Is it really that common to be in charge of a company and simultaneously lack the basic assertiveness necessary to say you're not going to cover lavish travel expenses?
This theme appears in the comments here a few times. The gist seems to be "Why not just confront the person?"
There are a few different answers to this one. The one you postulate is that the CEO lacks assertiveness. Presumably this is not a terribly common case.
A second situation is that the CEO is sufficiently assertive in the general case, but there are major power differentials between the players. One of the other commenters pointed out that a first-time CEO might not feel comfortable telling one of the titans of the industry to fly coach. This is presumably also uncommon, but more forgivable, although that CEO will need to get over it fast.
My circumstance, and I assume that of others, is that I regard board matters as a long-term interaction of fallible people. Matters of face, allegiances, and frankly who's in a bad mood on what day determine outcomes as often as logic. My job isn't to be idealistic about what should or shouldn't matter; it's to maximize the outcome for the company. Sometimes that may mean picking a fight over nothing to prove a point. Much more often, it means saving my bullets for big game. Others have different styles, but I find this a useful tool to have in the kit.
That said, this sort of minor-conflict-annoyance backfired on me once. I'll see if I can bang together a blog post about that soon.
>> Matters of face, allegiances, and frankly who's in a bad mood on what day determine outcomes as often as logic.
This is so true. Matters of face can spiral out of control easily. I think you handled this specific one with real dexterity.
One related thing from my own experience - As groups grow you tend to get moments where the community norms that everyone took for granted can't be assumed anymore.
It always starts with a single person operating outside those norms. You're faced with the question of whether you have a one-off situation, or a systemic problem (of which this one moment is just the first inkling). Knowing which approach is the right one seems like it's frequently gut feel, but then again, if you know that you are going to need process or guidelines soon, you can use see those moments as an opportunity to get things right before you get bigger problems later.
It really depends on the board member is. Imagine you have a board member who has been one of the key people who have brought your VC funding. You're about to start up a series B and again, he's one of your rocks.
Now you're having some extra meetings to get things straightened out. You know he typically flies first class in any case. Do you want to ask him to inconvenience himself (which is really what you're asking him to do) so that you can use him to raise more money?
While youy may say that this is a basic lack of assertiveness -- I could see the board member saying, "You're missing the forest for the trees."
It will also depend on how independent the board member is. Some board members are relying on your companies success. Others may be just there for the ride.
It should less of a problem for startups, where all the board members will be investors.
It's probably intimidating to ask someone like Jim Breyer or Mike Moritz or John Doerr. I imagine that would be a conversation I'd be nervous to have :-).
