Good deal making requires balance. In my opinion, the biggest hurdle to getting deals done is either a tendency to be overly conservative or too much machismo.
Point 1) . . . far too often apathy and professional butt covering lead to missed opportunities.
Pont 2) . . . we should always strive to make the appropriate opening move . . . making the opening move is often the most difficult part of doing deals but being a tough SOB is not the same thing as being a good deal maker.
Amen, brother! I'm probably on the aggressive side when it comes to dealmaking - when I see value, I want to get something done, and fast. Few things are as frustrating as dealing with counterparties who are bogged down by bureaucracy or fear. But - inside your organization, deal advocacy has to be positioned correctly. It's great to be the guy who focuses on shareholder value and zealously pursues deals that enhance such value, while being up front about the risks and challenges. It's not so good to be the "deal cheerleader" on every potential deal that comes in the door, and gloss over or omit the messy bits.
As for opening moves, no question they serve you well as long as they are reasonable. I always like making the opening offer. Although it involves more uncertainty, over time I believe making the opening offer yields better results by setting the stage for the deal and allowing me to push the timing and process for getting the deal done. However, in my experience playing the tough guy and making an outrageous opening proposal is worse than not making a proposal at all. At best, the other party will treat you as if you didn't even make a proposal. At worst, you'll really need to do the deal, and you'll have to waffle your way to a reasonable position, your credibility shot to hell. There's just no percentage in doing that.