The October 29, 2009 edition of Prime Time Sports had a segment with Keith Law about the Blue Jays’ new General Manager. In specific, about whether or not he should hire someone with a tonne of baseball experience as a mentor; he is after all only 32. (Yes, younger than me and running a major baseball franchise. No, I’m not feeling career failure. Not at all…). The general feeling is ‘Yes’ and that regardless of age or experience you need a half dozen people you can respect to bounce ideas off.

Here is an ish transcript of what Keith said during one critical part of the conversation. I’ve cleaned it up a bit for clarity and added annotations for people not up to speed on the Jays.

What I’ve heard about those [Pat] Gillick (former GM for Jays when they won their back-to-back World Series) years is that their biggest problem was actually making a decision. Gillick was very big on ‘everyone in the room has to be on-board’. And that works fine if the room is small, but their rooms were really packed. Now if [Alex] Anthopoulos (the new GM of the Jays) is willing to just say ‘You know what? Two thirds of us are pointing in the same direction and I like it; that’s how were are going.’ You have to be willing to have advisors below you who vehemently disagree with you and still go in the other direction. And then everyone needs to walk out of the room and be fine with it. It was a huge problem with [J.P.] Ricciardi (the most recent former GM) that his advisors could not disagree with him. You were just not allowed. If he had already decided what to do you, couldn’t point in another direction. You couldn’t walk out of the room feeling like we are doing the wrong thing. That was unacceptable.

This comes back to the Devil’s Advocate idea and its lack could explain why second-time entrepreneurs have a harder time at things than they did the first time. On the flip side, you could use who the leaders of an organization surround themselves as a barometer of future success: ex-consultants and yes-men, not so good; people willing to say call out the boss’ idiot ideas is much better. The boss still has to be the one who makes the decision, but if they are not cultivating a culture where they can be disagreed with, then they are leading a sick company.