strategic consultant to:  

~ serial CEOs & CTOs in software, Internet, technology & digital media
~ experienced consultants in all fields to maximize their practices

I’ve been watching my clients CEOs, their teams, and prospective CEOs make difficult decisions during the past couple of years, in these unfavorable economic times. Knowing most or all of the perspectives of the players (since everyone seems to tell me everything), I started an evolving list of questions to ask myself when deciding on important choices, like when to start something, or when to stop something, or when to take a risk, or how much of what to believe.

So here is the list I’ve been evolving:
1. What do I really want at this point in time re: this opportunity?
2. What am I willing to risk to have it?
3. How long can I sustain that risk?
4. If I cannot sustain the risk (say, twice as long as I would expect to), will I have taken all the risk for nothing? What would be my “lost opportunity” costs?
5. What other opportunities do I have, or might I have, if I did not move forward with this? Can I sustain the stress of “not knowing” about what may show up if I do not move forward on the opportunity at hand?
6. What do I really know about this? Who said it?
7. Do I trust who said it? Is this person in a position to actually know about this opportunity and its risks? Does he or she have an agenda (obvious or hidden) that has nothing to do with me?
8. Am I hearing facts (i.e., that can be verified?) or interpretations, or wishes & dreams & delusions? How can I investigate this?
9. Who else can I ask about this, who might have enough experience to guide my choice, and tell me what I have forgotten to consider?
10. What is the worst that can happen? Can I survive that consequence and continue on or start again, if the worst arrives?

Please send other questions you might ask yourself, to open a conversation about this.
And good luck.