I have started and failed at many of my own businesses. Looking back, I found that when I failed, I usually focused on one important question, while avoiding another critically important question.

Question 1: What would make this a success?

This may look like a straight forward question, but it has many little hidden gems that will save your new startup if you do it properly. When you REALLY answer this question, you will eventually break through your own hype about the businesses and start thinking how you will track and measure the success of the business when it kicks off. Ignore the Facebook likes, the re-Tweets and all that, those measurements give you a false sense of success. Look at the things that matters, the amount of new clients, how much are they spending, how much it costs to get new clients etc.

Answering this question will also help you see if you have created a false expectation of the market conditions and what you expect from it. Answer this question in as much detail as possible, then go and sit down with a coach and discuss this issue. I love doing this with my clients. We laugh a lot at how we “convince” ourselves of how easy success will come and how we bend the truth to speak to our need for success.

Question 2: What would make this fail?

“Nothing!” was the answer I got from the two founders of one company. Yep, I am not lying, needless to say I walked away because they were also looking for me to invest. If you cannot see the weaknesses and vulnerabilities of your startup early on, you are bound to fail because you will do one of two things when times get tough. Number 1: You will ignore reality and fail to see what really is going on and you will soon run out of time and cash. Number 2: You will blame, blame, blame! It is the government legislation, it is the economy, it is some big corporate’s fault etc. You fail to take responsibility for your own blindness and let me say it, stupidity.

List ALL (at least 10) that can make you fail and ask yourself how you would feel when each happens and what you would do when each happens. Get used to the emotions because THEY WILL COME and then sit and think how you will respond. I suggest sitting with a startup coach, like I do with my startup clients.

Be gentle

When I do these two questions with my startup clients, I try to keep it humorous and fun because these are hard questions to answer. You might see things in yourself you really do not want to. If you are a startup and want to run some ideas past me, book an hour session with me via Skype and see where you are heading with your business. At least start off from a basis of reality and truth.