Obama's legislative mindset...

One analysis over how Obama wasn't able to live up to his promise when he was first elected in 2008 provided by Rich Miller of the Capitol Fax:

It’s generally considered a rule of thumb that politicians with mainly legislative backgrounds do not make particularly effective chief executives. The two worlds, and their required mind-sets, are vastly different.

And, for the most part, our state’s better governors and our country’s most effective presidents for the past 100 years or so have had executive experience before moving to the top of the ladder. I spend a lot of time thinking and writing about legislatures, and I’ve been thinking lately that many of President Barack Obama’s bungles can be traced right to this issue.

Obama never really ran anything before being elected. But, more importantly, he also learned over the years to think like a legislator. Judging from afar, I don’t believe he has truly changed his mind-set.
...
Obama firmly believed his success at working with Republicans would help him be a better president. Heck, I thought the same thing during his campaign. So far, we’ve both been wrong.

After he was elected president, Obama was no longer a member of a large, mostly collegial group. Many of the same people who once gladly worked with him immediately vowed to block his every move.

Instead of realizing that the game had completely changed, Obama continued to approach Congress as if he were still a member of their club.

You should go over to CapFax and read the whole thing. And then in that same posting you will see another POV by Tribune Columnist Eric Zorn.

Count me as one of those who believes that "executive experience" is what one should look for in a potential chief executive. As President you have to execute the laws and the policies just as any manager would in a private business. A presidential candidate should show that he/she can lead and prove his/her effectiveness.

Of course that's not to say that's the only thing that matters. Obama didn't have a large resume to begin with. Even if he did "conservatively" move up the ladder to prepare for the presidency - which would be ideal if not practical if you want to strike while the iron is hot - then there risks with that as well. To be sure lack of "executive experience" bothered me with McCain although he had a more significant resume than Obama. Although we could count McCain's US Navy service.