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. 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. 

Re-evaluate

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@thesalesevangelist.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.

Sales is a year-round activity with no off-season and no breaks, so it’s important for sellers to understand how to deal with stress, fatigue, burnout, and a lack of creativity. 

Dana Cavalea is the former Director of Strength & Conditioning and Performance for the New York Yankees. Coach Dana, who helps companies optimize performance and productivity, wrote a book called Habits of a Champion: Nobody Becomes a Champion By Accident.  

He became a coach after realizing the tremendous difference that coaches made in his own athletic career, and how they helped him overcome bumps in the road. 

Opportunity knocks

Dana, who originally hails from New York, chose to attend school in Tampa because he knew it was near where the Yankees conducted their spring training. When he got the opportunity to join the team as the guy who handed out towels and cleaned the weight room, he jumped on it. 

Within a few years, he earned a paying job as the director of strength and conditioning and performance, and the team won a championship during that time. 

He discovered, through that experience, that many executives, CEOs, and sales teams wanted to know how athletes prepare to compete at the highest levels. How do they deal with injuries and fatigue and the obstacles they face during a season? How do they keep showing up every day in the face of fatigue and burnout?

Individual protocol

People assume that high-level musicians and athletes feel good every time they perform, but that couldn’t be further from the truth. They’re tired a lot, but they don’t tell themselves that. They understand that fatigue is part of life and that you’re going to have days where you don’t feel great. The goal, Dana said, is to have fewer of those days and more of the days where you do feel great. 

To do that, Dana coaches people to focus on a couple of simple things that affect performance.

• Hydration
• Sleep

These factors can inhibit the way you function overall. To address them, you must have an individual routine specific to your needs that helps you perform at your best every single day. 

Some players like music that pumps them up, and other players like music that calms them down. Each person must have a routine and protocol that is based around their needs. 

But how do you get there?

You get there by testing things. If you sleep for six hours but wake feeling tired, that may mean that you need more sleep, or that you need to understand your 90-minute sleep cycles better. We must perform each day and test different things like the food we eat to determine what makes us feel better. 

How do I feel?

Begin by asking yourself the question, “How do I feel?” Phrased that way, the question takes you out of yourself and gives you a moment in the midst of all that you have going on to consider how you feel. People listen to a million different podcasts and listen to two or three books at a time, and we’re so busy that we don’t take time to think about how we’re feeling. 

We’re working to create a self-awareness that is super important to determining the strategies that will help you overcome your struggles. 

Sometimes we underestimate the impact of stress on our bodies. Sports are very competitive, as is business. Sales is extremely competitive. You must prepare and train to compete. 

Energy wins. You might be a more talented salesperson than I am, but if I have more energy, I’ll continue to show up every day while you take a day off. #SalesSuccess

The key is to keep your energy up by hydrating, sleeping, fueling, and training. Then, fill your mind with good stuff to crowd out the doubt and fear. 

Sports have a defined starting and ending point, but sales continues all year, quarter after quarter. There’s no break because each year leads into another. 

Expectations

If we do well this year, what will the people around us expect from us moving forward? They’ll expect us to do better. So now we’re constantly trying to push our threshold. Although what we did last year was good, it’s not good enough for this year. Expectations shift.

Some people, though, get comfortable playing things safe, and doing “just enough.” They don’t want to do more than they’re already doing because they know it will simply shift the expectation higher. 

People fear success almost as much as they fear failure. Sometimes, they sabotage themselves in order to avoid the pressure of accomplishment. 

Leaders can help their sales teams overcome these struggles by being honest. If a salesperson has hit his numbers for the month and he has a pending deal that he could close this month but he’s holding it for the next month, his leader must remove the need for the seller to impress him.

Creating clarity

Dana heard an interview with Mariano Rivera in which Rivera said his career changed when Yankees manager Joe Torre called him into the office and explained that Mo would always be his guy. As long as Torre was with the Yankees, he wanted Mo by his side. That freed Mo to relax and do what he was best at. He was freed from the need to prove himself. 

If you can reduce the need to prove yourself because you’ve validated yourself, you’re in a great position. When a manager does that for his team, it’s like glue for the team. 

Dana puts his clients on a morning walk routine that includes a 30-minute walk with no technology. It forces them to be by themselves without the defense of jumping into the phone. Without distractions, they can think about the things they actually want. They get the clarity of evaluating their current situation and their own performance. They have time to ask themselves questions about how things are going. 

Taking ownership

You may find that you have a leader or manager who isn’t leading in the way you need her to. In that case, it’s up to you to tell her what you’re struggling with, where you need help, and how she can support you. You can also ask for clarity around the work you’re doing. 

When you have the conviction to seek clarity without fearing the conversation, you’ll invite more clarity. 

Dana often encounters people who exude confidence. He calls it their birthright because it’s so natural to them. They know exactly what must be done in order to succeed. In most cases, though, your team will include really intelligent people who simply haven’t experienced enough success in order to feel confident. Coaches can navigate their sellers to achieve small, frequent wins that stack up and build confidence. 

Sellers can acquire confidence even if they don’t naturally have it.

On the other hand, Dana sometimes encounters finance people who allow the market shifts and trends to impact how they feel about themselves. He reminds them that the market will do what it will do, so these people must avoid being reactive to the external environment. 

Striking out doesn’t make you a loser, and losing doesn’t make you a loser. 

Dana got this advice some time back: People can either love it or shove it. Not everyone is meant to work with you and you’re not meant to work with everyone. That’s just the way it is. 

Starting point

Nobody leaves the gym feeling worse than when they got there. They leave feeling glad that they went. Training is your starting point. 

Not all sales are equal. Don’t compromise yourself in the process of making a sale. Some sales aren’t the right ones and they’ll be a death sentence for your company. 

Sales is a hustle and a grind, so you must approach every day with a vision of what you’re trying to create. We’re quick to judge ourselves against other people. 

Sales is a relationship game. If people know, like, and trust you, they’ll open up to you. If they don’t, they’ll be closed to you. Relationships take time and they aren’t one-sided. 

Burnout and stress are perspective-based. Stress is the result of pressures you put on yourself, and stress over time leads to burnout. 

If you try to be perfect, you’ll ultimately fail. Hit singles. Don’t try to hit home runs. If you hit a single every day, you’ll get a run on the board and another man on base. 

Create a healthy process for yourself and then execute every day. 

“How to Deal With Stress, Fatigue, Burnout” episode resources

Connect with Coach Dana at danacavalea.com or access his YouTube channel for more content. Grab a copy of his book, Habits of a Champion: Nobody Becomes a Champion By Accident.

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@thesalesevangelist.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.

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