When Hope becomes Delusion -- what do you do?

We all know how important it is to remain positive. In the face of insurmountable odds, the strong are those that are able to see the potential, the positive and the path to success.

The responsibility of the leader is to hold that hope and keep it alive for everyone in the group. During the critical months of the start-up, that optimism is a resource as valuable as an unlimited unsecured credit line.

As the chief evangelist it is often far too easy to drink the kool aid. So --

As a leader, what do you do to ensure that you are keeping your feet on the ground and that your hope has not become delusion?

As a professional who works with start-ups, what do you do to bring an entrepreneurial start-up clients feet back to earth without being perceived as the "negative one"?

Jason Fried and David Heinemeier Hannson of 37signals wrote a book entitled Rework that is worth reading. But that is not the point I want to make here. While they were writing it, they shared their process and talked about it on their podcast. Something that was captured here really struck me. Everyone was expected to bring their "A" game and everyone else was expected to expect it of them. Here's how that worked in practice: Jason suggested an idea for the book. Dave, who is a rather direct guy (some would say arrogant), questioned it. He did not question it in a way that was confrontational, demeaning, or dismissive. But he kept questioning it. He questioned it at least three different ways. Each time, Jason had an answer but he was also willing to flex to meet David's concerns. The conclusion of the matter was that David was convinced.

The spirit of the conversation was one of mutual respect. There was no posturing or posing. The solid ideas remained, the weak ones did not. No association was made between the ideas and the presenters of the ideas. The mutual goal was to find what works and discard the rest.

The ultimate application for the question posed here is this: consider every road dispassionately and fully until it ends. If no consideration points to likely success, it is time to call it a day. There will be other ideas and other companies.

As a founder of start-up, the other founder and I built a humorous but practical definition of our working relationship: I was clouds; he was the sunshine. But that was my role: I was the more experienced of the two of us and part of the reason the two of us got investment in the first place was that we could keep up that positive message but always present it in a way that appeared not only optimistic, but that it had some critical thought applied to it.

I think you always have to project a credible optimism - we think we're gonna do well not because mom and dad always told me I'm great, but because we have (the right team, right approach, a good product, we've learned from our market, etc., etc.).

That's not to say we were never self-deceived. Oh, that's happened too. Ultimately, it's helped to keep running some scenarios in your own mind to check the following:

• Your venture is profitable, or on the road to it
• You're picking up new skills, making new business relationships - paving a way to a better personal future even if the venture doesn't reach its potential
• Your sacrifice is worth your equity stake, if you have one. If you haven't calculated not only what your equity could be worth, but under what scenarios you'll be able to get actual money for the equity, then you're flying blind. What's all the rah-rah optimism going to get you if it really isn't (or isn't likely going to be) worth anything?

And a note of conscience:

• As a leader, owner, CEO, whatever of a start-up, you're asking others to risk their assets, their careers, working lives. Be sure you realize what you're asking for before you hype up what you're offering in return.