The High Price of Joyless Sales Manager

Salespeople are optimistic by nature. They have to be; if they weren’t optimistic they could never succeed at a job where the first communication they have with their dream client is most often a flat out rejection and where they lose more of the opportunities they pursue than they win. This is true even when they are succeeding wildly!

A joyless sales manager can ruin their sales team and destroy their capacity to win by demolishing their natural optimism.

The Devil’s Advocate

Every opportunity comes with enough risks, threats, challenges, and competitors that the devil needs no advocate. The sales manager’s role is to not to play devil’s advocate when discussing opportunities. When coaching the salesperson on the opportunity it is fair to challenge their strategy and to push the salesperson for their best thinking and their best performance—as long as it is done with the intention of helping them identify and obtain the ideas and the resources that they need to win the deal. It can’t be to simply play devil’s advocate—that role, without fully participating in strengthening the deal yourself—is too negative.

Sales managers who play devil’s advocate without participating in generating ideas that strengthen the deal strategy, without helping to obtain the resources that may build a competitive advantage, and without a good and positive sprit, end up tearing their salesperson down and destroying morale.

I’ll Believe It When I See It

A salesperson has to believe that they can win every deal. This belief sustains them through all of the challenges, through all of the periods when the deal is at risk, and through the trials and tribulations that are part of competing for their dream clients.

They have to read positive buying signals as positive. Doing so allows them to believe they can win the deal and to act accordingly, pulling out all of the stops to win the opportunity. When they believe they can win, they are naturally excited to share the good news with their peers and with their sales manager.

A sales manager who doesn’t share their enthusiasm can take the wind from their sales. The sales manager does nothing to encourage the aggressive, no hold barred behaviors that the salesperson needs to take in order to win by suggesting (or saying) that they will believe the deal only when they see it. A sales manager needs to share the belief that they can win. Period! Even when the deal is incredibly unlikely.

The sales manager may never see the deal. The deal may be lost. But destroying the salesperson’s belief—and with it their optimism and confidence—does nothing to advance the deal or increase the salesperson’s likelihood of winning the deal.

The Deal Is Not Good Enough

Most deals aren’t perfect. In fact, many are far less than perfect. But winning the deal is winning the deal. Maybe the price was lower than desired. Maybe the deal requires more work than is normal or anticipated. Maybe it is somewhat short of what you, as a sales manager, would have hoped it would be. And, perhaps the salesperson made a blunder that made one or all of these things true.

If you are a sales manager, before you point out all of the things that are wrong with the deal, how you could have done better, or what you expected, stop and think about the outcome you are trying to achieve. Is it your intention to build your salesperson up by building their desire and capacity to go and win future contests? Or, do you allow your dissatisfaction to rob the event and the salesperson of the joy of winning?

Winning by a field goal in an ugly triple overtime game is still winning. Would you have liked to win in a blowout? Sure. But winning is winning, and winners celebrate and are celebrated before they review the game films to decide how to prevent a close game in the future.


A joyless, pessimistic, or even realist sales manager does nothing to encourage the optimistic fighting spirit a sales force needs to win. They need to share the optimism and share the belief that the deal can and will be won.


    1. A sense of optimism provides the salesperson with the ability act and to compete against all odds. What does a pessimistic attitude provide the salesperson or your sales team? What does the realist, pragmatist provide your sales team in the way of hope and fighting spirit?

    1. When you challenge your salesperson’s deal strategy by playing devil’s advocate, what do you do to provide the ideas and the resources the strengthen the deal? How do you share in the ownership of the deal by playing devil’s advocate? How do you strengthen your salesperson’s resolve and their commitment to compete and to fight for the deal?

    1. Your salespeople believe that they will win deals that they will lose. What does it cost you to support them in their belief? This is not to suggest that you should allow them to believe they can win without ensuring they have done what is necessary to win. You don’t have to forecast long shot wins, either. But how do you help encourage them to try and to compete against long odds?

  1. Are you guilty of criticizing the particulars of a new win when it is reported? How does this build your salesperson’s capacity and desire to win more deals? What is better way to deal with deals that are short of what you need them to be? How could you celebrate the deal and postpone reviewing all of the mistakes until they can be done in a format that doesn’t destroy the joy of winning—and with it the fighting spirit?

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