How to Handle a High Achieving Pain so You Don’t Get Arrested

Sooner or later every sales manager must deal with a high achieving salesperson who is also a major pain in the butt. You know the type … they’ve been with the company forever, outsell everyone else by a huge margin, and they’re not afraid to let everyone know how great they are.

They don’t believe the rules apply to them, and they give you more grief than the rest of the sales force combined. Though they may appear in many shapes and sizes, the following is typical.

Clarence has been in sales with the company for 15 years. His sales are twice that of the next best producer. He has the top 5 customers and has excellent relationships with them. He is very demanding of every other employee when he needs something for his accounts. 

According to Clarence, everyone else is either incompetent, shiftless, or just plain lazy. He tolerates his sales manager and, often, bypasses her entirely and goes straight to the president with questions or complaints. Even though he’s a great producer, his sales manager feels he is disrespectful and undermines her authority and credibility with the rest of the sales team. What’s she going to do?

Before doing anything drastic, step back and analyze the situation. Ask yourself the following questions:

  • Why is Clarence not the sales manager? If he’s so damn good, shouldn’t he be managing the sales force instead of you? The answer is because he’s not sales management material. If he were the sales manager, most of the other salespeople would quit rather than work for him. Those who stayed would struggle because Clarence would be in competition with them. He’d be undermining them instead of guiding and helping them.
  • Why are you the sales manager? There are many reasons, but the main one is you were hired because you have the skills and potential to manage the sales force. You’re the pick!
  • Ask yourself this: What’s your primary job as the sales manager? It’s to generate the sales and profits your company needs through the salespeople. That means all the salespeople, including Clarence, the pain in the butt.
  • Now, thinking specifically of Clarence, is he an asset or a liability? Are you and the company better off with him, or without him? Be careful here. Step back emotionally and weigh all the pros and cons. What would you lose if you fired him? How long would it take to replace him? What would happen to the relationships that he has with the key accounts? How about any vendor relationships he might have? On the other hand, what would you gain?
  • Please note something very important about customer relations. We’re all busy. Often, as sales managers or owners, we’re so busy we do not develop the relationships we should with all our key customers. We leave it to the salesperson. That’s a mistake.

Your salesperson then becomes the only point of contact the customer has with your company. If that salesperson leaves, then you have no relationship. Any business you’re doing with them is in jeopardy. Smart companies have at least five points of contact with their major customers. Here’s an example of what that might look like …


Your Company                        Your Customer


Salesperson connects with:    End Users
                                                 Ultimate Decision Maker


Sales Manager connects with all the above (at least knows them)

Finance/Accounting/Credit connects with counterparts

Shipping/Logistics connects with their counterparts

President/CEO connects with President/CEO

The level of connection depends on the importance of the customer. It’s not practical to have strong relationships with every customer. However, you should have good penetration of at least your key customers … the ones whose loss could have a major impact on your bottom line.

The bottom line is you’re in control. You must assert yourself as the sales manager. In my opinion, firing someone is always the last resort. There are many reasons why the Clarences of the world act like they do. 

Why doesn’t really matter. What does matter is they understand their role within the company. It’s your job to insure they do what they are supposed to do without causing strife and turmoil. 

It’s OK if they are better salespeople than you are. Hell, can you imagine what it would be like to have an entire team of them? You’d be laughing all the way to the bank. So, if you decide to keep Clarence, you need to decide what the ground rules are. What’s acceptable behavior? What’s not? Where’s the line that you will not let him cross? Keep your ego locked up and figure out the best way to use your assets, including Clarence. Then act accordingly. Remember, you’re the sales manager.

It is very important not to be held hostage by any one salesperson. Initially, you may be vulnerable, but you can take steps to reduce that vulnerability. Many smaller companies get in a position where one person is the only point of contact with a major customer or vendor. They forget that the account belongs to the company, not the salesperson. 

As the sales manager, you need to spend a good deal of your time making sure that doesn’t happen. When a salesperson gets too big for their britches or when they threaten you, you’ve got options. When, or if, a salesperson leaves, the damage is minimized.

I’m Oliver Connolly, founder of Street Smart Sales Management. If you have any questions or if you want to explore how I might help you, please e-mail me at

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Oliver Connolly