Along with experience in the digital marketing world comes a certain knowingness - a sense that one's eyes are clearer, his sense of judgment more acute. There's an assuredness that we've seen all this before and that we can instantly recognize winners and losers and easily sort the wheat from the chaff.
You not only know this guy: you've hired him. Or maybe you are him. You understandably value the digital experience he's had at a half-dozen companies over the past 12 or 15 years. This dude can make it rain. Maybe he can. But his experience and sense of self often come with a heavy tax. The cancer that too often grows with experience is cynicism. And it's a killer.
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The smart CEO and the enlightened manager are acutely aware of how this disease presents itself and how quickly it metastasizes. Mr. Experience holds the informal meeting-after-the-meeting to let the younger sellers know that this plan looks an awful like what he saw when he was at XYZ.com. He airs his reservations about company direction in an email reply to the whole team. Sometimes his physical presence at a meeting - body language, expression - are enough to spread the pathogens of doubt and fear. At a time like this -- of industry consolidation and massive change - he is patient zero in an epidemic of cynicism in your company.
The tricky part is, he may not even know what effect he's having. And he likely believes that his approach coming from a place of generosity and helpfulness. I really love this company! If he works for you, you must act.
Call it Out. Have a closed-door meeting with your cynic and make it clear that he's entitled to his opinions and thoughts, but that the overt behavior he's exhibiting must stop.
Inside Words/Outside Words. Let Mr. E. know that you want to hear his ideas personally and create a secure channel to listen to him. But make it clear that once the door opens, you need him to support or stay quiet about direction and initiatives.
Consider the Alternative. Too many CEOs and CROs operate out of fear - fear that saying goodbye to experience means kissing off your potential revenue. But look carefully: does the revenue this guy is actually producing compensate your company for the sense of despair and doubt that's immobilizing your other team members?
You'd never tolerate an employee who came in and crashed your network every day, keeping a huge number of your employees from getting anything done. But we do it every day. Your company and your sales team have life-forces that thrive on possibility, hope and good intention. Know the difference between honesty and cynicism and do what you have to in order to give your team the environment they deserve.