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The Sales Evangelist

Sellers, Sales Coach, Donald C. Kelly

Sales leaders must help their teams perform at peak levels, so they must start by understanding how to effectively coach struggling sellers

I’ve seen this kind of coaching done badly in the past, and I’ve walked my own team members through these struggles. I’ve developed tips of my own and I’ve learned from Mike Weinberg’s book Sales Management Simplified

Questions to ask

All sales reps and sales leaders endure dark moments where nothing seems to work out. Despite the fact that we’ve been selling for years, we endure periods where we simply can’t close. Very often, when that happens, there are several key things we must address.

These situations don’t develop overnight, and they usually result from slippage in certain areas. Begin by answering the following questions as honestly as you can. You’ll never find improvement if you’re dishonest about your situation. 

  • Does the struggling seller have a desire to succeed and thrive in sales? If he doesn’t have the drive to succeed, no amount of training or coaching will help.
  • Why is this particular seller on my sales team? Did you inherit this seller? Did you hire him?
  • How did the seller get into this situation? What signs did you see along the way? 
  • What has been done to fix the problem? What steps has the seller taken? What steps have you taken?

One-on-one meetings

If you aren’t already holding them, schedule one-on-one meetings with your sellers. I’m a big believer in this method because these leadership meetings offer opportunities to connect with our team members. 

One-on-one meetings with sellers provide time to fine-tune and fix micro-problems before they become huge cracks that jeopardize the stability of our organizations. #SalesCoaching

These can be monthly, or weekly, but quarterly isn’t frequent enough.  

As you work with a struggling rep, you can determine the things that stopped happening. Did he stop planning his prospecting? Is he failing to manage his time? Does he fail to establish a plan for his activities?

If you aren’t engaging in one-on-one coaching, you won’t know what’s happening with your team. When you recognize the problems, you can implement solutions and guide your team members to the right solutions. 

These meetings should be knee-to-knee, eye-to-eye if possible. 

Conducting one-on-one meetings communicates to your reps that you care about their success. When you take time out of your schedule to share suggestions and guidance with your team members, it’s meaningful to your team. 

If something is important to your sales reps, it must be important to you. One-on-one meetings help you determine what’s important to your team members. 

If the rep is really struggling, you can increase the frequency of your coaching sessions. 

Changing mindset

When I was a sales rep selling software, I changed my mindset so that I considered myself the entrepreneur over my territory. Mike Weinberg suggests that you do the same by establishing a business plan for your territory or area.

Whether you’re a BDR or an inside sales rep, begin by determining a goal for yourself. For struggling sales reps, help them to create their own goals and then to establish a plan to follow. Including them in the plan gives them accountability. 

Begin with small goals over the next three months of the quarter. Consider what your financial goal will be. Then determine exactly how they’ll accomplish that. Identify the existing customers that you’ll engage.

Establish a time frame in which your rep will accomplish that goal. Remember to include consequences. Ask your reps what a fair turnaround would be. Then ask your reps what should happen if they don’t meet their stated goals.  

Very often your reps will establish tougher consequences for themselves than you might have set. 

Desire to improve

When you have a sales rep with an obvious desire to improve, bend over backward for that person. Move mountains for her. If she is taking advantage of coaching and she establishes an awesome business plan, reward her efforts. Find other resources that will help her succeed.

Get her books or send her links to relevant podcasts. Meet with her when you can, and email her when you can’t meet. Check in through the day and throughout the week. 

When your sales reps thrive, your business will improve and your company will grow. 

It’s far cheaper to help your sales reps improve than to begin the hiring process over again because you need successful sellers. #SalesTraining

On the other hand, if your sellers don’t have a strong desire to succeed, and they won’t dedicate the effort to improve, then it may be time to remove them from your team. 

In my own case, I had sales leaders who believed in me and who recognized my drive to improve. They coached me through my struggles and helped me get where I am today. 


Once you’ve worked through the plan over the course of 30-90 days, if your rep still isn’t improving, you must identify why. If you’ve done the one-on-one coaching and you’ve helped her create a sales plan, you may have to put her on probation. It can be an informal program, but you must establish a marker that she will hit within that probation period. 

Usually by this point, if the rep truly wants to succeed, she’ll show signs of improvement. Eventually, she’ll have to work on her own and prove that she can hit milestones without other people’s assistance. Without that ability, she’ll eventually have to move on. 

The Sales Evangelist Certified Sales Training Program helps sellers improve by identifying problems and developing solutions to address them. Many individual sellers choose our program for themselves because it’s worth the cost of the training to increase their success rate. 

“Effectively Coach Struggling Sellers” episode resources

Grab a copy of Mike Weinberg’s book Sales Management Simplified

If you’re a sales rep looking to hone your craft and learn from the top 1% of sellers, make plans to attend the Sales Success Summit in Austin, Tx, October 14-15. Scheduled on a Monday and Tuesday to limit the impact to the sales week, the Sales Success Summit connects sellers with top-level performers who have appeared on the podcast. Visit Top1Summit.com to learn more and register! 

You can also connect with me at donald@donaldk4.sg-host.com or try our first module of  TSE Certified Sales Training Program for free. This episode has been made possible with the help of  TSE Certified Sales Training Program, a training course designed to help sellers in improving their performance. We want you guys to go out each and every single day to find more ideal customers and do big things.

I hope you like and learned many things from this episode. If you did, please review us and give us a five-star rating on Apple podcast or in any platform you’re using – Google Podcast, Stitcher, and Spotify.  You can also share this with your friends and colleagues. 

Audio provided by Free SFX and Bensound.

About the Author The Sales Evangelist

Donald is the host of the popular sales podcast,"The Sales Evangelist". He is the founder of The Sales Evangelist Consulting Firm where he helps small companies develop killer sales process to scale their business and increase growth.

Donald is also an award-winning speaker, sales trainer, and coach. He's a big fan of traveling, South Florida staycations and high-quality family time. Donald has a belief that “anyone” can sell if they have the desire and receives the proper training.

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