"Elevate the question." Ask metaquestions in response to questions.
Question: "What's the best way to get to the downtown area during rush hour?"
Response: "Why do you want to go downtown?"
A possible answer is that there's a meeting at an office building. But there are alternatives to a face-to-face meeting using today's technology. You can remotely meet with picture and sound. Or the meeting can be located in a spot more accessible during the day, or postponed until you can spend less time travelling than meeting.
Question everything. One example: Cliches. Cliches belong to the realm of automatic living, providing convenient pocket-sized doses of conventional wisdom to answer just about any question. But they are simplistic "one-size-fits-all" answers that can stop one from considering a more useful solution.
"The odds are against us." Well, odds don't really take sides. This cliche reflects a bias of the speaker and likely influences the hearers in a negative way. While odds are cold statistics for the masses, based on incomplete understandings of the associated systems, individuals buck odds regularly -- simply by trying.
"Do, or do not. There is no 'try'." Sorry, Yoda. You do not know all. There are obstacles you may not know about in solving a problem.
"Work smarter, not harder." Or "Work smarter AND harder." Eliyahu Goldratt points out in The Goal that one can be 100% efficient doing something that is not very effective.
Measurements of efficiency, or the bottom line, or short-term results are input data. Use them as tools, not gods to be worshipped.
"The pessimist complains about the wind, the optimist expects it to change, the realist adjusts the sails." --William Arthur Ward. Consider being all three at once. The pessimist might ask the questions that need to be faced by the realist.
"Failure is not an option." Yeah, I didn't see that among the choices. But it is still a possibility, if only due to the forces of change outside your spheres of control and influence. "To meet with triumph and disaster, and treat those two imposters just the same..." -- Rudyard Kipling, If. If considered rightly, failure has benefits: It educates, it builds character.
"A man's got to know his limitations." --Harry Callahan, Dirty Harry. Yes. And provide for them and work around them, and extend them where possible. No, you can't fly -- but then again, you can.
"You are what you eat." Better: You are what you eat, think, and hang around.
"Don't look a gift horse in the mouth." Why not? Did you want a horse? Even if you did, you are going to take care of it, and need to know how healthy it is. If you didn't want a horse, don't look at its mouth, but insist that the gift-giver take it back.
"If it ain't broke, don't fix it." But it IS "broke", in the sense that it is not a perfect solution. Situations change. Needs change.
"A life unexamined is not worth living." Well, you might lose out on a lot of enjoyment thereof.
"Someone's not a happy camper!" I'd rather be a fulfilled climber.
"There's no 'I' in 'team'." But there's an i in fix, ship, deliver, win, accomplish -- what's your point? Teams are composed of individuals. Often folks that quote this are not great leaders.