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...

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