During a presentation, I was highlighting the blog post on finding a strategic PITA (pain in the ass), describing how it was originally inspired by a senior person at our ad agency who never fails to dissect our ideas in painful, yet tremendously valuable ways.
A number of the attendees were in advertising and were surprised someone from an agency could get away with taking strong stands with a client. The experience for most of them has been that the agency has to conform to what the client wants to do, with little challenging involved. They wondered how my strategic PITA gets away with what he does.
My reply was he is able to do it because we want him to do it. It's a waste to engage smart people with diverse perspectives and then expect them to hold their tongues and simply agree with what we want to say or do.
Whether someone has the experience and intellectual horsepower to be strategic is only part of the issue. The important part, particularly in client-vendor relationships, is whether you've given another person permission to take on the "pain in the ass" role you need. So, have you given your potential strategic PITA the go ahead yet to be truthful? If not, do it today!