leaders to identify skill gaps and performance issues and use this information to ensure coaching is delivered where needed.

A corporate culture of innovation


Suppose your overall company culture does not support innovation so that people are comfortable trying and occasionally failing. In that case, it will be hard to drive a culture of sales improvement.

Best Practices for continuous sales improvement

Some of these points have been lightly touched upon above; others have not.

Teach your sales managers to coach

Your sales managers are your secret weapon to scaling sales improvement.

  • Teach them to coach
  • Coach them, so they improve
  • Provide them a framework for coaching
  • Enable them to coach in both one-on-one and team settings
  • Teach them HOW to give feedback. Be precise, not generic.

Enable mentors and buddies to coach

Peer-level coaching can be powerful when correctly done.

Teach your sales champions and influencers the same skills.

Set up a buddy program for new hires, where buddies learn to coach.

Coaching is not a performance review or status update

During your coaching, identify one opportunity for improvement and focus on helping your seller with that one item.

Perhaps, using your conversational intelligence tool or simply sitting in on a sales call, identified a handful of areas the seller could improve.

  • Choose one item only
  • Help that individual to see that improving this area could benefit them in their job
  • Brainstorm ways to improve this item
  • Roleplay the ideas
  • Give the seller homework to practice
  • Document next steps in an email
  • Review, roleplay, and continue in follow-up sessions

Hire for coachability

There are two primary categories of mindsets when it comes to coachability.

  • Fixed – These people are not open to learning and growing
  • Growth – These people are hungry for development and improvement

As you interview, use questions that explore the potential employee’s willingness to learn and grow, demonstrating times when they have done so in the past. For example:

“Tell me about something you would go back and do differently in your career. What would you do differently?”

Understand competencies required

What skills and competencies are required to be successful in your company in a given role?

Which of these must you hire for, and which are you comfortable teaching?

Sales improvement will only happen consistently in areas for which you can teach and coach. You need to understand your competencies in this area.


Work closely with your HR team and sales leaders.

Use data to pinpoint opportunities for improvement

You can’t change what you don’t measure.

Identify the leading and lagging indicators you will use as part of your overall sales enablement strategy.

Use this information to pinpoint sales improvement opportunities as you identify the business, team, or individual challenges against these goals.

Final thoughts

For sales improvement and improvement in general, a coach can make an enormous difference.

Embrace the concept and get a coach for yourself as early in your career as possible.