Yesterday I read a frickin’ awesome post over at OnStartups.   Of course, I found it through my Twitter stream.  Love Twitter for this stuff. Dharmesh listed 23 awesome, and so true, questions that keep entrepreneurs up at night.   Having started 3 businesses to date, this list was spot on!  I’ve been kept awake pondering most of these questions.  (except for number 4, I don’t have an Uncle Larry)

Being an entrepreneur is hard.   I’ve already found myself asking some of these questions with Socially Booked.    Marc Cerenda, the CEO and founder of Ladders.com had a great post on being an entrepreneur today.  You should read it.

The next harderst thing to being an entrepreneur is being a sales person.  I’ve always operated from the premise that sales people are the CEO’s of their own small business and they are almost entirely responsible for their own success or failure.  They ARE, in many ways, entrepreneurs. This being said, I thought I’d identify 21 questions that keep sales people up at night.

21 Questions that Keep Sales People Up @ Night

1. Am I going to make quota?
2. Did I make enough cold calls today?
3. Am I cut out for sales?
4. Did I bomb on that customer call today?
5. Is my customer thinking about switching vendors?
6. Is product going to have the new version out in time?
7. How can I keep my customer from asking for a price reduction?
8. How can I compete with my competitors brand new product?
9. Does my manager think I’m doing a good job?
10. Am I prepared for tomorrows call with the COO?
11. Should I even respond to this RFP, what happens if I don’t?
12. Is the deal going to come in before the end of the quarter?
13. My customer won’t call back. Why?
14. I see the market changing, but my company doesn’t see it. What should I do?
15. Our product isn’t delivering like we promised.  What do I do?
16. Is the IT department (insert any other department) going to sink this, even though my buyer loves it?
17. What if the demo fails?
18. Legal won’t move off their position.  It’s going to sink the deal.  What do I do?
19. I’m way behind in updating the CRM system and my manager is getting pissed, but I have to much selling work to do.  What do I do?
20. I’m afraid the deal isn’t going to close.  Should I tell my manager?
21. How do I tell my manager my SE isn’t very good and it’s costing me sales?

I’ve got big money there are at least 100 more really good ones.   What did I miss?  Add to the list in the comments.   Excited to see what keeps this community up at night.