Shattering the Myth of Managing Self-Employed Salespeople

Become a better sales coach and sales manager today.

Whether someone works as an employee or is self employed, no manager can afford the time consuming and costly mistake of having someone on their team who isn’t a good fit. These tips will help.

8-Steps to Creating a Coaching Culture by Keith RosenIt’s not a shock that one of my deepest passions is writing and sharing my work in a way that delivers value to people, wherever they are located throughout the world. What continues to drive me to write are the emails I get from readers, thanking me and asking for assistance around incorporating what they have read, overcoming a barrier they have encountered or what they can do to embed certain changes within their organization.

I embrace and enjoy any opportunity to assist every reader. That said, here’s a timely inquiry I received from a manager and my response to this person’s issue regarding how to manage a team of self employed salespeople, which I’m sure is relevant for many managers and the reason I’m sharing it here today. As you read through this, I hope this also serves as a good reminder that, whether you’re a salesperson, manager, employee or business owner, you are not alone and there is always an opportunity to better your situation.

Hello Mr. Rosen,
I am currently reading your book “Coaching Salespeople Into Sales Champions” cover to cover for the 2nd time in the past few months. I have also re-read specific chapters on multiple occasions. I am a Regional Field Sales Manager for a National Company. Our teams that we also remotely manage are made up of Independent Sales Representatives and as they are self employed, we have to be always aware of the IRS 1099 requirements. A few months ago our boss read your book and became very enthralled by it. Now, we have begun “Coaching” our Sales Reps. Somewhat of a challenge because of the 1099 situation but we are getting through it. What are your thoughts about coaching people who are self employed? Your suggestions and/or comments will be greatly appreciated.

Abide by a Code of Conduct

 While there are legal/compliance issues to be mindful of when managing a team of self employed/independent contractors, be careful about making the assumption that, because they don’t ‘work for you’ you can’t hold them accountable. Think of it this way. There are still guidelines and expectations you have of behavior, skill and performance. These can still be shared with your team of self-employed individuals. It all comes down to how you position this to them. Rather than lay down a set of commandments, a quota and rules they must adhere to as if they were an employee, which is the challenging part of managing a team of self employed people, position it as more of a choice they can make if they truly want to be a successful producer within your company. In essence, enroll them in developing an ‘employee’ mentality.

After all, when you were going through that recruiting process to find the right people for your team, at one point, you shared with them what the job entails, their responsibilities and what your expectations were, regardless of whether they were self employed or not. At the end of the day, they are either meeting the expectations you have of them or they are not. Moreover, you can still coach them, support them and enroll them in making the certain changes they need to make in order for them to achieve their expected degree of success. So, it’s less about not being able to “fire” them or hold them accountable to a certain guidelines because you don’t have the legal authority to make them follow your rules and more about sharing with them a message of what you find your top producers are doing and the choices they have made when taking the position.

Time for Some Role Play

Here is an example of what that enrollment conversation could sound like. Keep in mind, it’s solely an example so feel free to refine in order to make it fit best for you.

“First, we’re excited about the possibility of working with you and having you join our team. We want every person who comes aboard and works with us to be able to achieve their personal goals. In order to assist you in doing so, we have identified some benchmarks, best practices and characteristics that our top performers engage in and possess. We are keenly aware this is a self employed position and that many people take this position because of the freedom and flexibility it offers. That being said, we still want to ensure we are able to offer you all of the support and resources you need in order to become successful here. Here are some of the benchmarks we have identified that, if embraced, enables people in this position to achieve their personal goals (list criteria, i.e. suggested coaching, meetings, reports, daily activity, skills to develop, processes to follow, mindset, etc.).

As you can see, this is not only limited to the person’s activity and effort but a great deal of their success depends upon how closely they follow our proven system, how coachable they are and how open they are to ongoing training and development. Those that have the ‘leave me alone and just let me do my job the way I want to’ mentality seem to be the ones who struggle most and wind up not working out. Then it becomes a waste of time and energy for everyone, which is what we do our best to avoid. Instead, we have found that the type of relationship we want to develop with our team is one of mutual support, trust and accountability, in the sense that we are both committed to the same goal. That is, making you a success here. While you certainly have more autonomy being self employed, those who choose to come aboard have chosen on their own to work within these suggested parameters, knowing that ultimately, it is what will enable them to meet their personal goals.

How well do you feel you would fit within this type of environment? (Why?)

If you feel this type of environment doesn’t work for you or if you’re looking for much greater autonomy that goes beyond what our current team is choosing to do, then maybe this position isn’t the best fit for you.”

Photo Credit: Blake Danger Bentley