What should a sales manager do when faced with a situation when a high-producing salespeople cannot follow company sales practices or engages in unethical conduct? I call them “Cowboys” and “Cowgirls” because of their desire to operate like they were in the American Wild West, without rules or much supervision. As a sales manager, I often had to defend keeping these rebels on the salesforce to top management. At some point, the benefit of keeping them on board may be offset by the cost and time spent fixing the collateral damage they created. One obvious issue is that the sales revenue they bring in is not easily replaced, not by others in the salesforce, and not through a new hire.
Cowboys and Cowgirls are not the salespeople that show up at the office late, spend too much time at the coffee machine, or are gossiping. Those tend to be low producers and are a different problem because discarding them does not result in a large hit to revenue. Sometimes there is even “addition by subtraction” because other people will become more productive when they are let go.
I have had the fortune and misfortune of having several Cowboys and Cowgirls work for me. They were all high-producing salespeople; some were the top producer. I had to determine if their superior performance was due to misbehaving, for example, misrepresenting the capabilities of the product, but that was rarely the case. They were successful in sales because they flourished with the greater autonomy being in sales provided. They felt rules were for others, not them, and would deliberately flout them. Their nonconformist behavior was usually the by-product of their high energy level and extreme eagerness to close business in the shortest amount of time, which when done by following the rules, brings praise, not scorn. These individuals were often charismatic and fun to be around. But sometimes their strengths, including operating independently, became weaknesses.
Perhaps the Cowboy or Cowgirl decided to cut a corner and not receive pre-approval to offer a discount or provide a resource at no cost. They may have scheduled another person’s time without checking with them first. Or, they may have aggressively pursued their prospect to the point where they annoyed them. Maybe they did not receive a prompt enough response from one of the internal product, marketing, or legal staff people from a request, and the salesperson insulted them. The Cowboys and Cowgirls often operated with the philosophy of asking for forgiveness afterward, rather than permission earlier. And they worried that not receiving approval would hurt their likelihood of closing the sale. So, they went ahead without consent and believed that their productivity would absolve them of most of their “sins.” And that was usually the case.
When deciding how I needed to handle the Cowboys and Cowgirls, as their sales manager, I classified their conduct into three categories: 1) Were the problems the result of impatience, over-eagerness or rules-bending; 2) Did they lie to or misrepresent either to the prospect or to sales management?; or 3) Was there a mental health issue, such as drug or alcohol addiction, PTSD, or a personality disorder?
If it was the first category, I reminded them that their conduct annoyed others and was not acceptable. This was sometimes successful, or perhaps they reduced their most egregious issues. They were often unaware of the severity and repercussions of their conduct. And they did not consider the impact that it had on others that watched their behavior and may decide to emulate them.
If it was the second category, I would give the person one warning and terminate them the second time it happened. I had a zero-tolerance policy for lying and misrepresentation.
If it was the third category, I would get the Human Resources department involved to assure that we considered the person’s condition and followed the company policy. These people were often able to close sales, but often were unreliable and had absence issues. It is possible that professional counseling may help them.
I tried to be as tolerant as possible to keep high-producing salespeople on my team. The reality is that eventually they will wear out their welcome and move on regardless. So, it is best to try to contain their bad habits as best as you can while trying to backfill with other salespeople that will be better than average producers for the long-run.
This is one of the most difficult challenges that a sales manager needs to handle. Is the revenue from a high-performing salesperson offset by the trouble they cause while they are selling? No sales manager wants to let a high-performer go, so you often need to have extreme tolerance and patience. Try to not be an enabler to the Cowboy or Cowgirl, or that will become very time consuming and will put you on a collision path with your manager. Top management puts pressure on you to close sales, but they do not like rules breakers or people that cause internal morale problems. Understanding their behavior and handling it according to the three categories can help you be successful in your sales management career.
Steve is an expert on B2B sales strategies and how to increase sales using tips and techniques that he utilized as a high-performing salesperson and sales manager. He was recently the Director of Sales and an Account Manager at Accuity, where he closed the largest sale in the company’s history.