It's very refreshing to see someone like Lenny this season. He doesn't fit the mold of the corporate wannabe oozing and schmoozing with sugar-coated BS. Lenny doesn't beat around the bush and will tell it straight.
He can be too abrasive at times though. The preview for next week's car dealership retreat ep shows him snapping at someone to shut up. Plus the preview from before the season started had him arguing with someone in the boardroom with a "what do you think I'm stupid?" I think that's ominous. He'll go far, but probably won't reach the finish line.